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An illustration of a lacy underwire bra. Dana Rodriguez for Vox

The best (or worst) $20,000 I ever spent: The money to start a small business

If there’s one thing owning a small business taught me, it’s that just because you can doesn’t necessarily mean you should. 

When people tell me they’re thinking about opening a small business, particularly in a goods-based industry like fashion, my first question is, “Do you have money?” I don’t mean having savings or good credit or the knowledge of how to take out a loan, although those things certainly help. I’m talking family money, access to friends who will think nothing of loaning you six figures interest-free: that kind of money.

People at parties — or, these days, in my inbox — don’t expect this question. They tend to not appreciate this question. It is, in fact, one of the more abrasive questions I am comfortable asking total strangers.

But people tend to only approach me, seeking advice, after learning that I once owned a lingerie boutique for a number of years. They want to know the trick, the secret sauce, how I opened a well-known business with no money and no experience when I was in my late 20s and how I did it for four years. They want affirmation that their idea is a good one, the one that will land them on 30 Under 30 lists, that will definitely make them money. They aren’t too interested in why my own business closed — they just see that I am relatively young, queer, and that I did it, and so, obviously, they can, too.

Still, if there’s one thing owning a small business taught me, it’s that just because you can doesn’t necessarily mean you should.

I started a business for the reason so many people do: I had an idea that I thought could make a difference. I wanted my work to have meaning — and, on the cusp of having to write my dissertation prospectus, I was no longer finding that meaning in my English PhD program. Committing an unknown number of years to the pursuit of a degree almost guaranteed to not result in a tenure-track position seemed untenable. I started to look elsewhere.

Bluestockings, my e-commerce lingerie boutique geared to the LGBTQ+ community, was an outlier. The store, solely focused on stocking ethically made goods from indie designers, including kink-friendly and gender-affirming underthings, was one of those late-night, drunk-on-the-porch ideas that, by all accounts, should have been forgotten the next morning, lost to the heady summer nights of Boston. That I ran with an idea I was not qualified for and had no resources for speaks to my desperation to get out of grad school by any means necessary, but it also speaks to the extent to which I, still very entrenched in academia, had bought into the idea that I should do what I loved.

In Can’t Even: How Millennials Became the Burnout Generation, Anne Helen Petersen articulates how the longstanding desire for “a well-paying job” has morphed into the cultural prestige of “a cool job,” which she calls a distinctly modern and bourgeois phenomenon. The cool job is “a means of elevating a certain type of labor to the point of desirability that workers will tolerate all forms of exploitation for the ‘honor’ of performing it.” The cool job is one that can be defined by that famous, and at this point excoriated, axiom: Do what you love and you’ll never work a day in your life.

When you “love” what you “do,” there is a slippage between the work and the self. When do you turn off? When do you stop working, if your work is your hobby, what you always want to be doing? Academia is the kind of industry that Petersen, herself an ex-academic, cites as thriving on this slippage. But so, too, is entrepreneurship — MLMs, for one, but also retail businesses, such as Bluestockings, that require an extraordinary amount of time, money, and effort, all with the reward of LinkedIn titles like “small business owner,” one of those great American archetypes that politicians of all stripes so love to cite on the campaign trail.

Personally, I had no money, and with my working-class background, I came from a family with no money. I was deeply in debt, already divorced, and financially illiterate, having made no attempts to learn how to manage my finances in my mid-20s. Like my other millennial grad student friends, all from various class backgrounds, I had the attitude of, “I’m already in so deep — what’s more debt?” But I was also part of that peripatetic but highly educated “creative class,” and I wanted to do work that aligned with my values, whatever that meant. While I would have been better off looking for temp work or even simply taking on more hours as a nanny, which had supplemented my income throughout graduate school, I instead took on more than $20,000 in debt through credit cards and loans to start a retail business, not fully understanding what I was committing to.

I spent a lot of money to start Bluestockings, ostensibly to do something I loved, to make a difference. In this, I’m not alone: How many millennials have driven ourselves deeper into debt in the pursuit of work that was our “passion”? How many folks have gone back to graduate school or taken out loans to move to a big city for job opportunities? Gone into credit card debt trying to keep up with the lifestyle the industry they worked in required of them? In some ways, my story is unique; in others, it is profoundly similar to many of my peers.

These days, my relationship to Bluestockings yo-yos between ambivalence and shock at my naivete and hardheadedness. I ran the store on the leanest budget possible for four years, never once taking a paycheck. I ultimately closed the store in 2018, unwilling to drive myself deeper into debt and also wanting to focus more on my writing.

But then, it would be dishonest to discuss the hardships without also naming the blessings: I met some of the best, most enduring friends of my life through the lingerie industry. Bluestockings is what got me onto Twitter, a platform that would become integral to meeting still more queers, writers, and creatives over the years. I learned more about running a business (mostly through mistakes) than I ever thought possible, lessons that would translate to every kind of work I would do in the future. It was ultimately Bluestockings — not academia — that opened up the doors for me to work at tech startups in New York, leading to marketing work that would pay my bills for years.

And then there is, of course, the people who Bluestockings did reach, the folks I’ve met in gay bars and at queer camp who told me they bought their first binder from my store, that the photo shoots and blog posts helped them learn to appreciate their bodies and aesthetics in a world saturated by the Victoria’s Secret cis-hetero norms. There is that.

As with so many things in life, it’s a mixed bag. I don’t know that I would recommend going into a significant amount of debt for the sake of doing what you love if you don’t also have a plan to get yourself out. It is debt that, thanks to a very recent, very generous book deal, I am going to be able to pay off very soon. The business debt and the accompanying credit card debt that paid for my living expenses during that time will be wiped out, a clean slate, clearing up a significant chunk of my monthly budget that I won’t have to spend on credit card interest masked as a “minimum.” Luck is what that is, sheer fucking luck, and I am dearly aware of it.

It’s hard to put a price tag on one of the most formative experiences of my life. Couching it in binary terms of “good” or “bad,” “best” or “worst” feels simplistic and disingenuous, both. The store, and my experience of small business ownership, is like an old relationship that started with the highest of hopes and ended with a mortgage for a house I don’t live in anymore but am still paying off. There are good memories, to be sure, but would I do it again?

What an impossible question.

Jeanna Kadlec is the author of the forthcoming memoir Heretic.


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