I Survived My First Year in Business: Notes to My Day 1 Self

Ah, the first year of starting a business—when every day feels like you’re building a plane while falling off a mountain hoping you construct a flying machine before hitting the hard, unforgiving ground. If I could grab coffee with the bright-eyed, bushy-tailed Day 1 version of myself, here’s what I’d say… aside from “buckle up, buddy!” 

Hey, You’re New to This—It’s Okay to Not Know Everything 

Listen, nobody starts out as a business guru. Not knowing everything from the get-go is part of the charm (or chaos). 

You will mess up, and guess what? That’s completely normal. I wish I was more forgiving of myself, because I took every minor mistake and error extremely personally, often falling into a pit of self-doubt as to whether I was cut out to do this. 

Each stumble is a step toward knowing what the heck you’re actually doing. Think of it as paying tuition at the University of Hard Knocks—eventually, you’ll graduate with honors in Getting Stuff Done. 

Sleep is Your Friend, Remember That 

You think pulling all-nighters is the secret sauce of successful entrepreneurs? Spoiler alert: It’s not. 

I was 29 when I started my company. Those long, college nights fueled by Monster Energy drinks and that procrastinator-energy surge you’d feel cramming for a final exam? Yeah, that doesn’t exist nearly a decade after undergrad. You’ll work 18 hour days, and you’re going to feel like garbage every moment. 

Burning the midnight oil night after night isn’t a badge of honor; it’s a one-way ticket to destroying yourself physically and mentally. Value your sleep as much as your busy-ness. 

Trust me, your brain—and your business—will thank you. 

You Built a Business, Not a Life Sentence of Busywork 

Creating a job for yourself where you’re the boss and the most overworked employee isn’t the goal, and I paid a self-development coach a lot of money to drive this point home with me so trust me, it’s the truth. 

Remember why you quit your 9-to-5? Automate, delegate, and for goodness’ sake, take a vacation. Build a business that works for you, not one that works you over.

Friends and Family Discounts? That’s a Hard No 

I’m as serious as a heart attack, but my friends (former friends at this point)— were my worst clients. 

I know you want to be nice, but here’s the deal: your mortgage isn’t going to pay itself with goodwill and exposure. Charging Aunt Sally full price isn’t mean, it’s business. Friends and real fans will support your work by paying what it’s worth. 

Freebies can wait until you’re the next big thing and can afford to hand out favors like candy. 

Besides, people change once money is involved. I have lost friendships because I went out of my way to accommodate a friend and they turned out to not be very appreciative and ended up taking advantage of your relationship. 

Master the Art of Sitting Still (Yes, Really) 

I call it the “Lounge Rule”, it means whenever I’m at an airport lounge (I know this sounds like humble bragging but seriously, fly as often as I do and you won’t care about that Amex Platinum fee) I spend no more than 15 minutes working, and spend the rest of my time not doing anything work related. If I can, I literally find a good seat, and stare out a window. 

This sounds odd, but there is a clear reason why I force myself to not do anything productive. 

In a world that never stops talking, learning to embrace silence is like finding an oasis in the desert. Meditation, mindfulness, just staring at the wall—whatever helps you clear the mental clutter. It’s not just about calming your mind; it’s about giving your best ideas a chance to get a word in edgewise. 

Not Every Chat is a Sales Pitch 

Yes, you’re excited about your business (and you should be!), but not every conversation has to lead to a sales pitch. 

Network to make genuine connections, not just customers. Sometimes the best business relationships start with a chat about the weather, not your product catalog. 

It’s All Worth It—Freedom, Baby! 

All the headaches, the learning curves, the “what have I done?” moments—they’re just stepping stones to something greater. 

The freedom to steer your own ship, the perks of calling the shots, and the satisfaction of knowing you built something from scratch make every challenge worth it. There’s nothing quite

like entrepreneurial life, despite its occasional resemblance to a rollercoaster you can’t remember boarding. 

Looking back, if I knew all this from the start, would it have been easier? Maybe. But then I wouldn’t have these entertaining stories and pieces of humble wisdom to share. Here’s to more learning, growing, and thriving in business. If you’re just starting out, take these tidbits to heart, but also remember to enjoy the ride—it’s one heck of an adventure.