Jan 265 min read

Know what game you're playing

Ever spent a lot of time/energy/effort trying to chase wins, and then realized after winning that it wasn’t what you thought it was? Or have you collected accolades and accomplishments, and find yourself wondering what’s next?

Sometimes it’s worth asking ourselves if we’re playing the right game, and if we know what winning actually means.

3 parameters to define your own game

Three problems with playing the wrong game:

Not knowing what winning looks like means we’re constantly wasting your resources
On a societal level, it’s inefficient to have people using up time, energy, social capital, money etc, pursuing things that don’t really lead to better outcomes (for themselves or others)
We get too caught up to focus on the bigger game

Often we think we’re playing on set rules or fixed outcomes that determine a win, and that it’s clear who’s doing better than others - get the most career capital, get the highest salary, have the largest number of followers, have the most prestigious career, find the best partner.

But what winning looks like depends on which game we choose to play. Winning could mean…

Staying in the game the longest - e.g. early startups in the current fundraising climate
Losing the least - e.g. making the fewest unforced errors (especially as an amateur tennis player)
Being more trusted - e.g. if you’re looking to build a brand or online presence
Being more exciting - e.g. if you’re looking to build a brand or online presence, quickly
Being the fastest - e.g. to be promoted among peers

The reality is, whatever field we’re in, winning is self-defined, regardless of external markers of progress. What others want, or what an organization wants, isn’t ever going to be as fitting as what we want for ourselves.

In defining the game we actually want to play, I found it useful to consider the following:

Time horizon
Stage of pursuit
Risk

Wins are defined accordingly, and adjusted as the three parameters shift.

Don't lose the forest for the trees

Whatever game you’re playing right now, we’re all in a larger game of life. We often lose sight of this, because nobody knows the score until the end.

This matters because some things are hard to get back once lost - time, health, energy. It also matters because what we do in our current window of time shapes our future. The thought, behaviour and decision patterns we set now will shape our habits, thoughts and strengths.

In this bigger game, the rules, if any, are not clear. Participants come and go. Parameters are constantly changing. Simon Sinek repurposed James Carse’s idea of the infinite game for business - where the game never ends and the goal is continuation and survival, rather than winning.

In life, however, I’d argue that it’s not about living longer, despite the billionsof dollars poured into immortality. It’s about living, truly, period. Quality of life - not luxury or decadence, but contentment, honesty, connection, living in your own skin and knowing that it is yours - is primary (take it from a palliative nurse).

So - what does it mean to win at life?

Some folks think of what they’d like others to say at their eulogy. I’m a little more morbid but also, realistic. Being Mortal cemented what I’ve seen in my own relatives when confronted with their own mortality.

Most of us are going to experience years of chronic disease towards the end of our lives, probably with considerable pain and inconvenience. My idea of “begin with the end in mind” (Habit 2) is: when you’re on your last bed, unable to move or function anywhere the way you used to, and there are hours where you don’t have visitors or company, will looking back on your life give you peace and comfort?

The street sweeper gets buried next to the CEO. All that matters at the end of the day is how big we showed up and how courageous we were. - Robin Sharma

Aligning the long and short games

Can we align?

The inclination is to optimise. To learn from the dying, set our direction, and reflect, track and pivot regularly so that we hit our goals and wins now, tomorrow, and at the end of our lives. And magically we will somehow hit all the markers of success.

I wonder if optimisation is a trap. It assumes it’s possible. It assumes self-awareness, and a constant identity. In reality, we’re all different people now from ten years ago, and we don’t know who we will be in a year. Most of us don’t even know if our self-perception is accurate.

It also detracts from living itself. Optimisation is doing-centred. The game of life, and regrets of the dying, are mostly being-centred:

1. I wish I’d had the courage to live a life true to myself, not the life others expected of me.

2. I wish I hadn’t worked so hard.

3. I wish I’d had the courage to express my feelings.

4. I wish I had stayed in touch with my friends.

5. I wish that I had let myself be happier.

I’m not sure anyone’s figured out how to win at both short and long games. But my approach is:

Play the short game (current stage of career and other goals) to learn, grow or enjoy.
Play the long one to win. It doesn’t mean we will have no regrets. And the tradeoffs are difficult. But it will make those moments easier.

And then both wins or losses in your current game will contribute to the overall victory. And you can play your current game as truly a game, rather than something that defines your identity or your worth.

Summary + Action / Reflection

In the short game, consider your time horizon, stage of pursuit and risk appetite, to define your wins. If you’re risk-averse, try increasing your risk tolerance a bit at a time - it gives you a little more wiggle room.
In the long game, know what will bring you peace, joy comfort in those difficult moments when you are alone with the raw core of yourself.
Win the long game. Enjoy the short games.

Reply this email and let me know if this makes sense - or if you disagree.

References and recommended reads at the end of this email.