While on our honeymoon, my wife and I went on a daylong excursion to tour Aruba. Among the stops was a 50-foot cliff jump into the ocean. Waves crashing into jagged rocks and a guy with a desk job seemed like a bad combination.

Since they knew the safe spot to jump, the tour guides went before us. There's no way I would've gone without them going first, but after a quick look to gauge the jump, I went for it.

It was awesome. And although it rarely involves a cliff jump in Aruba, we often take risks in life. Some calculated. Some less so.

I've taken several calculated risks. I went to Ohio State without visiting campus. I drove 400 miles to go on a date with a girl I met at my best friend's wedding. I relocated to New York City after one visit without knowing anyone there. I took a job in Washington, DC and agreed to relocate my family from Columbus, Ohio. I left the DC job to stay home with my twin boys and figure out what's next. I started a blog.

None of the decisions went how I expected. But every one worked out in its own way.

I chose Ohio State over my other options because of the breadth of majors, which paid off when I switched from engineering to economics. The girl from the first date 400 miles away is now my wife and my partner-in-crime in raising twin toddlers. After a tough six-month adjustment, living in NYC taught me that I could thrive in uncertainty. The rise and fall of the DC job empowered me to realize the folly of pursuing The Job (more on that here) and allowed me to reassess work's role in my life.

Stay tuned for how life as a full-time dad turns out. So far, so good.

What does it mean to take a calculated risk? In my experience with personal and professional risks, those that went well and those that didn't, a calculated risk has three key parts: a brain, a backbone, and a heart.

The Brain: A Decision-Making Framework
When the opportunity in DC became real, my kids were two years old and we were in the middle of a pandemic. We lived in a great house in a great neighborhood in Columbus, with top-rated schools, new pools, multiple parks, and (most importantly) a killer wine shop, all within walking distance. We were comfortable. Deciding to uproot from our Home-with-a-capital-h was intimidating. Having a framework to rely on was critical to making a sound decision.

In the past, my decisions mostly involved talking to friends. But being as cool as I am, I took a decision-making course in 2020 that has been game-changing.

Offered by Shane Parrish and Farnam Street, Decision by Design introduced a more robust framework. I took the course to help with the decision about relocating to DC (profiled here), but I now use the lessons daily. The most powerful lesson for big decisions is a concept called a pre-mortem, where you imagine how a decision could end poorly and how you might deal with it. This process allows you to see a decision from a new angle and helps find weaknesses in your thinking.

Dealing with decisions going wrong is more difficult without understanding that the decision could go wrong.

A talk with a confidant, a long walk, a decision journal (here's a good one), a decision-making course, a magic eight ball. Regardless of the decision framework you choose, it will help current decisions and allow you to analyze past decisions. The cycle of decision > event > feedback improves your framework, with improved decision-making a natural byproduct over time.

Although I was disappointed the DC job didn't work out, there was little collateral damage because I had a framework. And the best wine shop in the world is still three blocks away.

The Backbone: A Support System
In early 2021, discussions with the DC firm were in full swing, and we were close to finalizing a job description and timeline. Then I got The Call. Everything came to a halt when I learned that an immediate family member was diagnosed with pancreatic cancer.

Through rounds of aggressive chemo and multiple surgeries, relocation remained a possibility. We’re all fortunate that treatment worked. But having a front-row seat to the year-long battle made me realize how fragile life is.

Would I regret relocating farther from extended family? Or would I regret not taking the opportunity to change my family's trajectory? These questions were hard to answer alone. I was fortunate to have a support system to help handle the complexity of a family illness and a possible relocation. A support system grounds you while also serving to open your thinking.

Have you ever needed to turn off the music while navigating traffic? Stress forces your brain to narrow its thinking, which leads to blocking out anything creative. When we face difficult decisions, the inherent stress means we can't even see other options or more creative solutions. My support system pushes, challenges, and questions me, which forces me to think more creatively.

So think about who or what you can lean on when important decisions are on the table. Go to your family and friends. Or the gym. Or meditation. Or journaling. Or a long bike ride. As long as you have something to support you, ground you, and provide a fresh perspective, you'll have the strength to take your risk.

The Heart: Optimism
I relocated from Columbus to NYC in early December. Since I was young and cheap, I saved the relocation stipend and decided to pack and move with just me and my girlfriend of six months.

The night before driving the moving truck to NYC, a snowstorm hit Columbus and moved east. Leaving at 3am, we experienced a frozen-over windshield, horrendous visibility, and an SUV sliding backward toward us on the highway.

The biggest lesson was not to trust Budget rental trucks to have functioning windshield fluid sprayers.

It wasn’t only luck and some deity out there got us through to sunlight and clear roads, but also the belief that we would get through it. We believed we would make it to NYC.

Through a hellish snowstorm, traffic, the Lincoln Tunnel and parallel parking a 26-foot moving truck on E 89th Street, optimism got us through.

Not every step of every decision is going to be easy. As the great Ohio State coach Woody Hayes said, "Anything easy ain't worth a damn." Doubt will creep in when you're at your weakest, and the bigger the risk, the more doubt there will be. It will be too easy to quit, give up on taking the risk, and settle for the status quo.

Believing that things will somehow work out is critical to taking a calculated risk. Even with a sound decision-making framework and support system, you will need optimism.

A brain and a backbone are useless without a heart.

The next time you face the opportunity to take a risk, listen to your brain, backbone, and heart. Though there may be signs warning you against it (sometimes literally), take the leap anyway.