Entrepreneurship: Like Skydiving Without a Parachute… But With Way More Paperwork

Welp. It happened. Layoffs. The kind where you stare at your screen in disbelief, then immediately stress-eat everything within reach. And suddenly, I was faced with a decision: do I dust off my resume and jump back into the 9-5 grind? Or do I do the thing I’ve been daydreaming about for years—dive into my own creative business full time and hope for the best?

Long story short—I took the leap. I am now officially my own boss. Which is equal parts exhilarating and what-have-I-done terrifying.

Who Needs a Boss When You Can Be Five People at Once?

On the plus side, I never have to sit through another soul-draining meeting where Joe from accounting explains yet another system I will never use. The downside? I AM Joe now. I am also HR, sales, IT, and that intern who forgets to order more coffee.

This wasn’t part of the dream, by the way. The dream was me, sipping coffee in a perfectly curated home office, effortlessly signing new clients with a brand new fine point roller ball pen. Reality? Me, at 2 AM, Googling how to write invoices while questioning all my life choices.

The 3 AM Freakouts Are Free

Let’s be honest—starting your own business is scary. One day, you’re just a person with a cool idea. The next, you’re trying to figure out taxes and debating if you really need an LLC or if you can just wing it (hint: maybe don’t wing it).

There are 3am moments when I stare at the ceiling wondering if this is all a mistake. Should I just go back to a job with health insurance and an IT department that fixes your computer when it starts making weird noises? Maybe. But also... no.

Because then, miraculously something incredible happens—I land a client. Someone actually wants to pay me for my work. And suddenly, the fear takes a backseat to excitement.

The Learning Curve is a Lie (We’re All Just Figuring It Out)

Let’s be honest: nobody knows what they’re doing. I will undercharge. I will overcharge. I will end up designing a logo at 2 AM because I didn’t set proper boundaries. But I will also wake up every day knowing that every single thing I do—every spreadsheet, every awkward call, every “please, dear client, pay your invoice” email—is building something that’s mine.

And that? That makes it all worth it.

Should You Take the Leap?

If you’re thinking about it—do it. Yes, it’s scary. Yes, you will have moments of sheer panic. But also? You’ll never have to ask for PTO ever again!

And hey, worst case scenario? That sarcastic greeting card empire I’ve been dreaming about is still on the table.