21 Things No Leader Ever Regrets Doing

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You probably already have some regrets as a leader.

I know I do.

Not only as a leader, but regrets as a husband, dad, and friend too. Leadership is so complicated that sometimes it’s hard to know what to focus on. Add a global crisis into the mix and it’s even more confusing.

So, why is it that so many of us keep making mistakes at work and at home?

It’s easy to blame your crushing workload, the people around you, circumstances, or just about anything that moves.

But if you look for common threads, you’ll often discover the problem was not in the situation, it was in how you responded to it.

Put another way, it was who you were when the hammer dropped.

But you can also look back on other situations and see you handled things well. That you really have no regrets.

Challenges come and challenges go in life and leadership. The difference between great leaders and poor leaders is often how their character responds to crisis.

Great leaders adopt practices, attitudes, and postures that lead to much fewer regrets. And they make strategic investments and decisions along the way that other leaders don’t.

In the midst of it all, there are some things you can do as a leader that you’ll just never regret.

While I haven’t gotten every situation right in leadership (far from it), I took some time to make a list of 21 things I’ve never regretted doing as a leader. My guess is when you’ve done them, you’ve never regretted them either.

And if you and I keep doing them, we’ll have far fewer regrets moving forward.

The difference between great leaders and poor leaders is how their character responds to crisis.  Click To Tweet

1. Throwing your heart into whatever you do

I’m increasingly convinced that a white-hot sense of passion is one ingredient in churches and other organizations that are doing an outstanding job these days.

Far too many leaders are phoning it in. If that’s you, hang up.

Fully engaging the task before you with all your heart is one of the best shots you’ve got at making an impact.

Too many leaders are phoning it in these days. If that's you, hang up. Click To Tweet

2. Taking the high road

It’s easy to get pulled down into mud…arguing, jostling, and getting caught up in cheap accusations that lead nowhere good.


Take the high road.

You know what that is.

Be kind. Don’t fight back. Prepare to be misunderstood. Forgive. Show grace.

The high road isn’t an easy road, but it’s the best road.

You simply never regret taking it.

The high road isn't the easy road but it's the best road. You simply never regret taking it. Click To Tweet

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3. Saying you’re sorry

It’s easy to apologize when you’re new or just starting out. Everyone expects you to make mistakes.

It’s harder when you’re the leader.

It’s hardest when you’re a successful leader who’s been leading a long time.

Don’t fall into the trap of thinking you’re above reproach. You’re not.

In fact, I think the leader should be the FIRST to apologize (I outlined why and how to apologize well here).

So apologize.

4. Praying for your team

You will never regret praying for your team.

Pray for them by name. Ask them what specifically you can pray for.

A leader who prays for their team is a leader worth following.

A leader who prays for his team is a leader worth following. Click To Tweet

5. Pushing through your fears

It’s not that great leaders have no fears. Pathological people may have no fears, but otherwise we pretty much all face them.

Great leaders push through their fears.

In this post, I outlined 5 signs that fear is undermining your leadership.

It's not that great leaders don't have fears. They just push through them. Click To Tweet

6. Smiling more

You’ll never regret smiling more.

I know I look grumpy unless I remind myself to smile. I’m actually not grumpy most of the time…I just look that way.

So smile.

By the way, being on video and even Zoom calls every day will remind you of how the world experiences you. Smile. 🙂

7. Saying an encouraging word

Very few people I know would say they are over-encouraged.

Okay, no one I know has ever told me they’ve exceeded their lifetime dose of encouragement.

Encouragement costs you nothing as a leader but it means everything to the person you’re encouraging.

Think about that.

Encouragement costs you nothing but it means everything to the person you're encouraging.  Click To Tweet

8. Saying thank you

Ditto with thank you.

When a leader starts acting entitled, followers lose heart.

Treat everyone—including staff—like they were volunteers. Thank them regularly and sincerely.

Even your staff have other options. They can quit. And if you fail to show gratitude, they will.

9. Helping someone who can’t help you back

Leadership ushers in responsibilities, but it also brings some perks.

At some point, you might command a slightly higher salary than others, have access to an expense account others don’t, or even have more control over your time.

Don’t use the perks of leadership solely for your benefit. Help someone who can’t help you back.

Buy them something. Be generous with your time. Open your home. Give them access to something or someone they couldn’t gain access to without you.

Can they pay you back? No, they can’t.

And that’s the point.

Hint: The sooner you start this practice (even when you think you don’t have much), the better.

The best leaders regularly help people who can't help them back. Click To Tweet

10. Finding a few great mentors

Leadership can be a lonely journey, but it doesn’t have to be.

Finding mentors is something no leader regrets.

I look for leaders who are a stage ahead in life and the kind of people I want to be in the future.

11. Developing some replenishing relationships

Ministry can be draining. So can leadership.

You give all day and often go home exhausted.

Often, people will seek you out in your off time asking for “just a little more.”

My wife and I realized years ago that we need to have some friends who truly replenish us…the kind of relationships where time passes quickly and you leave feeling better than when you came.

12. Deciding ahead of time what your priorities will be

I am amazed at how often I have to re-establish priorities in leadership.

Deciding ahead of time what you will do and not do, when you will be off and when you will work, and whom you will meet with and whom you won’t will help you keep first things first.

If you don’t do this, you will never have enough time and always be disappointed with the results you’re getting.

13. Adopting a fixed schedule

One of the best leadership moves I made was moving to a fixed schedule.

What I mean by that is I follow the same rhythm to my work every week with very few exceptions. I pre-determine writing time, meeting days, and more.

An open schedule is a guarantee you’ll spend your time on everyone else’s priorities, not yours.

If you’re looking for ways to save time and a little more on adopting a fixed schedule, this post can help.

An open schedule is a guarantee you'll spend your time on everyone else's priorities, not yours. Click To Tweet

14. Discovering what fuels and drains you

Ever wonder why some days you go home feeling excited and other days you go home exhausted—and yet you worked the same number of hours?

Some activities drain you and others fuel you.

Figuring out which does what can change the effectiveness of your leadership so much.

Great leaders will spend more and more time on the things that energize them and less on the things that drain them. It’s that simple.

I outline how to determine that in this post.

15. Investing in your personal leadership development

You can think of conferences, coaching, books, courses, and development programs as expenses, or as investments.

If you think of them as investments, you will become a far better leader.

The best leaders never hesitate to invest in their personal development.

Becoming better at life and leadership is never an expense, it’s an investment.

Becoming better at life and leadership is never an expense, it's an investment. Click To Tweet

16. Taking meaningful vacations

Even when my wife and I were starting out and we had no money, we found money to take even a simple annual vacation.

It’s one of the best investments we’ve made over the years.

I say meaningful vacations because you’ll be tempted to cheat.

You’ll be tempted to say “3 days is enough.” No, it’s not.

You’ll be tempted to say “We can just stay home and relax.” And maybe you can. But I just want to catch up on household projects when I do.

Taking a meaningful vacation doesn’t mean you have to drop thousands of dollars on a European tour, but it does mean you need to rest and recharge. In this post, I wrote about why driven people (like me) generally suck at vacation.

17. Developing a hobby you love

I could almost be a ‘work is my hobby’ guy. Maybe you could be too.

I love what I do and even writing this blog and doing my leadership podcast were once “hobbies” that morphed into what I do full time. Work just doesn’t feel like work to me most days.

But I also realize I need interests outside of ministry and leadership. At least if I’m going to stay healthy and balanced.

It took me a bunch of false starts, but I’ve eventually settled on cycling, boating, and BBQing as hobbies (I’m a Big Green Egg enthusiast).

Despite what you think, you need a hobby.

18. Becoming an early riser

While there’s still a debate about whether early risers really do get the worm, I’m sold on getting up early.

I think you’ll never regret becoming an early riser because you simply get 1-3 hours to accomplish things when no one is texting you, bothering you, or slamming your inbox.

Guess when I write this blog?

I think one of the keys to success is simply beating the patterns most other people follow. For me, getting up at 5 or 5:30 a.m. gives me (and you) a 2-3 hour advantage over almost everyone—and everything—else.

Try it.

19. Getting to bed on time

I am also a sleep evangelist. Having cheated sleep through my 20s and 30s, I repented.

I try to get as close to 8 hours of sleep every night. I really believe sleep is a secret leadership weapon.

There’s evidence that people who are sleep-deprived operate with a similar impairment level to people who drink too much.

Leaders who are rested always bring more to the table than leaders who are tired.

The sleep experiments I outline in Point 1 of this post have become a permanent part of my life (and I highly recommend them).

Rested leaders always bring more to the table than leaders who are tired.  Click To Tweet

20. Eating better

Diet can have a tremendous impact on mental clarity, alertness, and even your quality of sleep.

Sugar and carb crashes happen to far too many leaders.

Cutting down on sugar and carbs has helped me not only lose weight but feel much better throughout the day.

21. Working out

For years I resisted working out, but in the last fifteen years, I’ve taken exercise much more seriously.

It’s still a discipline, but finding something I love (like cycling) has really helped.

And most of the productive leaders I know take their health and working out at least somewhat seriously.

Don’t imagine that age leads to an automatic decline. At present in my mid-fifties I’m setting or tying personal bests for cycling I set in my forties and trying new things like running and waterskiing.

Most people stop doing things as they age. But getting older can just as easily be an excuse to start doing things.

Most people stop doing things as they age. But getting older can just as easily be an excuse to start doing things.  Click To Tweet

Bonus: Carving out a daily time with God

Why is that the first thing to go in the lives of many Christians is our time with God?

Anchoring myself in scripture and prayer at the beginning of every day is a discipline I’ve never regretted.

You lead better when you hear from God.

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Carey Nieuwhof
Carey Nieuwhof

Carey Nieuwhof is a best-selling leadership author, speaker, podcaster, former attorney, and church planter. He hosts one of today’s most influential leadership podcasts, and his online content is accessed by leaders over 1.5 million times a month. He speaks to leaders around the world about leadership, change, and personal growth.