The Hardest Lesson I Didn’t Want to Learn in Business
- Uncategorized
- June 16, 2025
The Hardest Lesson I Didn’t Want to Learn in Business… My client defaulting on £3k they owed me, yet that was one of the best things that happened to my business.
And yet, I felt humiliated.
I didn’t tell anyone except my coaches at the time.
I remember lying in bed for two days, crying. Not the quiet, graceful kind of crying, the gut-wrenching, ugly sobbing kind. I felt exposed. Vulnerable. Terrified. I kept replaying the same thoughts: How will I cover my bills? What about the payments I owe? How will I pay my mortgage this month?
This isn’t about why it happened.
It doesn’t matter who it involved. The resolution? Yes, there was one, but even that’s not the point.
What is the point is what the experience taught me about business, boundaries, and the type of leader I want to be.
Lesson 1: In Sales, Boundaries Aren’t Optional
That situation forced me to confront something I’d been avoiding: the need for stronger boundaries. I’d been too flexible. Too understanding. Too available. I hadn’t yet realised that boundaries aren’t just for other people, they’re how we protect our energy, our time, and our financial stability. They’re how we build sustainable businesses.
I had to stop viewing boundaries as a rejection of others and start seeing them as a commitment to myself.
Lesson 2: Not Everyone Gets to Work With You
This was a hard shift to make. I’d always prided myself on being accessible, on giving people a chance. But here’s the truth: Not everyone gets to work with me. And that’s not arrogance, it’s discernment.
I started asking better questions on discovery calls, developed a clear set of criteria for who’s truly ready to work with me, and stopped trying to “rescue” people. I’m not your saviour, and you are not my project. We’re collaborators, or it’s a no.
Lesson 3: Red Flags Are Data
There were red flags from the beginning. Hints in their language, urgency that came from panic rather than intention, and evasiveness around finances. But I ignored them because I believed in their potential.
I’ve learned to stop betting on potential. What someone says on a call matters less than how they show up after they sign. If I sense misalignment, I trust that now.
Lesson 4: Payment Plans Need to Match the Relationship
One mistake I made was allowing payment plans to stretch well beyond our time working together. I thought I was being kind and accommodating, but what I was really doing was giving away too much power and too little structure.
Now, if a payment plan is in place, it’s within the timeframe of the container. That’s not cold, it’s clear. And clarity is kindness.
Lesson 5: This Will Happen. Plan for It
This kind of situation is almost a rite of passage for entrepreneurs. It’s not a matter of if, it’s when. And while that sounds grim, it’s actually freeing.
Once you accept that it might happen, you can prepare for it. You can tighten your contracts. Upgrade your onboarding systems. Get clear on expectations and reinforce them early.
Scaling your business means you’ll work with more people, and with that, the chances of a missed payment increase. Some people won’t share your values around integrity or financial responsibility. That’s not personal, but it does need a professional response.
I wouldn’t wish this kind of experience on anyone. It’s painful. It brings up deep stuff… fear, scarcity, shame.
But when it happens, it becomes a mirror. You’ll see where your systems aren’t strong enough, where your boundaries need work, and what you’re no longer available for.
It’s one of the hardest lessons I’ve learned. But also one of the most important.
And if it ever happens to you, I hope you’ll take a breath, stand tall, and remember: this doesn’t define you. But how you respond to it absolutely will.
And if you’ve ever struggled with selling or if it’s ever felt awkward or overwhelming, then my book More Heart, Less Hustle, is the book for you! You can find your copy here.
