Reflections of an Accidental Entrepreneur (On Reaching a Milestone)

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Ten years ago, if you’d told me I would one day be an entrepreneur or a business woman, I would’ve cringed. Either term sparked mild revulsion in me, even when applied to someone else. I never thought I’d one day claim both labels, and do so with pride.

I’m an accidental entrepreneur. As a child, I never had a clear picture of exactly what I wanted to do for work or where, but having a “cool job” has always been one of my two lifelong dreams. I started working when I was 16 and I’ve had some very cool jobs besides the ones on my resume: selling clothes at the mall, providing night security, driving passenger vans, dancing with a band in Mexico and desert farming. My favorite jobs rocked because of the dynamite combination of awesome people plus interesting tasks. One standout was a temp job in my twenties where I spent my days transcribing cassettes of school psychologists’ notes and ROFLMAO at my two coworkers’ silly antics involving latex gloves and motorized toys.

Inevitably, either the tasks stopped being interesting (when I’d learned all I could and there was no room to grow) or the people stopped being awesome. They stopped being awesome by leaving or changing – especially my bosses. It took me years to understand that my eventual clashes with most of my bosses weren’t because I was wrong or a bad employee, but because most people in power are uncomfortable supervising people smarter than them – especially if those people are more loyal to their own integrity than their boss or the organization.

Five years ago this month, one such clash motivated me to leave my last traditional position and relaunch my business. I’d started it in Mexico 14 years earlier, but hadn’t been full time in ten. Like the last time I went full time, I relaunched with a “let’s see how this goes” attitude, thinking maybe it would be temporary, or a bridge to some as-yet undiscovered “cool job.” But I’m still here, and I just hit a major milestone this month: Year Five. First-and second-year success rates of new businesses range between 20-80% depending on industry and structure. However, the consensus is that only half of new businesses make it to five years. Half!

I’m increasingly a member of a select minority, and I’ve leveraged several unearned privileges to get here. My parents gifted me their brains, a love of reading and learning and their teachings about dogged self-reliance. My father received money from family that helped him buy a home in a decent neighborhood with trees, low crime, and job opportunities. I’ve benefitted from having white skin. My college-educated parents encouraged me to go to college. A small inheritance, received after my mother and grandmother died within a few months of each other, funded my graduate school studies.

I’ve benefitted from unearned privileges to get here, and I’ve also faced unfair barriers – especially as a woman. I’ve had to deal with sexism as long as I can remember. I didn’t even like being female until my late twenties – I hated the male oggling, the not being taken seriously, and the way smart, capable female classmates faked incompetence to be liked. Sitting in my high school English class, watching such a scene play out, I made the conscious choice that if I had to choose between being liked or being respected, I would choose the latter. I figured that path was more in integrity and more likely to effect real change over time. It’s been an exhausting path, and while I now try to come across as likeable and competent, having that clarity has served me.

I’ve faced other barriers to business success I often underestimate. Even though I’m White, and reasonably middle class, I’m a pioneer. Neither my mother nor grandmother worked for pay. I’m the only female on either side of my family to earn a graduate degree, and arguably the only professional. My father was the first in his working-class bloodline to attend college, and he earned a Master’s from CalTech. I was the second person to earn a graduate degree, and my brother and I are the only cousins on either side of the family to do so. My family wasn’t particularly healthy or nurturing, and I’ve suffered from mental illness since I was a child. Also, I’ve had to support myself since age 18, and got through college thanks to small scholarships, my Citibank visa and up to three jobs at a time.

In short, I had no role models and little capital – social or financial – to set me up for entrepreneurial success. No one taught me how to run a business, build relationships or manage money. No one showed me how to manage office politics, go after what I wanted, dress professionally or make the uniquely difficult life decisions women must make to succeed. It hasn’t been easy, and I’ve made mistakes I regret, but I’ve learned from them. I’m still here.

I became an accidental entrepreneur because I was driven by a vision and values beyond the specifics of any particular “cool job.” I wanted the freedom to choose when to work, what to work on, and with whom. I wanted to do something meaningful where I also excelled and enjoyed myself. I wanted variety and power over the important decisions that impact my life. I wanted to enjoy rewards proportionate to my brilliance and contribution. And I wanted to all this with integrity. Even at the outset, when cash flow was left of zero, I turned down engagements with clients I didn’t respect, or who requested services I didn’t feel comfortable providing. It’s one thing to have values when your bank account is healthy – it’s quite another when you’re hurting. But staying committed to integrity with clients and partners has paid off in more joy and peace of mind, and an excellent reputation.

It hasn’t all been easy or pretty, but it’s all been good. No work, choice or life is 100% problem free. The real question is – what kind of problems do you prefer? (Or in the wise words of Mark Manson, what’s your favorite flavor of shit sandwich?). I far prefer the occasional client frustration, technical snafu, internet troll, travel exhaustion or cash flow issue over boring tasks, toxic coworkers, workplace politics, ineffectual bosses and income ceilings.

Not only that, I’m proud to be part of a growing movement of people taking full control of their work lives – of women taking control of their whole lives. In fact, women-owned businesses consistently outlast male-owned businesses, and our average revenues are growing. With all that I’ve learned, and all the benefits the entrepreneurial life brings, I’m feeling inspired and confident about being among the 30% of businesses who make it to Year Ten. Perhaps if I apply the same clarity, integrity, curiosity and patience that have served me in business to my love life, my second lifelong dream will be fulfilled by then too!