By Dr. Nathan Baxter
Every ambitious leader who responds to an inner drive for more eventually develops a relationship with pain.
The road to meaningful success is rarely comfortable. It includes failure, discipline, setbacks, conflict, difficult decisions, disappointment, and circumstances we would never choose. Yet ambitious leaders are often drawn to this road.
Why?
Because they understand something instinctively: Pain often precedes the prize.
Winning is largely about overcoming. People who love to win aren’t simply attracted to the outcome; they are energized by the challenge of getting there. Give them a problem to solve, an obstacle to overcome, or something others believe can’t be done, and you will often see them at their best.
That drive can produce extraordinary results.
It can also create extraordinary pain.
I understand this because I come from the same mold. Over the years, I’ve had to learn how to manage my own quest for more while remaining grateful for what I already have — and while trying not to damage the people around me who depend on my leadership.
Age is a great teacher.
I’ve learned that if I want to finish my life well, I have to temper my desire for the next mountain with an intentional investment in the people and things that matter most to me.
You can spend your entire life climbing mountains only to discover that you neglected the people you hoped would be standing beside you when you reached the top.
What is Leadership Pain?
I define leadership pain as the emotional distress leaders experience as they make decisions and pursue what they believe is possible.
One of my first conversations with a potential coaching client usually centers around a simple question: Where are you experiencing pain?
Leadership almost always creates some form of tension. Leaders see possibilities that don’t yet exist. They want something to become better. And closing the gap between what is and what could be requires decisions, change, risk, conflict, perseverance, and sometimes sacrifice.
After years of coaching ambitious leaders, I’ve identified six types of leadership pain that repeatedly surface:
- The pain of being misunderstood.
- The pain of never being satisfied.
- The pain of cheating the wrong people.
- The pain of integrity.
- The pain of receiving counsel.
- The pain of self-leadership.
In Part 1, let’s look at the first three.
1. The Pain of Being Misunderstood
Much of a leader’s mental energy is spent making decisions, solving problems, setting direction, and helping people move forward.
And sometimes leaders have to make decisions that other people simply don’t understand — or don’t agree with.
The leader may have information others don’t have. They may be considering consequences that aren’t obvious to everyone else. Sometimes there isn’t enough time to explain every detail of the decision-making process.
So the leader makes the decision.
And then comes the pain of being misunderstood.
This can be especially difficult for leaders who genuinely care about people. Good leaders understand that their decisions have consequences. They often wrestle with those consequences long before anyone else knows a decision has been made.
The deepest pain often isn’t disagreement itself. It’s the feeling that our motives are being misunderstood.
That can create a particular kind of loneliness, especially for the person sitting at the top of the organizational chart.
The Coaching Solution
I usually encourage leaders to ask themselves two questions:
First: Have I communicated as clearly as I reasonably can?
Don’t use “I’m the leader” as an excuse for poor communication. People may not agree with your decision, but whenever possible, help them understand the thinking behind it.
Second: Do I need to be understood in order to be secure?
A leader’s sense of worth cannot rise and fall with approval ratings.
I’ve watched leaders waste enormous amounts of emotional energy — and sometimes organizational resources — trying to appease everyone who misunderstood or disagreed with a decision.
Sometimes leadership requires the confidence to say:
“I have listened carefully, communicated clearly, and made the best decision I know how to make. Now I have to lead.”
2. The Pain of Never Being Satisfied
The pursuit of more can be both a blessing and a curse.
Ambitious leaders rarely experience satisfaction for very long. The may celebrate a major victory tonight and wake up tomorrow morning thinking about the next opportunity.
There is always another problem to solve.
Another goal to reach.
Another mountain to climb.
Driven leaders often feel most alive when they are in the battle — solving problems, taking risks, overcoming obstacles, and discovering just how far up they can go.
They want to know where the ceiling is because somewhere inside they are wondering: “Could I break through it?”
There is nothing inherently wrong with that drive. In fact, it is often responsible for much of what these leaders accomplish.
The danger comes when more becomes the destination instead of a tool.
If there is always another mountain, when do you ever arrive?
The Coaching Solution
The solution is not simply telling ambitious leaders to slow down, relax, and take another vacation.
They may need a vacation — but that doesn’t address the deeper issue.
The better conversation is about purpose.
What are you ultimately trying to accomplish with your life?
What does success actually mean to you?
Who do you want to become along the way?
Who do you want standing beside you when you get there?
And perhaps most importantly: What would it mean for you to finish well?
Ambitious leaders don’t necessarily need less ambition. They need directed ambition — a clear understanding of where they want their drive to take them.
3. The Pain of Cheating the Wrong People
Success takes time.
Lots of it.
And ambitious leaders are usually more than willing to put in the hours.
Seven-day workweeks can become normal. Working Saturday morning doesn’t really feel like work because you’re wearing shorts, drinking coffee, and answering emails from home.
That’s practically a day off, right?
The problem is that time is one resource you can never replenish.
You can make more money.
You can rebuild a business.
You can replace an employee.
You can pursue another opportunity.
You cannot recover last year.
And this is where successful leaders sometimes make one of their most painful mistakes: They cheat the wrong people.
Every yes is also a no.
If you give another evening to the business, that time has to come from somewhere. If you spend another weekend chasing an opportunity, someone or something else doesn’t receive those hours.
The danger is that the people most committed to us are often the easiest people to cheat.
- Our spouse.
- Our children
- Our grandchildren
- Our closest friends
They love us. They understand. They tell us to go ahead. Until one day we realize how much time has passed.
For some leaders, this leadership pain doesn’t fully arrive until later in life, when it shows up under another name: Regret.
The Coaching Solution
I encourage leaders to identify the people who matter most and then create an intentional relationship investment strategy.
Write down their names. Then ask:
If these people really matter as much as I say they do, what should that look like on my calendar?
Determine how much time and attention you want to invest in those relationships each month — and then protect those investments with the same seriousness you protect an important business commitment. Because someday your calendar will tell the story of what you actually valued.
More Isn’t the Enemy
Most of us know someone who seems slightly obsessed with their pursuits. Their default mindset can often be summarized in one word: More.
More growth. More impact. More opportunities. More success. Another mountain.
I don’t believe more is necessarily the problem.
The question is whether our pursuit of more is intentional.
Are we becoming the person we want to become?
Are the relationships that matter most still healthy?
Are we enjoying any of what we’ve already accomplished?
And are we pursuing success in a way that will allow us, someday, to look back without wishing we had climbed a little slower and loved a little better?
Keep climbing. Just make sure you’re climbing the right mountains — and that you’re not leaving the right people behind.
In Part 2, we’ll explore the remaining three types of leadership pain: the pain of integrity, the pain of receiving counsel, and the pain of self-leadership.