How to Build a Successful Side-Hustle

How to Build a Successful Side-Hustle

Let’s talk about side hustles this morning!

Y’all have probably heard me talk about how I recently quit a cushy product management job where I didn’t have to do much but was bored/frustrated all the time, and the only reason I was able to do that was that I have a side hustle.

I’ve always had an INTENSE need for freedom to pursue whatever interests me and I hate feeling blocked... low patience. Building a backup revenue stream has given me tremendous leeway to pick my projects and exit situations if they’re not working out. In my case, my side hustles have always been writing.

In college I built up a decent career as a games beat journalist and now I have a nice little fiction publishing business. Each of these took a few years of dedicated effort to get going. And my biggest takeaways from doing this a few times are:

1) being prolific AND social eventually attracts an audience
2) it doesn’t feel worth it at first but eventually there’s a tipping point where things speed up
3) ignore your critics

For the first point, you just need to make a lot of stuff. I had probably 20 books published before I started seeing real sales traction but then it got exciting. Soon it was making enough to pay my rent. Most quit when their first few projects don’t take off. Gotta push. More importantly, you have to TELL people what you’re doing. No one really gets “discovered.” People see what you’re doing, like it, and share it with people they know. Telling the right people is important too... your mom isn’t going to share your anime art with her friends.

For the second point, it’s true that you’re going to feel like you’re toiling for nothing for a long time. This is because building a body of work and an audience is a slow process. If, like me, you have no patience, you just have to focus on the work for the sake of the work.

I spent about a year working on the draft of my first book. This might not seem too long, but I was doing it full time and I can now crank out books in 1-3 months depending on length.

This year was agony. What was worse was that I lost money on it. A lot of money. But I learned a lot that year and improved tremendously as a writer. I might have been $4k in the hole (plus opp costs), but by focusing my time and effort I was so much more prepared to launch into the next few projects.

I took a break, licked my wounds, and jumped back in again after a small break. The next time I focused on volume over quality and improved even faster because I was trying out more things. You learn more by making 100 pieces of art than by tweaking 1 piece 100 times.

As my body of work grew, I got better at advertising and making marketing funnels and had more content to sell people and I watched as my $2 days became $5, $10, $30, $50 days. The day I first broke $100 in passive revenue blew my mind. Seemed insane. That tipping point was the point where it kind of snowballed for a long time, and once a thing gets its own momentum you can choose to either press the gas down or lean back and let it coast while you pivot to a new project.

As for the third point, ignoring your critics, it’s really hard but necessary. Everyone has an opinion and lots of them won’t like your work.

People will think your work isn’t up to their standards or isn’t “good” enough to “deserve” to make money. People will try to tear your stuff down because they don’t like your messages or they resent you personally. You can’t let it shake you, especially early on.

The first one star reviews I got on my books devastated me. I was so sad about it, took it personally, would go into depressive funks. When you only have a few books and a few reviews on them, it seems devastating (and this applies to any content medium).

Now, when I get a one star review (which is pretty rare these days), I just shrug it off. That person wasn’t the right person for my content.

And now I’ve got built in super fans that are always ready to stan my work.

The key really is to build up a group of people who love you because when someone critiques what you’re doing it just means they’re not the right audience for you.

It’s not personal (even if their attacks are personal) and you need to remember that.

And quality of work is really variable. Depends on your audience. What matters is connecting with people—not that your work is perfect. You’ll get better over time, and if you can connect to people’s emotions you’re 90% of the way to good art already.

Eventually your side hustle can become your main hustle, but you should think very carefully about whether that’s something you want. I tend to get lonely (as an extrovert) when I work solo and I’m still trying to find the right way to balance freedom and social needs.

It can also be a lot more stressful watching the up and down swings of your sales/donations/patreons than getting a guaranteed check in the mail every two weeks from and then of course there’s accounting, quarterly taxes, managing your advertising, etc etc.

Small biz is not for everyone.

It’s stressful and complicated and even if you have a manager it’s expensive and you need to trust them.

Plus! Businesses don’t last forever. Market conditions change. Tech changes. Competitors disrupt. Your passive income stream of today may not work in 5 years. Or 3 years! Things change quickly.

You have to be thinking about the future always.

I’m watching things like GPT-2 very carefully right now, for example. I would be surprised if genre fiction for independent authors (pulp romance, mystery, etc) is still a viable job for most authors in 5-10 years. More likely is that “authors” will guide AI with ideas.

Which means I either need to get in on the game early or find a new side hustle before my business gets buried by tech that can generate high quality content much faster than I can manually.

And this also implies that brands will become much more important. This is true today anyway to an extent. There’s not a huge qualitative difference between plenty of pulp authors but readers get attached to a brand that they trust and just keep buying those.

Figuring out WHAT your side hustle should be is really hard too. You don’t want to pick something that looks lucrative if you’re not that into it because you’ll really hate it when you’re generating content you don’t care about all the time. It won’t resonate. My two most successful business ventures started out as passion projects I did for fun and I just kept building on top of them until people wanted to pay for more. 🤷‍♀️

I suspect that following things that naturally feel fun/exciting to you is the best way to connect with fans. Your enthusiasm for the material can’t help but shine through and that speaks to people!

They’ll similarly pick up on if you don’t really care about the work.

This is why I sooo strongly believe in making space for yourself to play. Creative outlets and permission to explore lead down really interesting roads that you’d never follow if you told yourself “accounting will make me money so I’m only allowed to do accounting.”

You have no idea what’s going to make you money until you start trying stuff and putting your ideas out into the world.


From a financial perspective, I’m terrified of not going back to tech but I’m also not especially confident I’m going to find an employer who’s a good fit for me locally. Portland is an okay small tech market but there’s not a ton of exciting projects to choose from. That kind of leaves me with no choice but to keep playing my freelance games if I wanna stay here since the lacking-passion burnout applies to regular jobs as well as freelance work.

If I’m not excited, I’m not gonna be able to stick it out. But in some ways this is very cool! Sometimes constraints are the best way to push yourself toward success. If I know I can’t or won’t go back to being a PM in the local market, that forces me to get a lot more invested and creative with things that might have 10-100x payoff.

A final note about money—be very very careful if you’re chasing just the money. Understand why you want or need that money. Because ultimately money as an end in itself is unfulfilling.

You do not want to work a job you hate for 30 years to discover you didn’t need the cash. I like money as much as the next girl but I’ve personally found that the axiom about it being diminishing returns beyond a certain threshold is SO TRUE.

If your work environment is making you miserable or you hate your job or you aren’t spending your life in the way you really want to, don’t wait a decade to recalibrate.

Start today, even if it’s small. It’s silly but I think we all need to listen to Shia sometime.

Because the thing is that EVEN IF you don’t quit your day job, sometimes having enough revenue from a backup hustle is enough of a calming mental barrier to the stress that you don’t need to.

Knowing you can hit eject at any time is extremely soothing, and it also lets you plan strategically for when you DO want to eject. You can be methodical and calculated instead of rolling the dice.

I may have lost a few years of opportunity cost building a side gig but the experience of learning how to do it is priceless.