A few years ago, I went through a period where I longed to spend more time on one of my favorite hobbies: tabletop gaming. I really like sitting down with friends and playing a board game or a card game or a roleplaying game. The social experience, the thinking process, the handling of the components on the table — all of those things, and more, appeal to me.
At that point, I really felt like I wasn’t able to spend as much time as I wanted to on the hobby. I also knew that there were some people who had started making online content — YouTube videos, podcasts and other material — related to the hobby, and a few were actually making a living at it (like DiceTower, Heavy Cardboard and Shut Up and Sit Down).
I decided that it might be fun to try making some tabletop gaming material as a side gig. It would give me a good reason to spend more time with my hobby as well as some time learning new skills, and I might end up writing a few articles on The Simple Dollar about the experience.
So, I dove in. I started making YouTube videos wherein I reviewed tabletop games, made some top 10 lists and started a podcast to go along with it.
I spent a few evenings a week working on this material and changed my writing schedule so that I could spend every other Friday on it. I really leaned into playing a lot of games so that I would have things to talk about.
It did well, for a while. I built up to more than 1,000 listeners and 1,000 YouTube subscribers over the course of a few months and was able to get the YouTube channel monetized, so I was making a little bit of money with it. I could definitely see a path in which this built into a nice money-making side gig.
There was just one problem: it wasn’t fun.
After a while, I began to realize that this side gig was just killing my passion for the hobby. I was no longer playing games for leisure, thinking or social camaraderie. I was playing them because I needed to review something next week. I was nudging people to play games that I thought I needed to play so I could review them. I became really critical of everything I was playing, which sapped a lot of the joy out of the experience.
At the same time, much of my hobby time had turned into “content production” time. Rather than playing a game with my good friends, I would spend time outlining a video, writing a script, setting up a spot to record a video, recording a podcast, or editing a video or podcast.
I didn’t mind those things per se. They would be enjoyable work tasks. However, those tasks were directly eating away at my leisure time and other times in my life. Side gigs devour time out of your life, and if you’re turning a hobby into a side gig, you’re likely devouring a lot of time that was leisure time and turning it into professional time.
After a few months of feeling like the side gig was ripping my hobby apart, I decided to give it up. I stopped producing new videos, left the old ones up for a while, and then eventually took them down.
It was an interesting experience, one from which I learned a lot, but not one I wanted to continue. I learned a lot about video and audio production — nowhere near a professional level, but enough to do simple things and understand lots of issues involved. I learned a lot about a different kind of content production besides The Simple Dollar.
Most of all, I learned that a hobby doesn’t make for a good side gig most of the time.
Practical advice for turning a hobby into a side gig
Focus on time management
This is my first piece of advice to anyone who is thinking about turning a hobby into a side business so that they can dig deeper into that hobby. Rather than mutating the hobby into a side business, instead, look at time management practices so that you have more free time to devote to your hobby.
For me, the two most effective time management practices were developing a strong system for keeping track of the things I need to get done by using an ongoing to-do list and calendar, and developing ways to be more intentional with my time so that I don’t waste time being distracted. The more I applied both of those strategies, the more free time I found for hobbies I care about.
To start with a to-do list, I suggest simply starting with a small notebook or piece of paper, writing down things you need to get done as they come up, checking the list regularly to see what needs to be done, and crossing them off as they get done.
To start with being more intentional, I suggest turning off a lot of notifications on your phone and other devices, getting into a habit of regularly asking yourself what it is you should be doing right now and using “time blocking” to block out chunks of your day for specific things.
Lean into your other skills and expertise
You may end up finding with these time-saving techniques that you have more free time available than you otherwise thought, and you may find that you want to start some kind of side gig to make money.
If that’s your situation, I strongly encourage you to start from a skills-first or equipment-first perspective, not a hobby-first perspective.
Ask yourself what skills you possess that others would be willing to pay for, whether in the practice of those skills (providing some kind of service) or in the product of those skills (selling some kind of product).
Perhaps you have some carpentry and home repair skills, so you may be able to hang out your shingle as a handyman. Maybe you have graphic design skills, so perhaps you can start your own side gig as a freelance graphic designer.
You may also want to think about any equipment you have that would help you provide a service, like a car or a woodworking shop. For example, if you own a car, you might consider a side gig of being a delivery driver through Doordash or a similar delivery service. If you have a lawnmower, you might consider a side gig of mowing lawns.
Change some aspects of your hobby
What if you still want to turn a hobby of yours into a side gig?
The first thing to understand is that you will have to change some significant aspects of your hobby in order to pull this off. No matter what you do, you’re going to have to create some sort of product or service that people want and then sell that product.
There are a lot of forms that the product or service can take and almost as many forms that the selling of that product or service can take.
For example, let’s say you want to mow lawns. The product you’re selling to people is your service in providing a freshly-mown lawn. Your sales effort involves letting people know about the service and discussing terms with them, then you deliver the product (mowing their lawn), and then they provide payment (either before or after the service).
Another trickier example: if you want to make YouTube videos you have to realize that what you’re actually creating is something that will sell ads. The ads are the product being sold that will make you money, while the videos are the method for selling those ads (the better your video, the more viewers you get, the more ads that ship and the more money you make).
Your side gig is really the selling of a product. That’s what all side gigs come down to. You have to either create a product of your own, creatively sell someone else’s product or both. Online content is often just creatively selling someone else’s product via the ads that are placed around it, or a sales pitch to convince people to contribute to your Patreon or something like that.
When you want to turn your hobby into a side gig, you’re either reshaping your hobby to either be a product to be sold or a sales pitch for some other product. People won’t just give you money for practicing the hobby in the way you always have. You will have to reshape it so that either your hobby results in a product (which you then have to sell) or that your hobby sells a product (through ads or other means).
The more you have to change your hobby, the less leisure activity that hobby will become
The harsh truth is that those changes are rarely enjoyable changes.
In order to turn my hobby of tabletop gaming into YouTube videos and podcasts, I had to start spending a lot of time writing an analysis of the games I played, managing all of the details of video and audio production and then promoting the videos and podcast once they were produced. Even though I put in the effort to give more time to my hobby, that time was entirely eaten up by these new things I had to do.
Not only that, but I also had to start participating in the hobby in a way that was conducive to creating YouTube videos and podcasts. It wasn’t enough to just sit down with friends and enjoy a game anymore — I had to always be asking myself how I could maximize that experience in terms of producing a video or a podcast segment.
This eroded my enjoyment of the hobby. It was no longer leisure time. Rather, it had become professional time. Sure, some of it was still time with friends around a table, but even that time had to be thought of in a more professional way and a less leisurely way.
Here’s the big problem: before that, tabletop gaming had been true leisure time for me. It had been a way to truly unwind from the responsibilities of the other spheres of my life: professional work, homeownership work, family obligations and community responsibilities. The time spent around a table with my friends had been a way to unwind from all that, to truly renew and refresh myself.
Turning it into a side gig drained away that sense of unwinding and renewing. It took away much of the enjoyment. Instead, playing games became like pure research for a work project. It might be enjoyable, but it wasn’t leisure. It didn’t unwind me. I didn’t feel relaxed afterward. I felt more like I had just completed another step in another work project, one that was done with people I liked but was still work.
In short, I had lost that hobby, and I had to start finding other hobbies so that I had leisure time. I believe true leisure time is something that everyone needs in your life, but once you take something that was once leisure and try to turn it into a side gig, it’s no longer leisure, and you have to find something else to replace it.
During that time, my limited remaining hobby and leisure time became very focused on reading, hiking, homebrewing, and fermentation. I realized that I had “lost” my hobby and was now needing leisure time to get away from it, and for me, that was the final straw. It was truly no longer leisure, and I wanted it back as a leisure activity.
Consider partnering with someone to handle the sales aspects
It is worth noting that some hobbies naturally lend themselves very well to producing things that can be sold. For example, my father was very passionate about his vegetable garden and always produced far more vegetables than we could possibly eat or can, so he would often give the excess away. I had another friend who had a woodworking shop at home and would just make stuff for people for fun, things that he thought were fun to make and that they might appreciate.
In both of those cases, they eventually figured out ways to keep their hobby almost entirely as a hobby while making some money from it, and in both cases, it came through partnering with someone.
In my father’s case, he found someone who would just stop by, pick up whatever vegetables he had and sell them on his behalf. That person basically served as a middleman for my father’s vegetables. My father had no interest at all in selling them — he just loved to plant, grow, weed and harvest — but he was just producing more than he could use. This enabled my father to just put the veggies in a box and they would magically become cash. Sure, he could have made more by selling, but that would have turned some of his leisure time into working time, and he didn’t want that.
In my friend’s case, he would make wooden items and give them to a friend to sell on Etsy with a split in proceeds (about 80/20 in favor of the woodworker after shipping costs, but the woodworker had to pay for the woodshop materials). The woodworker’s friend would just list items on Etsy, whatever the woodworker made, and earn some money from it. The friend almost definitely made a higher wage per hour of time than the woodworker, but the difference is that the woodworker viewed shop time as leisure time, made whatever he wanted and did it at his own pace.
This only works for some hobbies, particularly those where a skilled person produces things from that hobby that have value to others. Partnering with someone takes all of the “business” aspects of it out of the picture so that the hobby remains just a hobby for the person doing it, with proceeds often covering costs and providing a little pocket money.
If this sounds like your hobby, consider partnering with someone who can handle all of the sales for the things you create and produce, so you can focus just on creating and producing and keep it as a hobby.
Don’t sacrifice your leisure to a side gig
Although I’ve focused on how turning a hobby into a side business might result in losing a hobby, the real concern is losing genuine leisure time. If you transform your main hobby into a job, you no longer have leisure time unless you make other structural changes to your life, and that’s a path that leads straight to burnout.
If you still wish to try to transform your main hobby into a side business, do so with the understanding that the hobby will no longer be your hobby and that your leisure time will evaporate unless you box out time for some other form of leisure. If that is all a tradeoff that you’re happy with, then make that trade.
For me, I’ve learned the hard lesson that my leisure time is really valuable to me and I don’t want to lose it, nor do I want to lose the ways that I spend that leisure time. Turning hobbies into side gigs not only kills the hobby but eats up the leisure time and turns it into professional time.
If you want to launch a side gig, rather than starting with your hobbies, start by looking at your skills and any equipment that you have. What are you good at? What do you know a lot about? What things do you have that could be used to provide a service or product to someone? Start from that direction rather than mining a hobby. Also, be sure that your new side gig won’t just devour your leisure time, or you’ll find yourself with an overwhelmed and unhappy life.