Business Life Lessons — What Matters Most When You’re In It For the Long Haul

(me, a few years into my first business — then, a decade later and a few years into my second)

I was scared as hell.

I'd been laid off again, and this time I had decided to turn my freelance moonlighting into the real deal and give this dream of full-time self-employment a fair shot.

I'd set up shop in my bedroom closet and was two months into my “design business for real” and determined to prove myself worthy of the EIN and business license I’d gotten to make it all legit.

Getting enough clients to keep it legit was another matter… 

At that point I was only doing a couple hours of paid work a week and spending the rest of the time trying to flip the equation. Back then the glamor of entrepreneurship was a glimmer; hustle culture wasn’t a lifestyle, and “online business” meant you worked on a computer and emailed people.

Mine is not a rags-to-riches story

With all the privilege that came with being a Western-born, middle-class white girl, I already had a leg up. Plus, I was ramen-for-dinner young, newly married, no kids or debt so even though it felt otherwise, in hindsight the stakes for failure were marginally low. By God's grace I stumbled my way across some wonderful mentors, and I plugged away, and even if I didn't know where I was going half the time, I went.

In the ensuing years there were lots of great clients and some lousy ones…interns, employees, contractors, a business partner…

I laughed. I cried. I made people laugh and cry. And things kept growing little by little over the next 12 years until one day about five years ago, it was time to part ways with the business partner and do a new thing.

A pivot. 

And I was scared as hell again.

It’s been 17 years now into this full-time self employment thing, and I don’t have it all figured out—in fact, that’s a huge reason WHY I love business because the learning is never-ending. But I’ve logged enough time in the trenches to understand what really matters. If I could tell my younger self all those years ago what I know now, man… I’d have saved myself from a lot of stress and pointless toils at the keyboard.

Here are my top 5 Business Life Lessons:

1. Do the best you can with what you know at this point in time. 

Will you do it better 6 months from now, 2 years from now? Probably. But don’t wait until you think you do know more.

2.  Entrepreneurship is the greatest journey of self discovery. Ever.


It literally took me YEARS to come to this realization, and it wasn’t through my own sudden brilliance. Someone practically had to hit me over the head with this fact. When they did, I honestly felt… stupid. Of course. In what other context does someone willingly, constantly put themselves at risk for ridicule and rejection with the intention of helping others and the hope of making enough bucks to put food on the table? Acting? Comedy? Politics?

Yes, being in business for yourself involves all that and more. Truly, treat yourself being business with the care and compassion you deserve. It doesn't matter how big your business gets or how long you’re in it—it's always personal.

3. These 4 M’s are make-or-break for any business: mindset, message, market, and money.

Mindset – get your head in the game (it all starts here and always starts here)

Message – get your story straight (you have to be able to communicate your value online and in real life)

Market – get in front of the right people (know what they need so you can know if what you have is what they want)

Money – get comfortable with it and your books in order (so you don't operate in ignorance or in the red)

4. It takes as long as it takes you. 

At some point in your business journey you’ll see some of your peers skyrocket to stardom. You’ll see others who never quite make it off the ground. You’ll set your sights on goals a mile high and miss them a mile wide. You’ll experience seemingly out-of-the-blue wins. And all the while you might feel like it’s taking years—YEARS!—to generate the kind of joy and profit you dream of. 

First of all, remember Business Life Lesson #2: you’re on a journey and your journey is your own. 

Secondly, only you can know what your “enough” looks like. Don’t define it by someone else’s.

5. It takes a village to raise a business.

I don’t believe in solopreneurship. 

You can be a business of one, but you can’t do business alone. All the times I’ve floundered and failed and stagnated were the times I wasn’t in a community, didn’t have a mentor or mastermind, and/or didn’t have biz besties to keep my head on my shoulders and my heart from falling off my sleeve. 

Community solves an infinite number of problems that come up in business. 

Community is what turns the mundane into magic.

We live in a time where it’s easier than ever to put yourself into communities of support and collaboration—online groups, business networking, programs, courses, coaching—so I hope you’ll go out now and find yourself one if you don’t already have it. 

These Business Life Lessons certainly don’t capture it all but these are the ones I find myself coming back to when I find myself swept up in the rush of the day-to-day and need to anchor into what really matters. I hope you’ll find them grounding as well—whether you're new to entrepreneurship or nonprofit leadership or seasoned—and bolster your efforts to grow a business that's successful and sustainable over time. 



Have a comment? Or a specific question about what you just read?

Email me—I really will respond. I love getting email from readers, and I’m happy to give you a quick strategy or tip to make sure you’re rocking your message and your marketing feels fun and productive!

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