Lesson 5: The Risk in Playing It Safe
For four years, I taught MBA students two nights a week while building my consulting business by day. On paper, it made perfect sense: prestige, purpose, and a chance to shape future leaders. But in practice, it nearly drained the life out of the business I actually wanted to grow.
By Wednesday morning, I was already 40+ hours into my week and running on fumes. I’d sit at my desk, staring at my to-do list, too tired to focus. Teaching paid a fraction of my consulting rate, and even though I loved the students, I started to feel the weight of what I wasn’t building.
I’m not a quitter, so I stuck with it—for four years.
Looking back, I realize it wasn’t the job itself that kept me there. It was what the job represented: a familiar identity. It felt safe. Legitimate. A nod to my old life in corporate—one more respected title to wear on LinkedIn.
But slowly, I began to see the tradeoff. The hours I spent teaching were hours I couldn’t invest in growing my business. And as I started working with large nonprofits across the city, something shifted.
The work I was doing with those organizations—helping leaders make tough decisions, clarifying strategy, driving change—started to feel deeply meaningful.
That was the real ROI:
More people off the streets.
More families fed.
More justice in the system.
It wasn’t just more fulfilling than teaching—it was more aligned with who I was becoming.
That’s when Daniel Pink’s framework in Drive hit home. We’re not fueled by carrots and sticks. What really drives us is:
Autonomy – control over how and when we work
Mastery – a chance to keep getting better
Purpose – connecting our work to something bigger than ourselves
Teaching gave me status. Consulting gave me all three.
Eventually, I made the hard call to stop teaching and go all-in on my business. It was a risk—but it was the right one. I found better income, deeper fulfillment, and a business that felt fully mine.
Here’s what I learned: the real risk isn’t in leaping. It’s in clinging to a “safe” option that holds you back from what’s next.
So go ahead and experiment. Try something new. See if it fits. But set a date to check in with yourself. Be honest about what you’re getting in return—for your time, energy, and heart. Tell someone your check-in date so they can hold you to it.
Then make your choice.
Because sometimes, the most dangerous move you can make… is not making one at all.
