The Impact of Regret on 8 Successful Entrepreneurs

Entrepreneur RegretsRegret is powerful.  It’s life changing.  It makes you go back and think about something that you should have done different.

Wikipedia defines regret as a negative emotional reaction to personal past acts or behaviors. 

The thing about regret is that it changes people.  You can’t change the past, but you can change the future.  Even more than that, by sharing your lessons learned, you can help others.

That’s why I’m excited that these eight successful entrepreneurs were brave enough to share their regrets here at Beat the Nine to Five.

The question I asked all of these successful entrepreneurs was:

What was your biggest regret and what did you learn from it?

The interesting aspect was there were some successful entrepreneurs that disagreed and had no regrets, while others shared important lessons learned.  Read to see what these entrepreneurs had to say about regret, and then share your answer to the same question in the comments below.

I’d love to hear from you and learn from you as well!  


Corbett Barr, Founder of Think Traffic

corbett barr regret

My biggest regret is having spent part of my life worrying about regrets.  Now I live without worrying about what I could have or should have done and instead focus on what I can or will do with what I have and am.

Find Corbett at Think Traffic or follow him on Twitter @corbettbarr


Leo Babauta, Zen Habits

leo babauta successful entrepreneur regret

My biggest regret (and really I don’t have any regrets) is that I didn’t figure this out sooner. I could have started my own business years earlier if I’d known I could do it, and if I’d had the confidence in myself.

Find Leo at Zen Habits or follow him on Twitter @zen_habits


Chris Guillebeau, The Art of Non-Conformity

chris guillebeau regret

My biggest professional regret is not starting sooner. I wish it hadn’t taken me so long to get going! But I’m glad I finally pushed ahead.

Find Chris at The Art of Non-Conformity or follow him on Twitter @chrisguillebeau


Dan Andrews, Tropical MBA

Dan Andrews Entrepreneurial Regret

I know it’s weird, I don’t have any memories of big turning points where I made the wrong move. Nothing I dwell on. As I move further along in my carrer, there is a more regular form of regret or consciousness – that I should be doing more, and doing better work, to help others.  Like a daily mini-regret – it also serves as fantastic motivation and imbues what we do with a purpose.

Find Dan at Tropical MBA or follow him on Twitter @TropicalMBA


Tom Ewer, Leaving Work Behind

tom ewer regret

My biggest regret by a huge margin was that I didn’t strike out on my own sooner. I walked straight into a part time gig out of college that quickly turned into a full time job and somehow fooled myself into thinking that I was achieving everything that I wanted to.

It took five years, one global economic meltdown and a prolonged period of stagnancy in my job for me to realise that I needed to take matters into my own hands. Around half a year later I quit my job and I’ve never looked back.

To anyone that is considering doing something — anything — my advice would be this: go for it. Life is too short to spend your days procrastinating. Get out there and make it happen.

Find Tom at Leaving Work Behind or on Twitter @TomEwer


Caleb Wojcik, Pocket Changed

Caleb Wojcik Regret

My biggest regret in my entrepreneurial journey is not finding my own health insurance policy sooner. For 15 months I paid an outrageous amount for my COBRA coverage through my previous employer. I had no idea how much money I was wasting each month until I found I out could get the same coverage for half the price. That was a multi-thousand dollar mistake.

Find Caleb at Pocket Changed or on Twitter @CalebWojcik


Miranda Marquit, Planting Money Seeds

miranda marquit freelancer

I think my main regret is that I didn’t go into this thinking about it as a business. When I started, I thought I would do enough to  pay the rent and supplement my husband’s stipend as a teaching assistant in grad school.

I wish that I had seen the business potential and planned a little better. As a result, my efforts have been haphazard at times, and I’ve had periods of extreme stress and burn out interspersed with the good. Also, I wish I’d raised my prices a little sooner than I did.

You can find Miranda at Planting Money Seeds or on Twitter @mmarquit


Jeff Rose, Good Financial Cents

jeff rose regret

I think the BIGGEST regret was not hiring a business coach sooner.   I’m starting my 3rd year of the Strategic Coach Program and loving it.  It has changed how I approach my business and my life each and every day.   That change in mindset is leading to exponential growth on all fronts and excited to see where it takes me.  Skies the limit!

A former colleague had always talked about the successes from his coaching programs, but I immediately dismissed it as “being weird”.   I didn’t get why you would pay A LOT of money to someone to “make you feel good”.   Even joining the program I was still a skeptic.    Now I understand how easy it is to get lost in the daily grind and how important it is to have someone looking over your shoulder.  To constantly be reminding you of your intended journey and to spend your time where you need to be spending it.

You can find Jeff at Good Financial Cents or on Twitter @JeffRose


Now it’s your turn –  I’d love to hear your answer to your biggest regret in the comments below.

If you’re new here, we’d love you to come back again soon and check out what Beat the Nine to Five has to offer. We’ll help you learn how to build a business so that you can eventually quit your job to become an entrepreneur (or anything in between). It’s your choice.

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  1. Inspiring post! I try not to have regrets and stay positive. But if I had to answer, it would be allowing the fear of failing to paralyze me into non-action. Throughout my life, whenever I did take action good things happened. One, the desired outcome or two, a valuable lesson learned. However, it did take awhile to figure out a setback or lesson learned isn’t a negative outcome. You have to shake it off, learn the lesson, and get back on the horse! Love this quote from Zig Ziglar I heard the other day. “Failure is an event, not a person.”

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