A Process for Career Experimentation


As we search for our best fit work, many of us get stuck in the planning and analysis phase.

We research a thousand possible career paths online, take personality tests, and all of the awesome stuff that our connections are doing on social media.

But there’s nothing that seems like the perfect fit for us.

So we continue in the planning, research, and analysis phase, until it becomes analysis paralysis.

And we continue spinning our wheels to the point where we get stuck. Then we find that after all of this time, we haven’t taken any real action towards finding a career path that we love.

That’s a story that I’ve seen unfold time and time again, from friends, people that I’ve mentored, and online in career discussion forums. 

In my view, I think that there’s a better way to go about. 

I think that the best way to learn is by doing.

And in the case of finding your best fit work, I think the best approach is to try and find that best fit work by experimenting via small bets.

It’s to develop sound hypotheses for what you might like doing. Then, from there, going out to gather data about each of those in a low-risk way to reject or confirm your hypotheses.

Throughout this post, I’m going to walk through a philosophy for career experimentation, propose a process for how to develop career hypotheses and then review how to execute and track them in a low risk way.

Let’s get started.

The Philosophy of Career Experimentation

At a high-level, to find your best fit work, I think you need to establish a high-level direction for where you want to go in life. From there, you try to figure out how to get there while enjoying the process.

And in my view, it’s critical to take action within that framework to gather information about the potential of your path.

That is different than how most career counselors will guide you, which is to spend endless amounts of time in reflection to hopefully generate an epiphany about your exact right path.

Ultimately, I think you want to gather information and external feedback quickly, and to do so in a way that is not going to have major downside for you if you find that the path you’re following is not as fruitful as you thought.

To do that effectively, I think you want to operate in small bets.

What is a small bet in this context? 

A small bet is a low risk action for the purposes of gathering information. 

To be more specific, I think there are a couple of key criteria for determining if an action is low risk:

  1. There is limited downside to you personally and professionally if it fails
  2. You can stop what you’re doing quickly and easily and pivot to something else

For example, a small bet would not be quitting your job to pursue your passion without a backup plan. That would have significant downside in the sense that it could have significant short and long term negative financial consequences.

A small bet would be more along the lines of trying to build something on the side to validate the idea. And then pursuing it to larger and larger degrees if it looks promising. Or, alternatively, pivoting if it seems like it’s not the right path.

That is where the experimentation aspect comes in. I think of a small bet as an experiment that you’re running to test a hypothesis about the viability of a potential work path. 

If the hypotheses did not work out as you expect it, you move onto your next small bet and treat that as an experiment to gather info. And you keep doing that until you find your best fit work.

So that’s the high level thinking behind the process. Now, let’s talk about how to approach it more tangibly.

How to Develop Career Hypotheses

In order to conduct an experiment, you need to have hypotheses to test. 

When it comes to finding your best fit work, there is a specific approach that I like to developing hypotheses for what that might look like.

I talked about it at a high-level in the last section, but here is more detail as to how I like to approach it:

1. Establish a Vision for Your Life

When it comes to work, I think that where many people get it wrong is they look at their work in one of two extremes:

  1. They make their work the center of their life and build everything else around it
  2. They view work as something that they are forced to do and cannot possibly imagine enjoying it 

Ultimately, I think the best way to approach work is to think about the life that you want to live first and then intentionally find work that fits into and enables that life.

And that starts with having a vision for the life that you want to build.

2. Try to figure out how to build the life you want while enjoying the process

Once you know what you’re ultimately working towards in your life, you can then think more about how to get there.

And your work is generally the key to the how aspect of achieving the life you want.

Your work is your source of income. And it is one of the primary uses of your time.

So finding the right work plays a massive role in enabling the life you want. And in enjoying the process of getting there.

The problem is that many people do not enjoy their work.

Maybe it enables them to have certain aspect of the life they want, like status, money, etc., but they definitely don’t feel a deep enjoyment of the work or satisfaction from it.

So this is where developing hypotheses comes into play. You try to develop some educated guesses as to what work enables you to pursue the high-level path that you want to go, but that you will actually enjoy.

And my favorite tool for doing that is called Ikigai.

We wrote a full post on Ikigai here, but basically it serves as the intersection of all of the following areas:

  • What you like
  • What you’re good at
  • What the world needs 
  • What can make money

You can visualize it like this:


If you can find that intersection, then there’s a good chance that you’re going to enjoy the process of building the life you want.

To make this concreate, what you want to do is work through Ikigai process (as outlined in the full post on Ikigai) some possibilities for what you may enjoy that also serve to take you down the path of the high-level life you want to build.

For each item in the center of your Ikigai, think of that as an individual hypothesis on which you can place a small bet to gather more info on the viability of that option.

As you complete the Ikigai exercise, there’s no fixed number of items in the intersection/hypotheses that you should have. In general, I’d say that 3 – 5 possibilities is a good starting point. Enough for testing, but not so much to be overwhelming.

A Quick Note on Work Context

While Ikigai is a great tool for developing hypotheses about work that you may love, it’s important to also bear in mind that your work context is going to play a huge role in whether or not you like what you’re doing.

There are a variety of things that contribute to the overall context of your working environment. 

They are things like:

  • Who you work with
  • Who you work for
  • Whether you’re remote or in person

So in order to enjoy your work, not only do you need to find work that leads you in the direction that you want to go and that you’re likely to enjoy, but you need to be mindful of the context in which you do your work to help you enjoy it.

I unpack the idea of work context more in the I hate my job: what to do post, and wanted to make sure I called out your work context as a variable to keep in mind as you’re going through this process.

If your work context is off, that may throw off your experiment. Be mindful of that as you’re going through this process.

How to Experiment in Small Bets

After having completed the Ikigai exercise, and come up with 3 – 5 or so possible hypotheses, now is the time to test them via small bets.

As a reminder, the point here is to take quick, low risk action to gather information about how a particular path feels to you, as well as it’s financial viability.

Here are some ways tangible ways that you can place small bets to test out your possible Ikigais:

Conduct Information Interviews

If a hypotheses for a path that you would enjoy aligns with an existing career path, then information interviews are a great low-risk way for you to gather more information about that path.

For this small bet, what you want to do is find anyone that is at all in your network or connected to your network that does what you want to do. 

From there, offer to buy them lunch or coffee, and simply ask them questions about what it’s like doing what they do. 

Here are some basic starting questions you can ask:

  • Tell me about a typical work day for you
  • What do you like about your job?
  • What do you not like about your job?
  • What skills do you most commonly use?
  • How did you get into your field?

Talking to someone who is actually in the role and experiencing it is a great low-risk way to gather information about that path.

Do an Internship

In general, this one is most applicable to people that are in school, but that is not always the case.

An internship is one of the best low-risk bets because it’s a short term commitment where you’re doing the actual work that you want to do with lots of guidance and support.

If you like the role, in many cases you have the upside of getting hired full-time so it’s easy to follow this path if you like it.

If not, then you gathered hands-on experience to inform your decision, and you can move onto the next thing.

Start a Side Hustle

A side hustle is a fantastic small bet because you don’t leave your job to pursue your passion full-time.

You’re doing the work, gathering information on whether or not you like it, and are seeing if you can actually make money doing it.

Plus, if you maintain the motivation to do the work on the side on top of your full time job and other responsibilities, it’s a good bet that you love the work.

Here is a good list of 40 possible side hustle ideas that you can explore.

Don’t limit yourself to just those ideas though. Ultimately, you can build the side hustle exactly as you want to build it.


A freelancer is someone who does a specific type of work, but not for a single employer.

You’re working on behalf of multiple clients and are typically doing work on a project-by-project basis. Sometimes on retainer.

The great thing about this path is that it gives you a lot of flexibility to control what you work on and who you work with. 

Additionally, it can be done as a side project, you it’s a great way to get paid to gather information about a particular field.

The easiest way to find work as a freelancer is through existing marketplaces like Fiverr, or Upwork.

upwork screenshot

Contract Work

Another good method for experimentation is doing contract work.

This is different than freelancing because you’re doing one job for one company, but only doing it for a fixed period of time.

Six months is typical contract length.

The nice thing here is that it gives you a fixed period of time to try out a particular role or company.

If you like it, many times the contract turns into a full-time offer. If not, you can easily move onto the next thing.

How to Reflect on Your Experiments

As you’re running these experiments, it’s essential that you’re diligent about reflecting on what you’re experiencing as you’re going through the process. 

You need to capture the specifics of what you’re doing when your work feels right to you or, alternatively, the type of things that are happening when you feel like “this isn’t for me.”

My favorite method for doing that is journaling and here’s a quick prior on how to do that effectively:

How to Journal 

My favorite approach to journaling  is the Jim Collins daily score method that he discusses on this episode of The Tim Ferris Show,

Basically, it works like this:

  • At the end of each day, log in a spreadsheet, one of the following ratings for your day:
    • -2: A particularly negative day
    • -1: A moderately negative day
    • +1: A moderately positive day
    • +2 A particularly positive day
  • In a corresponding journal, write about what happened that day and the reason you gave it that score

There are a couple of things that I find particularly valuable about that process. First, you’ll be able to spot patterns. So if you’re focused on a particular career experiment at a given period of time, and you spot lots of +2 days consistently, that’s a sign that experiment is resonating.

The second thing I find particularly valuable about that is this journaling process is you can then dive into the particularly awesome or negative days. So for every day that you rated a +2, you can go in and see what it was about that day that made it so positive. What did you do, what was your rhythm, what did you work on, and you can look at patterns.

For example, you may see that your most positive days involved a lot of creative work, as they did for Jim Collins, or you might find that your best days are spent with other people. Those can serve as valuable clues as to how you can best craft your life for the way you want to live it.

Bringing It Together

After you’ve run a few career experiments, captured some data, and then reflected on what resonates, hopefully you have a sense of which of your hypotheses looks the most promising as far as a long-term work path for you.

If you’ve been able to find work that you think would enable you to live the life that you want to build, or puts you on the path to that life, and you’re able to enjoy the process, it’s time to focus your energy on whatever that thing is, and continue to take steps along that path.


Career experimentation is an essential tool for helping you to find your best fit work.

It breaks you out of the process of analysis paralysis and get you out there taking action to get actual data about how you can move in the direction that you want to go while enjoying the process.

The keys to effective experimentation are placing low-risk small bets to gather information on possible career paths and then reflecting on how each bet goes until you find the one that looks like your best fit.

Once you’ve found your path and you can double down from there.

About the author

Dan Slocum

Dan is the founder of Best Fit Work and is a business professional with over 10 years of experience. He has been a hiring and people manager on multiple occasions, and has also gone through the hiring process himself at a variety of different companies. Dan writes to share content, tools, and resources to help people discover and thrive in their own best fit work.

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