Here’s The Email I Send Every Seller At 44

️ ️⚡ Today’s level up ⚡

You’re in a unique position as a tech seller—access to the latest trends, can transform large businesses, and have the ability to earn well above your corporate counterparts. But what is it all for? What is your personal why?

Now is the time to start seriously thinking about architecting your future autonomy. I can help you, and this email may be the spark you need.

Here’s the email I send every seller at 44…

"You've got 6 years left. Maybe 10 if you're lucky. What are you building that's yours?"

I send this to every strategic seller who hits 44 and books time with me.

Not to be cruel. To be clear.

Because at 44, the math gets real:

• 50% of your career is behind you

• Your earning window is shrinking

• Your energy for the grind is finite

• Your family is watching what you choose

The exact template I send:

"[Name],

You just turned 44. Congrats on making it this far in the game.

Real talk: You've got 6-10 peak earning years left. After that, ageism kicks in, energy shifts, and priorities change.

The question isn't whether you can keep surpassing quota.

It's whether you should.

Every year from here is a choice:

• Build their empire or build yours

• Chase titles or chase freedom

• Collect paychecks or create equity

What are you building that you'll own at 50?

If the answer is 'nothing,' we should talk.

-Brandon"

Response rate: 87%

Why? Because it names what they're already feeling.

The three readiness questions I ask on our call:

1/ "𝑊ℎ𝑎𝑡'𝑠 𝑦𝑜𝑢𝑟 𝑛𝑢𝑚𝑏𝑒𝑟?"

Not your quota. Your freedom number. The amount at which work becomes optional. Most don't know. The ones who do are already planning their exit.

2/ "𝑊ℎ𝑜 𝑎𝑟𝑒 𝑦𝑜𝑢 𝑤𝑖𝑡ℎ𝑜𝑢𝑡 𝑦𝑜𝑢𝑟 𝑡𝑖𝑡𝑙𝑒?"

Strip away "VP of Sales" or "Enterprise AE." What's left? If you can't answer, you're not ready. Your identity needs to exist beyond your LinkedIn headline.

3/ "𝑊ℎ𝑎𝑡 𝑠𝑘𝑖𝑙𝑙𝑠 𝑑𝑜 𝑦𝑜𝑢 ℎ𝑎𝑣𝑒 𝑡ℎ𝑎𝑡 𝑤𝑜𝑟𝑘 𝑎𝑛𝑦𝑤ℎ𝑒𝑟𝑒?"

Selling is a skill. But what else? Coaching? Consulting? Building systems? The sellers who successfully exit have skills that travel beyond a fancy sales title.

Why 44 matters:

It's the inflection point where successful sellers stop climbing and start calculating.

They've proven they can win the game. Now they're asking if it's a game worth playing.

The smart ones use 44-50 to architect their escape:

• Build side revenue while crushing quota

• Invest aggressively (not in boats or BMWs)

• Develop expertise people will pay for

• Create content that builds authority

• Network with owners, not employees

They're not quitting. They're graduating.

From someone else's P&L to their own. From carrying quota to creating equity. From strategic seller to sovereign operator.

The brutal truth:

If you're 44 and not building something you own, you're just renting your lifestyle from your employer.

And leases always end.

Usually, when you least expect it.

The email I send isn't comfortable. The questions aren't easy. The math isn't negotiable.

But the sellers who face it at 44?

They're the ones who are free at 50.

While everyone else is still hoping their company won't be restructured.

🐝

P.S. If this resonates at all, you’d be a perfect fit for The Accelerator Program. It includes a subscription to The Purposeful Performer (can’t wait to share all of the enhancements for 2026) + three 1:1 coaching sessions to get you pointed in the right direction. This offer expires soon!