⛰️ Trail & Error: Build your escape plan

Welcome back to ⛰️ Trail & Error, your guide to building a life on your terms. 

Most people don’t leave unfulfilling jobs because they don’t know how. The fear of instability keeps them stuck in roles they’ve outgrown—until they’re pushed out by layoffs, burnout, or sheer frustration.

But what if you had a roadmap? What if career reinvention wasn’t about taking a blind leap, but following a step-by-step process to build freedom, security, and meaningful work?

Let’s talk about it. 👇

Why Career Change Feels Impossible (But Doesn’t Have to Be!)

Most people trying to transition into fractional work, consulting, or entrepreneurship hit the same roadblocks:

🚧 They think it’s all or nothing. (Quit today or stay stuck forever.)
🚧 They overanalyze. (Another course, another certification—then they’ll be ready.)
🚧 They wait until they have no choice. (Layoff, health scare, existential crisis.)

But the most successful transitions don’t happen overnight.

They happen through a structured process—one that de-risks change and gives you the clarity and confidence to move forward.

The Reinvention Playbook: A Step-by-Step Process

After years of helping people transition out of the traditional job model and doing the same in my own career, I’ve seen what works. It’s not about “chasing passion” or “taking the leap.” It’s about following the 6 steps to reinvention so that the change you seek becomes inevitable.

This is the 6-part framework I use:

1️⃣ Recharge → Before making big decisions, restore your mental & physical energy.
2️⃣ Recenter → Define what actually matters (values, priorities, constraints).
3️⃣ Rewind → Go back to curiosity—explore ideas without pressure to commit.
4️⃣ Renew → Experiment with low-risk ways to earn outside a full-time job.
5️⃣ Recommit → Double down on what’s working, discard what isn’t.
6️⃣ Reinvent → Set long-term goals, build systems, and create lasting stability.

How This Works in Action

Meet Alex, a senior marketing leader at a fast-growing startup. On paper, he’s thriving—great salary, strong resume, respected in his field. But behind the scenes, he’s burnt out, stuck, and questioning what’s next.

Like many mid-career professionals, Alex has thought about consulting or fractional work but keeps hesitating:

❌ "What if I fail?" He’s never worked for himself before.
❌ "I don’t know where to start." Should he freelance? Build a brand? Get another job?
❌ "I have a family to support." The idea of walking away from stability feels reckless.

Instead of taking a blind leap, Alex follows the Reinvention Playbook:

1️⃣ Recharge – He takes a step back from reactive job searching and focuses on what he actually wants.
2️⃣ Recenter – He clarifies his non-negotiables: More autonomy, better alignment with his strengths, and income stability.
3️⃣ Rewind – He explores different work models—consulting, advisory roles, fractional leadership—without committing too soon.
4️⃣ Renew – He tests the waters by taking on one consulting client while still employed, validating that people will pay for his expertise.
5️⃣ Recommit – He gradually shifts his energy toward independent work, refining his positioning and pricing.
6️⃣ Reinvent – Within six months, he’s built a profitable, flexible business, working with 2-3 ideal clients without sacrificing income or security.

Alex didn’t jump without a parachute—he built one first.

This is how real, lasting career transitions happen. Not by quitting overnight, but by following a process that makes success inevitable.

Alex’s story isn’t unique—it’s the reality for so many mid-career professionals who feel trapped in a system that rewards predictability over creativity.

As Paul Millerd put it on X just today: "Your corporate job is a trade: reliable income in exchange for the quiet surrender of your deeper curiosities and creative instincts."

What if you could reclaim both?

If You’re Considering Fractional & Independent Work…

Right now, fractional work and independent consulting are exploding—but too many people jump in without a strategy.

🛑 They take the first client that comes their way (even if it’s a bad fit).
🛑 They underprice themselves because they don’t k now how to package their value.
🛑 They end up recreating the job they just left—just with less stability.

Following a proven transition framework ensures that when you shift to independent work, you actually build a career that works for you—not just another exhausting job.

You Can Apply This Today

If you’re thinking about making a transition, here’s your next step:

1️⃣ Reply with “reinvent” and I’ll send you my best resources on career transitions.
2️⃣ If you’re actively looking to transition from corporate to independent work, just reply 📩 and let me know where you are in your career journey.

The old career playbook is broken. A better way is possible. Let’s build it together.