The truth about side projects

**Update: We’ve officially launched the A Song A Day Indiegogo campaign and are asking for your support in building a product to streamline the song-sending process. Thank you for being awesome!**
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When I first sat down to write this — four month ago — I listened to “Farewell Transmission” by Songs: Ohia — I highly suggest listening to it either while or after reading.

Side projects are a beautiful thing. They’re a learning lesson, a creative outlet, a relationship-building opportunity, and if executed properly with market-fit on their side, they can even be profitable and grow into a fully functioning business.

I believe that everyone who has an idea for a side project should pursue it. Mine has arguably been the best thing to ever happen to my professional — and in many ways, my personal — life. I’ve learned more valuable lessons over the past ten months than I would have solely focusing on my skills as a content marketer. I’ve also met people who’ve quickly become dear friends, and I have definitely grown as a person.

Side projects can help you be better at your day job: mine has helped me better understand the operations of the startup I am working for, empathize with our founder, and has brought us a little bit of business.

Plus, what doesn’t kill you makes you stronger, right? (Trust me, I hate that saying just as much as you, but it has some merit here.)

That said, there’s a lot about side projects that most people don’t talk about — the nitty, gritty, dirt-under-your-fingernails side of side projects. They’re a commitment — your baby, and much like a baby (or puppy, for those who find that reference more relatable), they require a lot of time, energy, and commitment to raise them healthy and happy.

One of my personal heroes, Sofia Quintero said it much better than I can:

“When people and books say, “Do something you love”, they don’t necessarily mean that you are going to enjoy it, what they really mean is that you need to choose work that you still would like to do despite all the suffering required to make it happen. There is a lot of pain involved in the process of creation so you need to be very much in love with the journey.”

Based on my own experience and that of friends, here are 12 truths about side projects that I hope help you prepare as you prepare for this exciting journey!

1. You need to have a goal

My buddy Nathan Bashaw who helped build General Assembly’s Dash and Product Hunt, and just left his job to build his side project, a new kind of electronic book had some great insights around goals:

“Know your goal. Side projects can be great for learning a new skill, working with new people, exploring risky new ideas, and making a name for yourself — but usually not all at once. One of the biggest pitfalls I’ve personally run into doing side projects is not being clear on my goals and expectations. It might feel a little awkward, but it’s totally worth it at the beginning of a project — no matter how small — to sit down and write out what you want to get out of it. When you know your goal, it makes every decision down the road a lot easier.”

2. Everyone’s obsession with failure is annoying

My friend Matt Ström wrote a really great, succinct post on this. Yes, there’s something to be said about the lessons learned from mistakes or failures. There’s certainly nothing wrong with taking a risk and not being a success in the way originally intended. That’s what side projects are for after all!

Take risks, but make them calculated. Have a cushion or a small pool of funds you can tap for your project. I haven’t done this, and regret it strongly.

Quickly think through decisions before making them. and weigh the pros and cons. If things aren’t working the way you want them to, identify the issue at hand and take steps to correct them rather than just bailing. No idea what those steps are? Find a mentor who can help guide you through the process. In other words, try setting yourself up for success.

Like Matt says, “don’t play bad shows.”

3. Doing things that don’t scale is necessary, but can also be a distraction

I couldn’t agree more with Paul Graham’s advice to do things that don’t scale; this allows you to get intimate with inefficiencies and learn where there’s room for growth and scalability. You’ll identify what can be streamlined or delegated, and what responsibilities you as the founder need to hold onto. Most importantly, you’ll learn the true need and interest your users have in your offering.

It also takes a lot of fucking time.

I’ve done a lot of things that don’t scale for A Song A Day, but these things have helped me:

  1. learn how to scale community, and
  2. prioritize features for our future product.

It’s meant sleepless nights and weekends at home, but at the end of the day, it’s worth it for the experience and the lessons learned.

I’m crazy lucky to have friends like Danielle (left) and Maria (right) who spend their Saturdays helping me do things that don’t scale.

4. Even if you’re not technical, you need to be a good product person

This point is owed to Kate Kendall, the founder & CEO of CloudPeeps, friend of mine, A Song A Day’s very first advisor, and my boss at my day job.

The very first thing Kate told me was that I needed to become a better product person if I was going to be a founder. Yes, a web engineer can help you determine how to make the thing work more efficiently and effectively, but it has to be the leader of the company who determines what the thing should do.

You have to share concise and strategic direction. You have to know your product inside and out and how users are using it, for what. More importantly, you have to define a roadmap, roles, and responsibilities around execution.

You also have to be able to make small changes quickly. You have to make quick decisions and be constantly iterating, tweaking, and experimenting. Buzzword alert: you have to be agile. This takes discipline and a clear vision, which can be easier said than done.

5. Everyone has an opinion; analyze it quickly, make an action item, move on

Distractions come and go as often as cabs on Broadway. Everyone is going to offer you a differing opinion from a different perspective. You’ll hear opinions on features, business models, who you should talk to or work with, how you should make money, how quickly you should grow or not grow. It can be overwhelming.

These people have a vested interest in what you’re building and are deserving of your time — to an extent. Listen to them, but recognize these conversations as field research and an opportunity to spread the word about your project. Try not to overthink them or let them distract you. Go with your gut — you’ll be able to discern a good idea from a bad one.

After making your first handful of mistakes, you’ll get better at identifying which meetings are productive, and which are time-wasters. No matter what the outcome, identify the take-away, make an action item or identify the lesson learned from the experience, and move on.

6. It’s ok to say no

As a founder and an employee, you’re busy. It’s ok to say no to meetings, social occasions, and even casual family obligations (with discretion, of course). Sometimes it’s what you have to do in order to ship.

They might not understand right away, but if you articulate how much your project means to you and what you plan to do with it, they’ll get it. And they’ll be there for you when you’ve found more time in your life, just like you’ve been there for them.

7. They take a ton of time

Ask any non-technical person with a side project how much time they spend on it. I can almost guarantee you it’s at least 80% of their nights and weekends.

It’s been a struggle finding time for A Song A Day, and I am definitely not alone. Jonathan Miller, founder of Pancakes & Whiskey (one of my favorite music blogs), said:

“The hardest part of starting Pancakes and Whiskey was finding the time. Working a full time schedule, trying to attend concerts at night and manage the site during the day, there was no down time. After a year of this, I felt completely burned out. The best decision I ever made was finding someone whom I trusted to help me along the way. I would have done this sooner, but I was scared to let go and delegate important decisions. My biggest piece of advice would be to find a team you trust, and don’t be afraid to let them run with their ideas.”

8. It’s ok to live your life for god’s sake

Don’t allow yourself to get burned out. Need a little bit of social interaction? Go have that drink, walk, coffee — whatever it may be — with a friend or family member. Everything will still be there when you get back. You need to live your life, or else you’re going to end up resenting the project that you were once so passionate about. Get out. Do things. Make headspace. Then be productive as shit when you go back to work.

For me, this means going to shows. I went to this Courtney Barnett show during CMJ last year on very little sleep smack in the middle of A Song A Day’s accidental launch. Feeling like I shouldn’t go, I did anyway and had zero regrets. There’s few things as inspirational as Courtney.

9. Being a non-technical founder makes things harder

Knowing who to work with and how to manage the build isn’t intuitive. There’s a learning curve, and it’s steep. The best advice I can give is to talk to people, do your research, learn as much as you can about how things work, and then go with your gut. You’ll know when something feels right, and when it doesn’t. Don’t go for the first shiny thing that comes your way. Get references and feel people out. Treat finding a technical partner like dating. Not New York swipe-left-until-your-thumb-falls-off dating, of course, but like hometown, “looking for the one” dating.

10. Decision making fatigue is a thing, and it’s hard

If this is your first side project and you’re considering turning it into a business, know that you’re about to make a ton of decisions. You’ll eventually come to a point where answering the simplest questions becomes overwhelming because you’ve made so many decisions in a short period of time. Just today, one of my closest friends called me to invite me to go camping and see live music and I almost bit her head off because I couldn’t fathom the idea of making another decision. That’s just silly.

As the old saying goes: “How do you eat an elephant? One bite at a time.” Break things down, tackle one small thing at a time.

I should say that the first time I heard this adage was from the late, great Josh Greenberg — Grooveshark co-founder, tech genius, happy person, and overall nice guy — while speaking at an event I helped organize many, many moons ago. RIP.

11. Side projects cost money

Of course this depends on what your side project is and what skills you contribute to it, but your project will likely cost you some money.

Mine has cost me legal fees for getting set up as a business, contracts, NDAs, legal research around copyright, terms of agreement, etc. I also have some minor overhead costs with Mailchimp and database management, Kickstarter costs, etc.

Make a budget for yourself early on and start putting money away now to cover your ass when a surprise hits you later. :)

12. Side projects are ninja tools — use them

This truth was contributed by Tom Critchlow, founder of Fiercely Curious. In 2011, he launched a single page website called Fuck Yeah Spotify that stitched two APIs together to display the top tweeted Spotify URLs that day. He says, mostly it didn’t work, it looked ugly, and got less than 20,000 views the year and a half it was live.

After tweeting it to Spotify, he was invited to present the project at a Spotify meetup and later learned that it caused an internal debate at Spotify whether they should hire or sue Tom. He said that meeting influential people at Spotify opened some interesting doors for him and was a great networking experience.

When interviewing with Google in 2012, he found that a disproportionate amount of time during the 7-round interview process was spent talking about this little side project Fuck Yeah Spotify. He said:

“At the time this surprised me. Why would Google care about it? Turns out — the secret life advice you won’t hear is that shipping something is a differentiator. Most people have never had to register their own domain name or figure out how to make a logo despite not being a designer, let alone build something from the ground up. Turns out the ability to think for yourself and to get things done is important and Google ended up hiring me.”

The takeaway here is not that you should do a side project to get a job (though it’s not a bad tactic!), but rather to open doors, to do interesting things and to differentiate yourself from those who’ve never built anything. Build something; even if it doesn’t work — just put it out in the world and good things will happen.

Bonus truth: Coffee, Red Bull, and vitamin B are your friends

I know it’s not healthy per se, but these things will be your life-savers, especially in the early days. Embrace them, stock up on them. Another alternative is running and healthy substitutes. I know whenever I’m feeling low-energy, a run does miracles!

And sometimes beer — you know…for creativity.

About that Kickstarter campaign

When I first sat down to write this post a century ago, I had no other intention than to help people who want to pursue a side project. I’ve had so many “holy shit, this is a lot of work” moments that I couldn’t not share my findings. But with so many months passed, I do have an update about A Song A Day. We’re going to be launching a Kickstarter in mid-September.

**Update: The campaign is now launched. w00t w00t.**

If funded, the campaign will help build a product to streamline the song-sending process. Each person will still be hand-matched to a curator(s) at least for now, and each song will always be hand-picked. The goal of the product is to cut back on time spent and mistakes made hand-scheduling 200+ email campaigns each week and to give us the ability to add new features.

The idea is that we’ll become more scaleable and grow and be able to pitch our service to potential sponsors and… *gasp* …maybe even make money off of it. I’ll be sharing a link to it here when it’s up. In the meantime, feel free to sign up for our service and listen to some new, groovy tunes.

A few of our stars and film crew.

Have a truth to add?

I’d love to hear your story!

Thank you, friends, curators, and supporters!

I’d like to extend a huge thank you to everyone who contributed a truth or a point to this post, and an especially huge thank you to Matt Ström for reviewing, editing, and sharing feedback! And the biggest thank you to all of our A Song A Day curators, friends, family, supporters, helpers, roommates, videographers, volunteers — you’re all amazing and I have no idea what I’d do without any of you. I definitely would have lost my shit a long time ago.