Playing the long game vs living every day like it’s your last

Go about every action as thy last action

Marcus Aurelius

The conundrum between dreaming big versus having zero expectations has bothered me for a long time. Alongside it is a similar conundrum: playing the long game versus living every day like it’s your last.

Stoics are obsessed with death. Their philosophy is gaining momentum in my generation. While Seneca and Marcus Aurelius’ renouncing of worldly possessions seems at least to some degree hypocritical, their reasoning is so clear and sound, it’s infectious. Seth Godin’s recent blog asked about the things we do every day: what if it is the last time we are doing them?

Living every day like it’s your last sounds good on many levels. You surely aren’t going to do anything you will be ashamed of – anything that  you won’t feel that you’ve enough time to make up for. It is easier to perceive everything as having consequence. This is the key – people are drawn to anything that has meaning. This essay by Kevin Simler discusses what it is that gives us the feeling of meaning. He argues that it is consequence. For example, a wedding has a lot of consequences, hence, it is meaningful. On the other hand, standing in a queue for your coffee seems to be inconsequential, hence, it lacks meaning. It seems that millennials are especially drawn to meaning. Victor Frankl argues that meaning is the one thing that makes a difference in our lives.

Living life as if you have a gun to your head has a few advantages. You won’t delay. You will only focus on what’s important. You will take bigger risks.

While meaning is enhanced through this “every day is your last” philosophy, there are vast parts of life that are annihilated by it. If today is your last day, surely, you won’t be starting any projects that involve huge uncertainty – even if you feel it is the right thing to do. You won’t put yourself in positions of leadership where everything depends on you. It is just like making an investment decision. You certainly won’t be signing up with a pension fund if you are believe in Stoicism! On a more practical level, even I think that I might die within the next 3 years, it leads me to make decisions that are short-term. It’s hard to be creative when you think that your life is nearly over. It’s hard to have patience and keep investing into things that take time to develop.

There is another reason why Stoic philosophy has become popular in my generation. It’s easily confused with nihilism. Stoics portray dealing with luck as a pointless affair. Almost everything, except getting to understand yourself is pointless according to Stoics. Nihilism is a delightfully comfortable place. If nothing matters, one can stop striving – and no longer feel the pain of striving. And we all love a good painkiller. Floating downstream has nothing to do with Stoic philosophy, however.

Ultimately, Stoics want the best of both worlds. They urge us to live every day like it is the last while making investment decisions that will impact generations.