261: How to avoid taking career risks by designing experiments


How to design career experiments

Human beings are designed to want reassurance. Consequently most of us aren’t particularly excited about taking career risks.

If we’re going to make a career change we want to know that we don’t have to “start over” or if we’re going to take the time and effort to pursue something new we want to know that at least a guarantee that we’re going to love it at the end of all that effort.

The bad news is that it doesn’t work that way, there’s absolutely no magic pill you can take that’s going to give you the ultimate reassurance that when you spend all the effort you’re going to see nothing but rainbows and unicorns on the other end of all your hard work.

The good news is we know that as humans we want to have some reasonable reassurance that we’re heading the right direction. That’s exactly the reason that over the years we’ve quietly worked to develop ways to help align our clients and students with life and careers they love (before they actually get there) by test driving and experimenting prior to making the switch.

Ironically ever since HTYC Coach, Lisa Lewis, casually mentioned this idea of designing experiments in podcast episode 147, we’ve had constant questions about how to do this . We’ve been teaching people how to design experiments inside our flagship programs Career Change Bootcamp and Signature Coaching but we’ve never dug into it on the podcast.

Until Now! Take a listen here then read the guide below.

We’ve created 6 different examples of ways you can design an experiment to test drive your potential new career, company, industry, sector, or even the people you might work with.


Laura Morrison worked in sustainability for nearly 8 years for the same company moving up the ranks. When she finally decided she wanted to change careers later on she felt like she wasn’t even sure where to start. On top of that she felt like she wasn’t even totally sure what else was out there.

That’s why she came to us. As a student in CCB she quickly learned that having lots of comparison in a systematic format can help you quickly decide what direction is the best for you AND help you narrow down the list really quickly.

What does that even mean? Well much like trying all the porridge with the 3 bears and learning quickly that this one is too hot, the other was too cold and this one was just right, Laura connected with and had conversations with 2 groups of people.

  1. Those that were in jobs that she hypothesized that she might like AND/OR
  2. People in companies she thought were likely to align with her values.

This act of “Talking to all of the people in all of the places” led her to have over 20 different conversations.

More importantly she didn’t just learn that she liked mildly warm porridge, she learned she actually like oatmeal with cherries in it too!

Here’s an email from Laura showing exactly what she was able to take away from these conversations.

If you read carefully you may have also noticed one of her (and our) favorite questions to ask is

What makes you good at what you do?

Because it helps you understand what they perceive as the most important pieces of how to be successful at that job, where if you simply ask what is the most important to be successful about what you do, you often get a whole bunch of bull shit about degrees and things that people are “supposed to say.”

Remember you’re not looking for formality, you’re looking to uncover useful information that helps you decide what temperature of porridge you prefer and exposes you to things you never even thought of! (like almond butter in oatmeal…mmm!)


Think of this approach as “The Social Goldilocks” + a bit of “BAM” – Emeril Lagasse style!

If you’re not an Emeril fan then think about it this way:

Mike Bigelow, another coaching client and CCB student of ours, needed to change cities because his wife’s job was moving. He wanted to take that opportunity to be very selective and take a role with a company that he was really excited about AND would pay him over 6 Figures.

First he used a similar approach to Laura by having many conversations as he could in the industry he thought he wanted to be in as much.

Next comes the “amped up followup”: he would walk away from a meeting with a potential employer, after asking what are you struggling with, what are big vision questions you are wrestling with to make the impact you want to make over the next five years, what would make your life easier? Then Mike went and did those things. Unsolicited, unpaid, just for fun.

How did he do this? During the initial conversations Mike would hear someone say “I have this need” or “I need to solve this” He would then ask followup questions to learn exactly why and what was most important, then Mike would go and create a spreadsheet, a piece of code or equation and follow up. Here’s how that conversation would go

Remember that thing we talked about I’ve thought about it, created this thing and I want to give you it for free, enjoy.

Being a hiring manager and seeing someone so affected by a conversation, that listened so well, and so excited about the work you are doing that they go and do the work and send it to you says a lot of exciting things about the contributions that person can make if you bring them into your team.

  1. Mike was able to test drive and experience the work first hand and decide if it was something he had further interest in. (the experiment part of the experiment!)
  2. Almost nobody does this, so it causes you to stand out from nearly everybody else in the minds of his potential future employers.

Through this process Mike ended up building relationships with many people he had interest in working with. It later resulted in both interviews and ultimately several job offers that put him over six figures for the first time in his life.

More importantly than that he learned through the experiments that there were some types of work and companies that he simply didn’t enjoy, saving himself potentially years by helping him narrow down his list (the opposite of taking huge career risks).


One of my favorite things to help our students do is to test drive work in paid capacity.

Why? Because it adds a different level of stakes to the experiment. You now are getting an idea of what it’s like to design and deliver an end product or service for someone.

The paid research approach is exactly what it sounds like: You actually do the work or a portion of the work and …[dramatic music inserted here] get paid for it… but typically in a short term format like a project or contract so you’re not locked into it if you find that it’s not for you!

We’ve found that the two easiest ways to start with this approach are:

  1. Freelance on a small project in the area you’re potentially interested in.
  2. Take on a project that exposes you to the area you’re interested in within your current company.

Here’s an example of both of these:

Andrew was working with a marketing company and not totally satisfied with his company or his career. He suspected that he wanted to shift to a particular area of Social Media Marketing.

To test drive this, he took the tiny skillsets he had developed around the fringe portions of his job around social media and began doing that for a friends small business on a freelance basis.

This allowed Andrew to try out and get paid. Most importantly it gave him the answer to the question

“Is this something I want to dive further into?”

In his case it was a yes. He learned he needed certain types of creative freedoms and liked getting paid for it on a more regular basis.

You can do that too. Identify the most likely place where you can get a small project to start with. Where is the low hanging fruit? Do you have a friend that needs this, is there a section in one of the vendor companies you currently work with that needs help? It could be taking a portion of your current job that you enjoy and try to do it on a smaller scale project.

To make this even easier, there are entire websites built around this like Fiverr and Upwork. For pretty minimal time you can get set up there and take on small jobs.

In Andrew’s case he determined that he wanted to learn more about the strategy side of social media marketing and then he went back to his company and expressed that to his boss.

This turned into him taking on additional responsibility which led to him getting to further vet this type of work and ultimately earning him a pay increase.

Boom! Additional paid research!


Volunteering, although usually very helpful to the organization you’re helping out, can either be incredibly valuable to your experimentation OR a huge waste of time!

So how do you do volunteering in a way that’s hugely helpful for you AND them?

Use this question as a guide before accepting or proposing volunteer work:

Will the  volunteer opportunity expose you to the types of work, people, challenges, or  learning that you hypothesize you want to spend more of your time around?

If not, or there’s not a high degree of chance that it will, find other volunteer opportunities instead.

Here’s an example of a volunteer opportunity from our very own Lisa Lewis, a career coach on our team.

She was in a place of deep career dissatisfaction. She loved helping people and wanted to do it more. She had applied to graduate school and taken the GRE, but still had a little fear in her gut pop up saying “are you 100% sure that being a clinical mental health licensed practitioner is right for you?”  

She wasn’t sure, so she found opportunity to volunteer, for free in her spare time, above and beyond the 9 -5 to get a sense of if she wanted to take this on as a 40 hour a week commitment.

She found the organization Crisis Text Line that she had followed for years. They were accepting applicants for their crisis volunteer program. I thought that would be a good way to do the work of sitting with people and holding space for them when they are going through intense painful moments and helping them to become calm and resourceful and to take care of themselves when things aren’t okay.

It was fun for me because I loved that opportunity. I had a glorious time doing the work but oh my goodness by the end I knew it affected me so profoundly and intensely in just four hours of work a week that I knew I wasn’t wired to turn it into 40 hours.

Lisa Lewis

For yourself when thinking about it what are some of the organizations doing the type of work or the sector you are interested in? Do they have anything you can apply for to test out and run experiments to see if that work feels good for you? I’ve personally even done this with professional organizations and volunteering to organize their events, like the Society for Human Resource Management (SHRM) where I wanted to gain exposure to certain people so I could learn if I wanted to work with them.


I’ve found that one of the quickest ways to become involved with a certain topic, profession, industry or even type of work is to become a member of the media.

I’m not talking about becoming a card carrying member of the Associated Press. Instead I mean by writing, podcasting, creating video, or any other type of media, you can get an inside look at what a particular type of work is like AND if you enjoy it, it can pave the way to future opportunities for you at the same time.

For example, this very blog started as an experimental blog back in 2012. I wasn’t even totally sure what I wanted to do next and suspected that I would have a lot of fun helping people make big life changes and big career changes on a fulltime basis. So I started researching and writing down everything I knew about it. You know what happened from there (or if you don’t here’s the story on episode 100)

Another example is Dustin Hartzler. He started out his experiment by creating a few websites of his own. He found he enjoyed it and his experimentation evolved into paid research by creating websites for friends and small companies who needed them. Through this work he found that he was enjoying WordPress (a popular content management system for websites) he created a podcast and posted it on iTunes to expose himself more to wordpress and further his expertise. (which creating content forces you to acquire) This also brought him even more customers to his freelance operation.

After doing this he had really become a fan of Automattic, the company that created wordpress. This led him to pursue a career working with their company.

What started as an evolving experiment in the podcast, later on became his ticket to get him in the door for an interview when there are thousands of candidates that apply to Automattic regularly.

Dustin did this with podcasts but this can also be done with a blog, essays, articles, videos, a website, and any other types of media.


This last one is exactly what it sounds like:

Immersing yourself in intentional learning to help you understand whether or not you want to pursue a career direction.

Well the first thing that most people think of college or graduate degrees, it doesn’t have to be this at all.

In fact, I try to talk most people out of doing an advanced degree, not because they aren’t valuable, but instead because spending 30 to 70 thousand dollars and two or more years of your time often isn’t worth it for most people when they still don’t know whether or not that is going to get them to a career that they are excited about.

A bigger reason than the time and money is for most (not all but most) professions and skillsets there are many more less expensive options to get you to the same result. This is especially true now more than ever. Even compared to 10 years ago There are so many more ways and types of education other than just college.

That said, taking a class, course or school can actually save you many years of wasting your life, especially if it helps you avoid a bad career decision. Here’s an example:

Avery was burnt out on her high powered career in finance. She knew she wanted to do something much more creative but didn’t yet fully know what, she decided to pursue something that she had a dream about forever and wanted to explore. She quit and moved to Paris to go to a photography school!

In doing so she quickly realized that photography really wasn’t for her. This might sound like a failure but instead this actually saved her many years of her life as well as not having any kind of regret.

You don’t have to quit everything or move to Paris to learn what’s right and not right for you.

Instead you could start with a single class or by taking a course on Udemy or SkillShare. This can help you understand if you really actually like the subject matter or skillset. Remember to try to apply the learning before you make a decision to dive deeper or not. The appeal of learning something is often different that the application of that same learning because humans are wired to enjoy learning.


Now that you’ve seen these 6 examples, you can choose the one that makes the most sense for your personal situation. Or you don’t have to choose just one, you can combine them together. For example doing some freelance work for a company that you met through the social Goldilocks approach.

If you’re not ready to test out an experiment yet,  bookmark this page so you can come back to it when you are.  Also  share this with a friend who might need it!

Scott Barlow: Welcome back to Happen To Your Career. I’m incredibly glad to be here. We have an episode that has been a long time coming. It's been requested numerous times by our listeners, in a variety of ways, email, snail mail, carrier pigeon, smoke signals, texts, all the things. Because it's been in demand we have Lisa Lewis back with us to talk about designing experiments. Lisa Lewis welcome back.

Lisa Lewis: Thank you, always such a pleasure. Hello Happen To Your Career fam.

Scott Barlow: Well hello there, designing experiments for backstory was causally mentioned in episode 147, Lisa’s first appearance after she joined our team. Take a listen to that “Following the Breadcrumbs to Your Dream Career.” The concept of how to validate whether the career you are considering could be a great thing or not was casually mentioned. Am I getting that right?

Lisa Lewis: I think so and since it's happened we have seen more and more questions to know how to test drive and see what is a good fit. One thing I appreciate with my background in economics is how do I manage the risk. There is a lot of risk and uncertainty in making a transition. The smart ambitious top performing folks that come to us don’t want to make an ill advised decision so it's important. I can’t wait to get into it to make it clear as possible, if not easy.

Scott Barlow: We are going to take you through six different ways to design an experiment, six different examples of what we’ve called our test drive method and help you be able to create and design experiments for yourself. To do that we need to talk about why people are so interested in designing experiments and what we mean by it. Why do you think this comes up? I know we’ve had the request again and again. What do people want to get out of it?

Lisa Lewis: The people in our community are observant and smart and have seen other people in their networks and communities make career transitions of their own. It sometimes looks like someone burning the bridges as soon as they cross them saying I’m done with this business and company. They are trying to make something dramatic happen. There is little success to that. Some people make it work and find a way forward but it's more like throwing spaghetti to the wall to see if it will stick rather than being calculated and thoughtful. One of the things that makes an experiment so nice is it helps you understand the assumptions you have about work that might be a good fit for you rather than betting the whole farm and getting validation that it is a good fit so you don’t move into a new job and realize six months in that you have brought your old baggage with you. Finding a way to move forward that doesn’t bring the discontent with you and allowing you step into something that is more fun without huge risk and fear that you don’t move forward.

Scott Barlow: That is incredibly important. I think the subtle piece about moving forward and bringing the right things versus baggage is possibly the most important piece. I think many people are interested in designing experiments because they are afraid of making the wrong move. We have worked hard to help people reframe right versus wrong when you are exploring and trying to decide what can be a great career move. How do you think about that right versus wrong thing?

Lisa Lewis: It is so true. And I think I talked about this in 147, when you are thinking of making a career transition in terms of this binary operating system of right versus wrong you are creating a huge amount of pressure on yourself and the way you are thinking about the opportunities are just black and white, yes or no. In people who successfully make transitions there is a lot of gray areas in the middle. It doesn’t have to be an extreme one way or they are other. We are complicated human beings with a lot of different needs and desires and how to best prioritize those for what works for you can’t be done in a right and wrong framework. The answer on what is the best fit for you and what your family needs now and the risk and opportunities you want has to be more nuanced than that.


It’s funny we are talking about this framework of right versus wrong. I was listening to a podcast the other day that Susan David was on who wrote “Emotional Agility” which is phenomenal. She talks about “dead man goals” any time in our lives we are trying to avoid being wrong, avoid pain, falling down, not getting it on the first try are dead man goals because they are impossible for living beings to have. If you are going to try something new and allow growth and space to expand and learn you have to expose yourself to some risk. Rather than thinking of things in right or wrong framework, the reframe of creating better goals around learning and growing and embracing uncertainty, you can set yourself up to test that better through test drives and it can be important.


The other thing I think is important is the idea of wondering what inside of you is pushing your brain to a right and wrong framework? Why are you afraid of being wrong? Is being wrong a bad thing? Is guessing a need and not getting it completely perfect the first time a bad thing? What kind of opportunities is that limiting you from having the possibility to expand and explore? As kids we tried things all the time and messed up and weren’t perfect and it was fine and embraced as the process of growth. For our listeners growth and chances to learn and be the expert and to try something new and keep having the novelty and fun of having something come across everyday that challenges and pushes you is part of the fun of being alive. The underlying fear of making the wrong decision can be helpful to grapple with and healthy. What are your thoughts?

Scott Barlow: As you are talking I was thinking and I think at least in the U.S., and other countries too, we have through schools, how a lot of companies are set up, created or destroyed, whichever way you want to look at it, the childlike ability you are looking at. We have given and put a whole bunch of reward on being right or being perfect or not making mistakes. Unfortunately any type of experimentation where you learn, or from a life growth standpoint, your ability to grow requires you to make mistakes or you aren’t learning at the highest rate. One is impossible without the other.


If we look at those two juxtapositions on one side we reward as a society the perfection and lack of mistakes but for us to move along as human beings and to feel happiness requires constant learning and making mistakes on a regular basis and making big leaps and bounds to create a good situation in our career. It requires imperfection and going into it having wrong situations happen. When you look at it that way you can understand how creating test drives are more effective because you can go through, here is the thought process when we do it with our clients and Career Change Boot Camp students. You can go through and speed up the learning process which is the intent. Design an experiment so you get the learning without being in a job for four years. It's better in my opinion if you go through a bunch of them, you've spent a week, two weeks a month or three and it doesn’t work out because it means it's saved you years of your life. Guess what you saved like twenty years of your life. That is fantastic. What is your take?

Lisa Lewis: Totally. I think that being willing to put yourself into a position where you might not be as successful as you want immediately but in a much smaller contained capacity like an experiment as opposed to making this transition into a brand new job where you start with this learning curve and realizing after you’ve been there a year, six months, or even in the first week it's not the right fit and you’ve completely uprooted your whole life, routines, and patterns. That is a lot of risk to me. That seems really scary. If there are ways to bite off little chunks of the fear and uncertainty and test it out first to help make really strategically informed choices in the future that seems like the best thing you can do for yourself.


I’m excited to get into our six different ways to design and experiment, I want to throw in a curveball, you are needing a pre experiment experiment meaning you are in a position where you are comfortable in your job but not happy and experiencing growth but the comfort is really nice. The golden handcuffs of a really nice salary feel like it's too good to leave then you might need a precursor to this test drive which is opening yourself to opportunities to learn grow and get rejected in a smaller capacity. Maybe that means going to Starbucks and intentionally ordering the wrong drink to remind yourself this is what it feels like when I mess up and make a mistake and I can rely on myself and trust myself to fix it or call someone in your family the wrong name to feel that momentary guilt and panic that you did it wrong. It reminds you you can survive it and everyone makes mistakes and you can gain courage to do this bigger test drives.

Scott Barlow: I try to make that a part of my everyday life. I’m curious if you have. Even yesterday I pulled a shirt out of my closet I’m not comfortable in. Alyssa bought it for me and really likes it. I’ve kept it because of that. I put it on and immediately felt uncomfortable but I kept wearing it intentionally because I don’t want to get too into my comfort zone because that is where you stop growing as a human being. You can devise those small very low risk things. I mean what is going to happen if I wear that shirt into public, nothing, besides maybe people will like it. To your point, there are lower scale ways to build up to these experiments. If we go through these and you feel a huge amount of apprehension of any of these I would say start smaller with these mini experiments.

Lisa Lewis: I’ll share a quick tale of a mini experiment I did. I was, as many listeners know working from Bali for a couple months. One of the things that become an opportunity to do wrong and be rejected, in Bali the traditional way to get around is a vespa like scooter. You go from point a to b. Only tourists walk. If I wanted the true experience I had to get on one of these damn scooters and make it work. I had a bunch of limiting beliefs around myself of I’m not coordinated and have no balance, I’m so afraid. A poor sweet ex-boyfriend of mine got to hear all of my excuses of why being on a two wheeled vehicle was a terrible thing. And yet it was something I needed to do to be able to function in this environment. It had nothing to do with career. I had to put myself into a high growth learning environment to get access to other things important to me. It was a humbling experience to remember I wasn’t good at it at the get go, I could seek out help and get lessons, and I could make it. The things I believed about myself were all just stories I was telling myself. I was just as equally capable of driving one as anyone else. Once I peeled back the layers of my fear and got into it it has spill over effect. For you who are listening there is something like that in your life, a little thorn unrelated to career that can help your remember your own confidence and trust in your ability to take on something new, not be great in the beginning but find a way forward. That will set you up to tackle these six items or which resonate with you.

Scott Barlow: That is perfect. I’m sure if you have listened to any of our back episodes we have talked many times about how you can build tolerance to discomfort. What is uncomfortable now as you build the tolerance with things like riding a vespa when you are not a vespa person or wearing shirts you aren't comfortable with you build that much like a muscle. Once you have done that the things we are going to talk about become so much easier. Let’s assume you’ve worked up to that already. Let’s talk through these examples and we’ll give you a story to go with each one. Help you understand how they work. This first one we are dubbing the Social Goldilocks Approach. How would you describe that Lisa?

Lisa Lewis: This one is a tactic inspired by a fabulous student and client named Laura. When I think of Social Goldilocks the idea comes from tasting a bunch of different bowls of porridge to decide if it is too hot, too cold or just right for you. We think about this as Laura going out there and talking to all the people in all the places. She did a fantastic job identifying all kinds of sectors and organizations that could be interesting to make her next step. She wanted an opportunity to grow and new challenges based on past skills and experiences pivoting them in a new direction. She was willing to put herself out there and be bold vulnerable and brave and call people in all companies and roles to have conversations about their culture, what does a day on the job look like, what are some things they love. She had a fabulous question asking everyone, I believe was what types of skills make someone really good at this type of role. When they would say that they are innovative, willing to push the envelope, willing to hear nos to get yeses, and she could validate that with her strengths. Does that sound like me? Does it sound like they are describing me and I’d have fun? Or are they describing someone I know or could be but not the person I want to be in this next phase? She did tons of these conversations and could hone in to get the perfect bowl of porridge. Even as of this morning she had fabulous news for us on how it's going. She is in an awesome position because she was willing to have those conversations and seek out candid honest feedback from people about their roles without having to have the hungriness in her eyes when people think of the typical informational interview. The conversations ended up being more candid and honest which helped her to make such better decisions.

Scott Barlow: One of the reasons she did such a phenomenal job is she went into it as curious and looking at it as an experiment not looking at it as how do I get a job at this company. She went in to evaluate do I even like this company or the role the person is in. Trying to measure that with what she wants out of life and a career. After the experiment she was able to say this lines up well but these other things don’t. The cool thing is she had done the work building relationships with the companies so it was easy to go back and say there are these two organizations I’m excited about and I already know people there. And be able to go through and talk to them about roles that were not even posted yet. You will get to hear her full story on a future episode of the podcast. Lisa didn’t know that so she’s excited.

Lisa Lewis: I’m so happy. Her story is so awesome. It's so validating to see people we work with grab the bull by the horns, diving in, and seeing this level of results. I can’t wait for her to share her story with the Happen To Your Career family and community. Get excited over there.

Scott Barlow: If you are wondering about some of the back context of how she did this and called up people in companies it was simple, she would do research on LinkedIn to see who she was most interested in talking to and then she would, anywhere she had a weak tie connection, I can’t recall who made that up - being if I know Lisa and Lisa works for a company and I get hired at that company it's not a weak tie. Most jobs don’t come from your family or friends. Most come from, especially more hidden roles, is I know Lisa and she knows someone else who knows someone else. That is a weak tie. Not someone I know well.

Lisa Lewis: That is from the world of mathematical sociology. Something studied and coined in the 70s that is starting to gain more momentum now with tools like LinkedIn where you can map out other people's networks to see a sneak preview of what weak ties they have access too so you can make strategic requests for introductions and warm connections.

Scott Barlow: Think about it as your second and third level connections on LinkedIn. She did a fantastic job of that because she would find those weak ties and ask for introductions. It worked well for her partially because she was building relationships but the bigger value was to go through and understand this porridge is too cold, it's not good, or too hot. I’ve talked to 20 organizations and a couple are just right how do I dive deeper now that I’ve validated these are great for me.

Lisa Lewis: One last thing is part of this process has to be what seeing wasn’t great and the cold bowls of porridge. The test drive process is to get what doesn’t work for you as much as what does.

Scott Barlow: If you think of it like a science experiment generally you set out your hypothesis and doing a number of experiments to get one set of data you move forward with and publish. It's very much the same here. You will go through a number of things that aren’t a fit and that is okay because it means you are that much closer to validating what is a good thing. You might talk to five companies and realize they are terrible fits but you learn why and what you are looking for and how to double down to find what you do want, flexibility, creative freedom or whatever it is for you. Great point. Here is the thing. With this approach you can amp it up further. That is the next example. We will share a story too.


Think of this as now that you have talked to all the people and called up companies and talked about roles and you think you have interest but you still want to validate further how do you do that?

Lisa Lewis: If we think about it as being a scientist and creating hypotheses and experiments. Experiment 2 is the Amped Up Follow-up. We had another awesome client Mike who took a similar tactic to Laura in that approach talking to a lot of people in a bunch of organizations he was interested in. He had a much narrower focus. What makes his follow-up amped up he would walk away from a meeting with an employer, after asking what are you struggling with, what are big vision things,questions you are wrestling with to make the impact you want to make over the next five years, what would make your life easier? Then Mike went and did those things. Unsolicited, unpaid, just for fun. Hearing someone say I have this need and need to solve this he would go and create a spreadsheet, a piece of code or equation and follow up. He might have sent a thank you after the conversation but a couple days or weeks later following up and saying remember that thing we talked about I’ve thought about it, created this thing and I want to give you it for free, enjoy. Being a hiring manager and seeing someone so affected by a conversation, that listened so well, and so excited about the work you are doing that they go and do the work and send it to you says a lot of exciting things about the contributions that person can make if you bring them into your team.

Scott Barlow: If you want to hear Mike’s entire story you can go back to episode 174 where we brought him on. I thought this was so cool. I’ve hired 600-700 people over the last ten years and I’ve rarely seen people do something like this. It makes a massive difference in impression. Think about if you are the hiring manager and someone comes to you and says you know that thing you said was really valuable to you but you didn't have time or bandwidth to get to? Well I went ahead and did it. You already know Mike knew it would be incredibly valuable because he had taken the time to dig deep enough. Here is where it was more valuable he told me multiple times where he did the work and realized I don’t want to do this. I’m not interested in it and realized if he was spending large amounts of time doing that it wouldn’t be a good thing for him. That happened once or twice throughout the process. That was more valuable sparing him potential years of grief being stuck doing that than even the small tidbits of positive things he learned. He got good reinforcement too and built massive relationships because no one does this, even though we are trying to change that.

Lisa Lewis: There are so many people that come through our doors and send us emails and say I’m not sure I’m going to like the work. What an easy way to talk to someone and hear about what they are needing and give yourself the time and space without pressure or their knowledge to try it out and see if you enjoy answering the need. If the answer is yes then boom. That takes tons of agonizing and questions off the table and validates it can be great and it was fun for me in this one context and I bet it'll be fun for me if I get to solve more problems like this.

Scott Barlow: What is interesting out of those 600- 700 people I’ve hired I’ve had three people who have done this. Two out of the three did not do the project as I would expect as paid work. If I’m honest. If I was paying them $150,000 a year I would have been less excited about it but I wasn’t expecting it, it met the minimal need. If I was paying $150,000 for it what would have been a subpar project potentially was one way above expectations because where they were in the beginning. I bring up that to say it doesn’t have to be perfect. Mike could have labored on this for long periods of time and said it's not good enough and I can't turn it in but the valuable thing is he got to try it out and get the learnings to know if he wanted to dive in and then he got to add something really valuable because he got to give something that exceeded expectations which were zero.

Lisa Lewis: Absolutely, such a cool way to make a lasting impression on your potential future employer. Speaking of lasting impressions, shall we go to test drive experiment three?

Scott Barlow: Let’s talk about it. This is called Freelance Experimentation or we like to think about it as the Paid Research Method. Here is an example. Andrew was working in different social media marketing and other marketing and not totally satisfied with his company or his career. He determined something was wrong but didn't know what he wanted to do or double down on. One thing he did was started taking the tiny skills he had developed around the fringe portions of his job around social media and began doing that for a friends company on a freelance basis. He was helping his friend and getting paid what felt like a small amount to him but we later figured it was a high dollar per hour value because it didn’t take a lot of time. In this case one thing he learned was he liked having some additional creative freedoms and other learnings. The important part for him was that he had another outlet to design an experiment around. This is something that allowed him to try it out and get paid and be able to say is this something I want to dive further into. Based on the learnings I have how do I want to dive further? In his case it was a yes. He learned he needed the creative freedoms and liked getting paid for it on a more regular basis.


You can do that too. Be able to go through and identify a place where you can get a small project to start with. Where are the low hanging fruit? Do I have a friend that needs this, is there a section in one of the vendor companies I currently work with that needs a little of this whether it's social media or another skillset? It could be taking a portion of your current job that you enjoy and try to do it on a smaller scale project. There are entire websites built around this like Fiverr and Upwork. for pretty minimal time you can get set up there and take on small jobs.

Lisa Lewis: I love it. Something you touched on is the idea of this tactic and applying it in your own current employment. If you have a job and it's a 7 out of 10 for what you are looking for but you like the culture and organization you can take a pivot internally and try something new that is an expansion where your past background can be brought in and applied in a new way. You get paid to do work in your 40ish hour a week position to try new skills and see if you like it and can create a platform for you to make a bigger transition if you want to go elsewhere. Or it can be a really easy seamless way to solve the question of feeling unfulfilled itching for a new challenge within your current organization without a big interruption to your life.

Scott Barlow: I think that is incredibly valuable. Usually the mindset for people when they don’t want to be in their job anymore is I don't want to take on anything else. When you are frustrated it closes you off from opportunities right in front of you. When you get closed off you miss the opportunities. Almost every organization is going to be willing to let you take on another project. You want to do more and it’ll be valuable, okay. There will typically be someplace you can cross over and it doesn’t have to be huge.


What do we have next? It's a good one, Getting Your Foot in the Door Through Volunteering. You have a story where you have done this before.

Lisa Lewis: Yeah, and if you’ve listened to 147 you’ve probably heard this. The quick story is for my foot in the door volunteering experience i was in a place of deep career dissatisfaction. I loved helping people and I wanted to do it more. I had applied to graduate school and taken the GRE. 24 hours before starting graduate school I had a little fear in my gut pop up saying are you 100% sure that being a clinical mental health licensed practitioner is the right way for you to do this? I wasn’t sure. I found a straight off the rack opportunity to volunteer, for free in my spare time, above and beyond the 9 -5 to get a sense of if I wanted to take this on as a 40 hour a week commitment. I found the organization Crisis text line which is near and dear to my heart that I had followed for years. They were accepting applicants for their crisis volunteer program. I thought that would be a good way to do the work of sitting with people and holding space for them when they are going through intense painful moments and helping them to become calm resourceful and to take care of themselves when things aren’t okay. It was fun for me because I loved that opportunity. I had a glorious time doing the work but oh my goodness by the end I knew it affected me so profoundly and intensely in just four hours of work a week that I knew I wasn't wired to turn it into 40 hours.


For yourself when thinking about it what are some of the organizations doing the type of work or the sector you are interested in? Do they have anything you can apply for to test out and run experiments to see if that work feels good for you? I have a fabulous coaching client Angie who is looking to do something similar with a couple organizations she admires that need people in communication capacities. She has such a gift for communicating and being sensitive and thoughtful especially around health related topics that she has found organizations that need what she has and it's matching up what she can do with what she needs in a free capacity to see if it's good and developing relationships to turn it into a paid capacity.

Scott Barlow: That is awesome. I think as you are talking about Angie one of the commonalities is you can’t allow the ambiguity to stop you from trying. Many people will think but how? Start like with Angie, she took what she knew and applied it to identify organizations and now it's going to be approaching them and some won’t work out which is okay and part of the process which leads into the next example.


This is something that because we have a podcast and website and blog we have a number of people email about it. We’ve now dubbed it the Budding Expert Method. Think of this as developing expertise through different types of media like starting a side project with a podcast. That’s what I did and how this business came to be. It can be like starting a blog. It's crazy how many doors open and how many people you get to talk to when you make yourself a member of media in anyway. You get access to information that other people don’t have which means you get learning and stuff that doesn’t work too. Its possibly the biggest effort out of all of these but it allows you to trial and error building expertise in an area and through a blog, podcast or other media, youtube channel. There are a lot of ways to do this but establishing yourself as an expert, and forcing yourself to learn , to talk about others and putting yourself into the world causes you to evaluate the great areas of what you are considering and what doesn’t jive. Even if you aren’t doing the work you are developing a high degree of knowledge about the work and many times you get enough information to make a valid decision. What do you think?

Lisa Lewis: It’s interesting to think about it in terms of you. Had you not started the podcast you wouldn’t have started to be an expert and have two of the top ranked career change podcasts in Itunes. It might have meant that this business wouldn’t have existed or might have in a different way and it all had to do with you being brave and courageous without knowing the return just because it would be fun. What an incredible light and chapter of your career and what incredible changes you’ve been able to create in other people's lives because four years ago you and your friend Mark were being goobers and goofing around on podcasts and wanting to record these conversations.

Scott Barlow: I appreciate that very much. It may not have worked out and even prior to the podcast was the blog set up as an experiment of whether I liked doing that. The original blog was an experiment. Someone else who has done this is Dustin who developed a podcast around helping people with Wordpress. That is the back-end of most websites and a content management system. It stores the pictures and words and how they come together so it shows up how it should look when you look at the website. He did this but then as he went through and created episodes he decided he wanted to make a career change. He was having fun and got hired by the company that makes wordpress because he had so much expertise. That company was founded by Matt Mullenweg. Go back and check out Dustin’s episode. He’s a great example of that method. We have another one.

Lisa Lewis: Experiment test drive 6 is intuitive and simple but people don’t think about. Take a Class. I think of this as the Avery Roth, one of the coaches from our team who has a past episode. She wanted to explore being a professional photographer and creating that level of beauty in the work she was doing. So she enrolled in photography school. Going and quitting your job and throwing yourself into school doesn’t have to be that extreme. You can take a course on Coursera, or Udemy or one of these platforms that offers opportunities to put classes online like skillshares. You can take a class in person at a community college or center. Maybe you have secret dreams of starting a jewelry store. I have a client who launched her own Etsy store making handcrafted artisan jewelry and it's phenomenal. If that is interesting to you, she took a ceramics class and she loved making cool little bits and bobs and turned them into gifts and art pieces. Taking a class can be a fabulous way to test drive if you like it and if it resonates with you. Or is it something where for only the cost of your tuition and time you’ve learned it's fun but nothing you want to devote 40 hours a week of your life to.

Scott Barlow: That is amazing. First of all I didn't know about the Etsy store so that's even better. As you hear these examples and stories I’d encourage you to do this. We have realized after helping thousands of people make really big life changes, that is what career changes are, massive life changes, and doing so we’ve realized it's more about the marathon not the sprint. You have to develop momentum. If you heard one that sounds way easier and you could get excited about or how you could make it happen I’d advise you to go head on into that one. Stop considering. When you get stuck in your head and try to evaluate 42 different ways to be able to decide exactly how to do the experiment will cause you to do no experiment and you’ll learn nothing which defeats the purpose. Just build the momentum. Once you realize how easy it can be and how valuable it can make your life and career you will want to do it more and in different ways and carry it in other areas of your life. What advice would you have for people as they are thinking about designing their first experiment and how to go about this?

Lisa Lewis: My biggest advice is something we wrote about in an article for the muse a couple weeks ago. Fear really likes to paralyze you from taking action. One Of the coaches I love and learned a lot from, Todd Herman, says fear cannot paralyze a moving target. The challenge I would throw down is how can you start to put yourself into motion? Just because something is hard doesn’t make it inherently better. Sometimes easy first steps are a great way to get the momentum going and help you develop confidence and trust in yourself for bigger challenges.


We’ve outlined the six tactics: Social Goldilocks, Amped Up Followup, Freelance Experimentation, Foot in the Door Volunteering, Budding Media Expert, Taking a Class Approach.


I want to throw down the coaching gauntlet and say which one of these six feels like the right thing for you right now that would be easy and what can you do before you move onto the next thing in your day? Before you go to the office or shut this off to go to sleep. What is the one single micro baby step you can take right now to accomplish or achieve one of these things? Is it writing an email to have a coffee conversation, looking up classes, going to the organization website of your favorite nonprofit or company you follow and sending them a pitch, going and putting your account on Fiverr or Upwork? I want to turn all of this knowledge into action. That is what differentiates people who make these transitions from the people constantly consuming more information and using the knowledge seeking as a delay tactic for fear to derail their progress.

Scott Barlow: We don’t like derailing progress. We like the learning and not the derailing. I encourage you to pick one of those out. If you want the stories we shared and the people we talked about in one nice pdf download go to happentoyourcareer.com/206. You will have everything about this episode and download the whole thing in a pdf you can take and use for first steps to design your own experiment. Make it happen.

Lisa Lewis: I love it and one other thing I want to throw out there. If you are committed and you want to make a change one thing we talk about in our Muse article is getting accountability and telling people you are doing this. If I can be the accountability buddy for you and you want to send me an email at Lisa@happentoyourcareer.com and let me know which challenge you are going to take on and the first step I would be so honored and excited to support you and cheer you on and add resources and things that might help if I can. I want to offer that as an opportunity for those of you serious about making a change. We want to be a part of your success story.

Scott Barlow: You heard it hear first. Lisa@happentoyourcareer.com. Lisa thank you so much for making the time. You are in Hawaii by the way, we didn’t say that. All the birds you heard in the background. She’s just hanging out, normal tuesday.

Lisa Lewis: One thing I was thinking about in Hawaii, there was part of this journey where I took the work and turned it into something that was location independent where I felt I had to be apologetic. I’m really sorry I am in Hawaii I know it's challenging. I want to take care of you but I’m asleep during those hours. The more I hide from the accomplishment that I created this work the more as a coach that I’m not standing to my own values and integrity as having my clients shout from the rooftop who they are and own it.


Thank you for giving me an opportunity to say I’m actually really proud of all the ways I’ve transitioned my business being based in Washington D.C. To take with me to travel and honor my values of spending time with friends and family scattered across the globe and taking advantage of the adventurous side of myself. Has it been challenging? Yes. I'm sure there are CCB students who have felt the challenge of not getting an immediate reply from me but to be able to find ways through, live this life on my terms, and treat this as my own experiment of can I continue on and be location independent and could I create a coaching practice where I coach from a different continent every couple months and help minimize career dissatisfaction and optimize career happiness to new people, new markets, new environments is so fun and exciting to me. I imagine you are still running these experiments too and being a scientist in your own life. Thank you for giving me my own moment where I could step into my integrity and own that it's been hard work, getting up really early and crazy hours, but for me to get to serve people and help in the way I want as 100% myself has been the most validating cool thing to accomplish and to talk and help other people too.


If you want to figure out what work fits you, find the fulfilling career that lights you up and gives you purpose, and you want help making it happen, coaching can help you step-by-step. Want to find out how?

Go to https://www.happentoyourcareer.com/coaching/ to apply.


Download the pdf on the Six Experiments at happentoyourcareer/206.

powered by

Ready for Career Happiness?

What Career Fits You?

Finally figure out what you should be doing for work

Join our 8-day “Mini-Course” to figure it out. It’s free!