️ ️⚡ Today’s level up ⚡
You’re in a unique position as an experienced tech seller—with access to the latest trends, you 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 letter may be the spark you need.
Here’s the email I send every seller at 44…
"You've got six years left. Maybe ten 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 "Strategic Account Director," 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 surpassing 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’ll benefit from completing The Clarity Challenge—a short reset to regain focus, control, and direction. It’s the first step every Purposeful Performer subscriber and member takes to architecting autonomy.
