Considering Quitting Your Job To Pursue Your Side Hustle? Ask Yourself These 4 Questions First

I’m an INTPB&J—which is to say, I don’t subscribe to personality types.

I can’t say I think there’s any one type of job that better suits people with certain personalities, or that people need to pick a career based on their personality types. And I certainly don’t factor my personality type into my own career choices.

That said, I believe there are some personality types that might be better suited to certain careers. I’ve freelanced and I’ve full-timed, so I believe I have some perspective on what kinds of personality traits might make someone better suited to one or the other. To figure out if self-employment is right for you, consider your answers to the following questions.

How Much Stability Do You Want?

Full-time jobs provide an undeniable sense of stability. There’s no such thing as true stability (I say it constantly, because I mean it), but freelancing requires being comfortable with more uncertainty than you need to accept in a full-time position. If the idea of having several periods of unemployment per year makes you queasy, you might not want to be a freelancer. Maybe your side hustle should stay your side hustle—and there’s a lot to be gained from that.

It’s about more than personality or personal preferences—you may be in a situation in which your own career instability affects other people, and for what reason, freelancing can add extra stress.

Are You A Self-Starter?

Freelance requires a degree of self-starting that might not fit your personality type. It’s not accurate to say freelancers are hustlers while full-time employees are not; I’ve had plenty of full-time jobs that required a constant hustle. I’ve also had freelance jobs that were relatively chill and involved sending a few emails per day.

What is true, though, is that downtime when salaried can simply be downtime. You are still paid your salary. Downtime when you’re a freelancer costs you money. If you don’t use that time to find a new project, you pay for it. That’s not always a bad thing—many people get into freelancing for the increased downtime, and many are comfortable with the pay cut it requires. But it might not be the perfect fit for you, and if you don’t want to use your downtime to seek out new projects, freelancing could be tricky.

How Patient Are You?

Being a full-time employee requires you to stick with unpleasant circumstances for longer. Some companies offer opportunities to transfer teams or locations, but it’s rarely a guarantee. If you hate a coworker at your full-time job, there’s very little you can do about it. In my experience, the people you most want to leave are the least likely to do so. I call this the Annoying Paradox—because it’s annoying. And a paradox. People stay at jobs for an average of four years, so waiting for someone you hate to up and quit is a slow strategy that will likely lead to disappointment.

As a freelancer, your jobs are temporary—whether you like it or not. If something isn’t working out, you don’t have to stick with it for too long. As a highly impatient person myself, I love the chance to constantly move onto the next thing. If you want to be able to quit easily when something is bad, freelancing might be right for you.

Are You Humble?

Don’t answer that—it’s tautologically impossible to get right.

It’s also the wrong question. The right one is: what type of humble are you? There’s a level of humility required of both freelancing and full-time work—possibly because being human is a humbling experience (not to be too graphic, but someone once changed your diapers). For freelancing, you need to be humble enough to ask for more work opportunities constantly. For full-time jobs, you need to be humble enough to let your boss direct your work. Also constantly.

That’s not to say all bosses are tyrants who will tell you exactly what to do at every moment of the day, or that freelancers are forever begging for the glorious chance at employment. Rather, unless you’re running a company, you have somebody managing you at a full-time job, and unless you’re insanely in demand, you have to ask for more opportunities as a freelancer. It’s a matter of what you feel comfortable being humble about—would you rather ask for more, or be asked for more? Which is more tolerable?

It’s not as simple as saying freelancers are commitment-phobes and full-time employees are corporate sheep, though I do love sweeping generalizations like that (and why are we so rude to sheep?). Before deciding if freelancing is right for you, consider the answers to the above questions. Sometimes, I think the right career for me is retirement—and honestly, I’m probably right.