Optionality is Killing Your Momentum

A few weeks ago, I wrote about one of the hardest words in business:

No.

At the time, I was in the middle of a decision-making process that forced me to drink my own champagne.

Behind the scenes, I was evaluating how and where I was spending time, energy, and resources—because since launching MSP Sales Partners in January, we’ve seen a sharp uptick in new enrollments.

That kind of growth is welcome. But it comes with a cost.

And that cost? Is time.

One of the few zero-sum games in business.

The Tough Calls

After long conversations and some honest analysis, we made the difficult decision to retire our community—a group I loved building. Weekly calls. Open conversations. A shared mission.

And just this week, we also announced the wind-down of our Accelerator coaching program—a program I’ve run for nearly three years.

This one hurt even more.

We’ve seen clients quit their 9-to-5s, hit high six and seven figures, and build businesses that started from the frameworks we taught.

The alumni are some of the most impressive operators I’ve worked with.

And we had some incredible in-person mastermind events here in Cabo.

But here’s the thing…

While we were doing a lot of things relatively well, none of them were getting done as well as they could be.

And when I stepped back to assess, the truth was clear:

It was time to go all in.

The Emotional Weight of Letting Go

Logically, the decision made sense.

Cut three or four smaller revenue streams, reclaim 20+ hours a week, and redirect all that energy into a single, fast-growing business unit.

Simple, right?

Not even close.

Every time I went to send an announcement or shut something down, my brain fought back.

"Maybe just keep this one going a bit longer.”

“What if this doesn’t work out?”

“Is it really worth cutting off that revenue?”

This is the battle so many operators face—the tension between strategic logic and emotional homeostasis.

We know what needs to be done. But executing on those decisions? That’s where it gets hard.

The Curse of Optionality

Early in my career, a board member—Harvard educated, successful exits, the whole package—once told me:

Optionality is good.

For years, that shaped how I operated. Keep doors open. Maintain flexibility. Hedge risk.

And to be fair, as an investor, it’s sound advice. (There’s a strong argument for concentration, but argument for another day…)

But as an operator?

Optionality is a curse.

Because every additional “option” you try to keep alive adds complexity.

Complexity creates uncertainty.

And uncertainty leads to hesitation, half-measures, and stalled momentum.

So this season, we’re removing the optionality. We’re putting our eggs in one basket—MSP Sales Partners—and building a category-defining sales program for IT companies.

The Real Risk

Going all in might feel risky.

But I’ve learned: feelings aren’t always facts.

Sometimes emotions are like a funhouse mirror. They distort reality, making bold moves seem dangerous and status quo feel safe.

But the real risk?

Spreading yourself thin. Trying to do everything. Playing it safe in all directions—and never gaining enough traction in one.

That’s the trap I was on the verge of falling into.

Final Thought

If you're at a similar crossroads—juggling too many things, unsure which to let go of—here's what I’ll leave you with:

Clarity isn’t found in spreadsheets or whiteboards. It’s found in motion.

And sometimes, the boldest business move you can make is to say no to the good… so you can say yes to the great.