NICE TO MEET YOU, I'M SELF-EMPLOYED

Even though around 1 in 10 Americans are their own bosses, self-employment is still widely viewed as something of a novelty. 

If you’ve introduced yourself as self-employed at a party lately, you probably felt some pressure to explain what that means, exactly. Given the rise in misclassified gig workers post-COVID, that title can feel almost unintentionally deceptive: it could describe a self-made millionaire, a Lyft driver, a part-time Etsy artisan, or someone who would rather not admit they’re between jobs. Then there’s you. 

Just like every vegetarian is frequently expected to explain how they get enough protein, the world has questions for the self-employed. In a culture where working for someone else has been the norm for generations, being in business for yourself can sound risky, impractical, or — worst of all — like a cute little idea. 

If the question “What do you do for work?” brings up feelings of insecurity or defensiveness, you may be unknowingly getting in your own way. How you show up, put yourself out there, and own your role has a demonstrated effect on business outcomes. In other words, that unaddressed imposter syndrome can undermine you in real time. 

While you’re still struggling to feel like the qualified leader that you are, making a plan for how to field questions about your decision to become self-employed can boost your confidence and help you get excited to talk about your business. 

Here are our favorite scripts for handling the questions that used to make us feel sheepish in a way that welcomes good conversations about employment, fulfillment, and the future of the modern workforce.

The Self-Employment FAQ

Q: Is this something you’re doing while you look for permanent work with a new company?

A: Especially if you took up the mantle of solopreneur following a layoff, people may assume that your choice is a band-aid in a tough job market. Freelancing your way through a job search, planned hiatus, or a change in life circumstances is a completely legitimate path — and so is never looking back. 

The best thing you can do for your business is get clarity on your own intentions and operate accordingly. If you’re in it for the long haul, you will only hinder your growth by continuing to entertain options that don’t align with what you want. 

Q: How can you manage without benefits?

A: Most people rely on their employer for paid time off, a savings plan, and insurance. While it’s true that the self-employed have to source these things for ourselves, it’s rarely the insurmountable obstacle that it’s made out to be. 

Because solopreneurs have control over their own rates, we’re able to build in margins that cover the cost of self-employment taxes, 401(k) contributions, and self-pay insurance. Depending on existing medical needs, health sharing plans can be a viable, less-expensive alternative to marketplace insurance coverage. 

In the same vein, the autonomy that self-employed folks have over their schedules makes taking time away a simple matter of preparation. Where traditional employees have to submit a request to use a limited amount of PTO, we’re empowered to set our own vacation dates, work ahead, and go. 

Q: What about the gap in your resume? 

A: The work that you do while in business for yourself is the most authentic, representative work you’ll ever do. While adding “self-employed” to your resume with no further details will definitely come across as more suspicious than mysterious, it’s completely legitimate to spotlight companies you’ve partnered with as a contractor. 

In addition to client relationships, freelancers are also continuously building a portfolio. Should you decide to return to traditional employment in the future, you will have both your body of work and proof that you can manage the daily operational needs of a small business in your favor. 

Q: What will you do about your complicated taxes? 

A: Freelancers have to put more thought into tax strategy than W-2 employees, but with the right help, roughly two-thirds of self-employed people successfully file their own taxes. 

Freelance-focused accounting resources like FigWealth.io give solopreneurs a leg up on how to approach estimated tax payments, what can be claimed as a business expense, and how to protect assets. If you’re in the habit of simply waiting for your net direct deposit to hit your account, self-employment will force you to have a much more intimate understanding of your expenses, earnings, and financial goals. 

Q: How can you tolerate being alone all the time?

A: Many people who choose to go into business for themselves are at least somewhat motivated by the fact that they don’t enjoy working from a crowded office. That said, even those of us who used to dread unnecessary meetings and team-building events do need community.

For those who crave an in-person work environment, co-working spaces are a great way to get out of your home office on your terms. For mentorship, camaraderie, and inspiration, however, freelancers have to be intentional. 

Dedicated networking spaces like the Yacht Club can facilitate that crowd-sourcing, meme-sharing, second-opinion-getting vibe that self-employment often lacks. Remembering that there are around 16.5 million freelancers in the same boat makes it easier to find ways to be alone, together. 

Q: Aren’t you worried it won’t work out? 

A: Any rational person will have moments of self-doubt. The big misconception underpinning this question is that traditional employment is inherently more secure than self-employment. 

Especially in “at-will” employment states, everyone faces the possibility that their current income source could suddenly go away. Moreover, while it’s a nice professional courtesy, private-sector employees aren’t legally entitled to severance — or even a recommendation. 

Because freelancers are in the habit of constantly soliciting work and usually work with several clients simultaneously, there’s arguably more security in self-employment. At the end of the day, we all have to stay agile. 

Own Your Choices; Own Your Business

If explaining your life as a self-employed person makes you feel squirmy, remember that most questions are statements in disguise. People who feel restricted to a familiar path will be naturally curious about people who don’t. 

Keep promoting yourself and your business like you mean it — even on the days that don’t. You never know who may be looking for your permission to view employment differently.