“Be Your Own Boss,” They Said

A few months ago, while playing with filters on Instagram, I came across the “In 2021, I Should…” predictor. A roulette-style generator of “fortunes,” I decided to record my real-time reaction to my randomized fate. Drum roll, please! 

It read…“Start my own business.” And the (now-saved) evidence shows a true facial expression of “oh, hell no.” I rolled my eyes, laughed, and exasperatedly exhaled, “I don’t feel like it.” 

After an energy-sapping year of self-isolation, social restrictions, and widespread loss, this response felt natural and warranted. Many of us are pretty tired! Still, it made me wonder if I would have felt the same sans pandemic. 

My instinctive answer: Probably. 

I’ve often felt good at lots of things, but great at nothing. That mindset makes it difficult to envision myself as a business owner, because I’ve long equated entrepreneurship with being a foremost authority and exemplary master in your field. Additionally, the prevailing “be your own (girl)boss!” culture—you’ll know it by its millennial pink color scheme—attempts to convince us that becoming an entrepreneur is solely a matter of drive, not desire. 

The prevailing ‘be your own (girl)boss!’ culture attempts to convince us that becoming an entrepreneur is solely a matter of drive, not desire.

I imagine it’s a bit of both, if not a true need. People choose to become entrepreneurs for a multitude of reasons: Their ideas are too unconventional for a corporate setting; their lifestyle is too unpredictable for a 9-5 schedule; their skillset has been deemed obsolete by an overarching entity. But there are just as many justifiable reasons that people choose not to. Entrepreneur itself reports that building your own business can be more lonely, unsure, expensive, and time-consuming than the alternative.

The deciding factors, according to New York-based mental health counselor Natalie Capano, can be our personal values. “Values around work differ between people,” she says. “While some scoff at the idea of working under someone, others crave that stability and structure. Some people strive to make as much money as possible, while others just want to pay their bills and live a comfortable lifestyle.”

What I crave, I’ve learned, is a space to express my creativity. The setting in which I do that isn’t of utmost importance. At least not right now. That’s not to say I won’t ever be drawn to an entrepreneurial life, but routinely checking in with ourselves and our current circumstances can be key to helping us determine whether it’s a good fit now, or ever.

Clinical psychologist Nancy Irwin offers a few questions we can ask ourselves if on the fence:

  • Am I more comfortable leading or following?

  • Do I thrive on “good stress” or feel overwhelmed by it?

  • Do I take obstacles, set-backs, and “failures” as debilitating or as challenges?

There’s more! Forbes encourages us to question our tolerance for pain, response to uncertainty, and ability to self-motivate. Huffington Post also insists that we evaluate our comfort levels with risk, rejection, and sacrifice. Our true feelings toward entrepreneurship likely lie in whether we view these inquiries as unwelcome stressors or exhilarating challenges—because the lifestyle can arguably be more rewarding and liberating, too.

Ultimately, we must get honest about our personalities and where we’re truly comfortable.

While I ideate best alone, I can get nervous when presenting those same creations without any assistance. (I assume this means I need a hand puppet or ventriloquist dummy or something? IDK. Help!) And without any educational background in business, I can also feel ill-equipped and overwhelmed by the basic logistics of starting one. (Something, something, supply and demand?)

I know, however, that entrepreneurs have successfully done much, much more, even with much, much less. And when my responsibilities change, so might my perspective.

We need to acknowledge that there is always power in being an invaluable, reliable cornerstone of a community or team.

Until then, to counter the belief that entrepreneurship is a better life rather than simply a different one, we need to acknowledge that there is always power in being an invaluable, reliable cornerstone of a community or team. Ultimately, if everyone were a leader, who would they be leading?

“We live in a culture that tends to give all the props to the ‘stars’,” says Irwin. “But the introverts who quietly work behind the scenes serve vital roles. Any good entrepreneur will acknowledge this.”

Instead, we can become passionate hobbyists and gentle goal-setters. We can seek out mentors and embark upon intrapreneurships (in which, within an organization, we’re given the support and autonomy to innovate ideas, processes, and products beneficial to the company). We can invest in others’ projects and offer our services for equity. We can be someone’s inspiring muse or steadfast foundation.

We can rethink what self-worth means and untie what we do from who we are.

And we can rethink what self-worth means and untie what we do from who we are

We can find fulfillment outside of entrepreneurship because nothing and no one is sustained without support. This means we can, and should, take pride in listening to our gut instincts, taking mindful inventory of our goals, and prioritizing ourselves while helping others. 

There’s so much honor in that.


Danielle Cheesman was born and raised in New Jersey, where she lived until moving to Philadelphia to study journalism at Temple University. She has spent her years writing and developing editorial visions for music, art, and lifestyle brands. Now residing in Los Angeles, you can usually find her taking pictures, making playlists, or cuddling her pup. Say hi on Instagram!