The Joys of Failing Forward

Key Takeaways

  • There is often an attitude with adults when it comes to trying something new, where you try it once, you fail, and you don’t attempt it again.
  • When we are young, we tend to fail forward often as we learn the ropes in life, but as we enter adulthood and become established in our careers, we forget what it’s like and become afraid of failure.
  • The idea of failing forward is lifelong learning at its best; it helps you learn new skills, and keeps your mind active and engaged in to your later years.

I knew a gentleman that passed away a few years ago who seemed to do more in life after he retired than he did during his working years. He retired from the active workplace about 20 years before he passed, but during those 20 years, he became a sculptor, painter, author, and learned a new language. I was simply blown away by everything he’d accomplished during his retirement, but what it really showed me was the fact that he was not afraid to fail, since he hadn’t learned any of these activities prior to his retirement.

Imagine you have a two-year-old who is learning to tie their shoes, they attempt it once, fail at it, and say, “That’s it, I’m done!” We see this attitude a lot with adults, where they try something one time, fail at it, and completely give up. We’re afraid to fail, but we really didn’t develop this fear until we became adults and entered in to the workforce. When we first start off, we fail all the time, but we eventually made it work and moved forward in our lives.

This idea of failing forward is with us throughout our lives, but we somehow seem to forget how it works as we get older. Watching this gentleman go through the failing forward process near the end of his life got me excited for when I get to that point in life, that I need to remind myself it’s ok and even good to fail. I know many people who have retired and have trouble doing other things because they are afraid of failing, but it’s a part of our human existence.

We often think of failure as going backwards, but failing forward is like the child learning to tie their shoes: they don’t do it right the first, second, third, or maybe even tenth time. Perhaps they get it on the twelfth try, but they learned every single time they failed, they gained more dexterity, their brain worked out how to do the loops just right. They just had to keep attempting, to have the courage and commitment to fail, and eventually, some momentum takes place and they learn this new skill, tying their shoes.

As you enter in to a new phase of life, perhaps it’s retirement, maybe it’s a mid-career switch, or some other big change in your life, don’t be afraid to continue to fail forward. You’ve got a lot of years of experience, but don’t let those accumulated hours of failing forward keep you from continuing to grow and learn. It’s this continuation of failing forward that keeps us lively and keeps our brains active to help us in to our senior years in life.

Until next time, enjoy.


Inertia, often caused by being overwhelmed, keeps smart people from planning. TransformingWealth™ , Coyle’s proprietary approach, is designed to get your arms around the big picture so you can make informed financial decisions. Take the first step to living the Good Life Managed Well™, and schedule a complimentary TransformingWealth Preview Meeting.

Gary Klaben is in our Glenview, IL office and serves our clients who are now located all over the country. He has over 30 years of experience and is the author of Changing the Conversation, The Wealth Sanctuary and co-author of The Business BattlefieldWhether advising his clients, mentoring his team, or coaching entrepreneurs, he is always simplifying complexity and motivating others to take the next action that’s right for them.
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