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What to do when your side hustle becomes a drag

Let’s talk about “anchor problems” and “gravity problems.”

If you spend a lot of time online, you have probably felt, at some point or another, the irresistible urge to undertake a side hustle.

By a side hustle, I mean a project that you start with the fairly explicit intention of getting paid or amassing some kind of public acclaim, recognition, or clout. Maybe you’ve thought about launching a podcast, a newsletter, a YouTube channel, or an Etsy shop. Why wouldn’t you? We live in a content economy, in a culture that deifies entrepreneurship, and as ads from Squarespace and Wix will remind you, it’s so easy to build a professional-looking website for any fledgling business.

For those who go through with starting a side hustle, there’s a solid chance that after a while, something about it begins to feel burdensome. It could be that you feel like you can’t sustain a certain level of output, or that you professionalized a hobby to the point that it’s not fun anymore. For whatever reason, it feels like a chore.

What do you do when your side hustle has become a drag? You could let it languish, making vague gestures at “getting back to it” and feeling guilty about pushing it off into infinity. (Have I done that? Am I doing that right now with a particular project? Who can say!) You could also address it directly, asking yourself some expert-approved questions to help guide you toward a more sustainable approach.

Let’s go with the latter.

Ask yourself why you started your side hustle

When I was interviewing experts for this story, I wanted to know what questions people might ask themselves when their side hustle starts to feel like a drain, in order to figure out how to move forward. Across the board, they immediately came back to me with the same one: “Why did you start this side hustle in the first place?”

Maybe you got into your side hustle to make money. Maybe you did it because you wanted to exercise your creativity or because you were passionate about a cause. Maybe you did it because all of your friends had an extracurricular project going on, and you thought you should, too. By taking a step back and revisiting your original objective, you can figure out what’s really going on and begin finding solutions.

If your initial reason for starting your side hustle still resonates with you, you can then look at reframing the problem. Bill Burnett, co-founder and executive director of the Stanford Life Design Lab and co-author of the book Designing Your Life, suggests thinking through your challenge in terms of “anchor problems” and “gravity problems.” Say you’ve got a weekly newsletter dedicated to tracking new restaurant openings in your city because you love trying new spots and want to share that knowledge with others. An anchor problem might be the fixed notion that it has to be a weekly newsletter — or even a newsletter at all.

“Once you’ve decided that there’s only one solution, you’re kind of locked in,” Burnett says. As an exercise, try letting go of the anchors you’ve attached to your side hustle and then brainstorm other ways of meeting your central goal. What if you sent your restaurant newsletter every month instead of every week? What if it took a form that was more exciting to you, like a TikTok or an Instagram account?

Gravity problems, on the other hand, can’t be changed. “It’s just a law of nature, in which case we say that it’s not a problem, it’s just a circumstance,” says Burnett. A gravity problem can also exist in a situation where you could make a change but aren’t willing to do so. For instance, you could stock up on cold brew and send that restaurant newsletter every weekend on top of your regular job — but maybe you didn’t realize at the outset how much effort and energy the newsletter would require, and you don’t want to sacrifice all of your free time for it. (Burnout is real.) That’s a reasonable position to take. When you’re brainstorming solutions, you just need to work within that constraint.

By asking yourself why you initially started your side hustle, you might also realize that your answer guides you toward shutting it down. This can particularly be true when you started a project because your friends were doing it, or because you felt some sort of peer pressure to do so. “You’ve just got to be honest with yourself,” says Burnett. “Maybe instead of opening my Etsy site, I need therapy. Why do I care what my friends think, and why is this a measure of my success in the world?”

If the project doesn’t feel aligned with who you are and what you want to bring to the world anymore, that’s a good reason to set it aside, says Sara Noble, a life coach who works with creatives. With clients who are undertaking a new project, she likes to help them set “conditions for satisfaction,” which include ground rules for when to abandon that project. “Especially as creative people, I don’t think we do enough of putting down our projects and moving onto something else,” Noble says.

Dismiss the self-judgment, perfectionism, and “should”s

When you start reframing your side hustle, a little voice might pipe up in the back of your head, saying, “Sure, you could take your weekly newsletter down to a monthly pace, but you shouldn’t.” The little voice offers all sorts of reasons for that. You will have failed at the project! You told your subscribers you’d send it every week, and you aren’t keeping your word! Your more successful peers have high-profile jobs and operate weekly newsletters, so you should too!

This is very normal, so don’t fall into a spiral of judging yourself for judging yourself. “I think the biggest thing when people start a side hustle and then hit a wall is that there’s a lot of self-judgment and ‘what’s wrong with me?’” says Astrid Baumgardner, a career coach for arts leaders and creatives and the author of Creative Success Now: How Creatives Can Thrive in the 21st Century.

Self-judgment gets in the way of finding a sustainable solution for your side hustle. “Design only works in reality, right now, where we are today,” says Burnett. Instead of fixating on the most aspirational version of your side hustle, which doesn’t exist, accept your reality: You tried one version of it, it didn’t quite work, and you now have some valuable information to guide you forward.

Sometimes we heap the word “should” on ourselves, but sometimes it’s coming from the people in our lives, including well-intentioned loved ones. Instead of taking someone else’s “should” statement at face value, Baumgardner suggests treating it as a flag. “When you hear that word, ask yourself the question: ‘You might think so, but do I?’” she says.

If a friend says that you should monetize your sewing hobby, for instance, think seriously about whether that’s actually something you want, because while external encouragement may motivate you to start a project, it probably won’t sustain you in the long term. “If it’s not your goal, it’s not going to happen,” says Baumgardner.

Speaking of external validation, a major reason for feeling locked into a side hustle — even one that’s clearly not working for you anymore — is the fear of disappointing your audience or clients. After all, these are the people who have given you their time, attention, and money — who have, effectively, made the side hustle what it is. That’s real. But, says Baumgardner, “You have to let it go.”

It’s worth remembering that your audience is not an authority figure in your life, says Noble. (They’re not your parents. Repeat that again.) “If they’re really aligned with who you are and the work you’re doing, then they’ll be aligned with whatever path you take or whatever direction you decide to take it in,” she says.

Treat your side hustle as an experiment

After identifying your motivations for having a side hustle and reframing the challenges you’re experiencing with it, you can enter experimentation mode, where you test out changes to the project and see how they feel. Baumgardner advises adopting a spirit of open-mindedness during this process. “Maybe you had some idea about it initially, but allow yourself the freedom to see what this is like,” she says. “Constantly take in information: How do I like this? How am I using my strengths? How much fun is this? How difficult is this? And what am I learning?”

Depending on the nature of your side hustle, you can consider changing up the cadence, length, subject matter, or format of your product. If you’re struggling with a technical aspect of it, zero in on that challenge and seek out help from someone (or a YouTube video) who can teach you. You may also think about modifying other aspects of your life to suit your side hustle. If your side hustle is a big priority — as a source of income, a passion project, or a career advancement tool — then perhaps you’d be served by giving up your TikTok or TV-watching time to fit it into your schedule.

If it makes sense for your side hustle, you can even pilot a revamped version of it privately. Before Baumgardner launched a blog, which eventually became the foundation of her book, she gave it a six-month test run to see how she took to blogging, stockpiling posts without publishing a single word. Prototyping behind the scenes can also give you the opportunity to get feedback from friends and family before putting your product out in the world.

There’s no one length of time that’s ideal for running this kind of experiment, but you’ll want to give yourself enough time to really get into the flow of the changes you’ve made. That could be eight weeks or even several months, though if you’re testing out a new product privately, be wary of giving yourself too much time to gestate. “I think if it’s going on for more than a year, that’s an excuse,” says Baumgardner.

Indeed, while there’s a lot of value in analyzing your motivations around your side hustle and thoughtfully brainstorming other versions of it, this kind of experimentation also requires a healthy dose of not thinking too hard — that lack of open-mindedness and lack of rigidity that Baumgardner described. “Just do it,” says Sara Campbell, a writer and life coach based in Los Angeles. “You can go around and around in your brain for 100 years before you put anything down. Let it be shitty.”

In Burnett’s experience, once you enter experimentation mode, the terrible feeling of having failed on your first try tends to dissipate. He knows something about prototyping, since he is also an adjunct professor of mechanical engineering at Stanford and previously worked in product design at Apple. “Of course you did it wrong. You’re going to do everything wrong for the first five, 10, 15 prototypes,” he says. “When I was at Apple, we invented the first laptop. There were like 300 prototypes before we figured out, oh, the keyboard should be in the back and the trackball should be in the front.”

Your goal is to evolve the project and learn, and evolve the project until it works for you. “Don’t come up with two ways to do it, come up with 10 ways,” Burnett says. “Once you’re in that mode of thinking, the guilt goes away, the ‘should’ goes away, the comparing yourself with others goes away. Because curiosity about ‘what’s the possibility of the future of me?’ is so powerful and exciting and fun.”

Accept a certain ebb and flow

A side hustle is likely going to change many times throughout its lifespan, as your goals, needs, caregiving commitments, work, and lifestyle evolve. Campbell has experienced this firsthand with her own newsletter, which she started after winding down a startup concept, itself a side hustle. “I think in the evolution of my newsletter, I’ve hit the wall multiple times,” she says.

When Campbell’s startup folded, she became deeply depressed, and her newsletter, called Tiny Revolutions, became a way to talk about those feelings. “The first six months were me just writing about that topic, healing myself, what you go through. It was something I needed to do, and it came from a very raw place,” she says. As she started feeling better, that project didn’t resonate as much as before, and for a while, the newsletter became much more sporadic. When Covid-19 hit, Campbell dialed her frequency back up, writing once a week on topics like mental health and Zen Buddhism, which she practices. More recently, she’s brought it back down to a monthly-ish cadence.

Campbell believes that after four years of writing the newsletter, her readers trust that she’ll show up in their inboxes, if not always on a rigidly defined schedule. And her readership has more than doubled since she stopped writing weekly.

When it comes to side hustles, Campbell says, there’s some degree of seasonality that we have to learn to tolerate in ourselves — a certain ebb and flow that we have to accept. “When it starts to feel like a chore, to me, that’s when it becomes problematic, and that’s when I know I have to figure out a way forward,” she says. “I reframe it to be a journey of curiosity and exploration and not like, ‘I must publish this content on Friday at 8 am.’”


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