Lessons From Running a Passion Project

I’ve been running my side project for over three years and haven’t made a dime from it. Rather, I’ve invested time, energy, and career equity into it. When it did bring in some money, I put it right back into the project.

Why?

For one, return doesn’t have to equate to financial gain. I could list enough personal and emotional reasons to warrant a book. The three big ones for me have been: passion, community, and a desire to give back to the arts.

The project is A Song A Day, which is a collective of curators who send handpicked songs to inboxes around the globe daily. We focus largely on emerging and lesser-known artists.

It’s been a journey getting to that one-liner. The project launched as an impulse without a plan. I was living in Brooklyn and working full-time as a marketing manager for a tech startup. On a run one evening, I had an idea based on an annoyance and acted on it. I made a website and bought a domain that night. I thought I’d spend an hour a day sending an email with a song to some friends.

Sending the link to a few friends gave me the validation I needed, and I tweeted it the next morning. It got retweeted and a few hours later, A Song A Day was trending in the top five on Product Hunt. Within a few hours, a few hundred people had subscribed. So much for an hour a day.

The next few weeks were mostly sleepless and so much fun. A bunch of friends, strangers, and internet acquaintances volunteered to help curate, organize, and send emails. A beautiful community was born, mostly by accident.

I’ve made more mistakes than I’d like to count, but I’ve done some things right, too. The project has twisted, turned, dipped, peaked, and evolved. Instead of sharing my thoughts on how to start a side project, I thought it’d be more helpful to share the lessons I’ve learned running a passion project that has made me $0 but has brought me a whole lot more.

Illustrations by Sunny Eckerle

Lesson 1: Everyone has an opinion. Do your research, then go with your intuition.

I turn the ripe age of 30 this month and I’m just now learning to listen to my intuition. Prioritizing everyone else’s opinions about my own decisions led me to quite a bit of trouble. It was no different with A Song A Day.

I spent a lot of time meeting people for coffee or drinks. I heard so many opinions. I valued each of them because I had no idea what I was doing.

The positives that resulted were many great ideas and a sense of direction, which I had been lacking. On the flip side, it led to several costly moves that weren’t necessary at that stage, especially without a business model or an inkling of how to build one.

I spent several hundred dollars forming an LLC, which would’ve made more sense if we were making money or had employees. I spent time talking to lawyers on copyright issues that could’ve been Googled. I had an unnecessary (not like I had groundbreaking technology) non-disclosure agreement for curators created. These were distractions from what was probably most important: figuring out a sustainable model to grow the community.

(Some advice - like having a contract for engineers - was smart. There are services including Freelancers Union and Shake Law to help point you in the right direction, but you should always get professional legal help for something like that.)

The best advice I can offer is to feel over think. Educate yourself. Collect all the information that will make you feel secure. Analyze it, identify trends, do whatever you want to do with it. Then take a deep breath and ask yourself what you feel. Go with that! If it starts to feel bad halfway through, make an adjustment.

But don’t confuse impulse and intuition. You can be intuitive without being impulsive, and that's important to remember.

Lesson 2: Decide early if it's a business or a passion project.

So many people advised me early on to decide if A Song A Day was a money-making business or a forever passion project. I wish I listened, but I was overwhelmed. Instead, I focused on building the community, trying to get a product built, and looking for early stage funding.

It turns out that early-stage investors, incubators, and accelerators want to see a business model with real, researched numbers. And a technical co-founder. I looked for one of those and it never panned out. My theory is, I was either held back by fear or knew deep down it was a passion project.

Projects can cost a lot of money if you let them. Decide early on if you’ll invest your own money for a return later. If you do, identify an initial business model (it will change as you learn from your customers) and start charging for it day one.

You don’t need a complete product before testing the waters (my second biggest mistake). Hack something together with forms and Zapier or spreadsheets. Put up a product listing and call it a “pre-order” to test interest. Set clear expectations. Let your audience know this hasn’t been created yet or you have a limited supply and are testing demand. The response will help you set an appropriate price point. Transparency is a good thing, especially in this early stage.

For a passion project, explore ways to fund your overhead costs. That could be a membership fee, crowdfunding, donations, grants, a subscription fee to access a newsletter or other content, branded sponsorship, or advertisers. You have options.

Lesson 3: Don’t torment over your vision.

I had a vision for A Song A Day but was too scared to own it and share it. I also had fear-based decision paralysis.

Any decision is better than no decision. Choose a path and go all in. Something - your product, customers, competitors, politics, work - will change. Perhaps all of it. So be ready to adapt.

When making a decision, I’m a fan of Mel Robbins’ five second rule: count backwards from five and make a decision. It’s all about intuition!

Make a decision, set a goal and vision, put it on paper, and share it with at least a few trusted stakeholders. Choose people who’ll hold you accountable and lend a supportive ear. Eventually, with their continued support, you’ll be making quick decisions with ease and confidence.

Lesson 4: Do things now that will save you time later.

Get creative with ways to keep costs low and your time precious. This might mean automating part of your workflow or recruiting volunteers.

In A Song A Day's first month, I grouped subscribers by interests and manually matched them to a curator. I loved this! It was fun and I learned a ton about our earliest users. It was also extremely time consuming. Manually doing operational work is useful at first, but not sustainable.

To this day, I struggle with automation. I don’t like it. I enjoy the painful work. Do as I say, not as I do. If you’re running a passion project and don’t have much time to spare, invest time upfront in setting up systems and experimenting with automation. This can result in a project that practically runs on its own, allowing you to focus on the fun, creative parts!

Lesson 5: Give up control and accept help.

Giving up control can be hard, but you can't do everything yourself. We have to ask for help and delegate. Understand you'll be disappointed in people at some point, that’s life. Take what you learn from it and move on.

I’m not great at managing people. But in doing so, I’ve learned how to be better at it and also realized I don’t love it. That might change with time. But thanks to this realization, my career path looks a lot different from my friends with corporate jobs.

I’m much more comfortable with collaborating than I am managing. I actually love working with people. For me, seeing someone as a collaborator rather than an employee changes the dynamic. I’m now collaborating with a friend on a new project and it’s been incredible. We keep each other accountable, we delegate, we bounce ideas around. And we check in on each other’s life outside of work. It’s great! All it took was a perspective change.

Accepting help can be a positive experience.

When facing a new challenge or decision, there is no silver bullet. Make a small change that feels right, measure progress, and keep moving forward. Be mentally prepared for it to yield results different from your expectations. Whatever the outcome, take it for what it is and move on.

This project has evolved so much. I haven’t even touched on all the variations of products we released, the content we tested, and how we produced four concerts!

I thought the last change to A Song A Day - one of many - was going to solve all our problems. I was wrong. Seeing these self-imposed expectations burst can feel defeating if you let it. Instead stand up, brush yourself off, and try something else.

Today, I’m at a crossroads. I still love this project but it has come to a point where it’s draining more energy than it is adding. And that’s ok, it’s been three years! I’ve decided to test something new by simplifying in the coming months and look forward to seeing what happens.

I'd never go back in time and not do A Song A Day. I met dear friends through this project. I learned and grew more than I ever did in college. We introduced so many people to new artists. We helped hundreds, maybe thousands of artists sell music and concert tickets. We brought people together. I fulfilled several teenage dreams and dipped my toe in an industry I’ve always wanted to work in. And I did it by starting my own thing. How cool is that?

If you have a project idea and aren’t sure if it’ll make money or will grow into a business, just do it! Make the decisions that feel right. If it starts draining your energy instead of adding to it, make a change. Go with your gut and most importantly, have fun! Godspeed.