10 Lessons from 10 Years of Being My Own Boss

Pregame Group Session-3

As of this month, I’ve been my own boss for 10 years. TEN YEARS! I deserve a promotion.

It wasn’t my original plan. I was laid off during the recession, and ended up landing freelance clients. In order to start a business bank account, I had to form an LLC, and thus Pressler Collaborative was born.

I hate working from home, so I rented an office. (Fun fact: I was the very first person to move into the first WeWork on their opening day!) With an address and a bank account, things were starting to feel pretty official.

I’ve worked solo; I’ve managed a team. I’ve had zero clients; I’ve had too many clients. I’ve worked until 10pm; I’ve worked from Mexico.

When I opened Pregame three years ago today, running a business reached a whole new level with the responsibilities of having a physical location, employees, and the corresponding bills bills bills. I’ve been in bootstrap startup mode for 36 months straight, and it’s been the biggest rollercoaster of my life.

I can’t say I never looked back; I’ve been through at least three stretches of actively looking for employment. Nothing great materialized, and before long a new, exciting client would come along and pull me back into my business.

I was never chomping at the bit to escape corporate America. I loved every job I had and thrived as part of a team. I don’t romanticize or glorify entrepreneurship; it’s merely one business game some of us have to opportunity to choose.

I’ve learned enough for a book, but as a founder in startup mode and the editor of this magazine, I haven’t quite had the bandwidth yet to write it! So in the meantime, here are 10 eye-opening lessons from my first decade as the Boss of Myself.

1. Being Your Own Boss is a Platform for Self-Discovery
Want to see all your strengths and flaws up close, like microscopic-close, and not be able to escape them or blame someone else? Welcome to entrepreneurship, the journey of profound personal responsibility! Self-management demands a level of honesty that’s not for the faint of heart.

2. Vacations Cost Double
As a small or solo service business, if I’m out of the office, the business isn’t running. During vacations, I’ve either charged my clients less, hired someone else to cover for me, or just brought the laptop along for the ride.

3. Your Schedule is Flexible, and Also Not Flexible at All
Same as #2, if I’m not in the office, it’s not getting done. So taking that long lunch or doctor’s appointment can mean throwing off the whole company. And after 10 years, my friends and family still don’t quite understand that I can’t just spontaneously leave at 3pm or chat for an hour in the middle of the day. I try to take the interruptions in stride and remember that being adaptable is a good trait to develop.

4. Even if You Only Work 40 Hours, Your Brain is At Work 24/7
Capacity isn’t about hours serving clients, it’s about brain bandwidth. The ideas and task lists and business minutiae start swirling in my brain from the moment I wake up until I fall asleep, because I care. It takes a persistent effort in self-care to manage the mind when in entrepreneurial mode, so it’s vital to build in daily practices like meditation, sleep, and exercise.

5. Get Your Money Right
Separate your personal finances from your business finances.
Pay yourself a consistent salary.
Put money aside for taxes.
Replacing your salary is not enough; factor in your expenses.
Charge more than break-even.
There will be slow periods.
The slow periods will pass.

6. Don’t Spend It Till You Get It
They’re not a client until the check clears. Related: some people may skip out on their bill, and it might be inconvenient, expensive, or even impossible to track them down. WHATEVER I’M OVER IT NEVER MIND.

7. Doing What You Do and Running a Business That Does What You Do Are Two Different Things
If you want to cook all the time, get a cooking job, do NOT open a restaurant. A healthy business spends at least 25% of its time working ON the business instead of IN the business – that means marketing, sales, operations, and more. If you aren’t up for it, get the benefit of working for a company with a team.

8. It’s Really Nice to Get the Credit
When my company wins, I get the recognition for the win. That’s pretty awesome. I’ve also been taken much more seriously in almost every business setting. Not to mention opportunities for press coverage, speaking engagements, and awards.

9. You Will Appreciate Your Former Bosses
Even the bad ones, none of whom seem all that bad in retrospect. I realized that it’s impossible to know all the perspectives necessary to making difficult decisions from your seat as an employee, and you have much less at risk. I actually wrote an apology letter to an old boss for being a pain in the ass… maybe I should have cc’d the others!

10. There is No Formula for Success
This is actually #1, no matter whether you’re an entrepreneur, entry level professional, or stay at home parent. If you want a formula, get a formulaic job. If you want a template, open a franchise. Being in charge is a series of judgement calls, and the destination is always somewhat unknown. Get comfortable with that and enjoy the journey.

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