WorkPlay

Misunderstood Celebrations for Entrepreneurs

Small business milestones that your friends and family find perplexing.

Happy birthday to my small business.

On July 9th, 2022, WorkPlay Solutions officially turned one year old.

🎉🎉🎉🎉🎉🎉🎉🎉🎉🎉🎉🎉🎉🎉🎉🎉🎉🎉🎉🎉🎉

As a solopreneur, how should I celebrate my corporate birthday?

Reflections on the first year

When I recalled the moments that filled me with gratitude or enthusiasm, I realized the significance of these moments does not translate well to anyone with a “normal” job. But if you have leaped to become an entrepreneur or small business owner, you get it.

The life of a solopreneur can be lonely. Your friends and family don’t know where your time goes or why you grind so hard. There are no coworkers to high-five or congratulate on a job well done. There are thousands of details and tasks to complete, and the days can run together. With that in mind, I invite you to join me and celebrate the unseen glory of small business ownership.

Birth

Awwww. He has your mother’s eyes. And your father’s tax ID.

Dad jokes about my boss (me)

I found this stage of entrepreneurship irresistible. Any time someone would invite me to something, I would comment in a conspiratorial tone about how my terrible boss was making me work late. They inevitably asked in confusion, “Don’t you work for yourself?”

Yes. It’s me. (Awkward chuckle).

I’m convinced every solopreneur goes through this terrible dad joke stage.

Font paralysis

The mental train wreck when I started preparing my first estimate for a potential client:

(Stares blankly at the computer screen, not sure what app to open)

Wait, I don’t have a document template for estimates.

Wait…I don’t have a logo.

OH DEAR LORD, I DON’T EVEN KNOW MY FONT!!!

I am not proud of the paralysis I experienced. My wife just looked at my catatonic shell and said, “Doesn’t everyone just use Times New Roman for everything?”

Ahhhhhhhhhhhhhhhhh!!!!!!!!!!!!

First $$$

First thing I sold? I’m glad you asked. I designed ten sets of PVC Catapults for a university student orientation. We fired eggs at a target in a big field.

Happy Holidays

Uh oh. It should have been obvious. But it came as an uncomfortable Labor Day surprise. I don’t make any money if I get sick or go on vacation.

Social media magic

I’m not too fond of social media, but I feel obligated to use it to promote my business. I learned Instagram but put a fork in Twitter.

Pod famous

A few months after launching WorkPlay Solutions Podcast, I was in our local coffee shop. I had just ordered an iced coffee when a stranger turned toward me. She said,

I know that voice.

Where do I know that voice from?

Oh, I listen to your podcast!

She never said she actually liked the podcast. But, it was my first and only 10 seconds of creator stardom.

My first NDA

I signed my first Non Disclosure Agreement. Or did I? You’ll never know.²

Count the pennies

Starting the business reinforced the value of purpose, mission, and joy in your career. For eight straight months, I worked 40+ hour weeks, didn’t pay myself a dime, and loved every minute of it. I’m thankful for my amazingly supportive wife and her willingness to keep the family financially afloat on only her income for so long.

What about you?

I’ve shared some of the most meaningful moments in my first year as an entrepreneur. What is important to you?

Footnotes

¹ I hid the first footnote in one of the pictures. Can’t find it? Go back and re-read very, very slowly.

² My business coach told me, “Future clients may look at you poorly if you joke about Non-Disclosure Agreements.” He’s probably right. But it’s my birthday. 😎

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