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Don’t Play Games You Can’t Win
Don’t Play Games You Can’t Win

September 27, 2025

Read Time - 4 minutes


Authenticity is the daily practice of letting go of who we think we’re supposed to be and embracing who we are. — Brené Brown



When I stepped into my first campus leadership role, I followed someone with a very strong style—quick decisions, a commanding presence, a way of setting the tone in every room.

From day one, I couldn’t help but compare myself. People were used to that style, and I wrestled with two questions: Who will I be in this role? How do I show up so people know what to expect? And here’s what I eventually realized: if I tried to measure myself against the game that had already been played, I’d always come up short. The only way forward was to choose a game I could win—one that fit my strengths and the moment we were in. Anyone who has entered a new leadership role has probably felt that same pull. It’s normal. But the leaders who excel are the ones who stop chasing someone else’s scoreboard and start setting their own.

(And if you’re noticing that’s two weeks in a row with a Brené Brown quote—guilty. Sometimes you go with the voice that keeps hitting the mark.)


Why Leaders Get Stuck Playing the Wrong Game

Higher ed leaders slip into un-winnable games all the time because the environment subtly nudges them there. We inherit expectations, traditions, and comparisons. Teams acclimate to certain styles or what they are comfortable with. Systems reward external measures. We see what other departments are doing and assume we should match their standards.


And we find ourselves there for often the simplest reason:

We haven’t taken time to define success for ourselves.


When you or your team doesn’t know what “winning” means in your context, you look outward for clues—toward peer priorities or a predecessor’s playbook—and aim at the wrong targets.


That’s how leaders get pulled into games that don’t actually position them—or their people—for success:

  • Following a predecessor’s style and trying to lead exactly as they did.

  • Chasing prestige in rankings or awards that don’t align with your institution’s identity.

  • Budget envy when peer schools have larger donor bases or state appropriations.

  • Enrollment contests against institutions with demographics or pipelines that look nothing like yours

  • Workload comparisons across institutions with very different teaching and research expectations.

These comparisons are tempting—but without your own definition of success, you end up playing by someone else’s scoreboard.

Four Moves to Shift the Game

The good news: once you name the game you’re in, you can change it. Your task is to redefine the rules so they position you—and those you lead—for real success. Here are four moves that help.

1) Redefine Success for Your Season

Year one may be about listening and finding your bearings. Don’t measure your first year against someone else’s tenth.

2) Know the Rules Before You Compete

Every campus has priorities—the projects that get funded, outcomes leadership tracks, wins that get celebrated. Those are the “rules,” written or not. If you pour energy into goals that don’t touch those priorities, traction will be scarce. Learn what gets resourced and praised, what recurs in strategy conversations, and focus your team where it will actually matter.

3) Play to Your Strengths, Not Their Scorecard

Once you understand the rules, lean into what makes your unit distinct. Maybe you can’t outspend a peer—but you can out-collaborate, out-innovate, or out-care. Perhaps you won’t bring in the biggest first-year class, but you can be the school with the highest retention and graduation rates. Your uniqueness is your advantage—find it, claim it, use it.

4) Reframe Faculty Expectations Around Winnable Games

Help your team shift, too. Faculty may compare scholarship dollars, travel funds, or research support to wealthier peers. Rather than chasing impossible benchmarks, point to tools you do have: partnerships, mentorship, visibility, and community trust. Redirect the conversation to wins within reach—and build momentum there.

Because the truth is this defining winnable games isn’t only a leadership discipline—it’s a team discipline.

Try This Before Friday

In your next leadership meeting, take ten minutes to reflect (or discuss with your team):

  • What’s a game we can win this year with the resources we already have?

  • Are we playing any games right now that don’t set us up for success?

Small reframes can create big clarity.

The Bottom Line

Leadership isn’t about copying a predecessor or keeping pace with peers. Their path doesn’t determine your own and copying it doesn’t guarantee the same success. It’s about defining the games that fit your people, your mission, and your moment.

“Beating” someone else in rankings, metrics, or achievements can feel like progress—but only in the absence of defining what real success looks like for you. The real win comes when you and your team grow in alignment with the goals you’ve set for yourselves.

That’s the heart of what Brené Brown’s quote above calls authenticity—letting go of who you think you’re supposed to be and leading in a way that’s true to you. Personally, it frees you to lead with integrity and confidence. Interpersonally, it creates stability and trust—your team knows what to expect and can rally around a shared direction.

When you stop chasing someone else’s scoreboard and start building your own, your energy aligns with your true purpose—and that’s what gives leadership its meaning.



P.S. I’ve heard from many of you that you’d like a more structured way to go deeper with the skills we cover in the newsletter — and work on them in practical, step-by-step ways. I’m designing something with that in mind and would love your input. What’s one leadership topic you’d want included? Send me a quick note and let me know.



Whenever you're ready, there are 3 ways I can help you:​

1.) Get the free guide: Your First 14 Days. A clear, practical playbook for new leaders navigating their first two weeks in higher ed leadership. 2.) Coaching for Academic Leaders: A focused 1:1 coaching experience for higher ed professionals who want to lead with clarity, build smarter systems, and stay centered on what matters most. I work with a limited number of clients each quarter to provide highly personalized, strategic support. Send me a message.

3.) Professional Development Workshops: Interactive sessions for faculty, staff, and leadership teams that help reduce conflict, streamline decision-making, and shift culture with smart systems. Virtual and in-person options available. Sessions tailored to your campus needs.


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