From Suits to Sweatpants: My DIY Journey from Corporate America to Being My Own Boss

In 2013, I left the cushy confines of Corporate America—the endless meetings, the jargon bingo, the HR-approved bagels—and decided to become my own boss. Spoiler alert: It’s been a wild ride. Think less Shark Tank and more Survivor: Home Office Edition. 

The Corporate Escape

It all started with that itch. You know the one. It’s the “What am I doing with my life?” itch that no amount of quarterly bonuses can scratch. One day, I realized that I was spending more time daydreaming about starting my own business than paying attention to spreadsheets. (Apologies to Excel enthusiasts everywhere.)

So, I quit. Bold, right? But here’s the thing no one tells you about leaving corporate: it’s not like the movies. There’s no slow clap as you walk out with your cardboard box. It’s more like, “Wait, who’s going to do all the work I hate doing now?”

DIY or Die Trying

Starting your own business is like trying to assemble IKEA furniture without the manual or those tiny Allen wrenches. But instead of a bookshelf, you’re building your livelihood.

• Marketing? You’re now the Chief Marketing Officer.
• Finances? Congratulations, you’re also the CFO.
• Cleaning the coffee maker? Guess what, you’re janitor-in-chief too.

I’ve Googled more “how to” questions than a college freshman. (Yes, I have YouTubed “How to create an LLC” at 2 a.m.)

From Panic to Progress

The hardest part of being a DIY entrepreneur is that it’s all on you. The best part? It’s all on you. Every victory, big or small, feels like winning the Super Bowl—except there’s no Gatorade shower.

I remember landing my first client and thinking, “Wow, this might actually work!” Then I had to figure out how to invoice them without looking like a total amateur. Shoutout to Google Docs for having my back.

Lessons from the Front Lines

1. You Can’t Do It All: You might think you can, but spoiler alert—you can’t. Hire help or barter services. Trade your graphic design skills for someone else’s bookkeeping expertise. It’s like a business potluck!
2. Imposter Syndrome Is Real: There are days when you’ll feel like a fraud, but remember, everyone’s making it up as they go. Even CEOs Google stuff. (How to make a PDF is probably the most recent search in a CEO's web history history).
3. Celebrate the Wins: No one’s throwing you a pizza party, so throw one for yourself. You booked a client? Nailed a pitch? Survived the week? That’s worth celebrating.

The Sweatpants Life

Sure, I’ve traded my tailored suits for sweatpants, but here’s the truth: I’ve never been happier. There’s a thrill in building something from scratch, even if that something is held together with duct tape and late-night coffee runs.

Being your own boss isn’t about perfection—it’s about persistence. It’s about showing up every day, figuring it out as you go, and laughing through the chaos.

So, to anyone thinking about leaving the corporate world to go DIY Entrepreneurship, my advice is this: Jump in. The water’s fine. Just don’t forget your floaties.

And if you fail? Well, at least you’ll have a great story to tell on your podcast, when your next endeavor is successful. 

Cheers to the hustle!