The 10 Greatest Life & Leadership Lessons I Have Learned (So Far)

If we are going to lead well, we better learn well too. Here are ten life and leadership lessons I have learned that may be of help to you as well.

1. Relationships are more important than income or status.

If someone says they do not care about how much they are paid, they are likely lying, spiritualizing, or have a very large inheritance. Pay is important, but there are things even more important than pay, and one of them is relationship. Many years ago, I left one position to go to another. As I have looked back on that important decision, I have now realized that I was not going to work for the organization as much as I was going to work for the person. That person added far more value to my life than money could buy. Status and salary are important at times, but I would still place more importance on who I work with over how much I make.

2. Christians are still very, very human. 

Regardless of whether or not we have any religious beliefs, we all have a tendency to forget that the people around us, including those we admire, are imperfect. Everyone wants a hero, and it can be a big let-down when they prove to be just like us… imperfect. This is especially true of Christians. It was a sobering reminder to me the first few times, in the younger days of my Christian faith, that someone I admired did not live up to what I expected. Yet such let-downs helped me develop more realistic expectations for those around me.

3. You can be blindsided when you least expect it.

Like the ocean, life can be calm and smooth sometimes. But rogue waves can hit you when you least expect it. I will never forget receiving the call that my 13-year-old daughter’s MRI showed a brain tumor. Not that anyone is prepared for that, but I was far more comfortable with a life that was sheltered from unexpected disappointments. This experience served as a sobering lesson - I should never assume a season of calm will be permanent. In this life, we will have disappointments and shattered dreams.

4. Life is full of compromises, and that is not a bad thing.

We like things black and white. But life is seldom clear. There are many times when we have to give in order to get. While compromise can be devastating when used in the wrong places, it is an essential part of life, teams, and relationships. When our first daughter was born, my wife wanted to stop working to be home with her. I was supportive of that, but it did require compromise – I would have to work two positions and be home less often, and she would need to be ok with me being home less often (some may say me being home less was a gift to her!). Compromise is not always bad and is often even essential.

5. Impact does not require credentials or position.

We often confuse popularity or position with impact. The reality is that impact comes more often by sacrificial service than position. A great example of this was a man I worked with as a landscaper years ago. I recently learned that he had passed away from cancer and wrote this on his memorial page: “He was a special man who I met when I was a very new Christian. He had a great impact on my life in those early years of my faith. His humility, gentle spirit, and unwavering faith in Christ was a powerful influence to me and to many others.” A great example of impact over position.

6. A life of character doesn’t get any easier as you get older.

I thought that, as I grew older, it would be easier to have my intentions match my behavior and my thoughts match the thoughts that God has. I was quite a bit off on this one. A faithful life, a life of character and purity, doesn’t get easier with age. It is still a day-to-day commitment, with each day being a fresh start. I’ll never forget the words of a wise old pastor who was in his 80’s when he said, “I have a lot of time to think now. And this has reminded me of just how sinful I still am and just how gracious God is.” 

7. Lost or damaged relationships come with (imperfect) leadership.

When I was younger, I never could have guessed how many friendships, even close ones, would come and go in my life. Some of the changes are normal – people relocate or life circumstances make it more difficult to stay connected. But there are also relationships that are damaged or lost when difficult decisions have to be made. This is especially true when you work with people you consider friends or you disagree with destructive decisions a friend is making. I continue learning that relationships are fragile, fluid, and yet essential to a healthy and joyful life.

8. The winter season of your soul is very real and very normal.

I read a book called Spiritual Rhythm a few years ago. The author uses the four seasons of the year to look at life. I used to naively think life would be spring and summer all year long – fun, bright, and energizing. Dark, cold, and depressing had no place. Yet that is not realistic. In our spiritual lives, marriages, relationships, and careers, it will not always feel like summer. Winter is real, normal, and sometimes even beneficial.

9. The older I get, the less I know… at least about some things. 

When I was younger, I was very confident that I knew what was correct and incorrect in many areas. And that confidence, at times, was glazed with a coating of arrogance. The older I get, the more I realize that my beliefs are more opinions than infallible knowledge, and I therefore need to be careful where, when, and to whom I speak with an attitude of “I am right and you are wrong.” And, even if they are wrong, showing some generosity may be as important as trying to win.

10. Others must increase and I must decrease.

The first 30 years of our professional lives are spent in “advancement” activities such as education, credentialing, relational networking, and striving for a track record of effectiveness. I have found that, as we get older, things should shift from advancement activities to “investment” activities. Investment activities mean investing myself in the success of others, helping others advance, and giving others the opportunities for visibility all while decreasing my own advancement. This is a mindset shift at first, and one that can create some insecurity. But, just like others did for us when we were younger, it is important to do. And it can be a very rewarding season since it sets you free from the constant need to get ahead. To hold on too long to power, position, or status will usually result in a poor finish to your life both personally and professionally.

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Jay Desko is the CEO of The Center Consulting Group and brings experience in the areas of organizational assessment, leadership coaching, decision-making, and strategic questioning. Jay’s degrees include an M.Ed. in Instructional Systems Design from Pennsylvania State University and a Ph.D. in Organizational Behavior and Leadership from The Union Institute.