Managing Leadership Pain, part 1

by Dr. Nathan Baxter
Lead Self Lead Others, LLC


Every ambitious person who responds to their inner drive for more has an ongoing relationship with pain.  It is an emotionally challenging path to success and ambitious leaders would have it no other way.  Why?  Because they instinctively know that pain always precedes the prize.  As a matter of fact, if you remove failure, discipline, set backs, conflict, challenges, and difficult circumstances from the journey they will go find another path that presents the obstacles they need to thrive.


Winning is all about overcoming.  People who love to win know that the challenge is what makes the contest so inviting.  Overcoming pain is really what brings out the best in ambitious leaders.  This is why they rarely are satisfied with their level of success and what can appear as strange to those who are watching their life.


The following thoughts are for my clients and others who relate well to the paragraphs above.  Because I come from the same mold, I have had to learn how to manage my quest for more while remaining grateful and not damaging those around me who depend on my leadership.  Age is a great teacher and I have learned that if I want to finish my life well I need to temper my quest for more with making sure that I am intentionally investing in who and what matters most to me as I climb the mountain.


Let’s begin by defining “leadership pain.”  Leadership pain is the emotional distress a leader experiences when he or she makes decisions to pursue what they feel is possible.  One of my first conversations with a potential client is centered around learning where they are experiencing pain.  If they are not in pain then they are probably not leading.  Leaders naturally strive for something more; something better and they are willing to deal with the difficulties that stand in their way.


Coaching ambitious leaders always involves helping them manage their leadership pain among other things.  I have identified the 6 types of leadership pain that are most common and need to be properly addressed:

  • 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.

The Pain of Being Misunderstood

The mental diet of a driven leader consists of making decisions, solving problems, and telling people what to do.  This is at the very core of a leader’s identity.  Oftentimes, they have to make decisions that others do not understand or agree with.  They do not always have the time, the opportunity, or even desire to walk people through their decision-making process.  They just make the decision knowing that they will have to manage the pain of being misunderstood.  It just goes with the territory.


Leadership is about making decisions and being misunderstood at times.  Depending on the level of insecurity of the leader the pushback they receive from the decision can be extremely painful.  Why?  Because leaders (the great ones) are very much in touch with the implications of their decision and suffer first before they cause others to suffer.  The pain that they experience stems from their feeling that their motives are being judged causing feelings of loneliness in a leader — especially those at the top of the org chart.


The coaching solution centers around first, making sure that the leaders have effectively communicated to others.  Second, it is important to double check that their self esteem stems from their own character as opposed to the popularity ratings.  Countless resources have been wasted by leaders who overreacted to being misunderstood and then spent money trying to appease others.


The Pain of never being satisfied

The pursuit of more can sometimes be a curse rather than a blessing.  The reason being is that an ambitious leader rarely experiences lasting satisfaction.  They are fully aware that they are most fulfilled when they are in the battle for more: solving problems, taking risks, and putting in the extra hours.  Even though they may raise a glass in celebration of a win, they quickly go back to thinking about their next conquest.  They tend to wonder just how far they can really go.  Leaders really do want to know where the glass ceiling is located because they are convinced they can break through it and defy the odds.


The coaching solution is NOT to try to get them to relax and take a vacation.  This is often a common mistake leadership coaches make when trying to help.  The solution centers around helping them gain clarity as to their purpose in life and figuring out what it means for them to finish well.  They are wired with an internal drive that many do not understand and they will accomplish more than most so the key is helping them be strategic and intentional with their life.


The Pain of cheating the wrong people.


Success takes time — lots of time — and ambitious leaders do not mind putting in the hours.  7-day work weeks are fairly normal and they consider it relaxing when they work on the weekend because they get to work in shorts or from a different location.  To them, that is time off.  The problem with using up too much time in pursuit of their latest win is that time is a commodity that can never be regained once it is spent.  There is nothing a leader can do to regain the time they spent last year working on their successes.  Many times leaders will cheat the wrong people.  The pain shows up towards the end of their life in the form of regret.  They realize that instead of cheating their ambitious pursuits they cheated their family and friends.  Because time is a limited resource every leader has to chose who to spend time with and who to neglect.


The coaching solution is to help the leader create a list of people that matter most to them and then work with them to create an investment strategy.  This strategy helps the leader figure out how much time they need to invest in their key relationships each month.  As with any plan, it is important to review the plan with them and hold them accountable for managing their investments.


(part 2 of this article will address the other 3 areas of pain)



Everyone knows someone who seems a bit obsessed with their pursuits.  They usually stick out because their default mindset can be summed up in one word; “more!”  More is not bad as long as it is intentional and relationships remain healthy.


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