Episode Breakdown
Take Risks | Beyond The Grind #028
That feeling of being comfortable in your career is nice, isn't it? The steady paycheck, the predictable routine, the feeling of knowing your job inside and out. But what happens when that comfort curdles into complacency? What if the path of least resistance is actually a path to stagnation?
In our latest conversation, we dove deep into a topic that affects every ambitious professional: the willingness to take risks. It’s a conversation sparked by a simple headline that claimed not enough people are doing it today. This got us thinking about why we shy away from career risks, even when our goals and lifestyle aspirations demand more than our current reality provides.
For many, the word "risk" carries a heavy, negative weight. It sounds like something to be avoided at all costs. But as we explored, there's a universe of difference between a reckless gamble and an intentional, calculated leap of faith. The truth is, avoiding risk is often the riskiest move of all.
The Danger of Comfort and the Power of Calculated Risk
The most common trap we see people fall into is the comfort of a "good job." Korede shared a story about a friend's husband who worked the same government job for 15 years. He was secure and comfortable, but that comfort came at a cost: stagnation. He didn't want to change jobs or take on new challenges because of the fear of the unknown. That certainty became a cage.
As Allen pointed out, this is especially dangerous when the ecosystem you depend on suddenly changes, like a shift in government administration. When that layoff finally comes, you’re left with years of tenure but few updated, transferable skills. You haven’t been forced to innovate or see what’s happening outside your bubble.
This is why Tosin’s distinction is so critical: we’re not advocating for reckless gambles, but for calculated risks. When Tosin decided to leave his nine-to-five for entrepreneurship, he didn't just wake up and quit. He registered his business, built it up slowly, and made a strategic decision to leave when he had a foundation in place. It was still a risk—going from a guaranteed paycheck to the uncertainty of a startup—but it was an informed one.
As Allen puts it, the risk is about the same when you’ve done the work. You’ve diminished the unknown by doing your homework, running the numbers, and understanding the landscape.
"To me failure was like not trying to achieve the things I wanted to in getting to a certain age and be like man, I'm old if I fail now, it's really hard." — Allen
How to Build Your Courage and Take Risks Intelligently
So if you’re feeling that pull to do more but are held back by fear, how do you start? How do you build what we called your "risk muscle"? It’s not about a sudden, drastic personality change. It’s about taking small, intentional steps.
Based on our conversation, here are a few ways to start flexing that muscle:
Start small. You don’t have to quit your job tomorrow. A risk can be as simple as finally registering the LLC for that business idea you’ve had for years. It’s a small financial and emotional investment, but it’s a powerful first step that makes your dream real. Or, if you’re in a W-2 role, it could be volunteering for a project outside your normal duties or drafting a proposal for a new initiative.
Surround yourself with challengers. The people around you matter immensely. If your circle is full of people who only tell you what you want to hear, it’s easy to stay comfortable. You need friends and mentors who will hold you accountable to your goals. As Allen noted, you can’t be the sole driver of someone else’s dream, and you can’t expect others to drive yours. Accountability is the engine of growth.
Reframe your relationship with failure. Many people don’t take risks because they’re terrified of failing. But what if you fail? Tosin encourages us to look at failure as feedback. It’s not final; it’s an opportunity to learn and improve. Walk yourself through the worst-case scenario. Ask yourself, "And then what?" More often than not, you’ll realize that the worst that can happen is not only survivable but also a valuable lesson.
"Don't treat failure like you need to look at failure like feedback... So what if you do fail? Failure is not final." — Tosin
Ultimately, the goal is to get it right just one time. Every attempt, every "failure," is just another data point on the road to success. If you don’t take the leap, you’ll never fail, but you’ll also never grow.
For the full, unfiltered conversation on calculated risks, overcoming fear, and building a life beyond the daily grind, watch the full episode on YouTube. And for more insights like these delivered straight to your inbox, be sure to subscribe to our newsletter.
“To me failure was like not trying to achieve the things I wanted to in getting to a certain age and be like man, I'm old if I fail now, it's really hard.”
“Don't treat failure Like you need to look at failure like feedback... So what if you do fail? Failure is not final.”