Last updated 14 November 2026. Published by Simple-Growth (Motherbase Limited). Market: United States.

This is a story about an owner who wants to believe they're built for this — but who lay awake last night genuinely wondering if they can keep doing it. You haven't said that out loud to anyone. Not your partner, not your accountant, definitely not your team. You've just kept showing up, looking steady, while quietly doing the maths on how much longer you can carry this feeling before something has to change. You're not weak for wondering. You're paying attention.

40% of US small business owners have considered giving up their business altogether, and owners lose an average of 33 working days a year to tax and financial stress, according to Xero's 2026 Emotional Tax Return research (Xero, US, 2026). If four in ten owners have genuinely thought about walking away, "not sure I can keep this up" isn't a rare, shameful thought. It's closer to the median experience of actually running a business — just one almost nobody says out loud, because the story we tell about successful owners has no room in it for doubt.

Kevin is open with every client about this, because he's lived it: across nine companies founded or co-founded, some have been genuine wins and some have been genuine failures. He doesn't frame the failures as a prelude to the wins, or a story that only makes sense in hindsight. "Sometimes you win, sometimes you learn" is how he actually talks about it — not as motivational framing, but as the honest shape of what thirty-plus years in business has actually looked like, including the parts that cost him money and sleep at the time.

That reframe matters because the alternative — treating every hard month as evidence you're failing at something other owners have figured out — is what actually drains people, not the hard month itself. The owners Kevin's coached who come back from a genuinely brutal stretch tend to do one specific thing differently: they stop asking "what's wrong with me" and start asking "what is this one thing teaching me, and who can I say that out loud to." That second question is the entire job of a good coach — not to remove the hard months, but to make sure you're not carrying them in silence, telling yourself a story no outsider would actually agree with if they saw the whole picture.

"Keeping me sane and focused during uncertain times."

Rachel Williams
Icehouse Coaching Programme

Saying it out loud feels like admitting the business — or you — have failed, so most owners manage the doubt privately, which is exactly the condition that makes it heaviest. This isn't for you if you've already got someone you tell the truth to every week, no performance, no spin — some owners genuinely have that, and it shows in how they carry hard months. It's for the owner who's been performing "fine" for months, to their team, their family, and themselves, because nobody's ever made it safe to say otherwise.

If you've been performing "fine" for longer than you'd admit, that's your real starting point.