Self Employment: Year One

IN case you’ve just tuned in, I opened a business last year. It’s a little upholstery shop in St. Paul that focuses on education (though I also offer services)

In that year, I’ve tried to fill my online presence with confidence and optimism, with enthusiasm for the journey, and gratitude for the uncertain future.


But if you know me in person, you know that reality was a lot more complicated.


A high school friend once told a story about his childhood dog. They put in one of those invisible fences, and every day the dog would test it, just to see if it was still there. Then, one day, he got a running start and barreled through, full steam and howling, hellbent for freedom, whatever the cost.

That’s how this year has felt for me. For years, I’ve tested the boundary of self-employment, gauging the danger before stepping back into the familiar. Are all my fears still there? Yup. All the reasons not to leap?? Yup. Scary scary scary. Better hang out in the yard.

But MAN I could see the other side, and it looked pretty good.

So last spring, I finally put my head down, got a running start, and barreled forward, yowling and wide eyed, hoping like crazy I could make it to the other side.

Self-employment is not for the timid or meek. I knew that this year meant getting up every day and doing something scary, meeting someone new, solving a different problem. I knew that all the planning in the world wouldn’t fully prepare me for The Unexpected. I knew that once I started, I couldn’t easily change my mind. To stand any chance of success, I knew I needed to be as visible as possible . . . and that I might fail anyway – not in obscurity, but with everyone watching, everyone knowing I’d tried my hardest and come up short. Who wants to do that?????

Let me tell you a couple things about Cynthia.

#1. I hate 4 way stop signs. I mean HAAAAATE. Like, I can occasionally get myself worked up a full day in advance about having to go through one, and will find ridiculously convoluted ways to avoid them. Why? Because I DON’T TOTALLY KNOW what will happen when I get there. What if I’m turning left but the other driver doesn’t see my signal? What if we get there at the exact same time? What if I wait too long and the other driver gets annoyed at me? What if they run it? What if I think it’s my turn but they think it’s their turn??? Do you see how stupid this is? And I know it’s stupid, but the heart wants what it wants, and my heart wants to know EXACTLY WHAT’S GOING TO HAPPEN ALL THE TIME AND TO AVOID POTENTIALLY AWKWARD SITUATIONS LIKE THE PLAGUE.

pizza and coke

#2. I love pizza. Especially free pizza. But if someone says, “I’ll pay if you call it in” then there will be no pizza. Because Cynthia hates the phone. And Cynthia REALLY hates talking to strangers. What if they can’t understand me? What if they ask me a tricky pizza trivia question I can’t answer? What if I just burst into flames and die right here?

#3. I studied classical music in college. Want me to memorize 5 Italian arias, 3 German art songs and a French folk song? No prob, Bob. But do not DO NOT ask me to scat or improvise in any way. Seriously. Not one bloody measure or I’m going to change majors immediately. Show me exactly what I’m supposed to sing, when I’m supposed to sing it, and we’ll all get along just fine.

The point is this: Cynthia is not a risk taker. I like my comfort zone and my well-laid plans. I despise uncertainty. If you need me, I’ll be hiding in the corner, hoping to avoid all confrontation, embarrassment or unstructured human interaction. (People are scary)

That would be why I spent 15 years trying to achieve my goals from the shelter of other people’s businesses.

Not surprisingly, it didn’t work that well.

Eventually, I had decide: keep hoping my goals would come to me. . . or put on my big girl pants and go meet them.

You guys, I still don’t know what happened.

One day I was reading, “You are a Badass” and the next thing I know, I’m giving my notice and typing up a business plan.

And like the initial climb and inevitable fall of a roller coaster, I spent a fair amount of time wishing fervently for a way to abort mission. Most days, my inner voice sounded like Edvard Munch’s, “The Scream.”

I always thought the right path feels intuitively, you know. . . RIGHT. But it’s hard to listen to your inner voice when your Fear of the Unknown is on full-volume banshee scream repeat.

But as the Anais Nin quote goes, ”

“And the day came when the risk to remain tight in a bud was more painful than the risk it took to blossom”

There simply came a day when I had to admit that I desperately wanted more.

Fortunately (or not) I’ve known enough self-employed people to know what I was in for. And I knew myself well enough to appreciate that this decision would stretch my absolute limits. I warned my husband that this year would be rough: for me,  for us, for our family. I repeatedly consoled myself: ‘It’s a two-year lease. Worst case scenario, you crash and burn for two years and then you quit.’ I battened down the hatches and dug in my heels.

This year took a super conscious effort, an act of will I hope never to repeat.

I called up SCORE and got a business mentor (she rocks)


I read and listened to motivational and inspirational books.

I drowned myself (and everyone else) in motivational quotes.

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I listened to songs like, “Confident” and “Firework” and “Superwoman” at full volume on shameless repeat.


You guys: I made a vision board.

I was seriously intolerable. Whether you care about upholstery or not, I talked your ear off. I exhausted my list of phone contacts, calling mentors in a panic when the shop was quiet. I constantly checked my bank account, doing the math on how many months until I was flat bust broke.


One morning in September, when everything seemed to be breaking and the universe was almost certainly conspiring against me, I sat at a stoplight, gripping the steering wheel and screaming, “LISTEN UP UNIVERSE!!!!!! I’M NOT F@#&*NG AROUND HERE!!!!!!”

I’m sure I looked as crazy as I felt.

Then I stopped by Workhorse Coffee and bought a Pfeffer.  Congrats on surviving another day, scared out of your ever-loving mind. Yay!


I never planned on owning a business. I’ve heard these wonderful stories about born entrepreneurs who always knew they wanted to own a business, even if they weren’t sure what that business might be. Maybe they own one business for awhile, and then go try some other completely unrelated business.

I’m sorry, WHAT??

I’ll tell you right now: If I close up shop at the end of my lease, I’m never owning a business again. I opened this business because I wanted THIS SPECIFIC BUSINESS to exist. And I wanted to work there.


And even for this business, it’s been a stretch. This year, employment has been all-consuming.

I’ve been a mediocre wife, a disconnected mom.

I’ve been a terrible friend and a completely negligent housekeeper.

I stopped sleeping, threw up, and lost weight.  Then I stopped working out, started eating garbage and gained weight. Even when I DID make it out for a run, I spent most of the time mentally balancing the checkbook.


I kept a stress journal and downloaded guided meditations to my phone.


When my mom retired, I cried behind her shop, feeling scared and alone, ashamed that I’d put my family at financial risk by chasing such a foolish dream. . .


Why am I sharing this?

Because I think transparency is gift that we give to each other.

It’s so easy to pop onto social media and think that everyone out there is braver and prettier and richer and happier than us. It can be so demoralizing. I think the truth is empowering.

I’m sharing this in case someone out there needs to read it.

In case someone out there is thinking they’re not brave enough or extroverted enough or smart enough. In case someone out there is scraping together enough courage to run at their own invisible fence, whatever that fence might be.

I want to tell you: You’re braver than you think. You can be scared and do something anyway. You can learn things, you can meet new people. You are who you choose to be.

Maybe I’m sharing this because I need to admit how scary this year has been. By business standards, the risk was tiny. By Cynthia standards, it was almost insurmountable. I ran through fire to get here.

And you know? I’m still standing.

Not just standing. DANCING. Because I’ll tell you, it’s pretty good on this side of the fence. My teeny, tiny business is doing okay! I’ve met all kinds of awesome people!! I no longer wake up in a panic (most nights) and I’ve started to run again, woo hoo! I’m restoring balance in my home life (though my house is still a mess).

Most importantly, I’ve learned that so many of my limiting beliefs were a mirage. I’ve cultivated strengths in myself that I never expected to possess. 


I don’t know where this road will take me, but I like the view looking forward. . . And no matter what, I’m glad I started traveling this strange new path. It’s changed me and I like this Cynthia better. She’s still afraid, but her fear isn’t running the show. One day at a time, she’s struggling to be the person she really, wants to be. . . And she’s getting there.







6 thoughts on “Self Employment: Year One”

  1. I hope you will share this articulate, personal, powerful piece of writing (and your soul) broadly. I’m filing under #womenyoushouldknow

  2. That spoke directly to me. So needed it. I’m still in the throes of this damn hard day after Day grind. I do all the same things you do to get up day after day with a new view. It’s so hard.

    1. Hello Mary,
      I’m glad this resonated with you, and thank you for leaving a comment! I’ve sure needed to hear from other self-employed people this year . . . I do hope things get easier for you bit by bit. Your website is lovely!!!! We’re headed out to Theodore Roosevelt National Park next month, I see places in Jamestown and Fargo to purchase your product! Looks like an excellent breakfast option for our family to take out on the trail 🙂 🙂 Best, Cynthia

  3. Thank you for posting…. I have been battling that fence and so afraid to bolt past it. My husband has been pushing me but I step back every time. I have lots excuses but you gave me a new insight and I thank you.

  4. Bless you for stepping out and sharing Cynthia!
    I have been in business for self for 20 years. The first 3-4 years were contract with clinics. I started my own business name from a home base in a friends house, moved on to a clinic starting over in a new region and 10 years ago I was on top of the world opeining my first location down town. I had a receptionist, brought on another therapist. Brought on a number of contract people, went on maternity leave twice. Kids are in school and I have a chiropractor working with me now. I’ve seen some great years. 20 years in and I feel I’m rebuilding and reorganizing and I’m tired.
    I love what I do but sustaining a business on my own is lonely and not really fulfilling.I’m either busy or distracted. I want to make a difference in a big way.

    The past summers have been better with the mide set of “I’m resilient to that which does not serve me.” I know money comes and goes but it has to flow. There will always be enough. I just wish I had the opourtunity to do more good with it.

    Thank you for stepping out of your shell to share what we all feel when we go into business. We need to focus on the time freedom that comes with not being tied to a boss you pays our bills.

    We need to be intentional on our business actions, be intentional on family time, be present and intentional on time for self!

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