The $50K mistake I made (so you don't have to)
A dear friend texted me Wednesday morning: “Heya… I’d love to catch up when you have time.”
He’s a former colleague from my Red Robin days. Both of us were executives who left within six months of each other to start our own thing.
We jumped on a Zoom the next morning, and for ninety minutes, we did something we rarely do: we looked back.
We laughed about the early mistakes in our entrepreneurial journeys. The false starts. The things we got embarrassingly wrong.
During the convo, I said:
“I wish we’d had someone like us back then. Someone who’d already done it. Someone who could’ve just told us where to start.”
I felt that in my chest.
Because here’s the truth: When you’re a successful executive deciding to leave and build something of your own, you’re surrounded by people who think you’re crazy. Or people who’ve never done it themselves. Or people selling you courses that don’t account for the fact that you’re not 25 and willing to hustle for pennies.
It’s hard to find people who’ve actually walked the path you’re on.
So you end up doing what we did: winging it.
And winging it cost us. Both of us. At least six months and for me, $50,000 in wasted effort.
Here are the three biggest mistakes we made. I’m sharing them because if you’re thinking about making this leap, or you’ve already made it and something feels off, these might save you the same pain.
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Mistake #1: We started with the logo, not the offer
The first thing I did after leaving corporate? I registered an LLC. Picked a business name. Hired someone to design a logo. Built a website with brand colors and a mission statement.
I felt productive. I felt official.
But I had zero clients. Zero conversations with prospects. Zero clarity on what I was actually selling.
My friend did the same thing. Six months later, we both realized: we’d built the packaging before we knew what was inside the box.
Here’s what we should have done first: talked to people.
Not networking. Not pitching. Just conversations. Asking the people we used to work with, the ones still in corporate, what they were struggling with. What kept them up at night. What they wished someone could help them solve.
Because your offer doesn’t come from what you think you’re good at. It comes from what the market actually needs and is willing to pay for.
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Mistake #2: We built businesses around what we’d always done, not who we actually are
I spent 18 years as a CIO. So naturally, I thought my business should be “technology consulting.”
My friend spent his career in tech leadership, as well. So he assumed he’d be a "Fractional CTO."
We were both wrong.
Here’s what we learned the hard way: Just because you’re good at something doesn’t mean you’re energized by it.
I wasn’t energized by technology. I was energized by helping leaders think differently, drive change, and build cultures where people actually wanted to show up.
My friend wasn’t energized by purely being an advisor. He was energized by building teams and de-risking tech investments for CEOs.
The business you build has to fit who you are, not just what you’ve done.
If you ignore this, you’ll build a second career that feels just as draining as the first one you left.
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Mistake #3: We tried to figure it out alone
This one hurt the most.
We were both smart, capable, experienced leaders. We’d built teams, managed budgets, solved complex problems.
Surely we could figure out how to start a business on our own, right?
Wrong.
The isolation nearly broke both of us.
Every decision felt heavy. Every setback felt like proof we’d made a terrible mistake. Every time we saw someone else’s success on LinkedIn, we wondered what we were missing.
We needed community. People who were a few steps ahead. People who could say, “Yeah, that’s normal” or “Don’t waste your effort there.”
But we couldn’t find it. So we had to create it ourselves… calling each other at random hours, swapping stories, cheering each other on.
It kept us sane. But it wasn’t enough.
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Here’s why I’m telling you all this:
After that Zoom with my friend, it reinforced something. The mistakes we made weren’t unique. Almost every expert I coach makes the same ones.
They start with the logo before the offer.
They build businesses around their resume instead of their wiring.
They try to figure it out alone.
And they waste months, sometimes years, circling before they find traction.
So I built something to fix that. Something free and has more substance than fancy formatting.
It’s called The Unignorable Business Blueprint, and it’s the guide I wish we’d had when we were starting out.
It walks you through the five foundational steps you need to figure out before you waste time and money on websites, branding, and business cards:
Identity — Who are you built to be, really?
Problem — What struggle do you solve for others?
Products & Services — How can you solve the problem?
Your Offer — What’s the ONE thing you could sell right now to get paid fast?
Your Channel — Where will you show up consistently?
It’s not a one-page cheat sheet. It’s an in-depth guide with questions a coach would ask you at each step, real examples from people who've done it, and a clear roadmap so you’re not winging it.
Again, it’s free.
Download The Unignorable Business Blueprint here →
And if you want to go deeper—if you’re ready to build this with coaching, community, and accountability—Patricia Wooster and I created The Unignorable Business Studio for exactly that reason.
Because experts like you shouldn’t have to figure this out alone.
Your coach,
Chris
