How I Run a Side Project Without Burning Out

The 4 rules I use to keep a side project fun for 18+ months. Includes the one rule that prevents the project from becoming a second job.

The side project graveyardMost side projects die in month 3. The pattern is well-documented: high energy at the start, declining energy through the middle, abandonment at some point in months 2-4. The reason is usually not the project. The reason is that the project stopped being fun and started being work, and the moment a side project becomes work, the side project loses to the day job, the family, the rest of life, and the long list of things that have actual stakes.I have killed more side projects than I have shipped. The killed ones are not because the projects were bad. Most of them were good ideas. The killed ones are because the project turned into something I had to do instead of something I wanted to do, and once the project is in the "have to" category, the project is in the same category as exercise and eating vegetables. I do those things, but I do not love them, and the side project never had the same health benefits as vegetables, so the side project loses.After about 4 years of this pattern, I figured out 4 rules that have kept the current set of side projects alive for 18+ months. The rules are not original. The rules are obvious in retrospect. The rules work because they prevent the specific failure mode that kills most side projects, which is the project turning into a second job.Rule 1: the project is for fun, with optional moneyThe first rule is the most important, and the one most side project advice skips. The project is for fun, with optional money. Not "for money, with optional fun." The fun is the point. The money is a possible side effect.This rule is hard to internalize because most side project content is about making money from the project. The framing is "I have an idea, I will build it, I will sell it, I will replace my day job, I will be free." That framing works for the 0.1% of side projects that become companies. It does not work for the 99.9% of side projects that do not. The 99.9% need a different framing, because the "make money" framing is a treadmill that does not pay off, and the treadmill is what kills the project.The "fun, with optional money" framing is the one that has kept my current side projects alive. The blog writing factory is fun. The static site is fun. The self-hosted email is fun. The fact that the blog writing factory makes $14 x N dollars a month is a small bonus. If it stopped making money tomorrow, I would still work on it, because the work is fun. The fun is the point. The money is a possible side effect.Rule 2: the project gets at most 5 hours a weekThe second rule is the cap. The project gets at most 5 hours a week of my time. The cap is hard. The cap is non-negotiable. The cap is the part that prevents the project from becoming a second job.Most side project advice talks about "timeboxing" and "weekly reviews" and "setting boundaries." That advice is good for projects you are obligated to do (e.g. a day job, a class, a family commitment). It does not work for side projects, because side projects do not have the same obligation, and the obligation is what makes the timeboxing work. Without the obligation, the timeboxing is just a number on a piece of paper.The cap works because the cap is a budget, not a goal. The cap says "I will spend at most 5 hours a week, and any hour I do not spend is a win, not a loss." That is a different framing than "I will spend 5 hours a week, and any hour I do not spend is a failure." The cap is the framing that converts the time spent from a chore into a budget. The budget is the part that has a finish line. The chore does not.The cap also forces prioritization. When you have 5 hours a week, you do not work on things that do not matter. You work on the things that move the project forward. The cap is the part that makes the project ship, because shipping is what moves the project forward, and shipping is the part of the project I want to spend the budget on.Rule 3: ship the smallest possible thing every weekThe third rule is the cadence. Every week, ship the smallest possible thing. The smallest possible thing is a post, a commit, a deploy, a fix, a release note, an email to a user, anything that is "the project produced an output this week."The cadence matters more than the size. A weekly ship is a habit. A habit compounds. A project that ships something every week for 52 weeks has shipped 52 things, and the 52 things are a body of work, and the body of work is the project. A project that ships nothing for 6 months and then ships a big thing at month 7 has shipped one thing, and the one thing is not a project, it is a one-off, and the one-off is what the project becomes when the project stops being a project.The cadence is also the part that keeps the project fun. The fun is in the shipping. The fun is not in the planning, the designing, the architecting, the "I am going to build the perfect system." The fun is in the "I made this thing and now the thing exists and now I get to use it." The cadence forces the fun to happen every week, and the fun is the rule that keeps the project alive.Rule 4: take 2 weeks off, twice a yearThe fourth rule is the recovery. Take 2 weeks off, twice a year. No project work. Not "less project work." Zero project work. The two weeks are the part that prevents the project from becoming a chore.The 2 weeks off is the rule I have been most resistant to, and the rule that has the highest payoff. The first time I took 2 weeks off, I came back to the project and noticed that the things I had been working on for the last 3 months were less important than I had thought. I dropped about 30% of the in-progress work and shipped the remaining 70% in the next 2 months. The 30% I dropped was the work I was doing because I had momentum, not because the work mattered. The 2 weeks off surfaced the difference.The 2 weeks off also has a side effect. The 2 weeks off is the part that makes the project a side project, not a job. A job does not give you 2 weeks off twice a year to do nothing related to work. A side project does. The 2 weeks is the perk. The 2 weeks is the part that makes the project feel different from a job. If the project stops feeling different from a job, the project has stopped being a side project. The 2 weeks off is the rule that keeps the project feeling different.What the rules do not doThey do not guarantee the project will make money. Most side projects do not make money. Mine make a small amount, which I am grateful for, but the small amount is not the point. The point is the project. The point is the work. The point is the shipping. The money is a possible side effect, not the goal.They do not prevent the project from occasionally feeling like work. Some weeks the project is not fun. Some weeks I do not want to work on it. Some weeks I skip the 5-hour cap because the project is in a state I do not want to leave. The rules do not prevent that. The rules are not a guarantee of permanent fun. The rules are the discipline that lets me come back to fun after the un-fun weeks.They do not scale. The 5-hour cap is for one person. The 2 weeks off is for one person. The cadence is for one person. If the project grows to a point where I need to hire someone, the rules stop working in the same way, and the project has to become a company. That is a different project, with different rules. The side project is the side project. The company is the company. The 5-hour cap does not survive the transition to a company.What I would tell past-meIf I could go back and tell past-me one thing, it would be: the side project is for fun. If the side project is not fun, the side project is wrong. The fun is not a luxury; the fun is the engine. The fun is the part that makes the project survive the un-fun weeks. The fun is the part that makes the 5-hour cap feel like a budget and not a chore. The fun is the part that makes the 2 weeks off feel like a perk and not a punishment.I would also tell past-me: do not start a side project for the money. The money is a possible side effect. The money is not the point. The point is the work. The point is the shipping. The point is the thing you get to use on Tuesday because you made it on Sunday. The money is what the market says about the thing. The market is not always right, and the market does not get a vote on whether the project is worth doing.Who this is forAnyone who has ever started a side project, gotten 3 months in, and abandoned it. Anyone who is starting a new side project and wants to set it up to survive. Anyone who is in a side project and is feeling the burn. The rules are not original. The rules are the distillation of 4 years of side projects, of which about 75% died and 25% lived. The 25% that lived followed these rules. The 75% that died did not.The honest partI am not always good at following the rules. I have skipped the 5-hour cap more times than I can count. I have gone 4 months without a 2-week break. I have shipped something every week, but some weeks the "thing" was small enough that I am not sure it counts. The rules are aspirational, not perfect. The rules are the part of the project I am trying to do better, not the part I have mastered.The reason the rules are worth writing about is not that I am good at them. The reason is that the side projects I have, the ones that are still alive 18 months in, are the ones where I have been at least partially good at the rules. The projects I killed, the ones in the graveyard, are the ones where I was not following the rules. The correlation is not perfect, but it is strong, and strong enough to make the rules worth sharing.Want a prompt pack to start your own side project?The Blog Writing Factory includes a "project plan" prompt that walks you through the 7-section plan in 30 minutes. The plan is the cheap part. The plan is the lever. The plan is what makes the side project survive the un-fun weeks.Buy on Gumroad. $14

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