Regret Minimization is a Powerful Motivator in Life


Before being hired by CWS, I had to do a personality profile that literally was an all-day affair. One of the questions I remember required me to fill in the blank after starting off with “Happiness is_____”. Without much reflection, I wrote, “living life without regrets.” 35 years later I still believe this to have a lot of validities.

The Importance of Living Life Without Regret

Regret minimization is a powerful motivator in life. In fact, Jeff Bezos used this decision evaluation tool to convince himself to start Amazon. He had a lucrative hedge fund career on Wall Street and was weighing giving that up to venture west to Seattle to start an internet business. When he told his boss about what he was contemplating he told Bezos that he thought it was too risky, especially because he would be giving up so much by leaving Wall Street. Bezos, upon further reflection, looked at it very differently when he decided to imagine himself as an 80-year old man looking back on his life, knowing that much of what often would keep us up at night as we grow older would be things we regretted, especially risks we did not take. He was convinced that he would look back with more regret by not having taken the risk of pursuing this idea than if he had failed to do so. That made the decision relatively easy for him.

With this in mind, my wife and I just took my daughter to college so I thought I would jot down a few pieces of advice knowing what I know now to hopefully increase the chances of her having a very meaningful college experience.

Regret can come in two forms: Regret related to commission (actions we take) and regret related to omission (actions we do not take).

I have found that the former can obviously lead to the most long-lasting, life-changing forms of regret since they can lead to catastrophic consequences while the latter tends to lead to forms of lingering discontent.

Rather than just focusing on regrets, however, I thought I would focus on actions that would lead to regret minimization. Before going into the details here is my summary of what not to leave college with:

A child


Not getting involved

Achievement being the primary source of your self-worth

Unhealthy relationships

Procrastination tendencies

Not caring

Poor health

Bad habits

Bad memories

No friends

Much of life (and investing) is winning by not losing. If we can be clear about what to avoid we have gone a long way towards winning the game of life because we can then focus on opportunities and challenges.  With this in mind here is a more expanded discussion of what I see as major categories of regret I would hope my daughter would avoid during the next four years (at a minimum).


Pregnancy I’m jumping right into one of the most awkward topics and yet the consequences can be so negatively impactful I believe it belongs at the top.

Take precautions. Visualize your career and future getting derailed by having to raise a child before you’re ready. Consume alcohol in moderation as it can often lower our guard and inhibitions much to our regret the next day or later in life. As they say in AA, “Think through the drink.” Temptation is very hard to overcome but, it is also extremely satisfying to have used our higher level of thinking and skills of discipline to overcome it. Obviously, the best thing to do is to avoid putting ourselves in tempting situations, to begin with but if this does not happen then try to keep the consequences at the forefront.

Unhealthy Dependence Many of our best and worst habits are formed in college when we are experiencing independence for the first time. We all have our higher and lower selves. The latter prey on our base needs and insecurities and if we don’t continuously work on elevating our higher selves then we run the risk of turning to unhealthy actions in times of stress and insecurity that can lead to a dependency on alcohol, drugs, sex, shopping, video games, other people, gambling, etc.  We then place these compulsive needs ahead of much more healthy investments of our time, talent, and treasure which can lead to disastrous consequences.
Getting in a car when the driver has been drinking With Uber and taxis there is no reason to take the risk. There is zero upside and the potential for 100% downside.
Cheating Do not overemphasize the importance of grades at the expense of self-esteem and doing your best. Even if you get an A you will always know you didn’t earn it if you cheated. Ask yourself why you were not sufficiently prepared and work on being more so in the future. The measure of one’s worth is not the grades he or she gets, but whether one knows deep down if they were fully committed and invested in whatever it is one sets his or her heart and mind too. A’s may not always be the outcome but overall the results on a cumulative basis will be outstanding and allow one to build up great habits that will serve you throughout your life in very satisfying ways.
Unhealthy relationships What you have to offer is very special and not everyone is worthy of your time, attention, love, and physical attributes. There is no need to lower your standards because you are worthy of those who want to be better when they’re in your company. Ideally, 1 + 1 should equal more than 2 and if it doesn’t then don’t sweat it as there are many others out there who can complement you wonderfully if you remain patient and don’t work too hard at seeking it out.
Avoiding relationships It is better to have loved and lost as they say then to never have loved at all. All worthy paths have a huge risk of heartbreak but the growth that can come from a relationship even if it doesn’t work out can be extraordinary. The only perfect person is in our imagination and we can learn so much about ourselves when we are willing to enter into relationships. Avoid unhealthy ones to the extent possible by staying true to your values, but don’t hold out for perfection because it does not exist.
Isolating Get involved in organizations and participate in class and talk to your professors. Get in the game of offering your gifts to others. It builds up the muscle of courage and becomes a positive feedback loop. People will also feed off your positive energy and contributions and you will be a magnetic pull versus a repellent.

Ask for help if you need it. Don’t let yourself fall into a deep hole academically, socially, or emotionally. You are not alone in whatever you are struggling with and people want to help or are just waiting for someone to open up to them because they want to do the same. Vulnerability breeds intimacy and intimacy is the foundation of all lifelong relationships, many of which are formed in college.

Not being prepared You worked so hard to get into college, don’t look back in regret that you weren’t prepared for your classes and exams. As Russell Wilson says, “The separation is in the preparation.”
Financial Irresponsibility Challenge yourself to enjoy the game of staying within an agreed upon budget. Limits and constraints can be great discipline/habit builders in life and lead to tremendous creativity and helping one to set priorities.
Don’t be too rigid Some of my best memories are spontaneous experiences. Don’t be afraid to try something new or go somewhere new on the spot provided you can manage your other priorities. Have fun!!

I know you will have an incredible college experience. You will continue to grow, take on new challenges, make lifelong friends, and evolve into an even more incredible woman than you already are. When you look back four years from now I hope you have very few regrets and incredible memories.

The University of Chicago is lucky to have you!


Over to You:

Over your own life, what do you do to minimize regret? Do you factor in potential regret when making important life-changing decisions? How has it worked for you?

One comment on “Regret Minimization is a Powerful Motivator in Life
  1. Bob Serr says:

    Excellent, thoughtful and well stated. I needed these when I was a youngster. Your children are very blessed to have you as a father.

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