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1323 6th Ave N.
Nashville, TN, 37208

The Skillery is a Nashville coworking space with resources and programming for freelancers, entrepreneurs, small teams and independent professionals, all aimed at making work meaningful, satisfying and unabashedly fun.

Entrepreneurship, and the weight of doubt

Blog Posts

Welcome to our blog, where we share stories and profiles of the entrepreneurs and events that call The Skillery home.

Entrepreneurship, and the weight of doubt

Nicole Keiper

Next month, I’ll be celebrating five years of being my own boss. (I’m a freelance writer, and working with The Skillery is part of what I do.) It’s worth celebrating — I’m proud, and thankful, and still a little amazed. The latter mostly because I went into self-employment thoroughly terrified, and carrying the weight of a false start on my back. 

About seven years ago, I walked into my boss' office in the newsroom at the local daily paper, and quit. I had no plan, no savings. I had no safety net. But I was miserable, and I really wanted to not be miserable.

After two sleepless, anxiety-ridden nights, I walked into my boss' boss' office, and — tearfully and contritely — asked for my job back.

I admit this with no small degree of embarrassment. It wasn't an experience that made me feel powerful or bold or focused or capable of launching my own business. But it’s probably worth admitting anyway, because I’m pretty certain I’m not the first person with entrepreneurial hopes who kept buckling under the weight of her own doubts. 

I’m also not the first person to find a way around those doubts.

. . .

The process of working up the nerve to take the entrepreneurial/self-employment plunge is, I imagine, vastly different for every one of us. We’re coming from different backgrounds, with different expectations and needs and thus, fears. Short of a huge financial buffer — and probably even including that — there’s nothing that can totally erase those fears. But something that helps: finding and leaning on mentors and fellow entrepreneurs.

It seems obvious, but for a lot of us, the idea of striking out on our own feels necessarily … alone. We focus in on the work and the business and the industry, and try to tamp down the conflicting emotions. But building a foundation that helps support us emotionally can be just as important as one that supports us financially.

It’s hard, being self-employed. Every task is your task, every problem is your problem. And your boss can get pretty demanding. Having people to turn to — people who’ve done what you’re doing, who’ve been where you’ve been — can make a huge difference, first in giving you the confidence to take the leap into entrepreneurship, then in giving you needed moral support as you move forward.

It never gets easy, even if it does get easier.  

When I finally did make the leap, I wasn’t altogether leaping — I was shoved, via a pink slip. I wish I could say I had an epiphany and a jolt of confidence and, head held high, jammed my flag in the ground. But, as it happens, I was sniffling into a glass of whiskey while former colleagues consoled and encouraged me.

Ultimately, it was their encouragement that got me to move forward on my own, and stop sending resumes out. And it wasn’t blanket encouragement, but their encouragement specifically — these two former colleagues sat where I was sitting a long while back, made the choice to go solo, then built up a client base, replaced and surpassed their salaries. They’d done what I wanted to do, and had a long list of things that did and didn’t work that they were more than willing to share with me.

They were also willing to help if I felt lost, answer questions, pass my name along, hold me up a little while I was feeling shaky. And that, I think, is what silenced my personal doubt phase. It was getting rid of the “on my own” feeling.

Independence is beautiful, and it’s what drives a lot of us toward self-employment and entrepreneurship. But there’s independence, and there's feeling like you’re out in a raft in the middle of the ocean, straining your eyes for dry land. 

Friendly advice from someone who's had a long slowdance with doubt: Take time, before you cast off to build a support system, stocked with strong shoulders and welcoming ears. If you’re struggling to find others who get where you're at, feel encouraged to come by The Skillery. Our place is full of folks who've been there, and who are there, and — a point of big pride for us — are really, really nice.