I had a short, yet pretty successful career in financial services, but – as I wrote in the FAQ – work wasn’t my life. I worked to live, but as long as I was in an office all day I made sure to work intelligently, thoroughly, and with an eye toward meeting great people and building great relationships.
Those great relationships materialized and were a big part of my professional experience, and when my countdown to resignation reached the ‘one week left’ mark, I started putting together a list of people I wanted to make sure I said goodbye to more personally. I made it through 95% of my list in the two weeks after I gave my notice (~100 people), but while I received uniformly encouraging and positive feedback, one thing stood out unmistakably: company executives were by far the most enthusiastic supporters of my decision to take off!
The average employee’s response was encouraging, with hints of light-hearted jealousy and frequently including expressions of job dissatisfaction. The average response from executives was “dive right in and don’t miss this chance!” One executive explicitly told me that with the opportunity to take a few years off, I would be crazy to return to the corporate world instead of diving head-first into entrepreneurship. Inspiring, but not quite what I had expected.
These responses had me thinking – why would the most objectively successful employees at my company be the most enthusiastic supporters of my leaving. They all knew that I did good work, so I doubt they wanted me out. On the other hand, they all knew that this wasn’t just a long vacation, so they weren’t just trying to keep me happy.
It didn’t take long to solve the puzzle: executives were more encouraging because they got where they were by taking calculated risks.
They knew that my ‘career risk’ was worth taking, and knew that living life on the edge is significantly more enjoyable than simply cruising by on what’s comfortable. My inner economist likes the idea of calculated risk (particularly because it’s the name of an economics blog by Bill McBride), and Amy and I are certainly taking one. While we’re certain that we’ll be financially secure during the next few years, we’re not set to retire for life. My goal over the next few years is simply to make sure that our calculated risk-taking pays tremendous dividends. I’m certain that it will.
posted by jayhorowitz
Our Take on Freedom: Escaping the 9-to-5 Before 25 
I love it! I think the executives were also encouraging because they wish they would have done the same thing when they were younger. They might even wish they had the courage to do the same thing right now. They probably have the money to do it but they probably gave up on those dreams a long time ago.
@David – I definitely agree with your thoughts, although what was really interesting was one executive who had done the same thing in 1987 and completely loved it. She was particularly encouraging because it was such a fantastic experience for her.
[…] I gave my notice I wasn’t shy about why I was leaving, and people were very supportive. “To travel the world with my wife for a few years” drew a lot more questions than […]