What I couldn't promise my wife Tabbi...

(Formerly The AI-Powered Business Advisor)

_{Issue #5 — February 03, 2026}

My wife Tabbi and I were sitting at the kitchen table. A stack of bills between us.

We had just signed a mortgage that was giving us financial stretch marks. Two car payments. Kids in private school.

And I was telling her I wanted to leave my corporate job.

^{Tabbi and I with our boys on a trip to Xenia, Ohio, in 2007 to ride bikes through the countryside on repurposed "rails to trails" railroad track routes.}

She needed to feel safe. I needed to be free. And those two things felt like they were pulling us in opposite directions.

Here's the part that matters for you...

- Why safety and freedom seem like opposites (but aren't)
- The one and only promise I could make that night
- What's actually waiting on the other side of the freedom vs. safety trade-off

I couldn't promise her how it would turn out.

I couldn't show her a spreadsheet that guaranteed success. I couldn't point to a war chest overflowing with riches to make her feel safe and secure. I mean, I was so broke just walking past the bank would trip the alarm.

And I certainly couldn't tell her "don't worry, I've got this all figured out."

All I could promise was my energy and my effort.

That's it. That was the offer. "I will put everything I have into this. I can't promise the outcome. But I can promise I won't hold back."

If you're reading this newsletter, there's a good chance you've had a version of this conversation. Maybe with a spouse. Maybe with yourself at 2am. Maybe with the voice in your head that keeps asking "but what if it doesn't work?"

I've had this same conversation with four different clients this month. Different names. Different industries. Same fear wearing different clothes.

"What will my family think?"

"What if I fail publicly?"

"Maybe I should wait until..."

The lyrics change. The song stays the same.

And if you've already made that first leap... if you're a few years into consulting but find yourself stuck in feast-or-famine, constantly chasing the next client, wondering if this is really what you signed up for... there's a second version of this conversation for you. It sounds like:

"I left corporate to have more control over my life. So why does it feel like I just traded one boss for a dozen clients who all think they own me?"

Same song. Different verse.

Here's what I've started to realize after 20 years on this side of the table...

Thomas Sowell said it best: "There are no solutions, only trade-offs."

In the beginning, that trade-off is real. You're exchanging the feeling of safety for the uncertainty of building something. Some people make that leap all at once. Others build on the side while they're still employed. Either way, there's a season where you're carrying more risk than feels comfortable.

And yet...

The corporate safety was never real to begin with.

Last week I wrote about the gilded cage. The bird sitting inside with the door wide open, saying "because I'm safe." Amazon just laid off 30,000 people who thought they were safe. One HR decision. One "strategic realignment." And suddenly everything they'd built for 10, 20, 30 years was gone.

When one entity controls 100% of your income, you're not safe. You're dependent. The feeling of safety and the reality of safety are two different things.

But here's the part that surprised me...

The trade-off is temporary. What's on the other side is not.

Twenty years in, I have MORE security than any corporate job ever gave me. Not less. Here's why:

My income is diversified. No single client controls my future. My skills are portable. My relationships are mine. And when things change, I have the agency to adapt.

I haven't saluted a boss in 20 years. I haven't begged for a raise. I haven't been in a corporate political cage fight. I haven't sat in a meeting wondering if I'm next on the list.

And unlike the consultants who escape corporate only to build themselves a new prison... I'm not a hostage to my own business either. I'm not chasing every prospect, saying yes to every project, letting clients dictate my schedule and my sanity.

Has it been a crazy ride? Absolutely. There were months early on where I wasn't sure how we'd cover the mortgage. There were clients who didn't work out. There were pivots I didn't see coming.

But here's the thing...

Every problem was mine to solve. Not something happening TO me. Something I could work on, adapt to, figure out. And over time, that agency compounds into something that looks a lot like security.

The freedom path doesn't mean choosing freedom INSTEAD of safety. It means going through a season of trade-off to arrive at a place where you have both.

Whether you're still sitting at that kitchen table deciding whether to make the leap... or you've already jumped but haven't quite found your footing yet... the path forward is the same.

You have to be willing to walk through the uncertainty. With good information. With wise counsel. With everyone who matters bought in.

Tabbi and I are still at that same kitchen table 20 years later. The crushing debt burden we carried back then is gone. Not because we got lucky. Because I learned that I can give myself a raise anytime I want. Win more clients. Use my skills to justify a premium price. Smart money management and the freedom to control my own income changed everything.

The kids are grown. And neither of us would change a thing.

One more thing that made the difference...

I invested in people who were a few steps ahead of me. People willing to point out the quicksand and show me where the bridges were.

Former Major League Baseball pitcher Vernon Law said it well: "Experience is a hard teacher because she gives the test first, the lesson afterward."

Trial and error sounds noble. But it's the most expensive education you can buy. Paying for guidance from someone who's already walked the path is the shortcut that actually works.

If you've been having this conversation with yourself... whether you're standing at that kitchen table wondering if you should make the leap, or you've already jumped and you're ready to build something more stable... I'm hosting a free training on Thursday.

It's called The Gray Hair Premium and it's about why this specific moment in history creates a unique window for experienced professionals. Why the thing corporate America rejects is exactly what the consulting market pays premium for. And how to move through the trade-off with the best information possible.

➜ BusinessBreakthroughAdvisors.com/The-Gray-Hair-Premium

I can't promise you how it turns out. But I can show you what's possible when you stop settling for safety that was never real... or chaos that doesn't have to be permanent.

See you Thursday.

Dale

Want to dive deeper? Check out these related articles:

👉  The Prosperous Consultant | Issue #4
👉  The Prosperous Consultant | Issue #3

You might also find these interesting:

🔎  The Trust Reckoning: The Shadow Side of Force 1
🔎  Client Value Journey: Stage 1 – Aware

P.S.: When you're ready, here are more ways I can help you...