When I think about the moments that have shaped my career, many of them have involved taking a risk. Not a reckless risk, but a calculated one.
Over time, I’ve come to believe that calculated risks are necessary for growth and fulfillment, both personally and professionally. That doesn’t mean every risk is worth taking, but it does mean that growth often requires us to step into something new before we know exactly how it will turn out.
Growth Usually Begins Before You Feel Ready
One of the biggest risks I took was leaving the University of California, Berkeley after my first year to enter the NBA Draft.
From the outside, it may have seemed like an easy decision because I was projected to be a high draft pick. But it wasn’t easy for me.
I was really enjoying being a college student, and at the time, players didn’t typically leave school after just one year. It wasn’t part of my original plan. I had unexpectedly exceeded my own expectations, and I was nervous about making such a significant jump.
What ultimately gave me confidence wasn’t knowing exactly how things would turn out; it was believing I was ready to work. I had faith that if I was willing to put in the work, I could give myself the best chance to succeed.
I’ve realized that waiting until everything feels certain isn’t always possible. Sometimes growth begins before you feel 100% ready.
Risk Isn’t About Being Fearless
Years later, I faced another decision that challenged me in a completely different way.
Working in the front office of an NBA team was already a dream. After having the opportunity to play in the NBA, being able to work in a front office felt like a double dream. Those positions are hard to come by, and many of my friends thought I was making a mistake for considering leaving to attend business school.
To be honest, I understood why they felt that way. I even delayed my enrollment for a year so I could continue working while I thought through the decision.
One day, I visited a class, and I remember feeling excited by what they were learning. Topics like the present value of money reminded me of contract buyouts. Analytical modeling connected to how we evaluate different outcomes in basketball. Leadership and team dynamics had been part of my life for years, but now I had the opportunity to study them in a completely different way.
I realized that if I dedicated myself to learning what was being taught, I would leave business school better than I entered it.
Would that lead to another job, or something completely different? I didn’t know. What I did know was that I needed to continue growing, and the information I was being exposed to lit me up.
What Makes a Risk Worth Taking?
I’ve learned that taking a calculated risk isn’t about ignoring uncertainty. It’s about preparing for it.
Before making a significant decision, I try to ask myself a few questions:
- Have I learned as much as I can about this opportunity?
- Who do I know that has done something similar?
- How will this decision affect the people who count on me?
- If everything goes wrong, how will I make it work?
- Will I be at peace with the outcome?
Those questions don’t guarantee the right answer, but they’ve helped me make decisions with greater confidence because they’re grounded in preparation instead of emotion.
Every Risk Doesn’t Lead to Success—But Every Risk Can Lead to Growth
One thing I’ve found is that every meaningful risk teaches you something. Some decisions work out exactly as you hoped. Others don’t.
Either way, there’s something to learn if you’re willing to reflect on the experience.
After making an important decision, I think it’s worth asking yourself:
- What did I learn?
- What would I do differently next time?
- How has this prepared me for what’s next?
Whether a risk led to a new opportunity or simply a new perspective, I’ve found that it always contributed to my growth.
Don’t Chase Risk. Chase Growth.
Neither leaving school for the NBA nor leaving a front office role for business school came with guarantees.
Both required preparation. Both required faith. And both required accepting that I couldn’t know exactly what the outcome would be.
Over time, I’ve learned that the goal isn’t to take risks for the sake of taking them. The goal is to continue growing.
If you’re willing to prepare, keep learning, and thoughtfully consider the decisions in front of you, you still may not be able to eliminate uncertainty, but you’ll allow yourself to keep growing, and in my experience, that’s often where the most meaningful opportunities begin.
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