Risk Taking – Tips on Making Decisions

Life is full of influential moments, they happen everyday. There are fewer moments that define who we are. Even making the decision to NOT let a moment define you can, in turn, be a defining moment. These moments are etched into our story as a necessary part of our experience.

Can you define your moments?

For me, making the decision to move to Florida after college was one of those moments. In hindsight, it changed everything. I want to share a quick story and what I’ve learned from it.

My Search

I graduated from college engaged to Liz and needed to get on the ball with getting a job. A family friend approached me about becoming a Junior Partner at Merrill Lynch. It seemed to be a great fit. I loved helping people, I loved money, I passed the tests, they offered me the job, I had a soon-to-be wife to care for; check, check, check, check, check. It looked like I was on my way.

Looks can be deceiving.

The Call

The call came from a great family friend, but it was not what I wanted to hear. He wanted me to meet a buddy of his running a real estate sales firm in Florida. Quite frankly, I didn’t want to go, but my Mom encouraged me otherwise.  When I left, the offer was pretty simple.

“I know you’ve got a job lined up, but I would love for you to fly down and take a look at what we do.  If you don’t like it, no worries.”

Instead of signing the papers the next day at Merrill, I caught a plane to Florida and it became part of my story.

What My Florida Decision Taught Me About Decision Making

1.  When you’re unsure, ‘Do Something’: When I graduated, I wasn’t exactly sure what I wanted to do. Brainstorming is great and necessary, but action is better. Go do something. When I was in limbo, I started waiting tables. It allowed me to make a ton of connections that I still have today and money was never a necessity when looking for a job. It also gave me a deeper understanding that I loved working around people.

“You often find YOUR thing by doing SOME thing.” – Mike Ashcraft

2.  Leaders take risks:  It is not coincidental that I was reading John Maxwell’s “21 Indispensable Qualities of a Leader”, particularly the part that says ‘leaders take risks’. Those three words were all I could hear on the plane flight to Florida. In reality, Merrill Lynch was safe: fiance, family, home. Now don’t get me wrong, that’s a tough industry, but the surrounding circumstances were safe. Florida was risky. It taught me to listen to the whispers and give them a shot.

3.  The difference between Risk and Recklessness: There is a huge difference between taking risks and being reckless. However, the line between the two can be very thin and hard to recognize. When determining that line, I consider a few things. First, legality. If its illegal, it’s reckless. Second, danger. What danger does it pose? Is it perceived danger or a true threat? Third, who else is at risk. If your risk involves your family, you have to be responsible to that decision first.

4.  Decisions can be tough, ‘Responsibility for a decision is tougher’: I will never forget the day we packed up the U-Haul and I pulled out of my parents driveway. In my mind, I stopped crying by the end of the street, but I’m pretty sure it was somewhere in Georgia. Wrestling fear and excitement is a bear. It pulls at every emotion as you accept responsibility. Once I made my decision, I had to go make it right and you do too. Even if making it right is learning from it, don’t get caught in the quicksand of doubt.

Questions: How do you make decisions?  What risks have you taken?


If you'd like to read the full story of my Florida experience and how it led me to where I am today, check out my ebook "I Am Here"

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