Even Great Leaders Have Big Regrets

Regret is a natural part of the human experience. There will always be things left undone and unsaid, time wasted, words fumbled, and mistakes made. Regret can be used to avoid future missteps: part of the entrepreneurial trial by fire that leads to refinement.

On the other hand, regret can weigh on your mind and spirit. Listen: there’s no way to today avoid regret. Not as a leader, an entrepreneur, or as anyone and anything under the sun. What we must do, though, is recognize regret immediately so we can pivot.

Don’t cause yourself to suffer unnecessarily: heed warnings before it’s too late to change course.

When All is Said and Done, this is What Great Leaders Regret Most

Regret #1 – Compromising values and integrity.

I don’t know a single person who doesn’t immensely regret taking a path that breaks their personal sense of morality. These ill-gotten gains will always be stained with the stench of compromise. As a leader, you must establish what you’re willing and not willing to do in pursuit of your goals.

There will be times when you’re presented with opportunities – opportunities that could be very lucrative – that demand you work with people and in ways that you can’t sign off on. You may temporarily regret not taking these opportunities, but you will avoid a lifetime of torture by sticking to your principles.

Regret #2 – Dwelling on paths not taken.

There are thousands of directions we can take in life. It’s so easy to fall into a cycle of “what if” and “I should have.” If we’re not careful we’ll become so fixated on an alternative reality that we don’t fully take advantage of actual reality. Regrets are like mud – they have a way of getting people stuck.

You can’t change the past. Regret, at its best, fuels self-reflection and improvement. At its worst, it leads to despair and doubt. Dwelling on regret just leads to an unending and painful cycle.

The key is to focus on the future, making choices that avoid the same mistakes.

Regret #3 – Neglecting physical, mental, and emotional health.

Entrepreneurs are inundated with the notion that they must give up everything in the relentless pursuit of success. Don’t get me wrong – leadership and entrepreneurship alike are challenging. It’s grueling work that demands resolve, dedication, and sacrifice.

Unfortunately, though, there are plenty of professionals who sacrifice the wrong things. You can’t undo the damage you do to your body over the years. You only have a small window of time where you’re in your prime, and self-neglect is going to catch up with you.

Your health is what enables you to keep going: staying sharp, active, and capable well into your twilight years. The quality of your life in the long term is worth prioritizing. After all, what’s a financial empire worth if you lack the fortitude to enjoy it?

Regret #4 – Trading family time for financial gain.

There’s not a single person, who, on their deathbed, would say that they regretted spending so much time with their family. There are plenty of people, however, who say they regret working so much – and missing out on the lives of their children.

We, men, have this drive to be providers and breadwinners. Traditionally, it’s the role we take on. We see it as the most important thing we can do for our family. But I want to challenge that notion. Men, step up. Be a present role model. Make family time sacred. Non-negotiable.

All the money and financial security in the world won’t make your family feel loved.

So, what do we do with regret?

Like failure, regret presents an opportunity. It’s a chance to reexamine ourselves, change course, and achieve greater success moving forward. The difference is this: failure lasts for a moment. Regret can last for a lifetime.

Refuse to dwell. Regret should be there to remind you to make better choices, not to beat you over the head with your worst moments. Don’t focus on the feeling: focus on moving forward with confidence and conviction.

And we must act sooner rather than later. Don’t let regrets linger any more than they must. When your behavior is resulting in regret, change your behavior!

How do you recover from personal and professional regrets? Share in the comments.