Why Not Now?

How a text message forced me to stop coaching around the problem and start solving it.

A client sat across from me, furious.

“We’ve done all of this and we’re back to square one.”

ICP built. Playbook done. Comp plan in place. Months of work. And not a single deal moved.

That conversation kept happening. Different client, same words.

Eventually I had to admit the thing I’d been stepping around for years. I was coaching everything except the thing that mattered most. Sales.

𝗧𝗵𝗲 𝗰𝗼𝗺𝗳𝗼𝗿𝘁𝗮𝗯𝗹𝗲 𝘁𝗿𝗮𝗽

For years I had a business that worked. Good clients. Good conversations. Two, maybe three days a week of real work.

Comfortable. And that was the problem.

Because in every quarterly review, the same thing surfaced. The top line wouldn’t move. Coaching only works when there’s demand. And as markets got crowded, demand stopped being a given.

Sales solves a lot of problems. When it’s firing, the operational noise quiets down. When it isn’t, everything gets louder. More frustration. More blame. People stop adding to the pipeline and start clinging to what’s left.

I could see the problem in every business I worked with. I just couldn’t fix it.

𝗧𝗵𝗲𝗻 𝗮𝗻 𝗲𝗺𝗮𝗶𝗹 𝗮𝗿𝗿𝗶𝘃𝗲𝗱

It was from Alex Goldfayn. An invitation to see what his system, Outgrow, could do inside a practice like mine.

I’d read the lots of sales books. Every one of them told you how to think about selling. How to handle the objection, how to structure the team.

None of them showed you how to actually do it.

Outgrow did. It was the doing.

The decision in front of me was simple. Get certified in January, or wait until April.

Naturally, I picked April. A bit more time. A bit more runway. Get a few things in order first.

It was a lie. The same “later” I’d watched a hundred clients hide behind.

𝗧𝗵𝗲 𝘁𝗲𝘅𝘁

Then Alex sent a message.

“Why not now? What’s stopping you from helping yourself and your clients make more money? Do you think it’ll be that different in April?”

I read it a few times. It landed because it was true. I was letting life happen to me. Waiting for a better moment that was never going to announce itself.

Twenty years has taught me this: if you’re not sure where you’re going, you’ll still end up somewhere. But if you know exactly where you’re going, the path gets easier. The waiting is just fog.

I booked January.

𝗧𝗵𝗲 𝗸𝗶𝘁𝗰𝗵𝗲𝗻 𝗰𝗼𝗻𝘃𝗲𝗿𝘀𝗮𝘁𝗶𝗼𝗻

I told my wife it was a big investment. Significant. She asked the obvious question. Why this, why now.

So I talked her through the whole thing. Sales is the number one problem for the people I work with. Solve sales and you fund everything else. You give a business the budget and the breathing room to fix the rest.

She listened. Then she said, “Yeah, that makes sense. You need sales to grow.”

I needed to hear myself say it out loud as much as I needed her to agree. By the end of that conversation, I wasn’t apprehensive anymore. I was certain.

𝗪𝗵𝗮𝘁 𝗵𝗮𝗽𝗽𝗲𝗻𝗲𝗱 𝗻𝗲𝘅𝘁

I flew to Chicago. Got certified. Rebuilt my practice around one thing instead of ten.

The first three months were uncomfortable. New language. New rhythm. Calls I hadn’t made in years.

But by the end of those three months, I’d closed three clients.

From a standing start. From a business I’d just decided to blow up because it was too comfortable.

Most growth doesn’t die from a bad decision. It dies in the gap between deciding and doing.

So let me leave you with the question Alex left me with.

That hire you’re waiting on. That system you’ll implement next quarter. That conversation you keep putting off.