As many of you know, I stepped away from the corporate world and recently I came back. I didn’t leave because I was burned out, or fed up, or chasing some viral “I quit my job” moment. I left with intention (but left the door open behind me). My goal was to test a long-standing dream. After years of working on my side projects (mentoring/coaching, training, writing) I wondered what it would feel like to go all-in. So I bought myself a year. Not a new car. Not a vacation. A year. What I learned: the dream was real. But so were the trade-offs.

There’s a growing narrative online that glorifies solo/entrepreneurship and makes traditional jobs seem like the enemy of freedom. That’s not what this post is about. This few paragraphs are all about understanding what you want, trying it for real, and learning what happens when your passion becomes your paycheck.

Tip of the Week: Leaving your corporate job might indeed change your life... but not always in the way you expect.

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The Theory Behind

Doing what you love can feel like work...because it is. There’s a quote you’ve probably heard: “Do what you love, and you’ll never work a day in your life.” But research suggests otherwise. According to a Mayo Clinic study, burnout is lowest when we spend around 20% of our time on personally meaningful work. Past that point, the gains diminish considerably. Self-Determination Theory tells us that motivation is driven by autonomy, competence, and connection. When your passion becomes your job, those drivers shift. You now have clients, deadlines, invoices. It’s still meaningful... but it’s also a job. And that’s okay, as long as you’re aware of it.

Most of us regret not trying, more than we regret failing. When Jeff Bezos left Wall Street to build an online bookstore, he used a tool he called the Regret Minimization Framework. He asked himself: “When I’m 80, will I regret not doing this?” The answer gave him the courage to leap. Psychologists Kahneman and Tversky explained this through Prospect Theory, which shows how we overweigh potential losses in the short term. But over time, we’re wired to regret inaction more than failure. If you’re on the fence about testing your dream, ask yourself: will I regret failing, or never finding out?

The corporate world has perks, and we shouldn’t ignore them. Spend five minutes on Reddit and you’ll find threads full of former entrepreneurs reminiscing about corporate life. Benefits, paid time off, team camaraderie, structure, mentorship… all things we take for granted until they’re gone. According to Vroom's Expectancy Theory, motivation depends on the belief that our efforts will lead to clear, valuable rewards. Corporate roles often have well-defined paths and feedback loops. Outside that system, you create everything from scratch (including your sense of progress). Some of us love that freedom. Others miss the structure. Neither is wrong, but social media definitely glorifies one side.

What I’ve Learned

You need to know whether your passion is a job, a vocation, or a hobby. There’s a framework that says our work can fall into three categories: A job (pays the bills), a vocation (gives meaning), a hobby (brings joy). For a year, I tried intersecting all three by trying coaching and public presentations as a job. Spoiler alert: It changed the relationship. It didn’t kill the joy, but it added pressure. Deadlines replaced spontaneity. Revenue replaced flow. The trick is not to avoid this shift, but to choose it consciously.

Make It Happen

If you’re feeling the itch to try something different, here’s how to explore it without going all-in too soon:

1. Name your curiosity. What’s the idea or project that keeps tugging at you?

2. Use the Bezos Regret Filter. At 80, will you regret not exploring this?

3. Break the lion into kittens. Start small. One project. One client. One class.

4. Aim for 20% time. Carve out a fifth of your week to test your passion. That’s where fulfillment peaks.

5. Pay attention to your energy. Ask yourself: Which parts of this work energize me, and which ones leave me drained? Often, your body sends the signal before your brain catches up.

6. Keep the corporate door open. Don’t make your leap dramatic. Make it strategic. It’s okay to return.

7. Reflect at six months. You’ll gain clarity fast. Let your next decision be informed, not impulsive.

I took a year to scale what I’d been doing on the side for years (coaching, giving presentations, building community). It’s been an incredible learning curve, and I’ve grown it into something real, with a team behind it now. The past few months, I've been fortunate to help many in their journeys. If you’re exploring something similar, or need support with coaching or presentations, just reply to this email - I’d be happy to help.

Leaply,

Jorge Luis Pando

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