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1000 Bad Decisions 

Some time ago, I was in a conversation with someone I have known for years. He was in a season of great personal struggle.

He couldn’t understand why his life was falling apart. His marriage was about to end. His job was hanging by a thread. Both of these situations were a result of some serious errors in judgment. He wanted a quick fix and assumed all he had to do was make a couple of good decisions now and he would once again have the life he wanted. My friend was half right. Making the next right decision would set him on course to realizing a better quality of life. However, one good decision does not negate a thousand bad ones. My friend has yet to realize it will require many more good decisions to undo the bad ones.

Over the course of their career, leaders will make thousands of decisions.

These decisions shape the legacy and future state of their leadership. In the best case, leaders are attentive and aware of the trajectory of their leadership. In the worst case, leaders (like my friend) may be realizing the consequences of a thousand poorly thought-out decisions. Similarly, these leaders will have to shift the overall trajectory of their leadership through good decision making. 

The ratio of good to bad decision making is a simple concept to understand. However, it can be challenging to apply. Amid the constant demands and pulls of leadership responsibilities, how is a leader supposed to figure out the trajectory of their leadership? Even more, how does an overworked leader identify and determine a desired future state of their leadership? We believe intentional pauses and reflection allow a leader to construct a vision for their future. And, by constructing the right vision of their future leadership, they are more likely to make decisions which align towards a positive trajectory.  

The end of the year is a time to ask yourself some important questions related to your future state of leadership.

Here are four questions to get you started: 

  1. At your future retirement party, how will people describe the kind of leader you were? 
  2. How will you know if you were successful as a leader? 
  3. If your career ended today, how would others describe your legacy?  
  4. What needs to change between your current and future state of leadership?  

Regardless of where you are on your leadership journey, it is never too late to consider your direction.

If you would like to take a proactive step in this direction, you might consider attending one of our four Milestone Leadership Intensives in 2022. You can find more information here. 

Here’s cheering you on and wishing you tremendous leadership success in 2022! 


Erik Dees is a partner with Milestone Leadership. The opinions expressed are those of the author.

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