Should I start a side project?

Don't wait on ideas that will be fun and lead to growth

5-min read


A few weeks ago I had the opportunity to join a virtual panel to talk about side projects. It was a fantastic conversation where I shared my reasoning for starting this newsletter and, more broadly, how I think about using my free time productively. I’m glad to finally take some time today to share my thought process and framework with you all.

There’s a logical journey we all should follow when deciding whether we should start a side project. Typically, side projects are born out of hobbies or skill gaps. Gridology, for example, was born out of a hobby: I love to write and wanted to create a focus and theme to empower me to write weekly—something I hadn’t done since college. Other side projects were started out of desire to try something new. For example, I learned how to code in Python so that I could complete a high-impact project at LinkedIn.

At their core, side projects must be additive to your life. The best ones should be fun and challenging. They should be enjoyable and cause personal or professional growth. Side projects must age like wine: they get better, more impactful, and more fulfilling over time. There are thousands of ways we all could spend our free time. The trick is to identify the projects that generate the best ROI. Here’s how I sort through lots of ideas so that I’m certain I’m spending time on only the best ones.

On the x-axis, we have the question: How much will you learn? Growth is an essential part of taking on a side project. Improving can mean getting stronger physically or adding a new skill to your personal or professional toolkit. The best side projects lead to an intended and marked change within you. All growth isn’t created equal. Be sure that the side projects you pursue lead to growth that you care about. For example, I don’t care about my singing ability. While taking voice lessons may lead to a better vocal output, it’s a wasted effort. At the end of the day, my singing ability is just not important to me. I’d rather learn other things.

On the y-axis, we have the question: How much fun is it? Side projects shouldn’t feel like work. By definition, a side project is something done on the side. There are no deadlines, requirements, or grades. You set the rules. Having fun as you complete your side project is a critical to set yourself up for success. It’s easy to do something for a day or a week, but enthusiasm, motivation, and effort will wane if you aren’t having fun. Don’t ignore your energy—let it guide you to new and exciting side projects.

Understanding the Grid

When using this grid, a guiding principle should be to not lose sight of the definition of a side project. Here’s how I define it:

A fun initiative to pursue in your free time that leads to personal or professional growth.

If the project isn’t fun, it’s a chore and not a side project. If the project doesn’t lead to growth, it’s a hobby and not a side project. If the project doesn’t lead to either, it’s either something you’re doing to unwind or a waste of time… and not a side project.

Start Now

The side project you’re considering will lead to growth and be fun. The top right quadrant is where every side project you pursue should land. These types of projects propel you forward in your personal or professional objectives. However, just because a side project falls in the top right quadrant, it doesn’t mean that side project will stay there forever. As each project progresses, you must constantly reassess much you are learning and how much fun you are having. These levels can (and will) change over time. This is expected. When the work becomes more frustrating than fun, take a pause. When the growth curve slows, take a pause. Last year, for example, my fiancé and I had created a joint Instagram account that shared fun hypothetical situations with our audience. In the beginning, we both were having a lot of fun coming up with the account’s aesthetic, brainstorming interesting hypotheticals, and building our community through growth hacking and ads. Over time though, we grew disinterested—and that’s okay! The project was fun for a while… the energy and learning just had a relatively short shelf life.


The side project you’re considering will lead to growth, but may be cumbersome and unenjoyable. This is where skill based projects usually land. Do you want to learn a new coding language? Do you want to learn design or how to draw? Do you want to learn how to be a better writer? Projects in this category tend to be personal or professional moonshots that constantly feel too hard to get started. The projects usually are written on some type of a bucket list, yet you’re never quite sure how much fun you’ll have doing it. More research is typically required to see if the project is something that you could find interesting. When I was deciding whether or not I wanted to learn how to code in Python, I took part of a very short class from Google as a minimum viable test. Python was out of my wheelhouse. I thought about the experiment like a startup would its new product: What’s the lowest energy thing I could do to see if I’m enthused to learn what I think I want to learn? Once I discovered that learning Python was, in fact, actually a fun undertaking, the project moved to the Start Now quadrant.

Tinker & Produce

The side project you’re considering will be fun, but you can’t yet determine how it would lead to growth. Projects in this quadrant usually start out first as hobbies. Do you love to run? Do you have like playing the guitar? Do you love watching comedy? Your natural enthusiasm for a topic has grown naturally overtime. Typically not much thought in improvement has ever entered your mind. To you, performing the activity is just plain fun. How good you are at it or the potential of making money from it has rarely (or never) crossed your mind. To identify intrinsically motivating side projects, start with what you already love, and start small. For me, I finished Jack Butcher’s Visualizing Value online course. I’ve always had fun designing logos, creating PowerPoint slides, and taking photos. However, I’ve never spent any time refining my craft or doing any legitimate learning to improve. This course marked the first time I’ve ever paid money or carved out specific time to improve my design skills. I’m tinkering here. Did I like learning more about something I had previously just enjoyed ad hoc? I did! So I’m now committed to improving this newsletter’s branding, transitioning from startup Gridology 1.0 to more focused Gridology 2.0.

Introspection Required

The side project you’re considering will not lead to growth or be fun. These are projects that typically get on your radar due to external factors. In order to transform these project ideas into real side projects, more introspection is required. Are you really interested in this idea? Do you want to pursue it for the right reasons (fun or growth)? If the project is a way to make a quick buck, then it’s probably not worth spending time on it. This category will come to life with a personal example. Several of my friends have taken up improv. Without introspection, I may be quick to join them. However, on closer reflection, I realize that public speaking while not knowing what I’m going to say is actually a frightening idea for me. That said, I recognize I could probably benefit and grow from the experience. Rather than immediately hopping on the improv bandwagon, I should commit to more vetting. I could run a minimum viable test: Instead of immediately joining an improv group, perhaps I watch a few videos online or go to more improv shows. Try on the idea without completely purchasing it.

Grid Shortcomings

There are two shortcomings with this grid:

  1. The grid doesn’t take into account how fame and monetary success play a natural role in project prioritization. While professional success is certainly an important component of life, let me offer you a different frame. Would you rather be successful at something where you constantly have fun and grow or would you rather be successful at something that offers no growth and no fun? All things being equal, I’d hope you’d choose the former. The idea here is that the amount of energy you have from having fun and improving will create a more sustainable project momentum for the long haul.

  2. The grid ignores current skill level. Yes, and by design. Side projects can be for those looking to learn something completely new or for those looking to refine their craft. Your current ability should have no bearing on your decision.

So, do you have an idea that’s been festering in your mind? Do you think it will be fun? Will you learn something? If so, what are you waiting for? Start small, and get going. And, of course, if I can help in any way just give me a shout. You know where to find me.

Life’s only as confusing as you let it be,

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