The 2020 Win Moment (Part 1)

A Rare Pocket of Time for Changing the Game

Reading Time: 5 minutes

This is Part 1 of a three-part exploration on this personal, organizational, and political post-election moment. Stay tuned for the remaining parts in the series.

The Game-Changing Moment We Are In

November 7th, 2020: the day of one of the largest collective sighs of relief of our times. The U.S. election was called for the Biden-Harris ticket, and jubilation ensued.

It was palpable as cities across the land erupted in dance and cheer. It was even more palpable against the backdrop of both the pandemic isolation and the protests for racial justice that have been our reality this year. This was a breath of fresh air, and seeing the celebration in the streets was too.

Of course, many do not share that sense of newfound, erupted solace. Many hoped for a different outcome but lost. And that got me thinking about games. It got me thinking about how to win; not how to achieve victory, but what to do with a win once it’s achieved, how to experience winning in such a way as to make a difference to the game.

Can you do something with a win that makes the win-lose, zero-sum binary disappear? What does a game-changing moment such as this ask of us?

Yes, the experience of a win, particularly one as big as the 2020 U.S. Presidential Election is a celebratory event. But are there ways to win and convert the game from one of winners and losers to one of mutual gain or positive sum?

And further, what can we learn by this exploration for other so-called games we play, personally and organizationally?

How to Win and Change the Game Forever


Here’s a standard game on a personal front. You set a goal for yourself. You figure out what system to set up to make success more likely. You coordinate the resources you have and make a plan that makes the goal achievable -- money, education, friends, guidance, coaching. You go after it. You do the damn thing. Congratulations. What next? 


Here’s the standard game on an organizational front. You and your team, your department, your startup, set big hairy audacious goals for the quarter. You convene a strategy meeting, delegate, maybe bring on outside consulting. You set the systems and marshall the resources and rewards systems needed to make goals achievable. You go after it, iterate, report back, pivot, debrief, stretch, make mistakes, grow. You do the damn thing. Congratulations. What next? 


Here’s the standard game in 2020 politics. The Democratic Party sets a big goal of taking over the White House from an incumbent President. A grassroots movement steps up in ways and to extents unseen in the history of our nation, in support of the ‘establishment’ strategy. The movement and the establishment undertake massive campaigns to educate and mobilize an unprecedented mass of voters. They do the damn thing. Congratulations. What next?

Sure, in all of these three scenarios and frames, there’s likely some sort of debrief, a rendering and recapitulation of what worked, what didn’t. But mostly it’s a big party and a move right on down the road to the next benchmark. 

Life moves fast. Business moves faster. Politics moves at the crushing speed of the constant now. 

A moment of a win is a prime time to investigate the game. Life, business, and politics are otherwise full of pressure. And the more pressure, the more we get the tunnel effect: under pressure, we tend to lean on our standard operating procedures. And those routines are often what get us into troubling ruts and inhibiting myopia in the first place. 

A win is a pressure release valve moment not to be squandered.

Upending the Standard Game Approach

So what if we slowed down the win and take the opportunity to reassess the game we’re playing? What would that look like? How would the game change?

The Personal Emerges Without Coercion

Over time I’ve read countless self-help books and leadership tomes, listened to Tim Ferriss podcasts, read Naval’s tweets, and opted-in for numerous workshops on productivity. I’ve sought out coaching to get out of my own way to achieve the goals I’d lobbed in front of me. Some of these worked wonders. 

The standard (over-simplified) track goes like this: set the clear goal, make the explicit commitment, and then go do the damn thing. 

For example, years ago, I decided I wanted to write more poetry and put my work out there. I did a Project Design: placed a clear goal down on paper (“publish three poems in literary journals by March 23rd of the following year”) and went after it. I did publish, but not nearly on the timeline I set. And in a sense, I needed the strategy to get it done. But in a sense the calling lived on a level below the domain of productivity measures. 

As David Whyte writes in The Three Marriages,

Many of our personal pursuits, whatever they may be, may be kicked into action, spurred into motion, by a good assertive strategy. But any meaningful pursuit -- any “deep hunger” as John O’Donohue wrote in Anam Cara -- can be drained of any “presence of love” when the fulfillment of that hunger is undertaken with an “excessive concentration on our work and achievements.” 

For any personal pursuit to be successful, a strategy might help, but more than that, a sort of silence is important. It’s about getting in the right relationship with the future you, with the calling that is inviting from a more timeless background of our days. It’s really about getting out of our personal headspace, and getting into conversation with the thing that is bigger than you calling you into emergence.

In a sense, the “deep hunger” or calling of our lives does come to fruition without getting out of our personal way. So instead of concerning ourselves merely with achievements and deadlines for these meaningful personal pursuits, it’s also about slowing the roll, getting into the right view, changing the game before it’s even played, and building a bridge to the future you.

Stay tuned tomorrow for The 2020 Win Moment (Part 2) exploring how to make use of an organizational win to change the innovation game.

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