The Depress(ing)ed Entrepreneur

I was a good student and a smart kid who did all the right things. I finished college with flying colors and even went to graduate school. Earning a master’s was incredibly challenging, in large part to undiagnosed and untreated anxiety and depression, made worse by strict deadlines and extreme workloads.

Despite the loneliness and incredible stress, there was always a clear path. Do the work, do it well, work hard, and you’ll get the rewards. The rewards- a published thesis, a degree- were supposed to lead to more opportunities. That’s how it works. That’s why I busted my ass, right?

I moved across the country, from Florida to DC, leaving everything behind to chase the seemingly endless list of museum jobs that the nation’s capital offered. I mean, there’s literally a museum on every corner. The same week I moved, a sequester took effect, a wholesale budget cut across the whole government. The museum jobs I sought were frozen.

But, I did the work. I got the reward. I wanted to level up. I applied for all kinds of jobs. Teaching at community colleges, writing for non-profits, entry level desk jobs, youth programming, support staff at schools…literally, all kinds of jobs. For months, nothing. I was even rejected from *volunteer* positions for lack of experience or the institution’s lack of budget.

I did eventually get a (very) low-level federal job with no room to advance but quit after just a few months because everything about it made me miserable. A superior (I had five immediate bosses) couldn’t remember my name and called me “honey.” A mouthy eighteen-year-old called me “sweetheart,” and said I should be grateful he did my job for me. Powerful men, men that run our nation, told me to smile and look happy when I was on my way to the bathroom. A sixty-year-old co-worker dragged me into a boss’s office after complaining about a throwaway comment someone made in front of me. This co-worked frequently made far worse comments but hated the kid he snitched on. My joints swelled from standing on marble floors and my sinuses revolted when I was on an outdoor rotation, switching between a 65-degree arid building and the 100-degree swampy humidity.

I left. I walked dogs instead, earning little money and a lot of dog bites, but at least I was free from petty drama. (But not condescending men- I have never been cat-called, harassed, or followed by men more than during this period of my life. One time, a man followed me in his car, offering me rides and commenting on my clothes until I hid and he got bored and drove away.)  

Graduate school taught me that I work best alone and on my own time. I wrote the bulk of my master’s thesis- 175 pages- without a single deadline imposed on me. I graduated from a three-year program in two and a half years. Some of my favorite days were spent in the library, poring over microfiche, or sitting in a café, furiously typing, perhaps across from a friend, also working on something. Recently, I wrote an entire sixty-thousand-word novel just for fun. I do not work well in an environment with forced meetings and micromanagement. “Find me a job where I can be alone and just get shit done,” I begged.

Around this time, miserable and depressed, I dug into an idea I had half-started in Florida: a teen girl magazine. For girls, by girls. I worked tirelessly building a business plan, website, ad campaign. The original idea was not overly successful, so I took a business class, changed the name and retooled. New name, new logo, new website, new everything. When I finally felt as though I was gaining some success, I lost everything. Through a bizarre series of events, literally a year’s worth of work- poof- gone.

I rebuilt again while working part time. If nothing, I was dedicated to making this business a success. I focused on hosting events. If nothing else, working with teen girls throughout college made me a great group facilitator. And I’ve always liked public speaking. I can make pretty much any topic interesting.

After countless missteps with selling my workshops to organizations, I decided to host my own workshops. To me, nothing felt more like an uphill battle than asking small-budget organizations for money, no matter how good the program is. Even a large budget organization that sells cookies but will remain nameless, laughed me out of the room for asking a measly $500 fee to host a half-day workshop for 25 girls, nearly three hours from my house, all materials included.

I took confidence classes, hired a business coach, bought books, said affirmations.  People who practice affirmations and positive mindsets seem to be rolling in abundance! The principles of attraction and abundance war with my anxiety and depression daily. Nothing seems to work. This is where I am, banging my head into the wall, over and over, at increasing speeds.

I’ve tried every single piece of advice that’s been given to me. Most of it is similar- “have you thought of calling this person or this organization?” I’ve called, emailed, followed up. I’ve tried mindset exercises, deep breathing. I’m in therapy and take SSRIs. I lean on my network.

I’ve even applied for plenty of “real jobs,” full-time jobs with benefits and security, where someone tells me what to do, and I do it, and I get paid the same every paycheck. Where I trade my freedom and anxiety for stability. Where there is a clear path to success, like the one I knew so well in graduate school. In theory, I am qualified. In practice, I am told I am not- that my experience doesn’t count, that I’m not qualified enough, that I am not a “good fit.”

I was rejected for "not having enough experience" by a job whose description LITERALLY, word-for-word, matched my resume. I was offered a paid internship, then had it recanted at the last minute- after I had given notice- for someone who already worked for the organization.

I am at my wit’s end.

I want to quit. My passion for empowering tween and teen girls hasn’t dulled at all. The business, though, wears me thin.

Deep down, I know comparison is the thief of joy, but it’s still painful to see people with an inferior product fly past me. It’s frustrating to hit so many dead ends- even with groups I’ve worked with for five years. It sucks when every possible partner is a fortress- schools, libraries, charter schools, after-school orgs, etc., that is terrified to spend money on a new, unknown quantity.

To hear “no” would be better than what I hear most often, which is nothing. It is silence. And it is deafening, even after five years of neglect.

And before I hear one more person say “just follow up, go volunteer somewhere, just do X,” I want to grab them by the shoulders and scream, “YOU DON’T GET IT.” In DC, prestigious volunteer positions have waitlists. I’ve been on them, I *am* on them- even after being told that I’ll never be hired by those places, because they don’t hire from their volunteer pool. In DC, the school boards are isolated fortresses. I’ve worked with the biggest one for five years on an annual project and still, no one can tell me how to get hired by a school. I emailed every. Single. Girls school. In the city every other month for two years to no avail- literally, not even a no, just a no response. And no, they do not allow outsiders to put up fliers.

It hurts my soul to work and work and work, creating wonderful experiences, promoting, only to realize that I must cancel the event because no one is signed up.

I am sick of being Sisyphus, pushing the boulder up the hill, only to have it crashing down on me over and over.

I’m tired and I’m worn out.

Now, I’m faced with a decision, do I keep pushing, keep trying to run free and make the world better? Or do I try- yet again- to get a “real job?” Do I bury that passion and that desire? 

Either way, I feel like a fucking failure.