What game are you playing?

We're not all playing the same game. And that's okay.

Imagine giving chess advice to someone playing poker. That’s what most career advice sounds like.

I recently spent time with a group of my business school classmates. It’s been four years since we graduated, and life has taken us all in different directions - geographically, professionally, and personally.

As we caught up, the conversation naturally turned to career paths. At one point, someone (let’s call them the advice-giver) turned to another (the advice-receiver) and said, “Maybe for your next job, you should focus on getting into a brand name company.”

What struck me wasn’t the suggestion itself (it’s a commonly held belief in business circles) but how mismatched it was with what the receiver values. The advice-giver was projecting their own definition of success: prestige, perceived stability, and maybe even external validation. But the receiver had never signaled that those things mattered to them.

In fact, everything about their career so far points to something else entirely: a desire to make sense of ambiguity, to stretch beyond what's comfortable, to build rather than maintain. They've thrived in startup environments, chosen winding paths over linear ones, and rarely made decisions based on conventional notions of security.

I realized then that not everyone is playing the same game - and that’s okay. One person might be chasing influence at a Fortune 500, while another is optimizing for impact, flexibility, or creative autonomy. One isn’t better than the other - they’re just governed by different rulebooks.

The trouble starts when we forget that. When we assume our goals are the goals. When we offer advice without first understanding what someone else is truly optimizing for. It’s like giving chess strategies to someone playing poker.

Some examples of games:

• The Game of Wealth

• The Game of Status

• The Game of Prestige

• The Game of Impact

• The Game of Freedom

These are not mutually exclusive but they are defined by different metrics of success.

When we’re in school, we are all (generally) playing the same game - get good grades, excel at extracurricular activities, get into a good college, make your family proud. But once we leave controlled environments like school, we start to play different games and optimize for different success metrics.

If you are feeling behind in any way personally or professionally, ask yourself: What game am I playing? What are the rules and metrics of that game? Am I truly falling behind, or am I just measuring myself against metrics of a game I’m not even playing?

And the next time you’re tempted to weigh in on someone’s choices, try asking first: What game are you playing? And what game are they playing? If the two of you are not playing the same game, take a step back and reframe your feedback accordingly.

The most powerful thing we can offer someone might not be advice - but curiosity.