Choose your next project with this exercise

Ever feel stuck deciding where to go next? Do you either have too many ideas, or none at all? How do you pick a new project to work on? How do you decide where to go next?

Similar to writing articles and naming things, I like to break creative blocks with systemization and combinatorics. Here's my current (work-in-progress) framework for choosing new projects.

The working identities model

This process gets inspiration from the book Working Identity: Unconventional Strategies for Reinventing Your Career. In it, Hermania Ibarra lays out a model for exploring and creating your many different "possible selves":

Your working identity is not a single internal entity. Instead, you have multiple possible future selves.
The only way to discover these selves is by performing experiments that involve interaction with other people.
At first, you will have several small possibilities. As some of them grow, they will begin to push out other identities. This could include your current self.
Why take this approach? Because it removes the paralyzing fear of having one true career path for the one true self. It's easier and safer to make these decisions in an iterative fashion, where you can pick up tacit knowledge.

source: https://waitbutwhy.com/

I love how this approach shatters the myth of finding "your true calling", and instead encourages exploration, experimentation, and play. Big decisions are scary, tiny trials are fun. The idea that you have one true job you are meant to do never rang true to me. How could I be destined to push buttons on machines that didn't exist when I was born? Did God know what JavaScript was back then?

Brainstorming identities

Blue Ocean! Go wide! Get weird! There's something freeing about thinking in multitudes. It's easier to come up with twenty or thirty ideas than it is one. If you haven't already, I recommend reading the story of the many pots: (edited below for length)

A ceramics teacher divided the class into two groups. half would be graded solely on the quantity of work they produced, the other half on quality.

On the final day of class he would weigh the work of the “quantity” group: 50 pounds of pots rated an “A”, 40 a “B”, and so on. Those being graded on “quality”, however, needed to produce only one perfect pot to get an “A”.

Well, come grading time a curious fact emerged: the works of highest quality were all produced by the group being graded for quantity.

While the “quantity” group was busily churning out piles of work-and learning from their mistakes — the “quality” group had sat theorizing about perfection, and in the end had little more to show for their efforts than grandiose theories and a pile of dead clay.

Approach this exercise with the zeal of a six-year-old who wants to be an astronaut one day, with a backup plan of cowboy. Here's an example list I came up from this exercise.

Even if you aren't looking to change your entire career, I find the "identity model" helpful. Everyone has multiple identities across different contexts. You are not your job title. Depending on who you ask, I am a software engineer, father, husband, or slowest guy at the Crossfit gym.

If it helps, you can think of the identities as paths, and then identifying projects among those paths.

Explore your possible selves

Once you have some ideas, start fleshing out what these possible futures look like. If you can, find ways to step back. It's hard to see past the blinders of habit and daily routine when you are immersed in them.

Here are some questions I've been trying out:

What would going down this path get you?
What are some constraints that could stop you?
What are the risks of going down this path? What could it cost you?
What do you know that could help?
Who do you know that could help?
What are some potential projects?
What are some potential experiments?
What questions do you have about this path?

Explore communities

By socializing with people outside your immediate world, you are able to gain knowledge and insight about other worlds you could not find anywhere else. What are some places you where could hang out with people one step away from where you are now, either online or off?

You may find "communities of practice", groups working on something, and "learning to be".

Most opportunities come from personal connections. To get a job in a new field, you'll need new connections.

Design experiments

If you aren't careful, you can get stuck in the "exploratory" phase forever. Well-designed experiments help prevent that. A use experiment:

Is small as it can be, but no smaller. You want something that isn't intimidating to take on. Scale experiments with your commitment level. Commit two hours, if that works commit two days, if that works commit two weeks.
Preferably involves interaction with other people. You'll gain a lot more knowledge from others than from "soul searching."
Should have a discrete end and success criteria. How will you know when to stop, and if it worked. "How it made you feel" is a valid pass / fail metric.

10 Experiment examples

Write and share an article. Does it resonate with other people? Did you enjoy writing it?
Submit articles for guest posts and paid writing opportunities. This method has the bonus effect of additional feedback, exposure, and maybe enough money for a sandwich or two. In this scenario, gatekeepers become useful feedback sources.
Build a landing page, show it off and get feedback from potential customers. Writing it will give you internal feedback, and pitching it will give you external feedback.
Have a service idea? Offer a "free 30-minute consultation" version to others. Alternatively, a paid but heavily discounted option.
Rewrite your resume aimed toward the job you want.
Apply for the job you want book interviews, even if you don't intend to take the job. (job interviews are a resource)
Joining communities counts as experimentation. Try to ask interesting questions, help others, and have a good reply game.
Ask someone who has done what you want to do about it. Have specific questions and things you want to learn so don't waste anyone's time. Use the "Who do you know that could help?" and "What questions do you have about this path?" from above to guide you.
Take on a bite-sized study project. If I was thinking about building a SaaS, I might try just setting up and hosting an instance of Bullet Train. Bonus points if you show it to others and get feedback.
Do some small, actionable learning, like a workshop or short course. Be wary of the wantrepreneur trap of reading & note-taking forever, tricking yourself into believing that's productive. Ideally, some work comes out of it and leads you back to #9.

What you could discover

When doing the experiments, here are some targets to shoot for (yes, another list, my brain is lists):

Do you enjoy it? (if not, the next questions don't matter)
Are you good at it? (or could you potentially / would you enjoy getting good at it?)
Would I be able to make a living doing it? (you can skip this one if you are looking at identities for fun)
Other findings (general fun facts you find as you go that may be useful in your journey)

As you do these experiments, drop identities once you feel you have enough negative signal, and double down on ones where it's positive.

Go forth and explore

Take some time to reflect, but not too much. Action produces information, and again, you want to avoid the trap of pontificating forever and never moving forward. What's something you've always wanted to do? Start thinking of possibilities, and ways to test them.

Treat it as an ongoing project. The list is never "done", you can come back and make changes over time. (As a new dad, I've had to adjust to the "small random bursts of work" mode over "long stretches of deep thought" mode.) The goal is to remove barriers. Get unstuck.

If you still get stuck feel free to hit me up on Twitter @GSto for help

Once you have some good experiments, start testing them. What did you learn? Where will you go? Who might you become?