Career change at 30 20 40 50

I think one of most interesting pieces of human nature and psychology is that we all drastically overestimate how unique our situations really are. We’re biased to think that *our* situation is special and the most challenging set of circumstances. We see this every day with people at all ages.

That said there are some real challenges (and even unique secret advantages) that you have when you’re making a career change at any age and we want you to know what those are! So we brought in 4 world renowned career experts to break down the challenges (real and perceived) of changing careers at 20, 30, 40 and 50+ creating a mini-guide for each decade of your life.

You can listen to the entire interviews here on the Happen to Your Career Podcast or click your age below to read the mini-guide.

Choose your age or scroll below and read the whole guide

Career change at 20

Paul Angone is a writer, best selling author of new book called “101 Questions to Ask in Your Twenties (and Let’s be Honest, Your Thirties too!)”. He’s a hilarious writer who knows people in their 20s better than they often know themselves and he’s become a friend over the last few years.

What are the Perceived Challenges of Changing Careers in your twenties?

“20 somethings who have big dreams and big goals who want to make a difference who want to make a lot of money who want to make an impact quickly realize that it's not going to happen as quickly as you envisioned. There's going to be a lot to do over moments along the way.”

Now the real perceived challenge here is that in your twenties it never feels like it’s moving fast enough.”

What are the Real Challenges of Career Change in Your Twenties?

“The bachelor's degree doesn't get you as far as it used to. You know now you see a lot of 20 somethings today feeling like well I'm unemployed, I have to get my master's degree. I already have thirty thousand dollars in debt. But let me add just another 50000 dollars and get my MBA as well because I guess that's what I should do because my bachelor's degree feels as worthless as a high school diploma.

Also the simple fact that there just are a lot of millennials out there. This means lot of people with a similar skillset and similar experience all applying for similar type jobs. So even though the job market has improved…It's still a competitive market especially for 20 somethings with a typical experiences. This creates some challenges taking jobs that feel like man this is not really a good fit or this is not the career path I want to be on or I'm really struggling here. So how do you do your best work in jobs that don't feel the best you know how do you bring your best self to jobs that feel really wrong. And I think sometimes that is the challenge of your 20s that really lousy jobs are kind of this 20 something rite of passage sometimes. But I quickly learned as well that you learn a lot in the jobs that you like the least and hopefully you learn the lessons quickly so that you don't have to go and get another lousy job. You can keep progressing and increasing your skill set and making connections so that your next opportunity is a better opportunity and then maybe also you're working on the side and doing you know the quote unquote side hustle as a twentysomething. I think that's more the reality now than it is the rarity that you're working a full time job.”

What are the Secret Advantages in your Twenties

Yeah the thing about your 20s and I do struggle and the ambiguity and the confusion that I see people working through as they're trying to find that path as they're trying to find that place that feels like home. It can feel very unnerving. It can feel very uncomfortable. And this doesn't seem like an advantage per se it seems like an uncomfortable place to be. But what I found out through my own story and then working with you know hundreds and thousands of 20 somethings at this point is it's in that place of transition when you're the most uncomfortable that you're actually making the most progress. And that if you're feeling those those feelings of angst or you feel like you're going through a quarter life crisis you know as we're saying these days.

Well gosh that is a great time to again be flexible to be open to be fluid you know to start realizing that your 20s really isn't about life going as you planned but it's about how you change and adapt and grow as it doesn't go as planned. And so again I think that's that's the opportunity there. But you have to capitalize on it and that's why I'm so big on being strategic about the questions that you're asking because sometimes it can feel like you're overwhelmed with questions and ambiguity.”

What advice would you give to people in their twenties

Paul (in the podcast interview) said he had emailed Seth Godin to ask him what was the question he thought he should include in his most recent book for people in their twenties (and thirties). Here’s what Seth sent back!

“What is fear holding you back from?” And “Is it worth it?”

Paul elaborated more on this too.

“The fear that is keeping me from taking that risk, Is it worth it? And most of the time it's not. If we look back at different times in our life where we have taken that risk when we held our self back and we felt anxious about it we felt depressed and we felt stuck. That wasn't worth it.

In your 20s I think you're going through a lot of breakups with your past with your school with relationships with your home as you move. There's a lot of break ups but as you transition it's okay that you fail. You know that it's almost cliche now that you will be comfortable with failing. You know you're going to fail a lot. You're going to take those risks but when you fail don't begin calling yourself a failure because you're not. And again you're not alone in this and even though everybody is making their lives look amazing on social media and were kind of overwhelmed with what I call ‘Obsessive Comparison Disorder’ on social media especially as 20 somethings we're constantly comparing ourselves. Every single post of every single day. You're OK you know and not everybody's life is as amazing as it looks on Instagram.

So reach out to people don't go on this journey alone. Don't be that person that's struggling to make it appear like you're not struggling. Reach out and pickup good resources to help you along the way. Help find mentors help find guides that will help guide you in that transition. Because even though you might feel lost you're also exploring but explorers get lost on purpose with purpose. So that's the goal. Intentional lostness exploring on purpose with purpose and bringing along guides along the way to help you do that.”

Want help making an intentional career change that fits you?


Join our free 8 day mini- course to begin getting insights into the “right career change for you” click here to learn more

Career Change at 30


We brought in Lisa Lewis, who is a career change expert and certified career coach on the Happen to Your Career team. She’s worked with countless thirty somethings over the years and if you’re in your thirties and want to make a career change it’s possible she knows you better that you know yourself! If you want to hear her whole story on the the Happen to Your Career Podcast listen to Episode 147

Here’s what she had to say about the challenges of changing careers at 30 or 35!


What are the Perceived Challenges of Career Change at Thirty?

“A good question because I think that the nuance between the perceived and the real challenge is so interesting especially for folks in their 30s. Thirty-somethings (and especially high performers and smart ambitious people) tend to put a huge amount of pressure on themselves to have it all figured out.

The Twenties felt like the decade of exploration and trying out new things and it didn't really matter. They were spending a lot of time doing other things that were important and just getting their lives together as adults.

But then there's something about when the clock strikes 12 on your 30th birthday. That seems to bring about this belief that you've got to have it all figured out and you got to know what you're doing and what path you're going to be on for the rest of your life.

One of the perceived challenges is feeling like “I’m not where I'm supposed to be in my career” and feeling the frustration and the pain between the expectation curve and the reality curve and wishing that there was more overlap. This big perceived challenge is this self imposed pressure an expectation that you must have found the one final job that you would be doing for the end of your days.

Paradoxically an interesting thing that also pops up as a perceived challenge for folks in their 30s is oftentimes they feel like they're just too far into whatever path they've been on to make a change. You feel like at 35, you've invested so much. You've come so far that it's too late to turn around. But yet you probably have another 30 to 35 years left in the workforce.

That that perceived belief that you know well I spent the past decade plus of my life working in environmental engineering or working in marketing and media and publicity or I've spent that working as a an educator you know as a fourth grade teacher can be really painful to think that because you've invested so much that there is no chance to make a pivot make a change make a correction and do something completely wildly excitingly different and go to a grad school to make a pivot from being a teacher into being a social worker or making a pivot from being an environmental engineer into being a natural resources economist or something else like that.



What are the real challenges of Changing Careers in Your 30s

“I think that a real challenge of being in your 30s is paying exquisitely close attention to the things that you believe to be true or not true about who you are what you're capable of and what matters to you and giving yourself permission to rewrite the script and rewrite those beliefs as bits and serves you in that specific era.

Just because your life has changed and you have new priorities and maybe you have a house and maybe you have two kids doesn't mean you couldn't have a say three months sabbatical where you take off and pull the kids out of school and go travel around the world.”

“There's no reason that some of the dreams that might have gone with less tethered lifestyle can't still exist for you. But your perception about what's available or not available for you can make a big big difference.”

“So giving yourself the space and the permission and the openness to keep pursuing the things that bring you joy even when the people and the models around you are tending to be a little bit more rooted a little bit more stable.

A lot of times in your 30s, for many women especially, is where you’re thinking about potentially having kids or wanting to be a really active role in their lives. And oftentimes this is where the Sheryl Sandberg “lean in principle” starts to pop up because there's it’s a real time to try to lean back a little bit in your career to create more space to be with your family. One of the beautiful things that Sheryl does through her book is talks about ways that you can have your cake and eat it too and continue to have fulfilling exciting meaningful work and ask for more and ask for more responsibilities and draw boundaries to get yourself the support that you're needing so that you don't burn out or or sacrifice really important priority time with family while also creating the time and space for what you need”


What are the secret advantages in your twenties

“I think being in your 30s is one of the best ‘secret weapon times' of your career. 

Being in your 30s gives you tons of time if you want to pull the emergency brake on whatever path you've been marching down and do something wildly different. You have so much time to do that.

You know enough about the world to be able to create a lot of value. You have gained enough experiences and skills to be wildly helpful. You are mostly sort of older millennials. So you've grown up with a lot of technologies that you feel really technologically fluent and easily able to dive right in with a lot of the millennials.

But you also are far enough along in your career that you can hang with folks in their 40s and 50s you know sitting in a boardroom or around a conference room table and be respected and valued like a top contributor and leader.



What advice would you give people in their tHIRTIES

If you are in your 30s you are old enough to know that asking for help is not a bad thing.

And if you are struggling and you're not asking for help then, you begin to realize you're bringing it upon yourself.

This is like a new and interesting way that a perceived belief or a limitation is getting in your way of doing what it is you want to do because you're at the stage in your career most likely where you've had enough time to build up some capital and you can afford to invest in things for yourself whether that's books classified as a graduate degree coaching, or therapy and all sorts of other stuff that can make a huge impact and a huge difference in your day to day happiness and your sense of clarity about what's next for you and the path and the accountability to make that change happen. And by the time that you're in your 30s you probably have a little bit more of an established community around you whether or not you are in a long term romantic relationship. You know you have had enough time to really develop some beautiful adult friendships. You are probably playing a new and different role within your family unit than you were when you were in your early 20s and you have so many other people around you that your happiness your fulfillment or conversely your sense of unhappiness or dissatisfaction can have ripple effects on. And we know that having dissatisfaction over the long term has ripple effects even for yourself in terms of your health your physical health your mental health in terms of your excitement and your energy level in terms of the way that you're thinking about imbuing your life and in terms of the people that you're attracting into your life and if you have the choice and the option to make a change and go after something that's a new and exciting. Why not set yourself up for success in every possible way.

Why not double down on taking a class and having a coach and reading the books and finding some mentors and doing everything else to make it as easy as possible because a lot of things going on in your life. It's no longer the same sort of like untethered freeness that a lot of folks in their 20s tend to experience. You know you have a lot of things that are pulling on your time and energy every day. So why not invest in systems and programs that will make it as efficient as possible for you to make a transition.

Want help making an intentional career change that fits you?


Join our free 8 day mini- course to begin getting insights into the “right career change for you” click here to learn more

Career Change at 40

Jessica Sweet of Wishing Well Coaching helps people specifically in their forties make career changes. She's been on many different sides of the issues plaguing people about their careers working as a social workerfor years and much later as a career expert who truly understands the modern landscape work.

What are the perceived challenges for changing Careers at 40

“So I think in their 40s people have sort of psychologically hit an age where a perceived challenge is their age. So you know when you're not in your 30s anymore. I think you've kind of crossed a threshold and you're sort of in this funny space which is middle age. So you're. You're too far into your career to feel like you can just drop everything and restart.

But you've got too much career left to just kind of stick it out. So I think a perceived challenge is being in this funny place where you're feeling particularly stuck and being at that middle age. So I think age has has a couple of different ways in which it's sticky at in your 40s so it's that it's being in that very stuck place where you're you're right in the middle too far and too to just drop everything and restart. But also too too much ahead of you to stick it out and then age also be a sticky because there's this perception of ageism. So people feel you know that they're going to be looked at and perceived as too old in the marketplace and be discriminated against and that there is ageism in the marketplace. You know it's not it's not totally unrealistic to think that that exists out there. So I think that's another way that just it just is a difficulty.”


What are the real challenges in your Forties

“Ageism is a real challenge. In your 40’s It does begin to be a thing. I don't think it's an insurmountable challenge but I do think it is a challenge for people.

I think another bigger challenge is that people are at this point usually you go into a job for several years so you know some people have had several jobs but a lot of people that I've talked to have been at a job for five, 10 or 15 years more and they haven't interviewed for a long time.

They haven't been they haven't kept their skills very sharp in terms of knowing how to get a new job. For example knowing how to network or keeping your network alive. Just being really on the edge of that type of thing.

So a real challenge is figuring out how do I kind of get back out there. It's almost like the dating scene you know you don't really know how to get yourself back out there again. Even figuring out what you want to do is a real challenge. And when you're at that stage that I talked about before where you kind of too far into to just give everything up and start again. And and you have too much career ahead of you to just stick it out and you should have woken up in the middle and then you realize you don't like your career being in that place where you where you realize you don't like what you're doing can be very very uncomfortable.

So that's that's a real challenge to to be stuck in the middle there and realize oh I don't like what I'm doing I need to figure something else out. I don't know how to do that. And and I can't I can't I'm really stuck between a rock and a hard place I can't stand and I can't get out. 


What are the secret advantages in your forties

One is the years of experience that people have. At this point you have a lot of experience under their belt. They've done a lot of things in their career they've seen a lot of things. (inserted from Scott I see people in their 40’s drastically underestimate how transferrable their experience is from one occupation to another)

And another thing is that whether you know it or not you probably do have a lot of networking contacts and most people that I talked to. That is the case. So it's an it doesn't have to mean that you have you know 500 plus LinkedIn contacts or that you go to networking events all the time you're networking contacts can be you know your neighbor your brother's friend it doesn't matter who you are how you're connected to these people. But at this point in your career and in this point in your life you do usually know a fair amount of people and those people those connections are advantages to you because knowing people having connections being able to reach out to people. That's the way that you will usually make that make that connection to your next position. So that's a real advantage when you're just starting out in your career. It's harder because you haven't had the the breadth of experience that you have. You haven't had the time to make that number of connections. And so it's a real advantage to to have done that already.


What advice would you give to people in their forties

So I would say “Don't stay stuck.” A lot of people that I talk to wait and they hope that something's going to change.

You know they said in their career and they think well you know something will shift for them something will happen in their jobs. For example; If you don't get a promotion. So you know something will show down sort of the way through. And sometimes yes that happens occasionally but a lot of times I've talked to people who have waited years and nothing's happened or now you know something's happened but it hasn't made them any happier.

the advice that I would give is be proactive and figure out what it is that you want to do. Don't just stick it out and hope for something to change and hope for something to happen to you. Instead figure out actively what it is that you want and and go make it happen because you can do that.

You do have the tools whether you know it or not. There are things that are working to your advantage even if you feel like you're in kind of the worst possible situation.

Want help making an intentional career change that fits you?


Join our free 8 day mini- course to begin getting insights into the “right career change for you” click here to learn more

Career Change at 50

Marc Miller has been there and done that. After a 20+ years at IBM, several  thriving tech startups, a painful stint as a high school teacher, a gig raising funds for the Jewish Community Association of Austin and a near fatal bicycle accident that changed his perspective forever he began working with people in their fifties who wanted to pivot. He now helps people career change and pivot.

Here's what Marc had to say about career change beyond fifty

What are the perceived challenges

“People in their 50s and 60s they have they have these things called ‘obligations' and they're usually large obligations. These are usually mortgages or putting kids through college when we're supposed to be at our peak earning years. Unfortunately what's happened to most of us as we went through two brutal recessions when we were supposed to be saving up for retirement.

The vast majority of people are still trying to save money so they may eventually someday retire.

The challenge is we feel we can't quite take the risk that the younger generations can because we don't have the career runway left. 


What are the real challenges

“Obviously the elephant in the room is age discrimination.

We are going through a massive demographic shift where we've been used to being in control. I was raised to be an employee to go work for a company that would take care of me. And after 30 or 40 years I would be able to go off and retire. Well two thirds of the way to retirement they moved my cheese.

We're now seeing rapid change with the economy. We're not used to that. We are seeing massive “creative destruction” happening at a ever accelerating rate.

Think of what the iPhone and smartphones have done and the amount of industries they've created but they've also equally destroyed even more. That kind of shift means we have to stay nimble on our feet. And that's something we were not necessarily expecting to do at this age.

So now it's a matter of learning how to shift and “bob and weave” like Mohammad Ali. Sorry that wasn't part of the plan.”


What are the Secret Advantages in your Fifties

I think the number one thing is we have our work ethic. We are used to coming to work getting the job done. I was raised to be employee. I wasn't raised to follow my passion.

I was raised to go get a job and it wasn't supposed to be fun. And so therefore if you tell me to come in and do a job I'm going to come in. We are going to show up by the way we're going to probably hang around for longer than the younger generations.

We're going to stick around and we are going to be loyal so that is that that is one of the key points is we are going to we are going to adapt. But you know what. When all is said and done at the end of the day you're going to be happy with our work.


What advice would you give to people in their Fifties and Sixties

“We are used to being in control when you're making these kinds of changes. You have to control. In other words you have no control over when jobs open you have. You have very little control. So number one you have to you have to be able to be able to move and react and and prepare and doing it differently.

A lot of our generation what we did was as we react as things happened rather than this to in this day and age you need to make your own opportunities.

Your next job or your next career is going to come through a relationship. This is one of the challenges that many of us in my generation. Our careers progressed because of relationships but very often those relationships have aged out. The folks who helped us get us to where we are today are have either retired, died, or no longer in a position of power.

So therefore you need to build new relationships. And yes it usually with people who are younger than you, so start forging those relationships because that's where it's going to come. Many of us have gotten used to it. We kind of forgot the fact that these relationships are what got us to where we are. “