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Happy Friday, {{first name | friend}}!
I saw a post few months ago that made me cringe.
An entrepreneur sharing how his business almost failed. How he couldn't pay his team. How he was sleeping 3 hours a night and eating ramen for dinner.
The whole thing read like a therapy session.
And here's the thing he was trying to do something smart. Share the real story. Be authentic. Connect with people.
But he got it completely wrong.
1. There's a difference between honest and helpless
Sharing struggles can build massive trust. When done right.
The problem is most people share struggles like they're still stuck in them.
"I was overwhelmed and didn't know what to do."
That's victim language. It makes people feel sorry for you, not trust you.
Better: "I was overwhelmed, so I had to get ruthless about priorities."
Same struggle. Different framing. One sounds helpless, the other sounds resourceful.
2. Focus on what you learned, not what you lost
Nobody wants to hear about your problems. They want to know how you solve problems.
Don't say: "We burned through $200K in six months and nearly went bankrupt."
Say: "We learned the hard way that runway isn't just about having money. It's about having enough time to figure out what works."
The struggle becomes a lesson, not a complaint.
3. Show the decision, not just the difficulty
When you share a hard moment, include the moment you decided to do something about it.
"I was working 90-hour weeks and burning out my team. I realized I was trying to do everything myself instead of building systems."
Then: "So I spent two weeks documenting every process and hired my first operations person."
The struggle sets up the solution. The solution shows your judgment.
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4. End with what changed, not what hurt
The point of sharing the messy middle isn't to get sympathy. It's to show transformation.
"That experience taught me to track cash flow weekly, not monthly. Now I see problems three months before they happen instead of three days after."
You're not the victim of your circumstances. You're the person who figured out how to handle them.
My take:
The messy middle is where the real story lives.
But there's a right way and a wrong way to tell it.
The wrong way makes you sound like someone who gets overwhelmed by problems.
The right way makes you sound like someone who gets stronger from problems.
Your prospects don't want to hire someone who survives difficulties. They want someone who learns from difficulties.
When you share struggles as learning experiences instead of sob stories, something powerful happens. People don't feel sorry for you. They trust you.
Because they know you've been through hard things and came out better.
Talk next week,
Stephen
P.S. This is exactly what I help clients with in business story consulting. We take the real, messy parts of building a business and turn them into trust-building stories. Not trauma dumps. Not victim narratives. Stories that show resilience and judgment.
