I've always believed in the value of side projects. Not because I'm a subscriber to hustle culture - I'm not. But because I believe in carving out time and energy to nurture my creative side. For me the appeal of being in tech has always been the ability to build something meaningful, but that's not always present in the day to day, especially in leadership. Last February I spent more time on review season than anything else. Necessary, but hardly fulfilling.

I read this book a while ago, called Marry Him (problematic title, might be a problematic read honestly although it was good for me at the time, but I did love the author's other book Maybe You Should Talk to Someone). One of the core points: don't expect to get everything from your partner. Healthy relationships need balance - friends, interests, separate identities. A good lesson for careers too, where even if you like your day job, you're still going to have bad days and - unless you're a founder with a high level of control and a strong team - it's unlikely to fulfill 100% of what you want.

Which is why I think a side project can be healthy for a bit of balance and a way to recharge. Here are five things that I think you can get from a good side project.

Remember how to ship. When did you personally last ship something? How many other people were involved in that, how much discussion and negotiation? How close did you feel to it, how much ownership?

This is the thing I love most about side projects, the feel that I get to ship something. Even if it's just a blog post, or a newsletter. It's my decision. I press go.

Try new things. At the day job, we're normally prescribed the set of tools and languages and they are probably fine. Consistency is necessary for an organisation, and there are of course real concerns around security etc that constrain the decision set.

But when it's just you and maybe a friend, what do you want to use? Maybe you have a secret desire to code in Haskell that is never coming to a corporate environment. Or maybe you just want to try Notion instead of Jira.

Shift your mindset. In your day job you have your role, and that can be great when it works to your strengths, but it can also limit you. Maybe you're an engineer who thinks they have product judgement but doesn't get much opportunity to try it. Maybe you're a product person who wants to code. Maybe you're in management and your primary output is a team, and you miss being an executor of things. Maybe you spend a lot of your efforts critiquing and want to remember what it's like to create.

You can be someone different in your side project, if you want to.

Collaborate. If I look back, all my best side projects have been with someone else. There's a reason for that - the right collaborator on a side project can be a chance to learn, gain a new perspective, or just deepen your relationship with someone you care about. The need to talk regularly and having something concrete to talk about - well there's nothing like it for deepening a bond. It can also help give you more of a sense of accountability, knowing another person is involved.

Of course the right collaboration partner is critical to it being a better time than going it alone. Choose wisely!

Decide rather than negotiate. Something I think about a lot is that whilst you might need to go to meetings to get your job done, no-one's job is to go to meetings.

It sure can feel like it though. Whether it's a full day of meetings, another negotiation about something you thought was decided on already, or a ping for a "quick zoom" you know is not going to be quick, it can be very refreshing to be able to just... make the decision you believe is right (or right for right now), and get on with things.

It's understandable that decisions get harder to make in larger organisations. But it sure is nice not to have to deal with that overhead from time to time.

So there it is, my list of five reasons why side projects can be regenerative to you. Have any more? Share them with a link to this post or hit reply to drop me an email.

It's February - the cold may be getting to those of us in the northern hemisphere and that new year energy might be running low. All the more reason to seek out some kind of joy and creativity; something just for you.

Wishing you a creative February.

-C

What I've been reading

Mastering Leadership (book) - I read this after my coach did a Leadership Circle Profile for me (basically a 360). It's not the easiest read, a bit grandiose and waffly in parts, but some core things that stuck out to me:

• The Inner game runs the outer game - basically what's in your head plays out in how you show up in the world.
• In it to win vs trying not to fail. In it to win is creative leadership. Trying not to fail is reactive. Creative leadership is a positive multiplier - reactive leadership is not.

Appreciated this article on some well intentioned management practices that can turn out not to work.

Enjoyed this on how to have a career in tech in 2026 - the answer is harder than it used to be. I still believe though! We just have to be more creative (like Toronto raccoons...)

This post on AI gains being contextual - data driven validation of my impression. I'd had minimal impact using AI in my day job, but when I switched to a different context it was a game changer. If you're in an organisation where AI is not yet impactful, but you want (need) to keep up, you need to find some problems interesting to you where it can be useful. Also appreciated this post - also from Maestro - on how AI might help us measure the impact of changes

The title is clickbaitey and I think some of the predictions are overblown. But I love the examples and the more creative mindset - why ship another document that people don't read when you can create an interactive tool?

Similarly clickbaitey but one of the more clearly articulated descriptions of how programming is changing and the value of systems thinking - I have to say, I am grateful to Claude for offsetting some of my deficits.

From mid-2025 but really appreciated this article on coding LLMs. Key quote

"Nobody cares if the logic board traces are pleasingly routed. If anything we build endures, it won’t be because the codebase was beautiful."

I think we have to start talking about identity threat for developers and helping them navigate a different world.

Just for fun: Can't imagine anyone following me and wanting to watch the Melania movie, but this review is worth the read - almost certainly more entertaining.

What I've been doing

• So excited to share that Jean and I have opened registration for our second course - the EM Survival Guide. Being an Engineering Manager in a post-ZIRP era has changed, and we want to help people navigate that. Early bird pricing through the end of February.
• You can now try my unhinged vibe coded quiz - what raccoon are you? I had so much fun putting this together and I love the art. Please share your raccoon on socials and tag me!
• After selling out our January cohort we've opened the next cohort (Apri) for DRI your career early.
• I joined Amy Yee on her podcast “Wired for Change” to talk about developers and leadership, and how that evolves - and doesn't - in the current AI / post-ZIRP era.
• I left DuckDuckGo and so now I can share what I really think about performance reviews - hugs to all my former coworkers who are facing down the February review season.
• I also wrote up some thoughts on scaling teams.
• I'm continuing to work with Twill, now as a fractional CTO. BRB figuring out what that means - more to come!