Mornings, Nights, and Weekends.

Finding the time to work on your side projects, from someone who’s been trying to figure it out for three years.

This picture apparently says a lot about me.

I used to envy my friends in engineering school who always seemed to be working on exciting side projects. They’d be motivated to stay up late in the machine shop cutting aluminum for some device they’d been planning all semester. I finished all my assignments just fine and got good grades but I never felt the need to get into this side hustle. Why do more?

Side hustle: the thing you stress about when you aren’t stressing about your 9–5

That changed when I started working on my first startup. Work wasn’t 9–5 anymore. It wasn’t due dates or deadlines. It was always on.

When that startup failed, I had a lot of free time but still had the mentality that free time was wasted time. So, I decided to learn Objective C (the iPhone programming language) and make HappyFeed. Since then I’ve had many jobs, but HappyFeed has always been my side hustle.

Even with hundreds of active users, it’s not always easy to put in the extra time on an unpaid project. When you are freelancing on three different projects (like this week) it’s even harder to find the time and focus. I thought it’d be worth posting about how and when I find the time to get work done.

Things that work.

1. Become a morning person

In college, working late nights was a badge of honor. You were more likely to see the sunrise from staying up all night than from waking up early. I’m still somewhat of a night owl, but my morning-person days tend to be my most productive (and lead to better sleep).

  • You have a fresh brain. You haven’t opened any emails yet, you don’t have a list of tasks for the day.
  • No distractions. Your Slack channels are all still sleeping.
  • You can relax in the evening. Now you won’t feel bad watching two or three episodes of The OA after work.
  • It just feels better. Seriously, try it for a week. Even one day a week.

2. Plan during your downtime

Planning is crucial for the Side Hustler, but work time is precious. To get the most out of it, use downtime to plan. Waiting for your sandwich to be made? Your date is running late for drinks? Bust out your planning-app-of-choice and write down some tasks for tomorrow morning. Just don’t split a bottle of Cabernet Sauvignon and expect to wake up at 6am.

3. Create mini-tasks

It’s been taking me too long to build out the web version of HappyFeed because “Build Website in Programming Language You Don’t Know” is a massive task. So, how I am breaking this down?

For this particular task, I could break it into smaller tasks like “Allow users to login on the website.” This could be broken down even more into steps like, “Sync API to website” and “Create login page.” The smaller the better.

4. Set artificial deadlines

When you are working for yourself on something no one is paying for, you don’t have real deadlines. Creating fake deadlines can help with overall planning and maintaining momentum. Usually I’ll set my deadlines on Sunday because Friday-Sunday have the most wiggle room for squeezing in extra work if needed.

5. Do the easiest tasks when you are least motivated

There are always some tasks that you will dread doing. Don’t feel like entering numbers into a spreadsheet? Just wait until you are experiencing the “Sunday Scaries” and crank it out with some old episodes of The Office playing in the background. Save the tough stuff for a motivated morning.

6. Say No

Entire books are written about the art of saying no, so I won’t spend too much time on this point. I tend to think of it like this:

So many successful people claim to have ruined relationships and alienated loved ones along the way. I’m doing a much better job than them if I’m just missing one Friday night out at the bar.

7. Enjoy the hustle

For me this means buying a six-pack of a locally brewed IPA, ordering in some Domino’s (don’t judge), throwing on some music, and having a Friday night hack night.

The next day I can wake up at 7am, drive up to the hills, and get in a 6-mile hike to clear my head. Maybe I’ll chase it down with some avocado toast before getting back to work around noon. I do live in California after all.

8. Let the good times roll

Just like this cat. (Source:

Every now and then, this magical thing happens — you actually get in the zone. You’re typing faster, you are free of distractions, and you are getting shit done.

…But then you realize it’s time for sleep or some other project.

If at all possible, do not switch over to that other thing. Focused work is a beautiful thing and you should prolong it as much as possible.

Things that don’t work.

1. Over-planning

Yup. I made an entry for “eat” this week.

I manage my time by putting blocks of work on my calendar. This becomes a mess when I over-plan. A task like, “look over crash reports,” might get missed on a Monday and get pushed further into the week. Often times, several tasks get pushed on a busy calendar and the stress starts to snowball.

2. Trusting your nights

It’s easy to say, “of course I’ll have time to look at those crash reports on Tuesday after an 11-hour day of freelance work.” It’s just as easy to watch an episode of something on Netflix and fall asleep early.

3. Television

Netflix shows are literally designed so that you will binge-watch. I’d be embarrassed to admit the number of times “one episode with dinner” turned into a whole night of watching Netflix. (I’ll get to those crash reports eventually.)

4. Mix it up too much

I love thinking of new ideas. There’s nothing more exciting than planning out a new app, buying a domain, and chatting about the potential with your tech friends. Unfortunately, this can kill your focus. Those crash reports will still be there after I wireframe out a little, right?

5. Dating

I hate to have to add this, but if I’m being 100% real with you, it’s a big one. Dating requires a lot of time for planning, can be very expensive, and potentially generates a lot of stress. If you’ve already been rejected by an accelerator this week, do you want to feel the cold shoulder of a ghosted second date? (Maybe she’ll want to split a bottle of Pinot and look over those crash reports with me?)

Pure romance

Final Thoughts

There’s no silver bullet to being productive and spending your leisure time working. Just make sure you care about the things you are working on and you’ll generally be able to find a way. Side projects can turn into a way of life so I would also suggest choosing habits that will keep you healthy in the long run both in terms of physical health and your relationships with others.

Each week in Building Happiness I’ll be covering a new topic about what it’s like bootstrapping a consumer internet company, HappyFeed.

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