Hi Friends,

Last Friday was my last day at Pricing I/O.

I was let go.

In 18 years of working, that's never happened to me before. I didn't know exactly how I'd feel when it did.

Turns out: fine. Genuinely fine. Pricing I/O is a great company doing important work. Marcos and I have a good relationship, and that chapter was real. I have nothing but gratitude for what I learned there.

But if you know me, I am an annoying optimist. The first few days are terrifying. But it’s slowly becoming the most exciting time of my life.

The last few days have given me real space to reflect on what I actually want. We're living through one of the most interesting periods in the history of work, and instead of rushing to fill the calendar, I'm leaning into that. This isn't a setback I'm recovering from. It's a beginning I get to design.

I suspect many of you have been through something similar or are quietly wondering what your next chapter looks like. So I want to share the steps I'm using to think through mine.

So, how am I planning what’s next for me?

Whenever a friend comes to me in transition and asks, "I don't know what I want to do next", I give them one book: Designing Your Life by Bill Burnett and Dave Evans. My answer is always the same: follow each chapter.

The last time I did the work myself was 10+ years ago.

So this week, I pulled my own copy off the shelf. Felt like the right moment to return to it.

The book opens with two questions before it lets you touch on strategy:

What do you believe about work? What do you believe about life?

Most people never ask these questions. They just follow the default path, school, first job, next job, promotion, and wake up one day wondering how they got there. Burnett and Evans call this designing your life on autopilot. These two questions are the off switch.

My Workview: Time Freedom

For the first time in my career, my answer has nothing to do with titles, comp, or the next opportunity. It's about time. Specifically, who controls mine. And yes -- it needs to cover our family expenses at some point.

I've missed birthdays. School events. Little moments you don't get back. I spent years inside big companies where the hidden job description read: scan your badge at the front door, scan it again to use the bathroom, sit in a glass aquarium under fluorescent lights while back-to-back calendar invites decided how your day would go. That hollow beep was followed by the hard clunk of the door unlocking. I still hear that clicking sound in my sleep.

That's not the next chapter.

What I want is simple: wake up, take the kids to school, move my body, follow my curiosity, build something with people I genuinely admire, and end the day fully present with the people who matter most. That's a good Tuesday. Everything else gets measured against that.

My Lifeview: Life is short

This one hasn't changed since I was 18. I was in a car accident that reminded me, viscerally, that nothing is guaranteed and life is incredibly fragile. That moment shifted something permanently. If life can end without warning, the only logical response is to be ruthlessly intentional about how you spend it.

Which is why this Naval Ravikant quote on a recent Chris Williamson podcast: "The only true test of intelligence is if you get what you want out of life. There are two parts: knowing how to get it, and knowing what to want in the first place."

That second part is the one most people never figure out. Life is short. Wanting the wrong things makes it shorter.

The step I'm in right now is called Life Design Interviews. Talk to the people in your life who know you well. Not to get answers. To gather signal. No one prescribes what's next. You just listen.

I'm in those conversations right now. Close former colleagues and friends who know me well. The process is working. And the most important thing I'm learning is to be patient with it.

This is the first time I'm not rushing for answers.

I'm going to follow my curiosity, specifically toward AI and what it means for the way people work. I want to be in the arena on that, not watching from the sidelines. But what form that takes is still being designed.

Will keep you updated on progress.

Til next time,

--Ali

P.S. If you're someone who is going through a similar transition, let me know. Happy to be a sounding board for you.

About Me: I'm Ali. I've spent 18 years at the intersection of strategy, growth, and B2B software & services. I've been the banker, the operator, and the advisor. Currently, I am funemployed and finally have time to explore work that lights me up. I write The Moat for leaders who want real frameworks, not recycled advice. I live in Houston with my wife Zohra, and two daughters.