How high-performers discover their ideal career and find meaningful, well-paid work without starting over —

A Career Change Guide

If you’re unhappy enough with your career to have found your way to this guide, then I have good news for you and I have bad news about the career change advice below. 

The good news is that by following this guide, you can change careers, find truly meaningful work, be well compensated and transform your life in less than a year.

The bad news is that everything you are currently doing to find meaningful work is wrong.

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Every complex problem has a simple solution, and it’s wrong.

H.L. Menken

You will NEVER find meaningful work by doing any of the following:

  • Learning to love your current job (doesn’t work);
  • Finding your passion (not really a thing);
  • Finding something that you’re good at, even if you don’t enjoy it (you’ll still be unhappy);
  • Realizing that money isn’t important (it is important);
  • Making a super amazing resume (mostly irrelevant).

If you’re looking to do any of those things, then I can’t help you. It’s been real. Adios. 

But, if you’re looking for help finding a career that fits you, provides you with meaningful work and compensates you really well, then you’re in the right place.

My team and I wrote this guide to help you understand the entire process of finding meaningful work, from where you are now, reading this guide, to where you want to be, working at a new job on an intentional career path that is meaningful, fulfilling and well-paid, ready to share this guide with a friend. 

This is the only guide that explains the stages of career change, the relevant sociology and psychology and stories of real people who we’ve helped along the way.

But I’m pretty sure my definition of “career change” is different than yours. Here are some examples of what I mean by career change.


Linnea told us her goal was to find a meaningful career with a step up in leadership. Seven months later, she achieved a career jump that was four levels higher to VP, and in a larger company.

Jessica designed her ideal career, and then created an opportunity in that career. She received a job offer with a salary of $130,000. We discussed it, and she accepted the position — after negotiating her compensation up to $380,000. She did all of this in just four months

Kristy decided she didn’t want mediocre work any longer. Instead she wanted all the best parts of being on vacation (traveling and wine tasting), combined with her favorite work activities (writing and managing operations). She created her own role as Chief Communications Officer for an online wine and travel company

Those examples aren’t even on the radar for most people (maybe you didn’t realize those things were even possible) but we get to share in these types of stories because we’re helping people like Linnea, Kristy and Jessica every day. 

Those examples are just the beginning.


What if you interviewed for a junior level position. Immediately after the interview you turn them down because it’s not what you want, then the company calls you with a job offer — for a senior level position. – I’ve seen this happen many times.

What if you could spend more of your day doing work that challenges you to grow in meaningful ways, but you did it with an organization and a boss that actually respects your needs as a human being? It’s possible. We’ve got hundreds of stories like this.  

I promise you one thing: to do work that is both fulfilling and pays you very well, you will need to drastically alter your mindset.

If you refuse to accept anything but the best, you very often get it.

Somerset Maugham

Here’s an example of what I mean that comes from real research.

Very few people on Earth have what they would call a “great job” and earn more than $100k annually. This guide teaches you how to become one of them.

But first I have to show you what NOT to do.


Years ago, my wife Alyssa and I moved to Portland, Oregon after I’d accepted a highly-paid but unexciting job as a Regional Manager for a franchise company. We bought a house – twice as expensive as anything my parents had ever owned. I started my new job, supervising 20 people. If I did well in my first year, they promised me a BMW. Suh-weet. I felt safe, successful, optimistic. 

But it didn’t last. 

My commute to work was three hours a day. My work schedule was 70-80 hours per week. I didn’t have weekends. I didn’t have time off. I never saw Alyssa. I couldn’t focus. I couldn’t work. I was scared. I gained nearly 50 pounds. I developed panic attacks. (I didn’t even know what panic attacks were before that!)

I began looking for a way out. The window. Not kidding. It was only two stories. If I “fell” (jumped) out the window, I’d probably just break my legs. They’d have to give me some time off… right? Would insurance cover that? Was that fraud? What if I got in trouble? Or got fired? I felt a panic attack coming on. I decided against the window.

Next to the office was a burger place. I decided to stress-eat myself sick and then tell them I needed to go home. I sat down and had three burgers, fries and a huckleberry milkshake big enough to fill a bathtub. It didn’t work. I got sick, but just nauseous enough to sit at my desk, writhing in pain. Not enough to go home. Damn.

I was trapped. Wife. House. Car of my dreams. No way out. Had to keep going. 

I went on this way for a year. Then one day, on the way to work, I had a panic attack so intense that I knew I was dying. In the car. Alone. On Interstate 5. Bumper to bumper traffic. No way for an ambulance to reach me.

I could see the headlines. “Fat loser dies in car because the real world was too hard for him. He is survived by his wife and his student loans.”


I didn’t die. But I decided something had to change. I brought my concerns to my boss, who listened politely. 

Three weeks later, he assembled my team, called me into his office, told me I was fired. 

But he did give me a choice. I could walk in the other room and tell the 20 people working for me that I was leaving, and he would give me three months severance. Or I could walk out the door without telling them and get two weeks pay. I needed the money. One last humiliation. I stood in front of my team and told them I was leaving. There were tears (mine). I was a failure. I apologized. I left. Me and my three months severance.

It is not because things are difficult that we do not dare. It is because we do not dare that things are difficult.


Driving home – my last commute – I decided to never live like that again. I spent the next 10 years searching for career fulfillment. I sat for over 100 job interviews. I transitioned to Human Resources leadership and conducted over 2,000 job interviews. I learned executive and leadership coaching. Along the way, I held many “dream jobs,” but then my dreams would change, and I would move on. And throughout the process, I was learning and growing and building my skills and honing in on what I really wanted. Finally, I started my own business helping people find career fulfillment. And I love it.


Scott is an author, coach (with 20 years of experience), and host of the Happen To Your Career Podcast – Which has been called one of the best career podcasts over 200 times by places like Forbes and LifeHacker.

His work has been featured globally on MSNBC, Glassdoor, The Muse, and many other publications. He’s regularly paid to speak at Universities and Organizations about meaningful work and career happiness.

He’s also the CEO of and now helps others avoid those same mistakes he made trying to find meaningful work.

Scott and his wife, Alyssa, live with their 3 kids in Moses Lake WA part of the year and somewhere else in the world the rest of the time! More about those adventures at!

He absolutely loves thinking he’s up on music before it becomes trendy (you can’t tell him differently) and his extended family tree takes a whiteboard to be able to explain.

He also dislikes writing in the 3rd person, but really hopes you love this guide!

I have a fulfilling career, but this isn’t about me. Or about the people we’ve helped find meaningful work. This is about you — your career change and what meaningful work means for you. 

So what does “meaningful work” mean? Here’s what I have found most people need to have a fulfilling career — see how many of these describe your current situation.


Here’s just a few of the most important pieces. You’ll find a complete list of the highest impact areas in Stage 3: Identifying your ideal career. Also here’s a link to my personal collection of much of the research, books and articles that have helped me form these conclusions.

  • Autonomy. You have control over how your work gets done. This includes creative control over your work and other times it means having flexibility to work when you want, like working remotely or taking time to be at a family event. 
  • Learning. Your job allows you to be a permanent learner. Every day, you learn something new about your work, your customers, how to be a better business person. You constantly learn new skills. Particularly those that you have curiosity about. 
  • Growth. Your job allows you  to become more than you are. A better business person. A better person, period. A better version of yourself. 
  • Creativity. No one wants to feel like a robot – learn to do one thing, do it over and over until you break and they replace you. Awful feeling. Your career allows you to activate your creativity by finding novel solutions to new issues. You are always doing / making / achieving something new.
  • Contribution. There are two kinds of contribution – what you contribute at work, and what your work contributes to others. At work, you know that your voice is heard and that your opinion matters. You believe in the company’s mission because you are helping to shape and guide that mission. And what your work contributes to others is about more than making money. You and your co-workers  help each other out. And your work makes life better for your customers.
  • Values. I can be my full self here – that’s how you feel when you think about work. You feel free to express and embody your values at work, and you know your co-workers will support you because you share the same values.

How many of those do you have? How many would you like? 

Career change is a mountain climb. It’s an adventure. It’s risky, it’s scary, it’s challenging, and if successful, it can be rewarding beyond description. But you have to make the choices that get you from where you are to where you want to be. I can guide you, but ultimately, you have to find your path up the mountain. 

This guide will help you determine if you’re prepared for career change, and if so, to provide you with specific actions that you can take to discover your path up the mountain.


Let’s talk about what I know, from experience, is not going to work:

  • You’re not merely trolling LinkedIn and Indeed. Job boards can help you find a new job. If that’s all you’re looking for, then feel free to go job-boarding. The overwhelming likelihood is that you will end up in the same situation that you are in now – unfulfilled, inadequately compensated, or both. Career change is not about finding a new job. It’s about imagining a new life.
  • You’re not starting over. Career change isn’t Chutes and Ladders. You’re not falling down and starting from the beginning. You don’t have to go back to school. You’re taking the personal strengths and professional skills that you have built throughout your life, and activating them to find meaningful work. Career change is not moving backwards. It’s moving upwards.
  • You’re not choosing between meaning and money. To feel fulfilled in your career, you need to derive meaning from your work, and you need to feel well-paid for it. Scientists – people in lab coats, probably wearing glasses, possibly with test tubes – have studied this question. You will not achieve career fulfillment by choosing either meaning or money. Getting up the mountain means finding both. And with that in mind…
  • You’re not taking a pay-cut. Repeat, you are NOT taking a big pay cut. You are not moving to the desert and living off of stuff that you find. You are not couch surfing while you journal about how money doesn’t matter. You are a talented, highly-skilled, dedicated worker. There is a place for you in the global economy where you can bring your abilities and expertise to bear on work that you find personally meaningful, and be well-paid for it. That is what’s waiting for you on the mountaintop.

Everyone who helped make this guide has been where you are. Just as unhappy. (or worse relatively happy with a “good job” but still not fulfilled) We’ve been just as scared. Just as sure that there was something better out there and just as unsure about how to find it. We got up the mountain, and we can show you how. 

And once you know how to do this, once you have acquired the skills to find or create opportunities to do meaningful work, you will always have the ability to do it again. So the next time you need to move on to the next phase of your career, you will know exactly what to do. Not start over, not troll job boards, but identify, locate and conquer your next adventure.

Go confidently in the direction of your dreams! Live the life you’ve imagined! As you simplify your life, the laws of the universe will be simpler

Henry David Thoreau

Learning these skills and applying them is not quick, and it’s not easy. So if you think this process is not for you – too much work, too much trouble, not worth your time – that’s completely understandable. Thanks for reading and best of luck.

If you’re still reading, if you’re ready to do the work to find your path up the mountain, to change not just your job, or your career, but your life, then your climb begins with this guide. 

The first stage is the most important, and the one that is most predictive of success. If you can accomplish stage one, you will probably make it up the mountain. 

Think you can do it? Put your boots on…


I’ve said a lot about how this process will be more challenging than you think (and that’s true).

As a palate cleanser, please accept this advice on how to make this process easier:

You do not need to read this entire guide.

Of course, you are welcome to read every word of this guide. It’s witty and informative and grammatically immaculate. Feel free to luxuriate in my ebullient prose.

But if you want to save a little time, take a look at the stages of career change listed below. After helping thousands of people change careers, I promise – one of these stages applies to you. Find the one that best describes your situation and click the link to jump to that section.

  • Only 4% of people on Earth work in what they consider fulfilling careers. Are you prepared to do what it takes to become one of them? We’ll help you find the answer – whether it’s yes or no.
  • You’ve decided to change careers. You’re going to climb the mountain. But there’s a lot of work to do first. At this stage, your goal is to prepare yourself, and the people in your life, for the difficulties you will face on your climb. We’ll get you ready.
  • You’re ready to climb a mountain, but which one? The next stage is to not only identify your new career but to imagine your new life. We’ll help you determine what it is that you truly want from your career change.
  • You know what you want. Or do you? You already have one unfulfilling career, you don’t need another. Before you hoist your pack and start clambering all the way up the mountain, we’ll show you how to design career experiments to investigate your potential new career. Call it test driving, wine tasting, ice cream sampling. The point is to try your new career before you commit to it.
  • You’re climbing! Finally! At this stage of the process, we’ll help you chart your path up the mountain. We’ll show you how to identify your signature strengths and reach the personal achievements, “a-ha!” moments and key realizations that will guide you the rest of the way.
  • You can’t do it. You’re not smart enough. Why did you think you could change careers? Whose stupid idea was it to climb a mountain, anyway? It’s too hard. You quit. This stage is about discovering a path forward when you are sure there isn’t one.
  • You did it. You got a job offer in your new career. You reached the summit, now don’t fall off. We’ll guide you through negotiating your opportunity and mastering your arrival. Congratulations.
  • Your new life on the summit is great, but it’s still life. You have a fantastic new career, but it’s not perfect. We’ll help you through the growing pains of adjusting to your new career and life.
  • As you continue to grow, evolve and change, we’ll help you make sure that your career grows and evolves with you.

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Only 4% of people on Earth work in what they consider fulfilling careers. There’s nothing wrong with the other 96%, it’s just that finding a fulfilling career is hard. The first stage in the career change process is to determine whether you are prepared to do what it takes to join the 4%. You want to change careers, but are you truly prepared to climb the mountain to meaningful work? 


Career change doesn’t begin with a thought, it begins with a feeling. And more likely than not, that feeling doesn’t come from your head, it comes from your gut. When you think about your career, how do you feel?

I’ve interviewed hundreds of former clients on my podcast and gut feelings are a common topic.

Alissa: “For me, having that intuition, it does help you kind of put that pause in things where you go, okay, something is off. Psychologists talk about the difference between your emotional brain and your logical brain. Your intuition is your emotional brain, but then you have to say, okay, logic brain, what do I do with how I feel? And that’s really where they get married together.”

Jason: “My coach helped me realize that following my gut or intuition has really helped me out. Being an engineer by default I’m analytical and don’t like to follow my gut. It was a kick in the pants and also her helping me understand what my gut is saying. Put your head out of it for a minute and let’s sit with it.”

Michal: “If something doesn’t fit or whatever your gut is telling you, you’re smart enough to know that, I got here and this is great, but I’m going to move on.”

What is your gut telling you?


You have questions – I know, I had the same ones. Let’s run through them.

  • Is career change really possible? Yes. We’ve helped thousands of people transition into fulfilling careers – we tell a few of their stories below. Think of how many impossible things have happened since January 2020. Do you really think that your changing careers would be crazier than any of those things? Yes, career change is possible.
  • How long does career change take? The amount of time it takes to change careers is different for everybody. It may take 30 days or 18 months. But you’re not going to make it up the mountain by sprinting to the summit. Career change is a process and it takes time. Our clients’ average career change takes 6-9 months.
  • But how do I know what’s out there for me, or how to get it? Of course you don’t know what’s out there for you or how to get it – if you knew, you’d already be doing it. Discovering new career options IS the process. They are out there. You will find them. You just need to begin. 
  • How do I begin? By reading this guide. Congrats! You’ve begun. Now keep reading — the guide is full of client stories that will show you how the process works.

Changing careers feels like a leap into the unknown. What’s out there for me? Am I going to land in a huge pile of money like Scrooge McDuck in his vault? Or will I be the Coyote chasing the Roadrunner off a cliff?

For the answer, we turn to our most trusted source – nerds. Here’s what science tells us about regret.

  1. We tend to regret inaction more than action. If you try something and fail, you are less likely to regret it than if you don’t try at all.
  2. The most common source of regret is the belief that we have failed to become the best version of ourselves. By failing to pursue our dreams, we set ourselves up for lifelong regret.
  3. Reversible decisions are more often regrettable than irreversible decisions. We are less likely to regret our choices if we believe that we had no alternative, and we did what we had to do.

If you’re a total nerd or maybe just a little emo, here’s my complete collection of research and notes on regret.

There is the risk you cannot afford to take, and then there is the risk you cannot afford to not take.

Peter Drucker

So, will you regret career change? You are more likely to regret not trying it than trying it. (Yay Science!!) And if you believe that your current career does not allow you to be your best self, then you are more likely to regret giving up on yourself than you are to regret fighting for yourself.

The key realization is that you don’t just WANT to your change career — you NEED to change careers. You have NO CHOICE but to change careers. This is where many people get stuck. 

Can you stay in your current career and be happy? Can you keep living your present life and feel fulfilled? If not, then you don’t WANT to change careers, YOU NEED TO CHANGE CAREERS. Once you accept that fact, you have no choice – you must change careers. And you will not regret doing what you NEED to do.

When I reached the point that I contemplated jumping from a window to get time off from work, I didn’t want to change careers – I NEEDED to do it. But it still took me almost a year before I began the career change process.

Laura, a former client, realized she needed to change careers three years before she began the process of doing so.

Another client, while walking to work one morning, contemplated stepping in front of a bus to avoid going to the office. Still, he remained in his career for five years before pursuing an alternative path.

This is what I mean by being ready for career change. We all WANT to achieve our dreams. We all WANT to become our best selves or live our best lives. But only when you realize that you NEED to do it, that you have NO CHOICE but to do it, will you be ready to pursue career change without regret.

Career change is hard, but so is staying in an unfulfilling role. Here are a few stories of former clients and how they decided it was worth their effort to scale the career change mountain.


Here’s Nadia, a former client, describing in her own words how she decided to change careers.

“It suddenly felt like all the doors were closed. I had nowhere to go. I had walked away from a very successful career and in my heart of hearts I knew there was no going back. I knew, practically, I could go back. But I knew I’d be miserable. And that was not what I wanted and I was desperately looking for a way out. And I was totally lost. I was despondent. I thought I’d made the biggest mistake ever. And then I found Happen To Your Career through Twitter, of all places. And then I thought, it’s now or never. I was at a turning point. It was like, something has to change. I had some savings. And it was a case of, let’s make this happen.”


Elizabeth felt pigeon-holed at work, relegated to a narrow set of responsibilities with no opportunity to learn or try new things. Friends, colleagues and her spouse noticed that she was becoming withdrawn, disengaged – not just from her job, but from her entire daily life. She would come home from work and seem defeated. Work that had previously been exciting became boring.

There were days when Elizabeth came home energized, excited. With reflection, she realized that those were the days when she got to learn something new. Elizabeth understood what was missing from her role – it was the opportunity to learn new things. She needed more responsibility for a greater variety of issues so that she could continue to grow in her work.

Elizabeth brought her concerns to her manager, laying out her ideal role. The manager promptly shot her down. She said Elizabeth lacked the skills to handle the responsibilities that Elizabeth wanted to take on – even though Elizabeth had been practicing those skills for 10 years.

At that point, Elizabeth knew she had to change careers. She knew what she wanted from her career. She knew that she couldn’t get it in her current position. And she knew her manager was not going to allow her to change positions so that she could achieve the things she needed to feel fulfilled.

Elizabeth pursued a career change. Seven months later, she had done it.


Laura never loved math, but she was good at it, so she became an engineering consultant. After a while, she got bored, went back to school and got a Master’s degree. With that new credential, she pivoted into sustainability consulting, and for eight-and-a-half years, she was happy. She progressed through four different roles at a high-growth startup in the future-facing sustainability field. It was exciting. She felt passionate about it. Until the feeling faded.

After eight-and-a-half years, there was nothing new for Laura to learn. She headed a team of 10 employees who were looking to her for guidance and inspiration, but she no longer shared their passion. Laura’s job became a burden. She decided to change careers.

Seven months later, she accepted a position in her new career.



  • Subscribe to the Happen To Your Career podcast. We have hundreds of interviews with people who have successfully changed careers. The podcast is a great resource to help you determine whether career change is right for you, and what to expect once you decide to go for it.
  • Read books about career change. I’d love to tell you that this guide is all you need to understand career change, but the truth is that there are a lot of great books to check out.You can hear interviews with many of their authors on the podcast.
  • Keep reading the guide. As we continue on, get ready for Stage 2…

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You’ve decided to change careers. You’re going to climb the mountain. But there’s a lot of work to do first. At this stage, your goal is to prepare yourself, and the people in your life, for the difficulties you will face on your climb. This includes (spoiler alert!) the moment when you will get most of the way there and then decide to quit. Sound scary? Daunting? Intimidating? It is. But we’ll get you ready.

The best to avoid failure is to make success inevitable. The way to make success inevitable is to plan for problems before they happen. Because I have helped thousands of people through this process, I know how it is likely to go — the fun parts, the hard parts, the parts that are going to make you want to quit. The great advantage of this information is that we can prepare for those problems now, so when they arise, we will already be prepared with a solution.

Taking a new step, uttering a new word is what people fear most.

Fyodor Dostoyevski

If you were planning a literal mountain climb, there would be lots of no-brainer equipment you would need — boots, coat, tent, sleeping bag, water bottle, Sour Patch Kids. That stuff’s easy. The tougher question is, who do you trust to guide you up the mountain? Who would you bring on the most challenging journey of your life? These are the people you need on your side for your career change, and now is the time to let them know that you need their help.


Stage two is a gut check. You’re about to undertake a difficult, complicated process to change your life. 

So — who’s coming with you? 

The first conversation you have may be with your spouse or significant other. This conversation will be a two-way street. You are going to need your significant other’s support, especially when the climb gets steep and you get frustrated. 

But your spouse or significant other also needs to hear from you. What will this process mean for them? What about money? You’re changing your life — what does that mean? Are they invited to your new life or are you leaving them behind? When you say, “I need you to support me,” what does that mean, exactly? 

This might be an easy conversation or it might not, but have the conversation now. Tell your significant other why you need to change careers. Tell them that you do not expect the process to be quick or easy. You need them to be there when your knees start to buckle and you think about giving up. Make a plan for any financial disruption. Make sure there is an open channel of communication so you can check in with each other while you’re going through the process. 

Another key conversation is to identify the friend who you’re going to call when you’re ready to quit. This is your personal Ghostbuster. When things are at their very worst… who you gonna call? This person. 

Prepare them. Tell them you are changing careers, it’s going to be difficult and complicated, and the day will come when you will call them to say that you are giving up on career change. When they get that call, their job is to convince you to keep going.


Career change is going to unbalance your life. Your daily routine will be disrupted. Your self-image will be disrupted. Your finances may be disrupted. You may feel off-balance. If other areas of your life are already off-balance, you may become overwhelmed. You may lose your balance and fall off the mountain. Your career change may fail. That would be bad.

Therefore, to whatever extent possible, you need to make sure that every other area of your life outside of your career is as stable as possible. Friends, family, relationship, finances — anything you can do to keep these aspects of your life in balance will exponentially increase your odds of completing a successful career change.

Assembling your team is a big part of keeping your balance. But be gentle on yourself. Don’t make the process harder than it already is. If you’ve been thinking about quitting smoking, now is probably not the time. If you’ve been thinking about changing your diet, maybe it can wait a few months. Career change is your challenge right now. Don’t pile other challenges on top of it. Climbing a mountain is hard enough — no need to add ankle weights. 


We know the career change process gets harder as it goes along. There are set-backs, reversals, rejections, promising leads that do not work out. As you climb higher, the path gets steeper, the air gets thinner, it becomes more difficult. Your patience may wear thin, but so may your rationality. Fear will begin to creep into your mind, and then flood it. “This isn’t working, why isn’t it working? What am I gonna do?” Fear will cripple your ability to make rational choices about your career path.

I know from my experience as a job seeker and a career coach, as well as from research, that the best thing you can do in a job interview is to show the interviewer as much of your true self as possible. If you’re “faking it,” “just trying to get through it,” “trying to give them what they want,” then you’re going to end up with a bad result. Either you won’t get the job, or, even worse, you’ll get the job, but the version of you that gets hired is not going to be your true self. And that will leave you back where you started — bored, miserable, unfulfilled, having wasted all of that hard work and sacrifice just to land in another unhappy situation.

Fear makes this problem worse. You should go into a job interview feeling relaxed, excited, eager to learn, open-hearted. Instead, fear makes you nervous, desperate, frightened, overwhelmed by a feeling of, “this has to work.” You feel like if you don’t nail this interview, the interviewer will push a button, a trap door will open under your chair and you will drop into a tank full of hungry sharks.

The best way to combat this fear is by surrounding yourself with people who can help you through your career change. There’s nothing worse than being alone when you’re scared. You think about how scared you are and that makes you more scared and the fear grows in your mind in a cycle until it consumes your entire conscious thought process. Break that cycle — surround yourself with friends. This is what your team is for. Also…


If you were climbing a mountain, you wouldn’t wear just one layer, you would wear several. That way, if the cold gets through one layer, there are others that will still keep you warm. These layers are a redundant system — they reinforce each other. An airplane has three redundant on-board computers, so if one isn’t working, the other two can keep the plane flying. Blockchain technology for cryptocurrency also works this way. Every cryptocurrency transaction is confirmed thousands of times to ensure that it’s authentic. 

Your preparations for career change should be the same way. You need redundancy. You need multiple friends, multiple reasons to keep going when things get tough. You need redundant fail-safe mechanisms to keep you climbing when you feel like you’re ready to give up. Again, your team is your most important asset. 


Full immersion means doing everything you can to dig into the process of career change — study it, learn about it, care about it. The people who are best at career change and have the best outcomes are the ones who are genuinely passionate about the process.

Who’s more likely to make it up the mountain — a climber who spends 30 minutes a day reading about mountain climbing, or a climber who thinks about it non-stop? The more time and energy you spend on career change, the better your outcome will be. Your mind will turn its energy to the creative problem solving you need to do to make your career change happen. Who do you know who can connect you to a certain company? Who can you talk to about a certain industry? How can you get in front of the person you need? 

Full immersion also doesn’t always have to mean “extra time”. You can layer it in to the existing parts of your day in the nooks and crannies of your schedule. Here’s an example:

What do you notice when you look at this? There’s all the normal parts of a day, it’s just the process of learning about and doing career change are layered over the top. In ways that don’t necessarily have to take additional time. I show you this because one of the biggest obstacles to finding and doing fulfilling work that pays well is time. 

If you tell yourself that there’s no time, there will be no time. But instead if you figure out how to use the time you have differently, you’ll eventually be very pleased with what’s possible. We all have the same 24 hours in a day.  

The Happen to Your Career podcast is a great way to be thinking about career change while you’re doing other things. There are also lots of great books about career change. And if you’re a to-do list person or a bullet journaler, make yourself some lists. What do you want out of your new career? What problems have you always wanted to solve? What industries have you always wanted to try?

Turn your mind to the problems of career change and let your mind amaze you with the creative solutions it thinks up.


Meet Linnea Calderon. 

Linnea is self-described multipotentialite (a term coined by my friend Emilie Wapnick). It means Linnea has a lot of different skills and interests, and sometimes has difficulty deciding which one to pursue. So, after 13 years in the financial services industry, and with a newly-minted MBA, she came to us for help to determine what to do next. At the time, Linnea’s job title was Senior Strategy Consultant. Less than a year later, she had a new job in a new career — with the title of Senior Vice President. In one move, she jumped four seniority levels.

After we helped her with her career change, Linnea came on the HTYC podcast to share how she did it. She attributes her successful career change to two points of emphasis — full immersion and extreme preparation.

Here’s how she described immersing herself in career change on the HTYC podcast:

Use a variety of different avenues and educate yourself, so one of the things that I did was along with the podcast, that I would listen to driving to work or at the gym, I also … bought books about specific topics that I was interested in. I’ll give a shout-out — How Do I Write This Email by Danny Rubin. Same thing with negotiation. That wasn’t my strongest point. So, after listening to Josh Doody’s podcast, I bought his book Fearless Salary Negotiation, read it, did the exercises. And so my advice would be to use different avenues and educate yourself during the process, because the more you know the more power that you have behind yourself and the confidence that you will have when you get to the point of when you want to go after your wants.”

And when it came to preparing for meetings and interviews, Linnea did her homework. Linnea moved up four job titles — that was an extreme result, and it came from extreme preparation. Here’s how she described her preparation on my podcast:

I would say one of the keys to my success was very in-depth preparation for every single interaction that I had, whether it was an informal coffee, whether it was an interview, whether it was following up in an email or a handwritten letter. Every interaction that I had or knew I was going to have, I prepared for to the nth degree. And so that way there was no question that I couldn't answer or anything that I couldn't be prepared for because I genuinely prepared a lot, probably more than I ever have."

What I love about Linnea’s story, aside from the great outcome, is that Linnea didn’t need any trick or special skill. She just worked hard on high impact activities — anyone can do that. 

When we showed Linnea resources to learn about career change, like my podcast and the books discussed on the podcast, she devoured them. When we taught Linnea how to approach people for informational interviews to learn more about their jobs, companies and industries, she threw herself into the process and worked hard to maximize every interaction. 

Extreme results come from extreme preparation. Immerse yourself in career change, do the work, and you can achieve well beyond what you think is possible.

What Extreme Full Immersion Looks Like – A Week in the Life

What do you notice when you look at this? In this schedule theres still all the normal parts of a day. However in this example there’s quite a bit of extra time spent on learning and doing career change too. This isn’t Linnea’s actual schedule but it is very similar to how she was operating.

She also went from a Manager level role to a Vice President level role – with a large organization. To make that happen, you don’t just do the bare minimum, you’re spending extreme amounts time, energy and effort to get extreme results that very few other people get. 

Linnea is not superhuman. She’s simply figured out how to use her gifts, talents and time differently to get extreme results. She invests in herself at an extreme level, she learns at an extreme level. You can too! 

Want to hear Linnea’s entire story in her own words? Here she is telling the story of exactly how she went from a Manager level role to a VP level role. Listen on the Happen To Your Career Podcast.



  • Listen to Linnea’s Story – Get an idea of how this works in the real world.
  • Build your personal “Team”. Identify 2-5 people (this includes mentors, coaches, friends and (select) family members) who will be on your Team to make sure you’re successful.
  • Communicate to people on your personal “Team” what you’re doing, when you’ll need them and what you will do when it gets hard. Use this template:
    • Hi [INSERT NAME]! I’m going to be changing careers and I would like your help. If you’re up for it, I would like to say/do [INSERT ACTION/WORDS] when I say/do [INSERT ACTIONS/WORDS]. Would you be willing to commit?
  • Not sure where to go next? Or getting stuck? Just want to move faster? Schedule a conversation with our team by clicking here. We will help you figure out the very best way we can help!

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Stage 3:
Choose Your Mountain – Identify Your Ideal Career and Life

You’re ready to climb a mountain, but which one? The next stage is to not only identify your new career but to imagine your new life. This is a fun one, but not an easy one. We’ll help you determine what it is that you truly want from your career change.

What’s fun about this stage, but also challenging, is that you have to dare to dream.

To know what you prefer instead of humbly saying ‘Amen’ to what the world tells you to prefer is to have kept your soul alive.

Robert Louis Stevenson

Yes, there is a list of characteristics of fulfilling work (below), but those factors have to be placed into a context. If you want to buy a car, I can tell you that it should have four wheels and an engine, but that doesn’t tell you what kind of car to buy. Just like you can’t take a strengths assessment or personality test and then BOOM out pops out a list of the perfect jobs that would be an amazing fit.


Here are the factors that make work fulfilling. Think of this as a checklist. If your job is missing any of these factors, then your job satisfaction will gradually erode until you feel unfulfilled. This list comes from my experience helping thousands of clients change careers, in addition studying the current research and doing research of our own. 

  • Autonomy/Flexibility. You work when and how you want to. You have input or authority over “how the work gets done”. You are not micromanaged, electronically surveilled, or otherwise made to feel like a tool in someone’s hands rather than an adult human who is permitted to use her judgement and expertise to execute her assignments. 
  • Challenge. Your work challenges you and pushes you to expand your capabilities. You are stretched outside your comfort zone, but not pushed so hard that you feel as if you’re drowning.
  • Growth/Evolution. As you acquire new skills, experience and expertise, you grow and evolve, and your job rewards that by growing and evolving with you.
  • Team. Your boss and coworkers are supportive. You don’t feel taken for granted or exploited. You and your coworkers are not put in hyper-competitive situations or otherwise forced to root for each other to fail. Simply put — you like the people you work with.
  • Impact and Contribution. You see a direct connection between your work and how it helps other people.  
  • Values. Your work is a reflection of who you are as a person — morally, ethically and professionally. You do not have to hide or compromise yourself in order to do your work. You do not have to give up on something you always wanted to try. You are able to bring your complete self to your job. 
  • Direction. You know what you are doing at work and why you are doing it. You understand what is expected of you and how these expectations fit your project’s goals and your company’s mission. You are able to ask for and receive feedback, to know if you’re meeting expectations and achieving both your goals, and your employer’s goals, for your work.
  • Signature Strengths. Your job leverages your strongest abilities so that you feel able to maximize your skillset in your work. You are not using one of your professional skills in your job while others waste away. You’re bringing every skill you have to your work.

And here are the detractors, the things that are going to ruin a great (even ideal) career situation.

  • Extremely long commute. On average, your trip to work takes over an hour. 
  • Instability. You do not feel that your job is secure and believe you could lose your role at any time.
  • Undermining. A series of unfortunate events negate your work. For example, several projects that you’ve worked hard on are all cancelled.
  • Inadequate pay. Your compensation doesn’t meet your basic needs or feels unfairly low.
  • Unsafe coworkers. Your coworkers or boss threaten your physical or psychological safety. For example, a coworker bullies you or a boss constantly yells. 
  • Underqualified. You are assigned work that is far beyond your capabilities and feels hopeless or continuously erodes your confidence.

So what do you do with all that? The list doesn’t tell you what industry to be in, what title to seek, what duties you should have (we’ll get to that in Stages 4 and 5).

You have to decide what you want. You have to choose which mountain to climb.


What is “clarity?” Clarity is not a flash of inspiration that hits you while you’re emptying the dishwasher. Clarity comes from the conscious process of reflecting on your real world experiences, deciding what’s important to you, consciously acknowledging those needs and then acting on them to the exclusion of all else.

Achieving this degree of clarity about your career goals is not easy. It requires hard work to delve into your experiences and really try to understand yourself. If you had a job you enjoyed, why did you enjoy it, and why did you stop enjoying it? If you had a job that went badly and you were laid off, why did it go badly? What was missing from the situation that you needed?

Clarity comes from having the real world experience to determine what you want, declare those priorities, and then act on those priorities, and only those priorities. Clarity means not compromising what you want because of fear or the expectations of others. Clarity takes courage.

Scott Anthony Barlow

Fear will encourage you to avoid this hard work. Fear will scream at you that you need money, and any job that you can find that pays you money is the job you should take. Just find a job and make it work. Fear will tell you to think about what others want for you. Everyone sees you as a lawyer — what will they think of you if you suddenly decide you’re a novelist? Won’t they be weirded out? Or disappointed? Ken Jeong left a successful career as a doctor to become an actor. When he told his doctor friends that he was quitting medicine to take up acting, what face do you think they made? 

If you do not have clarity about your career goals, then your career change will not be successful. And achieving clarity requires courage. 

A great way to approach this problem is to use the puzzle method

Think of the goal that seems silly. Think of the goal that seems impossible. What if you could achieve that one? 

That’s what Kristy Wenz did.


If you look at Kristy Wenz’s Instagram, you’ll think she’s on vacation all the time. Actually, she’s the Chief Communications Officer for, a role that she and the CEO devised specifically for her. She wears a lot of hats for WineTraveller and handles many responsibilities, including — you guessed it — travelling to vineyards and tasting wine.

How did she pull that off? By knowing what she wanted.

After 20 years in marketing and PR, Kristy wanted the usual trappings of fulfilling work from my list, above, but she was also looking for a few other things in her new career, as she explained on my podcast: “I knew I wanted to write. I knew I wanted to communicate with people. I knew I wanted to somehow be involved in food and wine and travel if I could because I love how it brings people together.” Kristy also wanted her career to connect her to history and culture. 

Travel? Wine? History and culture? Those aren’t career goals — those are stops on a European vacation, right? Wrong. Not only did Kristy create a role for herself that checked all of her unique career-goal boxes, she also found a situation that met every item on my list.

“I also needed something that was going to be flexible and allow me to work remotely. I put in a lot of time but on my schedule, which is wonderful, especially as a mom. I get to write, I get to be a manager, I get to jump in with ideas, I have a seat at the table and work with a dynamic group of people who are really amazing, and that was important to me, as well. Just working with like-minded people. People with similar values and the same goals and missions that I have. Everything fell into line and I honestly did not think it was possible even six months ago.” – Kristy Wenz

Kristy had the audacity to ask for what she wanted. She defined what she wanted and went out and got it in the real world. 


The first thing Kristy did was to take a hiatus from work. She and her family moved to Europe for several months. Kristy hoped the time away would give her clarity about her next step. It didn’t work. 

Kristy realized that clarity wasn’t just going to arrive. 

That’s when we began working together with Kristy and made a plan to help her figure out her ideal career change:

  • Create her “plan for inevitable success” (discussed in Stage 2). Kristy focused on taking one small step every day so she felt momentum including time with her career coach and other important people in her life. 
  • Build an ideal career profile (mentioned above). Kristy did exercises to gain a deeper understanding of her strengths and understand what levers needed to be pulled in her next job opportunity.
  • Conduct “career experiments” (discussed below in Stage 4). Kristy test drove some viable career options to make sure she was on the right path. 
  • Kristy wanted her new career to involve writing, so she got a gig working with a small online tourism and wine website to write some articles. (just one of several ways she was test driving potential opportunities)
  • Kristy realized that she loved writing but didn’t want to do it 100% of the time, which became a key piece of her ideal career profile. She realized there were other pieces of her past roles that she wanted to keep doing, like operations and marketing. 
  • As Kristy reflected, learned and experimented more, she also discovered career needs she’d never had, like the ability to travel as part of her job.

Once Kristy had developed her ideal career profile, she was able to pursue her ideal career:

  • Kristy identified a company with a mission that matched her career goals of incorporating wine, travel and history and culture into her work. It was a startup online magazine called WineTraveller.
  • As a career experiment, Kristy got a contract job writing for WineTraveller.
  • In the course of doing that work, Kristy realized that WineTraveller might need a full-time person to help with exactly the things she was interested in doing, specifically, writing and overseeing company operations.
  • Kristy approached the founder of WineTraveller about a permanent role and, over the next few months, negotiated with him to craft a brand new position specifically for her. 

Want to hear Kristy’s entire story in her own words? Here she is telling the story of exactly how she went from PR (public relations) to Chief Communications Officer. Listen on the Happen To Your Career Podcast



  • Listen to Kristy’s Story – Check out what it takes to create the ideal role for yourself.
  • Go through the Figure It Out–8 Day Mini Course to help you identify some of the most important elements that you need for your next career step and beyond
  • Take the Clifton Strengths Finder Assessment to begin to recognize and articulate your strengths
  • Use the categories mentioned above to write out what you want for each area (Use the Puzzle Method). Here’s a checklist to create your Ideal Career Profile. Then begin to prioritize and identify the top 5 items
  • Not sure how to read or implement your Clifton Strengths report? Or completing your Ideal Career Profile? Schedule a conversation with our team by clicking here

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Stage 4:
Do a Day-climb – Try Your New Career

You know what you want. Or do you? Before you hoist your pack and start clambering up the mountain, we’ll show you how to design career experiments to investigate your new career. Call it test driving, wine tasting, ice cream sampling. The point is to try your new career before you commit to it. That way, when you start climbing the career change mountain, you’ll be rock-solid certain that it’s the right mountain for you.

You know your Signature Strengths. You have identified your ideal career — possibly. You can’t be sure — you’ve never tried it. Before you commit to a path up the mountain, it’s time to run some experiments. Try before you buy. Test drive. Have a free sample. If you have identified a new career path for yourself that is truly a good fit for you, this will be fun. If not, then you will find out before committing yourself to the wrong path.

Try again. Fail again. Fail better.

Samuel Beckett

Career experiments take many different forms. They may be temporary positions, contract gigs or opportunities to try new roles at your current job. The goal is to use your Signature Strengths to practice the skills you hope to use in your new career. If you want to be a copywriter, can you get a contract gig writing copy for a tech company? Can you help work on the copy for the new website at your current company? If you’re interested in HR, can you help with the process of making your company’s new hire (you will be working with him… doesn’t it make sense for you to be involved…)? If you’re interested in software engineering, can you find an online class and see how you like it? Better yet, will your current employer pay for you to take it? You’re not looking for a full-time job yet. You’re just trying things on.


You fill your iPhone with numbers from the CEOs you’ve just met by interviewing them for your blog.

Wait… What?

That’s just one of the many ways that our client and HTYC Podcast listener Eric Murphy made a career change to his dream job.

Eric was working 10-14 hour days in his engineering role for the gas company in Las Vegas, Nevada. It was going well… except that he began to feel like he needed work that helped others. He realized working in the gas industry didn’t fit his values. He began to think about switching to work on a different energy source — solar.

He had no idea that he was so far off.


That’s exactly what Eric wanted to know! 

Eric wasn’t just trying to make a career change, he was also trying to figure out what career and company really fit him. 

We help every client through this process: 

  1. Determine your Signature Strengths. 
  2. Create your Ideal Career Profile
  3. Target only those companies and opportunities that fit your Ideal Career Profile. 

Eric was unique because he was simultaneously seeking jobs AND trying to discover his ideal role. 

If you’re thinking about pursuing career change but you don’t know exactly what career you want, that’s ok! Discovering what you want is part of the process!

What worked for Eric, and might work for you, is what we call the Test Drive Method


Honestly? Most of the time he just asked. You will be surprised how many people will say “yes” when you ask. 

But he was still nervous about asking for time from people, so here’s another unique method he used. Remember how he thought he might be really interested in working with a Solar technology company? Well here’s how he contacted their CEOs and got to learn about the solar industry at the same time.

Just because this test drive was right for Eric, that doesn’t mean it’s right for you. What creative solution can you find to the problem of meeting people in your prospective new career?

When we worked with Eric we helped him design a way to experiment that fit his goals and what he still needed to learn and explore,and helped him build relationships with people who could help him. 

There are many ways that we do this and there are 6 more common experiments that we use regularly to help test drive. You can find those here.



  • Listen to Eric’s Story – Get an idea of how it actually looks to conduct career experiments.
  • Review your Ideal Career Profile or Checklist (from Stage 3). Begin to identify several potential roles or Target Companies that could be a good fit.
  • Read about 6 most common experiments that we use with our clients to avoid career risk and design their own experiments and choose at least 5 experiments that fit your situation whether that is creating a blog, working a gig job, etc.
  • Getting stuck identifying potential roles or target companies? Or having trouble implementing a career experiment? Schedule a conversation with our team by clicking here.

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Stage 5:
Start to Climb – Pursue Your Ideal Career and Life

You’re climbing! Finally! And whaddya know, you’re good at it! At this stage of the process, we’ll help you use your Signature Strengths to move you up the mountain towards your new career. Get ready for personal achievements, “a-ha!” moments and key realizations. We’ll show you how.

Imagination is more important than knowledge.

Albert Einstein

Just as everyone’s ideal career may be different, everyone’s strengths are different, too. Your plan for achieving your ideal career needs to maximize your strengths and minimize your weaknesses. If you enjoy chatting on the phone and can quickly build a rapport with new people that way, then your career change plan may emphasize connecting with people on the phone. If you’re more comfortable meeting in person, then your plan should include seeking in-person meetings (COVID permitting). Conversely, if you’re uncomfortable in large groups, then you probably shouldn’t focus your career search on group networking events.

Leveraging your strengths builds confidence and momentum in your career change, and that will help you move through the inevitable setbacks and challenges you will encounter. If you reach out to five people and four don’t respond, but the fifth has a great 30-minute phone chat with you, then you have a win — points on the board, a feather in your cap — to build your confidence and keep you moving up the mountain. 

That being said, there’s a difference between not wanting to do something because you’re not good at it, and what you don’t want to do because you’re nervous. Don’t use “this isn’t one of my strengths” as an excuse to avoid the sometimes uncomfortable work of career change.

Be brave so you will be remembered.

The Odyssey by Homer

Here are two drastically different examples of how real people gave consideration to their strengths while crafting a job search plan. 


  • Easily having deep relationship building conversations with other people (when she was one on one)
  • Asking deep profound questions that allowed her to take genuine interest in others (and other people to quickly like her as a person)


  • Understanding what people need and want (what creates motivation and is relevant for others) 
  • Ideation and creation: Coming up with new ideas and creating something out of nothing


  • Get her to as many one on one conversations as possible with people that can help her or with authority to hire her (showcase her connecting and curiosity strengths)


  • Developed mini websites to get the attention of the CEO for specific job postings. (Showcase the ability to create and tailor to exactly what they need)

End Result: 

  • Had conversations that led to interviews and to her exact ideal role.

End Result: 

  • Skipped to the interview stage without having to fill out applications with several CEOs of medium size companies (yay!)

Full Backstory: 

Nadia, a former client, wanted to transition out of her teaching career. As a teacher, she was accustomed to meeting new students, getting to know them and connecting with them. She had a talent for it and she enjoyed it. Her strengths? Connecting with other people deeply 1 on 1 and showing genuine interest and curiosity through deep questions. Yet, when she approached her career change, she was apprehensive about the application processes, Resumes and CVs and even communicating with people via Social Media. Also she didn’t have anywhere near as much direct experience as other people she would compete with if she relied on sending in traditional applications.

This meant we wanted to leverage her strengths by getting into as many of those 1 on 1 conversations as possible where people could see how amazing she was and decide they wanted to work with her.

Full Backstory: 

When I was interested in finding a job that allowed me to work remotely (back before there were lots of companies that did remote work and competition for the few were really high) I was struggling to get attention. 

By leveraging my strengths of putting myself in other people’s shoes to understand their exact motivations and my strengths of generating unique ideas and them quickly implementing them I was able to get traction. 

I ended up taking a skill I had recently learned (designing websites) and creating mini websites complete with videos personalized to the CEO. 

It worked and it got me multiple interviews while bypassing the traditional application process. 


You can make it much easier and much more possible for you by considering how to apply your strengths throughout the process. We do this at Happen To Your Career with every person we help because it allows them to have a competitive advantage in an otherwise hard process. 

As a bonus, it helps people literally get hired for their strengths because they are using them from the beginning. Instead of trying to go through a traditional application and interview (the entire time trying to be someone they are not!)

Career change is an adventure into the unknown. The unknown will trigger fear in your mind, and fear will trigger resistance: “I don’t feel right about this.” → “This isn’t going to work.” → “I’m not doing it.” If you think it’s a bad idea to ask a stranger for a 15-minute phone call to chat about her experience at a company you like, then acknowledge that feeling, but interrogate it. Not everyone is best-suited to every form of interaction with other people. But be honest with yourself. Are you genuinely not good at talking on the phone, or are you letting resistance paralyze you?


Alissa Penny worked in HR (human resources), first for a manufacturing company and then in the public sector on behalf of municipalities. For a few years, she enjoyed it. But her husband got a new job, they moved, Alissa got a new job with a new municipality, and the new job didn’t go well.

Alissa became unhappy. Then stressed. Then extremely stressed. Then she began to experience periods of temporary blindness — her eyes would stop working. At that point, Alissa realized that her situation had graduated from “I’m not happy at work,” to, “My life may be in danger.” She needed to make a change immediately. She discussed career change with her husband, who was supportive. She quit her job.

As Alissa explained on my podcast, she wanted to continue working, but was unsure how to move forward with her career. She thought:

I still want to work, I enjoy working, I like the work that I do. So how can I make this happen in a way that I get to do what I like to do, what I do best, and really help the people that I have a huge passion for helping — municipalities, underserved employees, nonprofits, that kind of thing?

It was actually Alissa’s boss who suggested at her exit interview that Alissa consider consulting, but Alissa ignored the suggestion. A few months later, after working with Happen To Your Career, identifying her signature strengths and assessing her priorities for fulfilling work, Alissa realized that the thing she wanted most out of a new career was control — over her environment, her duties, her schedule. She still wanted to do HR, but on her own terms. Suddenly, consulting seemed like a good option.


Alissa, who had never worked on her own before, never formed a company, never run a business, decided to become an independent consultant. She reached out to 200 contacts offering her services. She received responses from two of them, and got no clients. Not what she was hoping for. 

Panic set in. How stupid, how embarassing, what a waste of time and money. Did she really think she could start her own business? 

But, she stuck with it. Even when she didn’t get any clients in the next two weeks. Or the two weeks after that. Or the two weeks after that. Until, all at once, she landed three clients. 

The lesson for Alissa was patience. Taking her business from nothing to something was harder and took longer than she expected. But it happened. She learned to just keep showing up, keep doing the work, and the business would grow. From the podcast — “I know that this time next year, things are going to look very different. And as long as I stay consistent, and I maintain my patience, they will be okay.”



  • Listen to Alissa’s story – Hear what the ups and downs feel in the real world.
  • Using the example above build a plan for your career change that leverages your strengths (take a hint from Stage 4).
  • Take a moment and review and update your resume and LinkedIn profile using checklists here and here.
  • Check out the HTYC Mini Guide to determine if you actually need a resume (spoiler alert: you may not!).
  • Not sure how to build a plan that leverages your strengths? Want to make sure you have an extremely effective interview? Schedule a conversation with our team by clicking here.

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Stage 6:
Mid Climb – Overcoming Setbacks and Adjusting Your Plan

You can’t do it. You’re not smart enough. Why did you think you could change careers? Whose stupid idea was it to climb a mountain, anyway? It’s too hard. You want to quit. This stage is about discovering a path forward when you are absolutely certain there isn’t one. There is. We’ll help you find it.

Everyone we’ve ever worked with (yes, everyone!) goes through some variation of this as they begin implementing their career change plan. 

This is the part when all the bad things happen. You realize you will never be happy. You understand that the universe does not want you to achieve your dreams. 

The Secret, The Alchemist, Tony Robbins — ALL WRONG! 

You lie on your bed, fully clothed, staring at the ceiling, listening to The Doors, wondering if anyone actually likes The Doors. You decide to give up, go back to your previous career. It wasn’t that bad, right? You did it for a while — what’s another 30 years? The stress will probably force you into early retirement, so maybe only 20 years, maybe less …

Honestly, I know it sounds mean, but I love this part of the journey, because I know how it ends.

Everything will be okay in the end. If it’s not okay, it’s not the end.

John Lennon

Think about every movie you’ve ever seen. Think about the moment when the hero is completely done for. Rocky is getting pounded. E.T. is dead! Marty McFly is on stage at the Under the Sea dance dissolving into oblivion while Biff is in the parking lot beating up George. It’s all going wrong!

And then what happens? Rocky fights back. E.T. wakes up. George punches Biff and Marty goes back to the 80’s. It all worked out!

The same thing will happen to you, it will just take longer than it does in the movies. You will reach the moment when you cannot go on, and then you will draw on the resources and the plan that you prepared for this moment. We planned for this back at Stage 2, remember?? 

Your friends and family will help. Your coach will help. The other people you identified to be a part of your team will help. You will look at how far you’ve come and you will know that there is no turning back.


You will also take a beat, analyze what you’ve done so far and assess what has worked and what hasn’t worked. If what you’ve been trying hasn’t been working, then what else can you try? 

This is a time to think about not only building up your existing skills, but also building new ones. You’re good on the phone, but could you be even better? You’re not great at job interviews, but you can improve. This stage is an iterative process of generally improving your career change skills to get you the rest of the way to the top of the mountain.

Mitch Hedberg said, “An escalator can’t break. It can only become stairs.” When your career change begins to go well, you will feel like you’re riding an escalator. Then the escalator will break. That’s ok — you can still take the stairs. Remember, you don’t WANT to change careers. You NEED to change careers. You will keep going. And you will make it. 

All of my clients experience difficulty in the course of their career change, but no one has described it to me more eloquently than Rob.


Rob struggled for a long time on his own in a very unsatisfying career before coming to me for help. Here’s how he describes the feeling that his career change was going to fail, and how he overcame it.

“No one wants to have an extended period of strife and grief and certainly, on the career side, you get to a point where it’s pretty rough. Coaching helped me the most in terms of having a little faith in myself. ‘You’re not the only one that’s been here. Yeah, this is rough, let’s talk about it.’ This idea that while it might seem that this is a solo endeavor, there are a lot of people out there who do want to help. I came to this process feeling like, ‘I’m just a failure,’ but I got through that and I owe that largely to our coaching sessions. There’s not an instant anything. You have to use your faith in the process of going towards your strengths and using those to guide you along that path and really building something that begins to look like a career.” 


I mentioned a bit of Nadia’s story in Stage 1: Considering Career Change. Nadia was a teacher in England. She loved her students and felt at home in the school community, but couldn’t avoid her growing sense that the work was making her miserable. When she decided to pursue career change, she felt scared, bereft, guilt-ridden and regretful. She was desperate to give up and retreat to her teaching career, but knew she couldn’t. Eventually, her career change process began to gain traction. 

As I was thinking, ‘Oh, there’s light at the end of the tunnel, I think I’m getting somewhere, the world changed. COVID arrived, and then all I’m hearing is, people are not hiring. I reached out to a recruiter and what I got back was, people are looking for experience. Come back in maybe six to eight months’ time when things are a little bit more settled.

When you’re moving from one sector to another, how are you going to have a network? My teaching colleagues are certainly not going to turn into corporate giants.

Nadia was also concerned that her network was too weak to support her career change into a new field.


Nadia adopted a few tactics to keep her career change on track. 

1) Accountability – First, she met with her coach (Phillip) every week to review her progress. This created a system that she didn’t have to think about to keep pulling her forward (don’t underestimate this) 

2) Getting Uber-Specific – They developed a spreadsheet and set weekly goals for her progress, down to the individuals who she would contact. This made Nadia accountable for her progress on a weekly basis. It also took ambiguity of exactly what she needed to do each week.


Everyone we’ve ever worked with that has the goal of getting paid very well for fulfilling work that fits them hits the same point in the process: They encounter a “skill wall”. This is the point where they realize that the skills required for getting meaningful work are different than what’s required for getting a regular job. 

This is where everyone runs into a wall and they often don’t see how to do the process any differently. To do it differently (and be successful) you will also need to up your skills.  

Nadia also worked on developing her skills. When she first approached us for coaching, she was not great at sending emails to reach out to people. We worked together to develop her skill and her comfort level in sending messages to strangers. Ultimately, that was the skill that made Nadia’s career change possible.

The magic of that was to say, let’s look at people who are currently doing these jobs. Let’s do some research and see who you can connect with. And that is where the door opened and the light shone.

Here’s a real example of Nadia’s upping her skills. This is one of the first messages she sent and also the email she much later sent that led to her getting a job offer.

Subject: Your SAP Position

Dear Jim,

My passion for learning with a proven ability to deal with complex issues systematically and creatively led me to seek a career in Logistics and Supply Chain Management. Whilst studying for the Masters I acquired hands on experience with SAP All-in-One and loved every minute of it. The value it brings to an organisation in terms of end to end solutions for all business processes and supply chain visibility was breathtaking.

My experience of working as a consultant brought into sharp focus the importance of a well designed implementation strategy. I transformed a faltering implementation into a success by initially focusing on the following three areas;

  • Mapping business processes – gained a deep understanding of their business functions and experienced them firsthand
  • Bridging gaps – between SAP functionality and the client’s business requirements, and by eliminating silos within the organisation
  • User acceptance training – educated myself on the impact employees had, and continued to, sustain along with an understanding of their psychological needs

Being endlessly curious, insightful and a natural relationship builder, I enjoy asking probing questions that help me understand even the most intricate business issues. I synthesise this knowledge with subject expertise, providing fresh perspectives and identifying new opportunities for growth.

The design of the company’s Application Management Cycle offering a lifetime solution, resonates deeply with me. A holistic approach with specialist knowledge, harnessing expertise to join up business goals with technological capabilities, and ongoing client care, is a recipe for sustained success. I would be proud to join your team and believe my strengths, energy and ability to learn new skills will serve your company very well.

I look forward to learning more about your company and discussing the value I could add as your next SAP Business One Consultant.

Thank you for your time and consideration. I hope to meet with you soon.

Yours sincerely,


Here’s the email that allowed her to make a connection (with someone she didn’t know) who later introduced her to her future boss. Take a look see if you can spot the differences. 

SUBJECT: We studied Bus. Analytics at ********** University

Hey Mike,

Forgive the impromptu email, I came across your profile whilst researching SAP Partners on LinkedIn. 

Turns out we both enrolled at ******* in 2015 and studied Business Analytics units together. Unfortunately our paths didn’t cross, though I felt a sense of kinship when I saw you were awarded Best overall Performing Student in your course, just as I did in mine!

What really grabbed my attention was your career journey from assembly line worker in ******** to Business One Consultant at ****** in ******; wow!  Currently I am looking to transition into SAP implementation and on the search for advice.

Specifically, I’m curious to know how you made the transition from assembly line worker all the way to SAP Business One Consultant? Additionally, what was it like to complete SAP certification?

If you’d be willing, I would love to have a 15 minute call with you to learn about your experiences and advice on what it takes to break into an SAP Consultant career. 

Just reply with a ‘yes’ and we can work out the best day and time that works for your schedule.

Many thanks, 


There’s a lot of psychology built into this email that we won’t even get into in this guide, however one thing you might notice is that it’s much shorter and very specific in what she is asking for. She even makes it easy on the other person to say “yes” to her request.  

BTW if you simply rip off this as a template and think it’s going to work for you, that may be an indication that you could also up your skills as you’re going through the process of your ideal career. 


Nadia found a connection on LinkedIn who currently worked at the company that Nadia wanted to join and had been in her university class. Although they never met at school, they had taken a class together and had both won awards in it. Nadia reached out to him for an informational interview, they connected, and that experience led then to building  a long lasting relationship with that connection. “I asked for a 15-minute chat. My shortest conversation was 45 minutes.” Eventually, Nadia connected with someone who offered to send her resume to a former colleague who worked at Nadia’s target company. That led to a phone call, an interview, and Nadia’s first job in her new career.

With hindsight, Nadia also attributes her successful career change to personal resiliency. 

You can have the most fantastic coach in the world, but if you are not resilient within yourself then it’s not going to work. We talk ourselves out of things without even trying.



  • Listen to Nadia’s story – Get an idea of how to keep moving forward despite setbacks.
  • Look at the plan you built (from Stage 5), make any adjustments if necessary to make your plan more effective. Don’t forget to tap in the personal Team you built (from Stage 2) to give you an assist!
  • Once you have an interview(s) lined up, prepare using the Interview Checklist. To dive even listen to the hand-selected HTYC podcasts on nailing your interview here and here.
  • Feeling stuck in conversations? Have an upcoming interview? Schedule a conversation with our team by clicking here.

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Stage 7:
Reach the Summit – Find Your New Role

They said you couldn’t do it. You said you couldn’t do it. But you did it. You got a job offer in your new career. You reached the summit, now don’t fall off. We’ll guide you through negotiating your opportunity and mastering your arrival. Congratulations!

When you persevere through the ups and downs of career change and arrive at the point that someone is offering you a job in your new career, your first inclination will be to just take it. Don’t quibble, don’t haggle — accept before they change their mind!

But, as you will have learned and re-learned throughout this journey, your unique combination of strengths make you exceptional. Once the organization has taken a sufficiently strong interest in you to make you a job offer, they won’t give up on you so easily.

I don’t have a lot of respect for talent. Talent is genetic. It’s what you do with it that counts.

Martin Ritt

Before you accept a position, take your time and make sure that you are getting everything you need to set yourself up for success. Whether that’s flexibility, vacation time, additional compensation or other benefits. You and your new employer will both be happier if you work together to assure that you are positioned to succeed in your new role.


Mike Krzyzewski, the hall of fame basketball coach, has said that luck is what happens when preparation meets opportunity. 

With that definition in mind, Karen was very lucky. Having worked in philanthropy for several decades, Karen was ready for a change. She wanted to move on from her current organization but find a different role in the philanthropy industry. Karen and I worked together to identify her signature strengths and design her ideal new role. 

Around this time, Karen’s employer hired someone new. Although Karen’s bosses told her the new employee would be under her supervision, when his hiring was completed, it turned out — surprise! — that instead of Karen supervising him, he would be supervising her. Karen was not thrilled.

However, this new employee had left a job at another philanthropic organization. Karen realized the new employee’s former job fit all of her criteria for the new role she wanted. And, because of her deep network of contacts in the philanthropy community, Karen already knew the CEO of this other organization. Karen told the story on my podcast:

I already had a good relationship with a lot of the people there and with the CEO there. So I reached out to him and said, ‘Hey, this might be kind of awkward, but you know, the position that just became vacant because we hired that person away from you — I’m interested in coming over there.

I had my ideal career profile that I could say, ‘alright, check that box, check that box, check that box, oh, you know, I want a little bit more time off.’ So I actually negotiated for that. I said, ‘I’d really love to have a few more days off.’ And so I got that. So it really does help you identify what you need what you can bring to an organization and where you should negotiate.

Within a few weeks, Karen had an offer in hand for her dream job. And because Karen had spent the time to identify exactly what she wanted, she knew exactly what to ask for in negotiations with her new boss.



  • Listen to Karen’s story – Hear how to negotiate to make a dream job even better.
  • Use the HTYC Negotiation Plan to create your customized strategy and make your dream job even sweeter!
  • Break open the champagne, do a happy dance, give yourself a pat on the back… just celebrate reaching the summit!
  • Need help negotiating your job offer? Schedule a conversation with our team by clicking here.

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Stage 8:
Master the Mountain – Thrive in Work That Fits

Your new life on the summit is great, but it’s still life. You have a fantastic new career, but it’s not perfect. We’ll help you through the growing pains of adjusting to your new career and life.

New job, new career, new life. If you know that it takes some time to break in new shoes, you know that it will take some time to break in your new life, too. If you’ve done your career change correctly and landed a job that leverages all of your many signature strengths for a high salary, then your new role is likely to be exciting, but also highly demanding and overflowing with new information for you to learn and apply at warp speed. You will be drinking from a firehose. You will be building the plane as you fly it. Very exciting, very challenging, but also potentially frustrating. Give yourself some time to adjust.

Everyone has only one true vocation: to find himself.

Herman Hesse

Now that you have done the hard work to improve your career situation, the next stage is to work on improving yourself. You may bring habits, attitudes, behaviors to your work that may slowly undermine even an ideal job situation. You have issues with authority figures, you may under-communicate (not acknowledging messages, not sending follow-ups, not making sure that instructions are clear), you may have difficulty with boundaries (getting too close to co-workers or not close enough). This stage is about fine-tuning your professional habits, which can make the difference between having a job and thriving in it.


Laura left her old career because work made her feel exhausted. After landing her dream job in a new career, she still went home everyday feeling exhausted. But, she was able to distinguish between the bad exhaustion of her old job and the good exhaustion of her new job. Here’s how she explained it on my podcast:

I’m being challenged. And I’m exhausted, because I’m working hard. And I’m learning every day. And there’s always room for improvement. Before, I would leave work exhausted because I was bored. I still leave work exhausted. It’s just that now the exhaustion is from flexing my brain and personal development and much more excitement about the work that I’m doing and being invested in it.




  • Listen to Laura’s story – Get an idea of how thrive in your role.
  • Listen to Melody Wilding talk about setting boundaries in your career.
  • Make a list of what skills would allow you to have a better quality of life? Is it drawing boundaries? Learning to have very difficult conversations? Asking for what you want/need in a way that works for you? Learning to allow yourself to be happier internally? Write them down.
  • Take the above list and determine simple ways you can practice these daily.
  • Want to know how you can thrive in your role? Schedule a conversation with our team by clicking here.

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Stage 9:
Ascend the Next Mountain – Evolve in Your New Life

Career change is an on-going, iterative process that will last through the rest of your career. As you grow and evolve, your needs and dreams will grow and evolve, also. Your career path will be a constant process of refinement to move yourself closer and closer to your ideal, even when that ideal changes. But now that you have the skills and have applied them once, you will always have them at your disposal. 

The statement I hear most often from people changing careers is, “I just want to find a career that I can stay in,” or, “I just want to find a company that I can stay in.”

But humans don’t stay in one place. They grow, they change. It’s unavoidable, even if it’s inconvenient. So, saying that you want to find a place you “can stay in” will not only place unfair limits on you as a professional, it will place unfair limits on you as a person.

You should not expect to find a new role in a new career and keep it until you retire. You should expect to continue learning, continue growing, continue refining your ideal career profile, and know that you will have the tools to pursue that ideal, even when it changes.


Now that you have made a career change once, you will always have the skills to do it again. Not necessarily because you are looking for an entirely new career. Maybe you’re just looking for what’s next in your current field. But you’ve been through it before. You’ll know the signs. When you feel that sense of purpose and contentment slipping away from your work, we can help you take the next step.

Living is a form of not being sure, not knowing what next or how.

Agnes de Mille

Tanya was a television and live event producer when she came to us for help changing careers. She enjoyed producing but wasn’t happy in the entertainment industry. She kept pivoting between entertainment companies, trying to find her place in “the business” — television, concerts, other live events — but nothing felt fulfilling. Tanya was ready for a change. But not only did she want to change industries, she and her significant other were making a move from New York to London. That meant finding a new career in a new city on a new continent, where she did not have a strong network.

Where do you start when you have no network? 

Tanya started by drilling down and identifying exactly what she wanted from her new career.

Ultimately putting in the work and effort, really paying attention to myself, thoughts, and gut on what worked and didn’t throughout my career, my wants, what I was looking for, my motivations, my minimums, ideals, etc. and putting it on paper. It helped me put myself in a different light evaluating my needs and wants. I could see myself through a bigger lens. I was able to properly position myself in this career transition, which was the missing key.

I did everything you coached us to do. The reach outs, massaging your network to get introductions and being bold and forward. I do that in my job, but was hesitant to do it in my search.


Once she knew what she wanted, she found a company that she believed could give it to her — Wanderlust. Then, she got after them.

Tanya’s efforts paid off. She landed her dream job with her #1 company choice: Wanderlust. As you can imagine she was ecstatic — for one whole year. But after some changes at the company, It quickly turned her dream job into a place she could no longer work at.


This time, finding her next opportunity was no problem for Tanya — she just ran through the same process that had brought her to Wanderlust. No fear of the unknown. No existential hand-wringing about what it would mean for her self-identity. Tanya knew that every step in her career was just one step. And when she was ready to take the next step, she had the tools to do it. That’s the greatest value of this guide — once you learn these skills and apply them once, there will never be anything to stop you from applying them again. These are skills you will keep for the rest of your life.

Career change is an on-going, iterative process that will last through the rest of your career. As you grow and evolve, your needs and dreams will grow and evolve, also. Your career path will be a constant process of refinement to move yourself closer and closer to your ideal, even when that ideal changes.

Now that you’ve gone through an overhaul process of career change to meaningful work, you have the tools to keep changing, tweaking and refining. Sometimes this means changing your role or company again (and it will be so much easier the next time), but most of the time it means taking tiny steps to move you closer and closer to your ideal career and life, like taking on a passion project at your current job.

After beginning her career with an academic position that did not suit her and successfully changing to a new academic position, Michal put a premium on making sure that her new role would give her room to grow and evolve as her career progressed. We discussed it on my podcast:

One of the most fantastic things that I love about my supervisor now is that when I interviewed he said that he doesn’t expect me to stay there forever. He wants to create opportunities for me to grow, and the highest compliment to him would be if I stayed in this role for a while and then moved on to something else. And when he said that, I said, ‘Yes.’ This is what the process is about — doing something that fits your life in that moment, and if it doesn’t fit, being flexible enough to think that I can always move on and I can always find something that fits better. Something’s going to happen eventually. Somewhere, something in life is going to come up. And so it is really impossible to find that perfect place where you’re going to stay forever.

Don’t have conversations because you are looking for another job. Have conversations with people who are doing things that are interesting because you’re interested in them. That’s going to open a whole world to you that you don’t know about.

Life changes, so will you and so will your career. That’s why Michal is always seeking to connect with new people. Even if you’re not in the market for a new job or a new career, keep reaching out, keep learning, keep making new connections. Keep your channels open. From Michal’s podcast episode:



Trying to refine your ideal career? Do these things now:

How can I help you?

Congratulations! You now know everything there is to know about career change! So get out there and be somebody!

No, not really.

I’ve been a career coach for over a decade, and I learn more about careers, career goals and career change every day. The reality is that every person is different, so every person’s ideal career is different, and every person’s career needs are different. And people change, so their career needs and goals change, too. Understanding your personal and professional strengths, and how to leverage them to create your ideal career, is a lifelong process. 

But if you’ve made it all the way to the end of this guide (and, seriously, let me say not only, thank you! But also, wow!) then hopefully you understand that simply by analyzing your career goals, recognizing that there is an ideal career for you and pursuing that ideal career, you are far ahead of almost everyone else. 

I’ll continue to update this guide with new stories and new ideas as I continue to develop and refine my understanding of career change, so please check back.

If you are interested in discussing your ideal career and how to achieve it, I’d love to chat. Please feel free to set up a time to talk here.

You can also check out my eight-day career change mini-course to help you get started on your career change. That’s available here.

And if you’d like to subscribe to the Happen To Your Career Podcast, you can do that here.

Thank you again. And best of luck with your career.

— Scott Anthony Barlow, Founder and CEO of Happen to Your Career

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