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What the Oregon Trail Taught Me About Leadership

I went to grade school in the 1980s. And if you’re of a certain age, you remember that going to the computer lab was a big deal back then. In fact, one of my favorite things to do when I earned free lab time was to play The Oregon Trail. My buddies and I competed, as only pre-adolescent boys can do, by seeing who could race towards Oregon the fastest. But none of us ever made it close to Oregon’s Willamette Valley. We pushed our digital families to the extreme, usually ending in their in-game demise of some disease like dysentery. 

I shouldn’t be surprised that my own boys (who now play the game on an iPad!) basically do the same thing I did back in the 80s. They push their crews fast, ignore the health warnings, and laugh when their characters give out. After watching this for long enough, I decided to give the game a try as an adult.

The first decision I made was on the crew. I ensured the crew had diverse backgrounds and talents. I read each character’s profiles, ensuring I had people who could fix things, socialize, and even negotiate. Next, I made sure to buy extra medical supplies and food for the journey. After all, I thought, you never know what kinds of obstacles are going to come up on the Oregon Trail! 

As I started the game, I chose “walking” as our pace because I didn’t want to burn anyone out. I also made sure to allow our team to rest whenever the computer gave me the option. I even had the team stop and talk to people on the journey so that my “social health” indicator stayed green. 

About an hour later, with my crew all still healthy and progressing toward Oregon, my son said to me, “You’re good at this game!” 

The Leadership Lesson  

What I learned from this gameplay was three things: 

First, I learned that to do well in the game, you must lead people well. In short, that means you ensure they’re fed, that they have medical supplies, and they can take breaks and rest when they need to. Additionally, you must ensure there’s enough social interaction for everyone to stay engaged and healthy. And in case you miss the implication, this is exactly how you lead people in real life as well! 

Second, understanding the “how to” of leading others is only the first part of it. The most important part is actually doing it. That means helping your team slow down when they get tired, and providing opportunities for social interaction when it’s needed — along with countless other things that you have to observe and act upon. This all takes awareness and a desire to help people. 

Lastly, to do all the above, you have to lead yourself well. It’s often easier to do these things for others than for yourself. But pushing yourself past fatigue, failing to rest, and neglecting to make time for social interaction will negatively impact your health — all things that can make you sick and make you less effective in leading others. 

So how can you apply the above lessons to your leadership as we enter the summer months? Think about these questions:

Do you need to provide your team with opportunities to socialize? 

Do you need to provide your team with opportunities to rest? 

Or do you need to focus on yourself? 

Do you need to socialize? 

Do you need to rest? 

The start of summer is a good time to take this quick assessment so that you can stay on track for the second half of the year. 

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Best of: 23 Things Golf Taught Me About Life and Leadership

As winter turns to spring, and as many enjoy Spring Break, here is a post from last fall about the lessons I learned from golf in 2022. I look forward to another year of learning on the golf course in 2023. But what I look forward to the most, is more time with my two sons as they learn from the game of golf as well.

Everyone who plays or follows sports has their view of which is the best. Of course, such notions are relative — there is no definitive or objective answer. That said, I think golf is the most applicable game to life. To illustrate, I am using today’s post to share what I have learned from golf over the last ten years. 

Before sharing the list, let me elaborate a little on why I have focused on the past ten years. As I have shared in other posts, I came close to walking away from the game of golf in my twenties. The love I had for the game came mainly from the fruits of it, which was the success I experienced as a high school golfer. When the success went away, and my scores increased, I began questioning why I even played the game in the first place. 

Here’s what I learned. 

  1. A performance based on results does not lead to peace of mind.
  2. Expectations are deadly. Just hit the next shot! 
  3. Doing enough will never be enough in golf or life. 
  4. More practice does not guarantee lower scores, but less practice guarantees higher scores. 
  5. Hurry leads to bad decisions, poor play, and less joy.
  6. The embarrassing shot you just hit was hardly noticed by the other golfers who are fixated on their next shot!   
  7. Your score is only one indicator (and often a poor one) of how well you played on a given day. 
  8. Beauty is only seen when you look for it, and it is everywhere on a golf course.  
  9. Golf is a game of recovery, not perfection.
  10. The game is best played, not analyzed.
  11. A conservative strategy, coupled with an aggressive swing, often produces the best results. 
  12. One swing thought is almost always one too many. 
  13. Learn the names of your playing partners, and cheer them on. Your battle is with the course and your soul, not with them. 
  14. What you think about, see, and believe about yourself affects your score more than your technique. 
  15. Great golf is almost always boring: keep the ball in play, hit toward the middle of the green (not at the pin), and two-putt. Repeat. 
  16. During a great round, you must contend with the inner belief that you deserve to keep playing well. More rounds have been sabotaged by insecurity than “choking.” 
  17. There might be nothing more satisfying in life than spraying a ball into the trees, humbly chipping it out to the fairway, and getting up and down from 100 yards to save par. 
  18. There might be nothing more tempting in life than trying to thread the ball through 20 trees and onto the green. I have made more double bogeys doing this than I care to admit, but the handful of birdies I have made have been awesome! 
  19. Putting is 101% mental and belief. My putting turned around when I started believing this.
  20. Negative self-talk does not end on the 18th hole. Learn to do away with it before you begin the round. 
  21. A certain amount of luck is needed to make a hole in one. But there is a certain amount of skill required to hit it close. 
  22. Golf was never meant to be played riding in a cart. Walking helps one see the landscape, hear their thoughts, and feel the life of the course. I learn this lesson repeatedly as most of my rounds are in a cart. 
  23. And regardless of what you shot today, there is always tomorrow. At least for now. 

There is no game like the game of golf. I say this as it has helped me learn more about myself than any other sport I have participated in. To the achiever, it is the most insidious game ever created. To the humble, however, it is a gift. A gift that teaches one that their self-worth will never be found in any game, pursuit, or result. 

And this last lesson might be golf’s greatest. Golf taught me that the only way I would find peace with it, as crazy as this might sound for some, was to look elsewhere. For me, it was discovering that Jesus really loved me — the broken, imperfect me, with secrets I would not want to print here and insecurities I could list for days on end — that freed me from the need to be good at golf, great at work, and the world’s best (even though I am one of the most flawed) husband/dad. 

Every time I am tempted to think I am turning into “someone” or that I am important, I am reminded to go tee up. 

A few shots in, and I am quickly humbled once again. 

Golf, it turns out, opens your soul to a lot more than just golf. 

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