Lessons From A $10,000 Mistake
Some mistakes are easy to spot, while others take months to reveal themselves.
This one unfolded over the last year.
It started the way so many good things do — with so much promise, and so much to be excited about. I met a potential client who was passionate, growth-minded, and ready to invest in her business. She had a compelling model, a pipeline full of opportunity, and a clear need for the kind of support I offer.
We kicked off with intensity. Built systems. Identified her bottlenecks. Rallied the team around a shared vision… The progress was real.
But payments? Her business always seemed to be “just one big deal” away from revenue that would pay all of us — herself, her team, her bills, and me.
At first, I chalked it up to growing pains. She was trying to stabilize the business and her personal finances. I’ve seen that before, and to be honest, I believed in her. So I extended grace. I kept coaching. I told myself the breakthrough was just around the corner — that she needed my help to earn the money to pay me.
It was a catch-22:
Keep coaching and accumulate a higher balance, hoping she’d become a long-term client who eventually caught up and got profitable?
Or stop coaching before she had the chance to become anything at all?
I kept going.
Today, I'm embarrassed to say she owes me over $10,000 in accumulated coaching fees.
Promises to pay have come and gone. I’ve paused our sessions. I’ve initiated collections. It feels terrible, and it’s not what I ever want this work to be. But when a business is bringing in revenue and still choosing not to pay its obligations, there’s a deeper issue — a clear misalignment in priorities, values, or readiness.
On paper, she was almost perfect.
Smart. Scrappy. Open to coaching. Hungry to grow. She had a stellar business model and high-margin services that should have predicted half-a-million dollars in monthly revenue.
But over time, the gap between potential and follow-through became clearer — and wider.
And that gap cost me serious time and money.
The hardest part?
She was so close to being the kind of client I love working with — the kind I build my entire business around. And in some ways, that made it harder to walk away. But I finally had to ask myself:
If this client came in the door today — knowing everything I now know — would I still say yes?
No.
That was the moment things clicked.
Not every promising client is the right fit.
Not every relationship is meant to continue.
And here’s what I’ve learned since:
Dream clients don’t just bring good vibes — they bring alignment, readiness, and a commitment to follow through.
Red flags are easy to explain away. But when your gut whispers, it’s worth listening early.
You can’t be the hero of someone’s growth if they aren’t willing to carry their own weight.
Clearer systems and language during onboarding can help shape a good-fit prospect into a dream client — before the first invoice is ever sent.
(In fact, I recently calculated I could hit my entire seasonal revenue goal with just 3 new dream clients — or 59 average ones. That’s 20x leverage for working with the right people.)
The work gets richer, the value gets deeper, and the outcomes get bigger when you’re aligned with the right client.
And — of course! — get paid up front.
So here’s what I’m doing next:
I’m building a coaching business I’m proud of — one that delivers massive results, has crystal-clear expectations, and protects both parties.
I’m tightening my onboarding process, trusting my intuition, and continuing to evolve my structure around the clients I’m best equipped to serve.
And it’s exactly why I’m intentionally creating space for my next few dream clients.
If you or someone you know is an ambitious business owner ready for clarity, systems, and strategic growth — I’d love to talk.
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Always learning,
— Andrew
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