The 4 Secrets to Successful Side Projects

In 1995, Craig Newmark started a mailing list alongside his full-time job. He wasn’t intending on building the world’s largest classified advertisements website. The list was simply a convenient way to alert friends of social events for software developers living in or around the Bay area.

That small side project turned into Craigslist – a site that today boasts billions of pageviews each month and is a leader both in classifieds and job boards.  But it took Craig four years to quit his full-time job and devote all of his time to his company.

Craig’s story isn’t entirely unusual. Much of the software we use on a daily basis was built on the side:

Side projects are a great way to test the waters with a new idea while also maintaining some peace of mind by not abandoning your full-time gig. They’re also a perfect way to hone new skills and offer a creative outlet where you can more risks without fearing dire consequences.

side projects

For all of the benefits side projects offer though, it’s not easy to keep them moving forward. Additional projects draw down your precious reserves of time and energy that are too often tapped out by your normal 9-to–5.  It’s hard to come home from work every day only to continue working. Like any other project, side projects offer a series of highs and lows. You’re bound to be motivated some days and not others.

So how do you maintain momentum on a side project when your full-time gig is draining your time and energy?

Luckily there are a few things you can do to make it easier to stay on track. Whether you already have a side project up and running or are thinking of starting one, here are some 4 invaluable lessons from successful side projects to help you keep moving forward.

  1. Put importance on the skill, not the finished product.

Before Dilbert was a household name, cartoonist Scott Adams held a number of jobs to pay the bills. In fact, while he was still employed at Pacific Bell, Adams would wake up at 4am to draw cartoons so he could put in a full day at the company. In his book How to Fail at Almost Everything and Still Win Big, Adams outlines a key strategy that helped to keep him motivated – he set systems rather than goals.

Side project system
Image credit: Business Insider

A goal is a specific objective that you either achieve or don’t sometime in the future. A system is something you do on a regular basis that increases your odds of happiness in the long run. So if you do something every day, it’s a system. If you’re waiting to achieve it someday in the future, it’s a goal.

For example, Adams could have set a goal of becoming a famous cartoonist. However, what would happen if he woke up at 4am for two years straight only to fail as a cartoonist? Deflating to say the least.

Dilbert side project
Image credit: dilbert.com

Instead, Adams created a system:

The idea was to create something that had value and…I wanted the product to be something that was easy to reproduce in unlimited quantities.

Within this framework, every morning, every cartoon – and his many other creative “failures” – was a learning experience.

More often than not, side projects will lead to little fanfare. The Gmails and Dilberts of the world are few and far between. If you expect every side project to end with a seven figure payout, you’re setting yourself up for failure. On the flip side, if you view every side project as a learning experience, you’ll feel less pressure and enjoy the process.

John Saddington, the Indie Developer responsible for Desk.pm and Teeny.tokyo, echoes these sentiments:

…building side projects is more of a mentality and lifestyle than anything else…When you start with a different motivation, such as building a company, then you’re enterprising, you’re being an entrepreneur, you’re creating a startup, not a side project. This is a fundamental difference that changes everything.

  1. Talk about it with anyone who will listen.

Jennifer Dewalt made a bold commitment when she decided to learn to code. Publicly on her blog, Dewalt promised to launch a new site every day for 180 days. Each site would be accompanied by a blog post, and the code would be live on her GitHub account for anyone to see.

Jennifer Dewalt side projects

Dewalt could have made a promise to herself secretly, offline, away from public scrutiny, but she took a risk and shared her side project with the world. Not only did this hold her accountable to putting in the work every day, she also had tons of supporters cheering her on!

Similar stories are everywhere:

In each of these cases, creators are building connections with their audience. They’re sharing the frustrations and celebrations that everyone can relate to. Readers learn from their mistakes, connect with their story, and support their mission. That’s pretty awesome motivation when you’re tempted to turn on Netflix at the end of your workday.

  1. Block it off on your schedule, and hold that time sacred.

Cal Newport might just be the most productive man on the planet. As Eric Barker explains in his article in The Week, Cal juggles a seemingly unlimited number of commitments including:

  • Working as a full-time professor at Georgetown University
  • Peer-reviewing academic journals
  • Writing books (four so far with another on the way)
  • Maintaining a highly active blog

Let’s also not forget that Cal is a husband and father. One of his keys to productivity is especially relevant  for wrangling side projects:

Assigning work to times reduces the urge to procrastinate. You are no longer deciding whether or not to work during a given period; the decision is already made.

Side projects can take up a tremendous amount of time. Assuming you’ll just somehow find the time is wishful thinking. You need to be proactive and set aside time beforehand to continue making progress.

Time block side projects

I first started freelance writing while also working full-time as a personal trainer. Even though I was working from 11AM until 8PM five days a week, I thought I would have the energy to take on 1–2 assignments a week. I haphazardly set due dates assuming I could always work on the weekends if I fell behind.

After only a few weeks, it was clear that this haphazard, I’ll-find-the-time-somehow approach wasn’t going to be sustainable. First, I never had energy when I got home at night to write. Second, working on the weekends left me feeling like I never had any time off.

By necessity, I built a system that I still use in some fashion today. Every working day is divided into a series of chunks. I assign projects and tasks to each chunk of time at the beginning of the week. Then all I have to do is execute my plan. I no longer have to think about what I’m going to do during a specific hour. This way, I make sure to fit in time for two main passion projects (writing and coding).

Accounting for each of my working hours also helps me stay realistic on what I can accomplish in any given day and keeps me from taking on more than my schedule can handle.

The main takeaway? Assigning a specific time slot to devote to your side project every day before you actually get there will help you protect that time from getting overrun by your other work.

  1. Set check-in points and know when it’s ok to quit.

Side projects should be fun. After all, you’re trading your time and energy for something that’s likely not going to lead to a huge payout. Working on a project that no longer interests you or that’s not moving forward is not fun at all, but the other option (abandoning ship) can feel a lot like failure, particularly after you’ve publicly told everyone about it.

The easiest way to avoid feeling like a failure while still giving yourself a way out is to set checkpoints at regular intervals. As a recent example, I committed to posting a JavaScript code challenge every Monday for 10 weeks (Admission: I missed last week because I was on vacation). The number 10 was rather arbitrary. I felt like it was easy enough to hit that I was sure I could succeed but short enough that I wouldn’t suffer long if I hated it. After 10 weeks, I’ll reevaluate and ask some tough questions that are applicable to any side project:

  • Is this still providing enough value for the effort and time I’m putting in?
  • If no one else read/noticed/used this, am I learning enough from building this project that it would still be worth it?
  • Do I eagerly look forward to working on this project or is it becoming a chore?

If, after 10 weeks, I decide that posting JavaScript code challenges is no longer worth it, I can stop without feeling guilty. Check-in points provide a way to make sure the time and energy you devote to your side project is still worth it.

  • If you want to start a newsletter, promise to send out at least five emails. If you’re dreading doing a sixth, stop. Everyone will understand.
  • If you’re learning to build a website, commit to at least building the homepage. If you’re not having fun, don’t worry about adding an About or Contact page. Cut your losses and find something else!

Success stories always praise grit and determination, pushing through when you’re tired, busy, and overworked. It’s just as important to be able to take a step back, take a candid look at your project, and understand when to call it quits and start one that will be more rewarding.

The 4 secrets to successful side projects:

  • Make sure you’re building skills that easily translate to other areas regardless of how the project turns out.
  • Talk about it often and share your story with others.
  • Block off specific time on your calendar to work on your side project at the beginning of the week.
  • Have fun! Set regular checkins with yourself and don’t be afraid to call it quits if you decide it’s no longer worth the extra time and energy.

What side projects are you currently working on? How do you maintain the energy and motivation to keep showing up every day? Don’t keep your productive secrets to yourself! Share them with us in the comments below.

About the author: Jeremey DuVall is a Happiness Engineer at Automattic and freelance writer on creativity, productivity, and self-development. Offline, he’s an aspiring outdoor adventurer, runner, and a carrot cake connoisseur.

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