Living with Constant Discomfort as an Entrepreneur
What they don’t tell you about the road less traveled.

When I visualized becoming a full-time entrepreneur, I imagined it unfolding much like a regular job.
Getting a job has a certain rhythm to it: Apply for work, interview, get a job, celebrate, train for the job, execute job solo, grow in experience, continue with the job until you promote, terminate or retire.
So, I honestly thought that starting a new business would follow a similar pattern with the same steady feelings that a regular job created. That by following known, logical steps, I could pretty quickly create the same security that a regular job provided.
Steps such as: create a business idea, make a business plan, get needed training/funding, open brick and mortar (if needed), market the business, get first customer, gradually grow customer base, expand business, continue with business or plan exit strategy.
Sure, I knew there would be unknown challenges such as lean economic times, poor vendors, difficulty getting customers, possible theft/fire…. And I have experienced many of those setbacks.
However, what I didn’t realize was the constant, never-ending inner discomfort that results from choosing the road less traveled.
Every morning I wake up and I don’t know how much money I’m going to make. I don’t know if I’m going to make my bills on time. I don’t know how the day will flow or if I will get any business. I have no idea if the work I’m doing is actually making a difference or if I’m just pissing in the wind. I don’t know where I’ll be 5 years from now… I don’t even know where I’ll be next week. And will I eventually go bankrupt or will I pull a Hail Mary out of my hat?
When I had a regular day job, I had a steady paycheck and a budget that I followed. I timed my bills to my paycheck, and I kept my bills manageable. I knew when I took time off because it had to be approved in advance.
Sure, there were unknowns such as illness and random expenses. But, for the most part, I knew where I was going to be next week and next month and next year. “Every Day is Exactly the Same” by NIN was my anthem.
Now I get up when I want, I take a day off when I want, travel when I want. I have a tremendous amount of freedom. I am bound by No One.
But where I am headed and where my business efforts will end up is completely unknown. I want to be SET, SECURE in my financial stability. But I’m not yet there with my entrepreneurial endeavors.
So sometimes I peruse the want ads. I think about going back to work for The Man. I fantasize about set paychecks and benefits and paid time off and the comradery of coworkers all stuck in the same boat.
THIS is the MEAT of the sacrifice of the road less traveled. THIS is the hardest part of the journey. Every day for almost two years, I’ve digested these fears and worries and concerns while foraging ahead without a known outcome. Living with the unknown and continuing to stay in the unknown is the hardest path I have ever taken.
It is highly uncomfortable with every fiber of my being. From when I wake up in the morning to when I fall asleep at night — it is always there, niggling at me like a hair in my eye that never goes away.
And I am all about comfort. I rarely wear high heels or pants because dresses and flats are a thousand times more comfortable for me. Is it any wonder that I have considered opting out of this self-imposed journey on an almost daily basis?
However, I know that I know that if I succumb to the all-encompassing comfort of a traditional job again, I will bathe and wallow in it. The motivation to stretch and push me in new directions will disappear faster than you can say W-2.
While my current path is vague, it allows me unlimited potential. While my business could sink like a stone, it could also take off beyond my wildest dreams. And that is what keeps me going on this crazy path. Living in the unknown brings unknown outcomes. And since I greatly desire a life that goes beyond a set income and two-weeks’ vacation a year, this is where I find myself.
From where I sit today, the sky is the limit. There is no glass ceiling. I could create a winner that takes off and provides safety and security (while maintaining my freedom and traveling lifestyle). I could create a business that’s better than any job I’ve ever had. It’s all there and available to me — the possibilities are truly endless.
But so is Failure. Its existence is the fuel of my chronic discomfort. Success has always come easy to me in a regular job: You do your work, keep your head down, and don’t make waves. With being an entrepreneur, you’re not succeeding UNLESS you’re making waves.
And, so, I choose to sit with this discomfort for days, weeks, months, years. It is NOT an easy price to pay. It is NOT for the meek or timid.
But I continue because the dreams and passions of my heart are worth it. The benefits that high success could give my friends and family are worth it.
And, most of all, I’m worth it.
