The 4 Types of Regret

We’re excited to announce the launch of The Daily Coach Network — coming this September. See details below.

He stood in the giant tunnel awaiting the signal to head down to the makeshift square stage that resembled a boxing ring as 20,000 people at Madison Square Garden in New York City, on a beautiful October night, were breathless, awaiting his performance. With the “go ahead,” Frank Sinatra double-tapped the cheek of longtime friend Jilly Rizzo and headed to the ring—to perform his first concert since his self-imposed retirement.

For the last song, Sinatra chose “My Way,” his semi-autobiographical contemplation of leaving show business and retiring. In the song, Paul Anka, the songwriter, starts the second verse discussing regrets—which Sinatra had a few.

Haven’t we all held on to regret over our careers — young and old?

However, as we all get older, regretting the mistakes we made in the past becomes a way of living. As Wright Thompson wrote in his wonderful book, “The Cost of These Dreams,” “All driven people experience a reckoning at the end of their life’s work, but when that work feels incomplete, or somehow tainted, the regrets can fester with time.”

Fortunately, bestselling author Dan Pink comes to the rescue. Pink’s latest book is called “The Power of Regret.” Pink conducted a worldwide survey, gathering over 16,000 regrets from 105 countries. He found that regrets fall into four categories.

1. Foundation Regret. Suppose I had only done the work if I had been more assertive as a leader. Suppose I had only worked harder.

2. Boldness Regret. Suppose I had only taken that risk five years ago if I had trusted my gut and started that business. Suppose I had only reached for the stars.

Pink writes: "If foundation regrets arise from the failure to plan, work hard, follow through, and build a stable platform for life, boldness regrets...arise from the failure to take full advantage of that platform—to use it as a springboard into a richer life."

3. Moral Regret. If I had only done the right thing. If I had been a nicer person.

4. Connection Regret. If I had only reached out and kept in touch, maintaining friendships would have been my priority.

As Pink proves, regrets are a part of everyone’s life. We must not allow it to impede our present days’ actions or affect our happiness. Pink proves regret is a normal shared human experience, which should allow us to remove any quilt or embarrassment. We must carry on—and spend little time regretting the mistakes. Rest assured, as we continue to age, we will find other regrets—but with Pink’s help, we will understand what category they might fit into, which could help us determine our actions. We might regret less by understanding these four categories before we make a personal or professional decision.

Even Sinatra had regret — just too few to mention.

Introducing The Daily Coach Network

Accepting Applications Now

The Daily Coach Network, led by three-time Super Bowl-winning NFL executive Michael Lombardi and Naismith Basketball Hall-of-Fame Coach George Raveling, is a highly-vetted membership community for business executives who approach their leadership development like athletes.

New England Patriots Head Coach and General Manager Bill Belichick and James Kerr, international best-selling author of the book “Legacy,” will kick off The Daily Coach Network’s monthly speaker series.

Limited to just 75 members, the community features monthly, exclusive guest speakers and connects you with other high-performance leaders who understand your challenges and will hold you accountable to your development — without a major time commitment.

Launching September 2023.

Learn more and apply here.