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  • Caroline Ridgway

Accidental Entrepreneurship & the Will to Persevere

I am an accidental entrepreneur. My career path has been a bit disjointed. The overall trajectory has been up and forward, but not within the same job description or even sector. I did not have a years’ long dream of owning my own company. There was no business plan I carefully honed and nurtured. I am where I am because of life’s unexpected turns. In this, I’m sure I’m not alone.

There’s a dichotomy in the working world I struggle with. On one hand, throughout my education and most of my professional life to date, I followed the path laid out for me, and endeavored to meet external expectations. It was about working hard, achieving, moving up, earning more. The ambition of upward mobility. On the other hand, I’ve chafed against the constraints of a traditional office setting, and always felt deeply that life is and should be about more than the financial and practical necessities of needing to work for a living.

Reality has a strong tempering effect. Upward mobility is, indeed, a nice ambition. It’s frequently not attainable. Saying someone should follow their passions and do what they love for a living is only marginally viable as advice.

Our jobs economy is shifting ever more towards gig workers, contract employees, side hustlers, and freelancers. In some ways, this could be construed as a positive development. On the employer side, it’s undoubtedly less of a financial commitment, saving on healthcare and benefits for salaried employees. For the workers, it enables a lifestyle imbued with more flexibility and diversity, counterbalanced by a weighty assumption of risk. The COVID-19 calamity has given us all a more nuanced perspective on the ins and outs of remote work and digital communications.

A hashtag in prevalent current use by the restaurant industry, so I’ve seen, and likely others, is #TooSmallToFail. Its implication is clear. A throwback to the previous financial crisis and references to the banks as being too big to let fail. Now, of course, it’s small businesses on the chopping block. In this instance, global disaster has not been wrought by systemic financial mismanagement but by the confluence of a naturally occurring, if historically devastating, disease outbreak, and varying magnitudes of social, cultural and political hubris.

I don’t know what will happen to the small businesses. My family has owned restaurants in our little city for almost 50 years, withstanding hurricanes, recessions, skyrocketing food and labor costs, and the vagaries of the dining public. Will this do us in? If, as some say, restrictions are necessarily in place for another 6 months, or a year, or 2 years, I suppose I have to assume yes, we’re done. No small business could withstand such a scenario. So, do we then witness the total collapse of our small business culture, which has been the backbone of (pardon the vague political illusions) what makes America actually great?

What will happen to my little business? The infrastructure of which consists entirely of me, my laptop, a phone, and an internet connection. I worry that budget decreases and staffing cuts will make it altogether even harder to find mutually beneficial client relationships.

On the plus side, I believe in the fundamental importance of the written word. Now is a time to tell your story unabashedly. It’s a matter of survival. Tell your customers why they’re important to you. Share anecdotes about what those relationships have meant over the life of your business. Be unequivocal about your local (or broader, if that’s your scope) impact. Dig in, hang on, and speak up, because it matters. What matters less is how we all got to where we are. The extraordinary thing is the will to keep going.

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