February 3, 2025

How the Conservative Approach Led to Welcomed Risk

 I was recently listening to a podcast discussing how we tend to take fewer risks as we grow older. Regardless of the type of risk, personal, professional, or financial; most of us naturally gravitate toward comfort and security rather than high-stakes opportunities. I would consider myself someone with a strong aversion to risk. I like to stick to what I know, follow the tried and true, and build a life that is predictable. That predictability helps ease my anxiety. If you’re anything like me, the unknown is a source of stress rather than excitement. Instead of focusing on potential upside, I often dwell on what could go wrong.

As I listened to the podcast, I started reflecting on how different my life might have been over the last 20 years had I taken more risks. What if I had prioritized impact over stability? It’s a tough question to answer because risk-taking has never been my natural instinct. I’ve always done my homework, played by the rules, and avoided shortcuts or gambles for quick wins. But as I continued listening, I had another realization…

While I’m not out here making reckless leaps, over the past few years, I’ve started stepping further outside my comfort zone, taking small but meaningful risks. I’ve leaned into the Modern Craftsman platform, stopped trying to please every client or potential client, and embraced unconventional partnerships and opportunities. The thing is, I don’t HAVE to do any of this. My career is stable, and I’m not searching for drastic change. Yet, at 39, I find myself choosing to push my boundaries. Ironically, this feels like the opposite of what most people do as they get older.

I think I’ve reached a stage in my life and career where I have the confidence to color outside the lines. I’m actively pursuing things that make me uncomfortable, participating in events that make me sweat, and exploring business ventures without guaranteed payback. By now, my career should be on autopilot. I’ve spent 15 years laying the foundation. I could just sit back and let it run. But I want more. More challenges, more opportunities, more fulfillment, and yes, even more uncertainty.

Looking back, I’m glad I took the safe road early on. It gave me structure, stability, and the foundation to build a life I love. Had I taken bigger risks in my 20s, I might not have had the same consistency or peace of mind. That measured approach allowed me to manage my anxiety, grow into a better version of myself, and ultimately, get to a place where I am ready to take more chances.

Fifteen years ago, if the phone didn’t ring, I would be in full-blown panic mode, stressed, anxious, and scrambling for solutions. Today, I welcome those moments of quiet. They give me space to think creatively, to step outside the box, and to explore opportunities that might lead to something even more fulfilling, even if just temporarily. The systems I built, my stubbornness, my insistence on doing things the right way. All of that gave me the confidence and resilience to handle uncertainty with grace. My approach wasn’t always perfect. At times, it held me back. But in the grand scheme, it got me to where I am today.

I may not be the most successful person in the room, but I’m proud of what I’ve built. I’ve worked with incredible clients, created beautiful projects, built a strong network of peers, helped more people than I ever imagined, launched multiple businesses, and created a lifestyle that (most days) makes me happy. I played a conservative hand, but it paid off. Now, I have more opportunities than I need, and I recognize how fortunate I am for that.

I’m not entirely sure where I intended this blog to go, or what the big takeaway is, but maybe that’s the point. If you’re at a crossroads in your life or career, do what feels right for you. Prioritize your mental health, your long-term success, and what truly fulfills you. What serves you today may not serve you tomorrow, so always keep the door open.

For me, that meant sticking to a careful, measured approach for years. I didn’t take huge risks, I didn’t put my family in harm’s way, and I remained conservative in my choices. That approach gave me the stability and confidence to take risks now. Not necessarily financial risks, but mental ones. Because at the end of the day, I finally understand that everything will be okay. It will all work out. And it’s not worth losing sleep over.

Today is just another day, and that’s a pretty great place to be.