Hobbies and Hustles

I recently read this great little article by Molly Conway entitled The Trap of Turning Hobbies Into Hustles. In it, she makes the astute point that when you attempt to start earning money from something that’s a hobby, it ceases to be a hobby any more – rather, it starts to seem like work:

I have a friend who is living her dream. She makes and sells leather pocket belts, holsters and ruffle tops for the steampunk/Renaissance Faire/Burning Man crowd. Her designs are worn and enjoyed by thousands of people; she’s created more jobs for Bay Area artists; she’s her own boss — and she hasn’t taken a real day off in roughly eight years. Because that’s what it takes to do what she loves. I admire […] her, but every time I’m tempted to listen to someone who says I should open a restaurant just because I throw a good dinner party, I think of her, and remember that admiration is not the same as envy.

That’s not to say there isn’t joy to be found in turning something you love into your life’s work — it’s just to say that it’s okay to love a hobby the same way you’d love a pet; for its ability to enrich your life without any expectation that it will help you pay the rent.

This hit home for me.

One of the cornerstone elements of our financial turnaround was that I was able to find a side gig that I was eventually able to turn into full time work – and you’re reading it. The Simple Dollar started out as a pet project I did in the evenings in our tiny apartment as I wrote through some of the ideas I was discovering and working through in order to turn our financial life around. It became reasonably popular and, while it never earned enough to make us wealthy, it did earn enough that switching to writing it full time was a real option because it also reduced our child care burden (since I was at home and had a super flexible schedule).

Writing has always been a hobby of mine, and while I was in the “honeymoon period” of my financial turnaround where everything was new and exciting and I was trying all kinds of new (to me) things, it was purely fun to write about those experiences. As time went on, though, I found that what Molly describes above as purely accurate. Suddenly, something that was a hobby to me was making money – which was great – but now it was burdened with deadlines and responsibilities and expectations – which wasn’t good.

Yet, here I am, still writing about personal finance. How did I make that work? How can I still keep writing about personal finance and earning an income at something that was my hobby without being miserable?

I think that what I learned from that transition serves as some powerful advice for anyone looking to turn a hobby into a side gig.

First of all, I had to accept that writing was no longer a hobby, but a profession. Prior to that point, writing was something I purely did for personal fulfillment. I have always loved taking my ideas and putting them down on paper, much like how other people love and are fulfilled by woodworking or crafting or fishing or cooking or whatever. However, it was never something I had to do in order to produce an income for my family. I did it when I had the time and when I had burning ideas inside of me and I did it solely because it fulfilled me.

When you choose to do something for money, particularly when it becomes a source of money that you or your family relies on, that relationship changes. You can no longer do those things when you feel like them. You have to keep at it, regardless of how you might feel at the moment.

Leisure activities are enjoyable because they’re things you want to do and you can do them at whatever level feels right for you. When you have to do those things for a living, that choice of what to do and when to do it goes away. It’s no longer your choice. Even the most successful writers out there, like Stephen King, sign contracts and have obligations for their craft. They can’t simply choose when to write and not do it if they don’t feel like it.

That’s the difference between a hobby and a profession. With a hobby, you want to do it and, if you happen to not want to do it today, that’s okay. With a profession, you have to do it, regardless of whether you want to do it today.

There are days when I wake up and the last thing I want to do is write. I have all kinds of other things I’d love to fill my days with. However, I have an obligation to write, a freelance agreement that I signed that provides income for my family (good) but has stiff consequences if I don’t write (bad).

That change from wanting to do something to having to do something is a serious change and requires a far different approach. It means that it’s no longer your hobby, but your profession, and you have to approach it professionally. You have a set schedule and requirements and it’s no longer the free thing that you used to do.

In the early days, when I did The Simple Dollar for fun, I wrote about whatever I wanted pretty much whenever I wanted. If I didn’t feel like writing, it was fine. Today, I spend several hours a day most weekdays doing some sort of personal finance writing-related activity. There are times when it’s purely fun, but there are a lot of times when I have to do it even though I don’t want to.

So, how do you make that change?

The first thing I figured out was that on the days when I’m feeling in the groove, I need to get as much work done as I possibly can. If there’s a day when the writing comes easy and feels good, I do everything I can to stick with it all day long and all night long, if need be. Once every few weeks, I’ll just tell Sarah that I’m in a groove and I need to ride that groove for as long as it lasts. I often talk about “flow state” on The Simple Dollar, and that’s exactly what I’m talking about here – if I have days where I can get deeply into a flow state and just keep writing and writing and writing, I do it.

What this does is that it gives me breathing room for the days when it’s not working quite so well, when I’m dreading writing or when I can’t get anything to come out. On those days, I can walk away and professionally recharge.

Without that ebb and flow, this whole thing wouldn’t work. If I simply stopped on those good days when I had two or three things completed, I wouldn’t be able to do this. On those days when I really feel motivated and engaged and excited, I have to get as much value out of them as possible.

Why? Nothing makes a hobby-turned-side-gig miserable faster than the days when you’re not engaged at all with your gig but you still have to produce work. You’re going to be miserable and you’re going to not be very productive at all. You are far better off those days simply walking away and recharging or finding other aspects of your work to do. In fact, if you keep doing this, if you keep grinding when the passion is zero, it’s going to become miserable and your quality is going to fall off a cliff and you’re going to lose the whole thing anyway. Trust me – I’ve been there.

if you try to turn a hobby into a hustle, be aware that you’re going to lose a hobby. When you start doing something for money, there starts to be expectations involved with it and you can’t simply pick it up when it feels fun and let it sit when it doesn’t. You have to pick it up every time, and that’s work, not leisure.

There’s nothing whatsoever wrong with that, and work can most definitely bring you joy, but there are times when you have to do it even when you don’t want to. That’s the difference between a hustle and a hobby – a hobby can be put down, while a hustle can’t.

Make absolutely sure that this is something you want to give up as a hobby. If it’s something you genuinely value as a way to escape, as something you can pick up when you want and leave alone when you’re not feeling it, you should think very carefully about whether you want to convert it into a hustle.

Thus, if you do go down this path, you have to find a new hobby. Your old hobby is no longer a hobby. It fills more of your time than you would ever like. That doesn’t mean it no longer brings joy, but what it means is that it no longer serves as a hobby, as something that provides leisure and escape from the routines of your life.

Ten or fifteen years ago, my main hobby was writing. When that went from hobby to side hustle, it no longer fulfilled and refreshed me. It was the thing that sometimes made me need to feel fulfilled and refreshed. I discovered cooking. I discovered hiking. I (re)discovered tabletop gaming. I (re)discovered reading. Those are my hobbies.

Writing, although I still love it, is my work. It is not a hobby. It is not an escape. It is not something I can pick up when I’m excited about it and put down when something else is more compelling at the moment.

I’m lucky in that most days I’m excited about it, but there are most definitely days when I have writing commitments and it’s the last thing in the world I want to do. That’s what makes it work and not leisure.

Finally, turning a hobby into a side hustle generally only works well if you’re utilizing skills and talents you have. If you love to knit, for example, but you’re a mediocre knitter who can turn out good stuff but slowly or bad stuff quickly, it’s probably not a good choice to try to turn knitting into a side hustle. It’s a great hobby, but not a great source of income.

Writing happened to work well for me because I can write reasonably good material (I don’t claim my writing to be great in any way, but I do think I can lay out points and tell a decent story) in large quantity and fairly quickly. That’s a skill, one that I utilize every day.

It’s my belief that turning a hobby into a hustle works best if you have several hobbies, you see a clear path to income with one of them, and you can apply strong skills you already have to that path. That way, you’re not turning your main passion into work and you’re able to do something of value that others will want and appreciate, thus ensuring at least some chance of success.

Good luck!

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