For Ambitious People

Here’s a question.. What are you most proud of so far in your life?

It was during a tequila-fueled discussion with my roommates one night that I found myself facing that same question. My answer? A party I threw senior year of college that I had planned and carried out in its entirety.

That might sound strange, but the party was valuable to me because I had used all my initiative and creativity to pull it off. I had also made everyone around me very happy. It was tremendously gratifying in the moment.

My roommate Robbie had a different approach. His proudest moments were all about doing things that would take him where he wanted to go later on in life. He had graduated college with good grades, and had been a part of the honor council. All of it had been out of a sense of duty to do what he was supposed to do, he explained. These accomplishments were checklist items, a way for him to feel confident that he was on the right path. Somewhere down the line, people would be really impressed by all that he had done.  

This conversation highlighted two different ways of attributing value to our lives. I call these two different approaches the “Now” Mentality versus the “Checklist” mentality. The “Now” mentality attributes value to whatever brings us engagement and satisfaction in and of itself. The “Checklist” mentality attributes value to whatever will bring us engagement and satisfaction indirectly. In this way, one who values something from a “Checklist” mentality sees that thing as valuable only because it will lead to something else he or she values in and of itself later on.

In the context of decision-making, both mentalities seem quite natural. If you are choosing whether or not to do something, you will probably consider both the enjoyment of the act itself and the results it creates.

However, based on my conversation with Robbie, and the time I spend with talented young adults who are trying to make big life decisions, the more wary I become of the “Checklist” mentality. In my observation, this style of attributing value can be dangerous, especially for those who are seeking success but don’t yet know what their definition of success would look like.

The dangers are as follows:

First, we sometimes assign checklist value to something when we don’t actually know enough detail about why that thing will be valuable down the road. For example, I took guitar lessons throughout my childhood under the delusion that somebody someday would care that I was a well-rounded kid who had studied guitar. Big time Checklist value there. However, I sucked at guitar! I hated it, and nobody cares at all about my efforts now. I should have done something I actually enjoyed. Remember, there is nobody who will evaluate your accomplishments at the end of your life and give you a stamp of approval. You just die happy or unhappy. So if you can’t pinpoint the future benefit of something you don’t really like, it may be worth reconsidering.  

Second, we can talk ourselves out of wonderful and fulfilling ways to spend our time if we make all of our decisions based on checklist value. Success driven people can get so focused on winning that they undervalue their own interests. If you love something, then you should need a hell of a good reason to justify omitting it from your life. Life is short. Do what makes you, you. If you love to read fiction, don’t spend all your time reading business news and exclude all else. If you want to work with kids, then don’t get talked into going to law school because it sounds more impressive to do so. Do what you want to do. Think big. Get creative.

In summation, the “Checklist” mentality does have its downsides. But hey, so does the “Now” mentality. A healthy balance is in order.Just remember, if you ever find yourself in a place where you feel trapped in a checklist mentality, doing only what you feel you must do, take a look at this short video. Remember, sometimes you just gotta say, “What the fuck!”