Playing the Long(er) Game

Most Monday nights, I go to a neighborhood bar and play board games with a group of people (now friends) that I found via Meetup.com when I moved to North Carolina in 2021. My favorite games are the mid-heavy strategy ones (like Dune) that are fairly complicated, are usually for 4-5 people max, and take 1.5+ hours to play.

These types of games require strategic choices and trade offs that impact my ability to position myself for future rewards or moves. And it takes a few turns to build momentum as I get more powerful cards and gather resources. Then it becomes a flywheel of power to help me leverage towards success - which for me is primarily a well-played game and secondarily a win.

Playing a longer game like Dune is a way to practice positioning and strategic choices like the ones that I’m making in my business. But even a complicated board game has specific rules, direct outputs, and limited chaos. It also has a clear win condition and ending point. It is a finite game.

Positioning and strategy work in business is much messier, complex, and chaotic. It feels riskier, more vulnerable, and harder to navigate, because it is.

And the business I am building is an infinite game. I want it to be a sustainable and dynamic activity that I enjoy playing over a much longer time than a Monday evening in a bar.

Another real life reality is that I’m playing the long game with my business efforts while also paying current rent and bills - mostly from a cash cushion I built up as a runway. It’s all a collection of choices and tradeoffs that hopefully position me for future work.

But a board game is a good metaphor to help frame my approach to reworking my business.

Making Moves

The starting point is with the hand I’m dealt, including the resources, skills, experience, and connections I’ve built and collected over time. This status quo is familiar and easy. It has a level of certainty and stability that are comfortable.

But now, it’s time to make moves, play the long game, and experiment with how this might work in the real world. I’m making choices about which activities I’m investing time and energy into hopefully building future momentum and traction.

Moves I’m making:

• Daring Studios Brand & Website: This is the scariest project that I’ve been avoiding because it feels vulnerable. I’m planning to entirely rework things here as a foundational anchor. I want this to be a more accurate map of how I’m positioned in the territory.
• Building Durable Assets: Getting a lot of the things in my brain in written articles that are findable, sharable, and evergreen.
• Launching a Podcast Project: I have an idea for a new business-related podcast for solopreneurs, freelancers, and creatives. I’m planning to do monthly episodes starting soon-ish.
• Publishing Consistent Newsletters: Like this one.

Letting Myself Sense & Respond as a Strategy

When something goes sideways in my plan during a board game - a card or spot gets taken by an opponent or maybe I don’t have the resources I need to make the move I want - I have to make another choice. It’s easy to sense when I need to shift my moves and respond to a wrench thrown in my plans because in a board game, it’s choosing another move off a finite menu of options.

In business and life shifting a plan when a wild-card’s thrown in is much more open-ended and unknown. Sensing that I need to pivot with my plan requires more attention and discernment on my part. And responding in a strategic way means keeping the overall direction in mind and making a good enough choice with the information I have right now.

It’s always a work in progress because no plan survives contact with reality. All we can do is sense the shifts and respond with a new move.

So that’s where I am with my business moves. I’m trying to make the strategic moves to position my business to play an infinite game.