The Exercise I Keep Coming Back To

A Tool for Clarity, Alignment—and the Truths That Time Doesn’t Erase.

Welcome to a new format inside 963—where the deeper work begins.

This is the space where reflection turns into action. Each installment offers a concise, actionable tool—whether it’s a framework, a mindset shift, a reflection prompt, a career exercise, or a product recommendation—drawn directly from the coaching and advisory work I do with founders, executives, and creatives navigating growth, change, and recalibration.

Some come from 1:1 sessions. Others are drawn from workshops or personal practices I’ve refined over the years. Now, I’m bringing them here, to support the work behind the clarity.

My intention is simple: to offer the kind of values-centered, strategically grounded guidance I share in private settings. No fluff. No gimmicks.

If you're craving more structured support, the first 963 Workshop launches later this year (!)—details below, along with how to inquire about my coaching offerings.

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This Week’s Focus

The exercise I keep coming back to.

When I was a freshman at NYU, one of my English professors gave us a deceptively simple assignment:

Write a letter to yourself four years from now.

Describe your life. Ask questions. Say what matters. Speak to who you hope to become.

He collected our letters, along with permanent mailing addresses—somewhere we’d still be reachable after college. Four years later, he mailed them back.

I had completely forgotten about mine—until it showed up at my family’s house: postmarked, creased, and written in my own handwriting.

Reading it felt like time travel. Like sitting face-to-face with a younger version of myself. She shared her dreams, her doubts, the people she loved. She asked questions that stopped me cold. She was wise in a way I hadn’t expected, reminding me of one truth I’d still be carrying four years later:

“There are so many things I’m unsure of in life.

But it’s interesting to note that death is not one of them.

Carlos will still be dead in four years.

And we will all still be mourning him.”

Carlos was my brother. His death shaped my entire worldview—what matters, what’s worth chasing, and what can never be undone. That sentence from my younger self still echoes when I face hard decisions. Because if death is a constant, then so is the question: How do you want to live?

The final lines of that letter have stayed with me ever since, quietly becoming my North Star:

“You better have cute style, be in good shape, understand your values, and not have sold out.

Love you, Jamie.”

It was simple. Even cheeky. But clear. That 18-year-old version of me understood the assignment: Live well. Be healthy. Know your values. Don’t abandon them.

That’s still the lens I return to when I need to realign.

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Now It’s Your Turn

Write a letter to yourself, four years from today.

Talk about what matters. Ask questions. Tell the truth.

Here’s how:

1. Set a timer for 10 minutes.

2. Write without overthinking. No editing.

3. Be honest about what matters to you right now—hopes, fears, questions, truths.

4. When you’re done, mail it to me. I’ll send it back to you four years from now.

Mail to: