7 Signs You’re Working on the Wrong Side Hustle For You
No, it doesn’t matter if you’re already weeks, months, or years in; starting over might be the only route to a happy ending.
It was a Sunday night, driving back from a weekend trip down to San Diego, and with each mile closer to home, the gnawing in the pit of my stomach heightened. It was one minute, one mile, one day closer to the dreaded Monday. But unlike most 9-to-5-ers, my Monday schedule wasn’t dictated by a salaried job or a whip-cracking boss; instead, I’d brought this anxiety all upon myself — and voluntarily so.
That night wasn’t the first, but it was one of the pivotal moments that made me reassess a very successful side hustle that had mushroomed into a life of its own — and had begun to take over mine.
That side hustle started out as a fun little experiment. It was an edgy secret project that allowed me to flex my creative muscles, test a new market, and see if it could generate any cash or profits — and it did. Unfortunately, one of the downsides of a financially “successful” side hustle is that in short order, it can start ordering you around. As we all seek to build the lives and businesses of our dreams, it’s tempting to dive in and try new things — but sometimes the best next step is pausing, pivoting, or letting them go. Here are 7 signs you’re working on the wrong side hustle for you.
1. You dread the day-to-day
I once watched an interview with Daniel Radcliffe (Harry from the Harry Potter movies), in which he discussed the downsides to fame. One of the biggest detriments to widespread fame and success was the paralyzing pressure to keep living up to it. In other words, after starring in such a successful project, he — and many of his co-stars — were gun-shy about taking on a new role.
What if they were one-hit-wonders? What if they could never come anywhere close to their earlier career success? What if it was all just luck or a fluke?
That’s exactly what happened to me: One of my side hustles blew up, and I froze. The project that used to be a fun, whimsical escape became a pressure-cooker to measure up to the prior week’s or month’s revenue and public reception. Even though I had initially enjoyed the process, with the pressure of a public audience and concrete numbers for comparison, I started to dread this hobby-experiment-turned-side hustle.
If or when your side gig starts to feel more intimidating and stressful than your full-time job, it may be time to hit the brakes.
2. The perpetual recalculation
While some people incorporate side hustles for “fun”, many do so with some financial goals or aspirations attached. However, if your side hustle’s success or income is significantly tied to the time you invest, and you find yourself constantly recalculating your hourly rate to determine if it’s worth it, you may already know the answer.
If you’re just waiting until that hourly rate outpaces your full-time gig as the greenlight to go all-in, awesome — maybe you’re already there! If, alternatively, you’re wrestling with the low time-to-earnings ROI and resenting the hours you’ve already put in, you may be re-creating an income stream you’ll soon grow to hate. If you don’t enjoy the process or don’t believe in the bigger-picture longer-term outcome (or financial success), then you are allowed to quit or seek another path.
3. The false escape plan
When you start a side hustle, you should ask yourself three questions:
- What’s my motivation?
- What’s my baseline goal?
- What are my boundaries?
If your motivation is simply to add another $500 to your monthly income, you shouldn’t feel defeated if you don’t see a quit-your-job escape plan on the horizon. Conversely, if your baseline goal is to replace your full-time income or build a business you can sell for enough cash to quit that 9-to-5, then you may want to be a bit more critical about your ROI trajectory. Likewise, if the only path to that escape plan crosses your boundaries by requiring 10 hours of work 7 days a week, it may not be the golden ticket after all.
For those who set out to create a side hustle that can serve as an escape plan, you should work backwards, calculating exactly what milestones you’d have to hit to make it so. If the cold hard truth is there is no realistic or lucrative exit in sight for the fledgling venture you’ve created, there’s no harm in pivoting the model or exploring other opportunities.
4. The time-expertise constraint
I have a good friend who has a side hustle he claims to love. He says it’s his dream job and hopes to make it his lifelong career one day. Plot twist: He’s outsourced all of the hard parts (the “work”), rather than taken the time to learn or acquire the expertise. In so doing, he’s padding his employees’ skill sets, but remaining stagnant in his own.
Why is this a problem? The issue is this side hustle has become a money pit, since he pays his employees more than the venture brings in, while he swoops in every now and then for the “fun” parts.
His rationale? He says he doesn’t have the time to learn the skills that generate revenue, since he’s too busy doing the “fun” parts alongside his full-time job. In essence, he’s become a glorified project manager for a not-yet-profitable venture.
If you’d rather invest your money in outsourcing than invest your time in acquiring the necessary skill set for your side hustle, you may be yearning the job of a manager, rather than a side hustling entrepreneur.
5. It’s run its course
I recently almost bought a business that’s for sale; it’s a very cool, fun venture that’s gone globally viral. In fact, it’s already traded hands once from the original founder post-virality. I won’t give it away completely, but it has to do with glitter.
This business started out as a fun little prank gig, then blew up beyond its founder’s wildest dreams. It subsequently — and rapidly — died down, just as unexpectedly. Since then, acqui-founders have attempted to revive it to its prior earnings unsuccessfully, spinning their wheels around why this one-hit-wonder won’t come back to life.
I hate to break it to you, but as someone who’s been there personally and seen a good friend with a multi-million-dollar viral sensation experience the same thing — some ventures are trends and fads that run their course. If you still enjoy the slowed-down side hustle and manage to make a profitable return, there’s no harm keeping it afloat. If, however, you’re perpetually disappointed that you can’t recreate those peak earnings and thus resent the venture’s comparative failure, maybe it’s time to pack it in. Few things stay viral forever, and you may have a better time seeking out a new media frenzy to feast your time and dollars on.
6. Due for a re-swizzle
When it comes to quitting jobs, I’m not the biggest fan. That’s not because I don’t love entrepreneurship or side hustles; it’s simply because I know I quit my 6-figure job far earlier than I should have, and if I could go back, I’d hang onto that stability for as long as possible while building my own ventures.
That said, sometimes your main job is the bottleneck on your side gig, and it’s costing you significant momentum and moolah. If you find that you’ve fallen in love with your side hustle and are out-earning your main squeeze, it may be time to re-swizzle — but that does not necessarily mean to send in your “Two Weeks Notice” and watch your health insurance go from $50 employee coverage to $500/month COBRA (true story!).
Consider these two options to maintain stability and income maximization:
- Flip the script and make that side hustle your main gig, while scaling back your main job to part-time or
- Tweak the business plan or your scheduled involvement to create a more scalable venture that isn’t limited by your daily or weekly availability
Five years ago, employers might have fired you for working on a side project. These days, they’re far more understanding that many employees engage in various income-generating activities, and they may need to accommodate your schedule if they’d like to retain your talent and expertise.
7. It’s monopolizing this
Moderately successful side hustles run one very major risk: They can lull ambitious go-getters into the guilt-ridden commitment to keep them going — even at the expense of other more fulfilling or lucrative endeavors.
If you started a successful service business, but your heart wants to create and monetize your own content, don’t succumb to the fallacy that you need to triple down on what’s working. If your side hustle is monopolizing your other business explorations, it’s limiting your potential and constricting your growth. If I’d allowed myself to be governed by the “triple down on what’s working” school of thought, I’d have a fraction of the revenue streams, opportunities, income, and stability that my side ventures have created.
The tail versus the dog
Side hustles are supposed to enable freedom, fulfillment, exploration, and income-generation; that’s why we pursue them. If your side hustle is stifling any of those four objectives and tying your hands, you may have let the tail wag the dog — and you’re the dog. The only wrong way to construct your career and income streams is by creating one you don’t love.