Why Risk Having One of These Regrets About Your Career?

People talk about the “risk” of entrepreneurships way too much as well as the fear of failure.

But the biggest risk I see in life is … REGRET.

I’ve posted about “regret” several times here at the EntreLab and even given talks mentioning my fear of regret that one person referred to as my “demon of regret.”

This demon of regret is one of the biggest motivating factors in living a life of purpose and passion that ultimately led me to entrepreneurship.

Regret is too big of a risk for me. It outweighs so much of the other stuff, which is why this quote by Teddy Roosevelt resonated with me so deeply about Living Life in the Arena.

Daniel Gulati, co-author of Passion & Purpose (which I hope to read soon), posted the top 5 career regrets he’s heard talking to career professionals. The simple statements in his article resonated with me and I’m sure will with you too so I thought I share them here and include commentary from me beside them:

  • “I wish I hadn’t taken the job for the money.” — I’ve often said money jobs are prison cells. Just ask your parents.
  • “I wish I had quit earlier.” — I don’t want to be at the end of my life with the limited time, talent and treasure I’ve been given and know I squandered it.
  • “I wish I had the confidence to start my own business.” — The day you start to think you have entrepreneurship mastered is the day you fail. Most entrepreneurs who are supremely confident (i.e. to the point of annoying arrogance and cockiness) are simply covering up for a massive dose of personal insecurity. I simply took a calculated leap. I wasn’t the best. I didn’t have the most talent. But I was confident in one thing — I didn’t want to waste an opportunity when it came! Each day is a new challenge with new obstacles. But each day you build on the previous day’s journey with some confidence in yourself as well.
  • “I wish I had used my time at school more productively.” — I loved those days and didn’t savor them as much either … but again, I had work to do. Squandering it playing videogames (how I lost my full-ride scholarship) and sleeping in more than I did would be folly to me and ultimately delay the joys I’ve had in my career, my business and life.
  • “I wish I had acted on my career hunches.” — I can safely say I sought to act on all the career opportunities I had before I started iThemes (I averaged a new job almost every two years professionally). I wasn’t complacent to sit and soak somewhere. I wanted to advance my career path … and when I attribute any success I’ve enjoyed as an entrepreneur, I always add this line: “I was at the right time, at the right place, with the right people … and I was ready.” I jumped when the opportunity of a lifetime opened itself to me.

Read the full article here at the Harvard Business Review.

But what about you? What are you risking today by not taking the next steps in living your life?




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