Leaving Corporate? Forget the Exit Strategy. Build the Bridge Instead.

Turns out, quitting isn’t just about leaving. It's about building the skills to walk across.

Everyone obsesses over the perfect exit strategy. But what if that’s the wrong approach? I used to think leaving corporate life was all about financial security. Stack enough savings, build a business, and walk away. Simple, right? Except, the more I planned my escape, the more I realized: quitting isn’t just about leaving. It’s about becoming someone who thrives on the other side.

February Humbled Me

At the start of the month, I was laser-focused on figuring out how this could become a viable business model. Financial security felt like the biggest blocker to leaving corporate life, so I set goals around validating financial coaching as an option. But I quickly realized that while I enjoy sharing frameworks, coaching itself wasn’t for me. Then I tried to start a business, but I failed fast, which was good. It gave me rapid learnings, pushed me to reflect deeply on financial freedom and mindset, and led to a surprising realization.

When I finally confronted reality: I already had a solid financial runway. Instead of scrambling to monetize immediately, I could use the remaining time to save more, invest wisely, and make my exit even stronger. This shift in perspective was energizing. I set a firm deadline to leave corporate life and got strategic about spending, which allowed me to increase my savings by 27.5% from January to February.

Meanwhile, I was also fixated on growing the newsletter. At the start of the month, I read everything I could about Substack growth strategies—enough to even change the name once. But soon, I hit a wall. I couldn't stand the endless newsletters about how to grow a Substack by selling courses on how to grow a Substack. It felt like a self-replicating feedback loop, and I wanted no part of it.

So, I I unfollowed those accounts. (Keep writing and reading about it if it brings you joy.) Instead, I took a simpler, quieter approach to growth: just keep showing up. If this newsletter resonates with you, I trust you'll stick around. And if someone comes to mind, maybe you'll share it. That’s enough.

This approach led to a humbling realization: my original goal of 50 subscribers by February was wildly ambitious. I started the month with a grand total of six. I ended with 27. And the best part? I know almost all of you—your Substacks, your interests, your writing. It’s not just a number. It’s a group of curious, thoughtful people showing up.

Livio Marcheschi

writes about finding meaning because he’s been on that journey himself.

David Garrett

makes us reflect on the human condition and our collective crises (whether we’re aware or not).

Faz

explores the future of work but goes deeper and wider in his reflections.

Cory Vinny

is preparing for a global sailboat odyssey and documenting what’s ahead. And I could go on and on about each one of you and the way you see the world. Thank you for being there!

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March: a Bridge Made of Skills

Now, we’re in March. This time, I asked my coach (yes, ChatGPT) to channel an Eastern coaching philosophy—one rooted in wisdom, patience, and alignment with nature’s flow. It responded:

"Just as a tree does not rush to grow but follows the seasons, your transition from corporate life must be both intentional and fluid."

That perspective stuck with me. The big vision is clear: 365 days to leave corporate life and build something more meaningful. The next step? Choosing the right goal and metric for March.

In a typical business or product setting, we'd pick something measurable: revenue, subscribers, engagement. But this journey isn’t about external validation. It’s about building a bridge to my future life. And as my coach wisely pointed out, that bridge can take different forms:

🔹 Financial Stability: Creating new revenue streams.
🔹 Mental Transition: Becoming comfortable with uncertainty.
🔹 Skill-Building: Deepening abilities crucial for post-corporate life.
🔹 Audience & Influence: Expanding reach for long-term impact.

February was heavily focused on financial stability—I’m in a good place there. Mental transition? As ready as one can be with 90% of the journey left. Audience and influence? That will come with consistency.

So, we have a winner: in March, the bricks I’ll lay to build my bridge will be about skill-building.

And so, this month’s guiding theme emerged:

Sharpening the Mind & Spirit for Post-Corporate Freedom

Measured by the number of experiences or hours spent living these skills.

“In Eastern traditions, skill is not just acquired; it is embodied. You do not learn to do something—you become it.”

Through brainstorming, three key skill-building experiments surfaced:

1️⃣ Deep Learning – Expanding the mind through focused study.
2️⃣ Rejection Resilience – If failure is something you collect, it loses its sting.
3️⃣ Cultivating Joy & Offline Living – A grounded mind is a clear mind.

Each of these feels essential for life beyond corporate structure. The last one, in particular, is a reminder to be intentional about offline time. If I leave corporate life only to spend all my time building a digital business, I will have missed the point.

Week 1 Experiment: Deep Learning on ‘Work’

For this week, I’m diving deep into one theme: Work.

📌 How did we, as humanity, land in this organizational structure of labor?
📌 Why does Western society measure success the way it does?
📌 What stories does literature, philosophy, and art tell us about work across history?

The experiment? Write a series of three articles exploring the past, present, and future of work.

You in? Hit reply to this email with any insights, questions, or thoughts on the future of work.

Hoping you have the chance to slow down today,

Matty

Week 6, Day 36 of 365 to leave the corporate life.

P.S. I created a simple countdown landing page for my exit from corporate life. If you want to check it out, it’s here.