Corey Wilks, Psy.D.

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Is Entrepreneurship Worth the Stress?

A few weeks ago, I got a short letter in the mail:

The Tennessee Department of Revenue was going to take me to collections and dissolve my business because I didn’t pay my taxes.


Entrepreneurship—solopreneurship in my case—is overwhelming and filled with uncertainty on a daily basis.

There’s so much you have to keep track of, so many things you have to get done, so many open projects that could take weeks or months to come to fruition…it’s easy for little things (like paying your taxes) to slip through the cracks.

My LLC is my main source of revenue. So if I can’t do business, I can’t make money. And everything I’m currently building, and the courses I already have out, would have to be taken down or they could be ceased by Tennessee.

By the end of reading the letter, I was sweaty, nauseous, and was sure my blood pressure had doubled.

But wait, I thought. My business is registered in Kentucky, and I have a CPA that handles all that. Why is Tennessee threatening to dissolve my business and ruin my credit?

After a series of emails and a few sleepless nights waiting for an answer, it ended up being a simple clerical mistake. Long story short, I used to have a business in Tennessee that I dissolved years ago. But for some reason, Tennessee’s systems hadn’t updated my information.

Two days after getting that panic-inducing letter, everything was taken care of.

But fuck, was that a stressful two days.

If entrepreneurship is so overwhelming and uncertain, and periodic panic-inducing experiences like this are just par for the course, why would anyone willingly sign up for this particular brand of torture?

Great question.

Something happened this week that resolidified why I choose entrepreneurship despite all the stress and uncertainty…

A few days ago, my girlfriend went to bed early because she felt unusually tired. Three hours later, she was in excruciating pain, running a high fever, and couldn’t keep anything down (I’ll spare you the details, but you get the picture).

I felt fine, so we weren’t sure what was going on with her.

She tried to ride it out, but her symptoms eventually got so bad, she needed to go to the hospital.

Could it be appendicitis? Food poisoning? Or something worse?

Her fever and dehydration were the most worrying symptoms.

It was the sickest I’d seen her in years.

So at noon on a Wednesday, I drove her to the hospital to figure out what was wrong.

I didn’t have to ask my boss for permission, worry about what my coworkers would think about me leaving midday, calculate if I had enough sick time saved up to take off, or commute 45 minutes from the office back home to take care of her.

I just left. Because I’m my own boss, I don’t need anyone’s permission.

I had the freedom to take care of a loved one on my terms.

She’s fine, by the way. It ended up being a vicious stomach bug. Some meds and IV fluids to address her symptoms and she got discharged that evening.

This is why entrepreneurship is worth the stress and chaos that comes with it.

Yes, I could’ve talked about how being an entrepreneur is cool because I get to meet awesome people, buy cool stuff and call it a business expense for a tax deduction, take a vacation whenever, work from wherever, productize my knowledge, get paid to share my thoughts, etc.

And all that’s true. Entrepreneurship can be cool as fuck.

But those things pale in comparison to:

  • Never again feeling trapped when a loved one needs you, but you can’t take care of them because your boss won’t give you permission to leave work.
  • The simple joy of walking out of my home office to make eggs and avocado toast with my girlfriend in the middle of the day (yes, we’re Millennials and avocado toast is delicious).
  • Having control over my time and having the freedom to spend it doing what I love, with who I love, whenever I want, however I want, wherever I want.

So is entrepreneurship worth the stress?

It’s a fucking rollercoaster of emotions, uncertainty, self-doubt, and white-knuckling your way through the day sometimes.

But I’ll gladly choose all that, because of the freedom that comes with it.

Because everything in life has a price.

We can choose to pay the price of freedom to have certainty, or we can choose to pay the price of uncertainty to have a chance at freedom.

What price are you willing to pay for the life you want to live?

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