I closed my small business after seven years in operation, and now I get a lot of outreach from fellow entrepreneurs who want to talk. Each time I sit down for one of these boss dates, thinking I am there to check in, to make space for a friend to vent and share, I find myself talking a lot. If you know me, you know I can easily do that, but in these moments it is in response to questions.
What I find is that others really want to hear about my experiences. Not the positive ones I polished to share, but the real ones that were scary, and that in the hardest moments I thought no one else could understand. In confidence, we recognize the fear and the hardship of ownership. The feelings you wrestle after giving everything of yourself and receiving so little in return. Whether it’s a missed paycheck or a skipped day off, the biggest subsidies that support small businesses come from the owners’ hearts, minds, bodies, and bank accounts.
Success (whether real or imagined), not transparency about the struggle, is what sells. As the face of a business, you must hold your head high and always answer the “how’s it going” questions with something synonymous to “great!”. But more often than not, this is not the truth. The truth is it’s hard as fuck, lonely as hell, and especially since the pandemic changed the rules to the game both socially and economically, a lot of days just suck.
Trust me, my brave friends, despite the depths of loneliness you are feeling, you are not alone. That doesn’t make it easier.
I’m starting to feel like a small business therapist. Am I qualified for this? I’m not sure. But I’m willing to give it a go because these are my friends and former colleagues. They are some of the most inspiring people I know, who wake up every day and give their energy to our local economy. They believe in the future of their small businesses. And perhaps the most important work these owners do is to lead others–their employees, customers, and community–to do the same.
A few weeks after I closed my business, I lent a chef-friend my hand saw so he could finish cutting up a whole hog when his broke in the middle of butchering. In our brief, yet way-too-long-for-a-sidewalk talk (I definitely would have invited him in if I had known we’d get caught up baring our souls), we commiserated about how hard it can all be, and he shared his plans for improvement. Between details about new programming that would hopefully grow the business over the coming season, he told me he knew that he couldn’t go back to what he was doing before–when he was working so much that at one point he was awake for ninety six hours.
Four days straight. That’s about about how long I was processing the fact that my friend was standing in front of me to tell the tale, after pushing himself that hard and that far. A part of me was in awe, but more than anything I wanted to call him up, sit him down, shake him, and say, “Slow down. Don’t burn out like me, because the day you can’t keep going, we all lose.”
What, you might think, could be important enough to put off the most-basic form of self-care—sleep—for four days? If you’ve never owned a business, felt the true fear of what might collapse and fall without your constant work, attention, and support, then you won’t understand. I once shared with another one of my boss pals that I had started wearing a mouthguard thanks to grinding my teeth at night from stress1. He volleyed that he had already been there, done that, and had woken up from a stress dream having bitten his mouthguard in half. I have had so many versions of conversations like these over the years. I repeat, you are not alone.
I frequently share advice with other owners that I learned the hard way; you have to take care of yourself so you are able to keep showing up. And I usually get the same response I always gave, “I know”. We know, but we don’t act as if we do. When you are the fuel and the fire behind a thing, if you stop, it stops. You are not an employee. Your shift never ends. We preach about sustainability and the communities we support, then dismissively say “I know” when told we need to physically and emotionally support ourselves. We’ll get to it, after the work, which must get done at all costs.
In a conversation over dinner with a mentor-friend, I confessed something I had been feeling as I processed the closure of my business; I began to doubt that small, sustainable food business models like mine could ever thrive. It wasn’t just me. Nearly every small business owner I know is struggling in some way, trying new strategies, staying awake for 96 hours straight to follow through on them, and wearing themselves down in the process. We give so much more than we take, hoping it will make a difference. And it does, but will it ever be enough?
My friend responded that in her work as a sustainable and local business advocate who supports and encourages entrepreneurs, she sometimes fears she is leading us all over a cliff. I assured her, we are all going to jump anyway. When someone tells you it’s a long way down to fall, you’ll probably just reply “I know”, because what’s behind you isn’t working either, so how bad could the leap be? If it doesn’t kill you it will make you stronger.
I can tell you from experience, that it helps to have a hand to hold when you’re scared before you jump, and to have someone who checks up on you to make sure the fall didn’t break you. If you’re out there working to sustain a small business: Take care of yourself and remember, you are not alone.

I’m going to assume that the majority of you reading along are not small business owners. If this prompts you to ask the question, “What can I do?” The answer is simple: Go out and support local businesses. It matters.
As we arrive at the season of peak consumerism masked as tradition, please don’t do your holiday shopping on Amazon. Take a stroll down main street in your town and stop into the boutique shops and sustainable food stores your neighbors own, visit that holiday art fair, or consider giving an experience, like a gift card for dinner at a local chef-owned restaurant. If you must shop online, make sure to order directly from small businesses—so many of them now offer shipping (because they have to if they stand a chance of keeping up with the man—and yes, I’m referring to Jeff Bezos).
It’s important to always remember that you are the customer, which means you hold the dollars and the power. You can choose to use them to prop up your local economy so it will continue to be there for you in the future.
My Latest…
Reading
Parable of the Sower and Parable of Talents, written 3 decades ago, tell the story of a dystopian, post-apocalyptic future caused by the accidental collision of climatic, economic, and sociological crises. And it begins in 2023. Buckle up, friends! If you’re starting to get worried about me because it seems like I’m living in a state of doom and gloom, know that I found myself thinking positively at one point, “Well, at least it’s not this bad!” I kid, but not really. I tucked into these books deciding it was far past time I got to know Octavia Butler and I’m sure glad I did. They had me thinking long after I turned the last pages.
“All that you touch
You Change.
All that you Change
Changes You.
The only lasting truth
Is Change.”
This newsletter, “slow living is destroying our productivity” from
, was one of my favorite short-form reads of the past week, and certainly on topic for what I was writing. Something that often comes up in business therapy chats is how overwhelming it can feel to keep up, like you’re building the plane while flying it. As a once proud hustler who is now trying to find self-compassion and peace in just being, I loved these thoughts on slow living:“What does it say about our culture that we view slowness and productivity as mutually exclusive? And then I thought . . . No wonder we’re all burnt out.”
Watching
American Symphony is an intimate documentary about life, art, and finding the strength to carry on. It is an insanely beautiful depiction of spirit and work of John Batiste and his wife, Suleika (I also recommend you follow
here on Substack). The film was just released for streaming on Netflix. I highly recommend you watch it and marvel at what these two souls have generously shared.It’s been a good week for movies in my house, and Brad and I loved Nyad, which is also streaming on Netflix and stars Anette Benning and Jodie Foster (whose performance gave me Taxi Driver vibes. I think we’ll re-watch that soon). I’ve been swimming a lot. It’s become one of my most important rituals of self-care, serving both my body and mind. I was inspired to finally join a lap pool and build up my strength since every time I find myself staring at a lake or body of open water, I think “I want to swim across that”. So you won’t be surprised that this film really spoke to me.
Thanks for being here,
Heather
P.S. If you’re a paid subscriber you can join in the comments (which keeps the community in and the creeps out). I look forward to chatting there!
This was during a period of time when I had the responsibility of funding, building, and then moving my business to a new facility, on top of my seven-days-a-week job of being the owner-operator of a whole-animal butchery. The pain got so bad it sent me to the dentist.
Thank you for putting this all into words. I feel every one of them in my tired, inadequately cared for body.
I know this story all too well. Thank you for sharing Heather 🫶