Leadership · · 7 min read

4 steps to playing the long game

Most things matter less than you think - when you put your long game lens on.

4 steps to playing the long game

Nothing matters as much as you think in the long run.

Don’t believe me? Take a look at your calendar or to-do list from three months ago. Scroll through some of your messages from a year ago with your best mate.

The stuff that kept you awake at night, had you put in extra hours, or agonised over the right choice, doesn’t seem such a big deal now, does it? Nothing much would have changed if you hadn’t done a third of it.

Now, think about some of the hardest things you’ve coped with. The stuff that felt unmanageable and you didn’t know how you’d get past. The odds are that it all worked out right. You probably refer to that and appreciate how you changed, grew, or learned.

When you look back, you’ve got a long-game lens. It's like a wide-angle setting for your brain.

When the long game lens is on, you see how individual choices, events, and upsets fit into the bigger picture and work those into your narrative.

We can do that for the past and often for the future, too. That’s how we set goals and make plans. But we struggle to do it for the present. It's why there's such a disconnect between strategy sessions and workplace behaviour—we get the long game lens out in the meeting room and put it away again when we get back to our desks.

When we can bring some of that long-game perspective into the present, we see our options, choices and daily events differently. We ask questions like:

  • "Does this take me closer to the end goal?"
  • "How will I talk about this in a year?"
  • "Is this the best use of my time?"
  • "What consequences will this have?"

As a blackboard outside a coffee shop will probably tell you sometime soon (but John Lennon said first):

"Everything will be okay in the end. If it's not okay, it's not the end.”

That’s all well and good, but it’s not helpful when you need to work out how to think differently now. If you didn’t feel like shit, you wouldn’t have stopped to read a quote like that in the first place.

Your long-game toolkit

To get you started, here are your top four tools for playing the long game:

  1. Perspective
  2. Purpose
  3. Patience
  4. Practice.

1. Perspective will take care of your pain

The closer you are to something, the more important it seems. Our brains are wired to put immediate threats first, which makes sense from an evolutionary biology standpoint. We react to the threats in front of us, to stay alive. This is great when we’re staring down a woolly mammoth but not so useful when we turn into reactive drama queens, panicking at every new email and catastrophising every relationship, project or meeting that doesn’t go to plan.

Given we’re so good at putting things into perspective in retrospect, it can be helpful to play Future You when everything seems unmanageable. Try thinking about your life as a book and about this disaster or phase as an event or a chapter. How would it fit into the broader story of what came before and what came next? What would this chapter be called?

Try writing a list instead titled something like '10 Reasons This Doesn’t Really Matter’ or ‘5 Reasons I’m Glad This Happened.’ For bonus points, read your list aloud. When we say things out loud, our brain believes us, and we’re naturally pretty good storytellers. Hack that annoying bias for good.

2. Purpose will give you perspective

It feels like our experiences are factual because they’re tangible. If you can see, smell, hear or taste something, it must be real… right? Wrong. Most of what we experience is just a projection of our shit.

Like Google, our mind runs on a series of filters, sorting through the metric tonne of sensory information available at any given time to present us with relevant results. This is great, if you’re a good Googler using the right search criteria. But if your criteria are unhelpful - or worse, if they’re unclear - the sorting function doesn’t work. Some things seem more important than they are, while the most critical stuff falls by the wayside.

It’s why you get to the end of a busy day exhausted but wondering what you achieved. In Essentialism Greg McKeown calls this the ‘paradox of leadership’—feeling overwhelmed and underutilised at the same time.

Perspective doesn’t work without purpose.

It's hard to see things for what they are if you don’t know who you are or what you care about.

McKeown calls this your ‘highest point of contribution.’ Simon Sinek calls it your ‘why.’ Call it what you like. The guts of it is that the minutiae doesn't seem so relevant when you’ve got your eye on something bigger and more meaningful.

Who cares if someone cut you off on the motorway or Ben in Accounting took the wrong tone in his email when you’re focused on building something important?

I don’t know your bigger purpose - maybe saving dolphins, bringing sustainability into the workplace, or being a present parent. It doesn’t matter what it is. It just matters that you have one.

Your life will always fill up with stuff, because you secretly want it to. All those pressing concerns are a helpful distraction from spending time with yourself. We avoid boredom because we’d have to face the truth about our super-important work and life things and wonder if this is all bullshit.

Taking the time to understand what you really value and the impact you want to have on the world might be scary, but the evidence suggests it’s worthwhile. People motivated by a strong sense of purpose tend to live more meaningful lives, have more satisfying relationships, and do better at work. These are nice things to have.

3. Patience will find your purpose

How uncomfortable would you be if I asked you directly - ‘Hey Charlie, what’s YOUR purpose?’

Some of you might be enlightened already and point straight to your LinkedIn tagline or Instagram bio. The rest of you would squirm awkwardly, make a bad joke, or stumble through a jumbled explanation, apologising as you went and secretly fearing that you might not have a purpose.

That’s OK. Most of us are banging around in the dark. It’s a long game, remember? Your purpose probably won’t come to you in a bolt of lightning, but will morph and shift over time. For on-the-job learning, the first step is simply to do things and notice how they make you feel.

When I work with clients, I ask them to notice how their energy changes when they do different things and react in different situations.

  • What lights you up?
  • What do you love the most about your job?
  • What do you hate the most about your job?
  • What do you get lost in?
  • What gets you all over-excited and annoying when it comes up at dinner?

Pay attention to those things, and you’ll start to work it out.

If you’ve spent the last decade working too hard or getting lost in your kids and don’t know what you like anymore, that’s cool. Just do some stuff. Maybe you’re an artist? Maybe you like gardening? Maybe you’re into social justice? Maybe you don’t know yet.

Start noticing, keep track, and when you find something that works, do more of it. Over time, your criteria will get clearer - and your search results will, too.

4. Practice will give you patience

Once you’ve thrashed around for a while figuring out what you care about, and you can sum it up in an Instagram bio, you will have a happy and fulfilling life, maintain a useful perspective on everything and become a Zen master.

…Or not. Knowing your purpose isn’t enough. You have to do something about it.

Knowing your purpose and not living in alignment with it will make you more miserable.

You can see how you’re wasting time and energy, but you’re still doing those things. Ah, transition.

Unfortunately, having a long-term vision doesn’t make it magically appear (sorry if you’ve read The Secret and thought it would.)

Everyone knows the "one day" guy. One day, they’ll write a book. One day, they’ll start their own business. One day, they’ll run a marathon. Maybe you are that guy. But one day will come, and if you didn’t write anything, launch anything, or pick up a running habit, the odds are against you.

In this way, playing the long game is a bit of a paradox. On the one hand, nothing matters as much as you think it does. On the other hand, your small choices add up to big change. James Clear writes about this in Atomic Habits, but every wealth advisor has been preaching consistent, incremental deposits forever. Compound interest is the 8th wonder of the world, and you can create compound payoffs in your life, too.

How we spend our days is, of course, how we spend our lives.
– Annie Dillard

When we use our long-game lens in the present, we channel our purpose-filtered search results to create small choices, habits and behaviours that get us closer to the big picture… and let the rest go.

To keep a healthy perspective on the present, do more of what lights you up - write that book, start that website, go to that class and take small steps to bring sustainability into your workplace and help autistic dolphins.

Do less of what gets in the way, and when something pisses you off, push it through your filter. Ask questions like:

  • “Is this worth my energy?”
  • “Does investing my time here take me closer to my long game?”
  • “What should I focus on instead?”
  • “How do I get rid of this from my life"?”
  • “Can I just let this go?”

Your long game is ultimately defined by your short term. So check how you’re reacting, what you’re choosing and what you’re saying.

Above all:

  • Figure out what you care about
  • Pace yourself while you make better choices
  • Let most of the other shit fall away. It doesn’t matter anyway.

Or, in the words of my daughter, scrawled on a Post-it note on my fridge:

“Do something today that helps you tomorrow.” (Charlie, 10)

- AM

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