Leadership: You Keep Using That Word
“You keep using that word. I do not think it means what you think it means.”
Inigo Montoya’s line from The Princess Bride popped into my head the other day while I was scrolling through yet another post about “leadership.” Everyone throws the word around—leading teams, leading projects, leading by example. But I started wondering if it means what most of us assume it does.
Simon Sinek pulls the idea of leadership back to something simpler and harder: bravery. Not the chest-thumping kind, but the quiet willingness to keep playing an infinite game when everything around you pushes for a quick finite win. In my own life, that bravery shows up most often in deciding when to say yes and when to say no. The difference between those two words frequently comes down to whether I’m chasing a short-term score or staying true to a bigger purpose that outlasts any single goal. If you’ve been following along in this series, you may recall that this bigger purpose could be considered your Just Cause.
The Bravery of A "Yes" or "No"
What do I mean when I suggest that bravery shows up with the decision between a “yes” and a “no”? Consider the decision to accept a promotion. For many, it’s a no-brainer—you’re offered more money, a new title, and acknowledgement of your expertise. However, the additional responsibilities and time commitments might distract from, or even derail, your Just Cause if the promotion isn’t related. Do you have the courage to ask the right questions? Do you have the courage to act on the answer? Are you brave enough to follow your Just Cause at the risk of outside pressure?
Short Game or Long Game?
Another example is continuing education or additional training, like going after an Executive MBA. A while back I sat down with my VP and asked about the value of something like an EMBA for our organization. He figured it might become really useful in about five years. There are a lot of ways to hear that. I didn’t know exactly how long the program would take on top of a full-time job and family responsibilities, but after six months or so of thinking it over, I decided it was time to start the process anyway.
On the work side, I was trying to be proactive—maybe even a little early. I really want the EMBA to pay off there, and I’m confident it will in practical ways. But the stronger pull for me was how it could serve my Just Cause: helping others Aim Up and improve toward their highest calling. In the finite game, it might have made more sense to wait until the timing looked perfect or the organizational need was obvious. Because it was my own initiative and not at the request of my employer, I was completely responsible to foot the bill and use only personal time. The assignments and time commitment pulled hard on my early mornings and energy I could spend elsewhere. There were weeks where it felt like a lot! Yet when I measure it against the longer game—meeting new people, building skills and perspective that let me show up better for people trying to make steady progress in their own lives—it becomes a different kind of choice.
Choosing to move on it when I did, even with the uncertainty, felt like a small existential shift: adjusting my own development path on purpose so I could keep contributing to something that outlasts any single role or deadline. The short-term scoreboard might look busier than I’d like, but the steadier direction feels more aligned with where I’m trying to head.
Note: To be transparent, my family trumps any external ambitions. If there would have been a cost that put the Just Cause of my family in peril, I would have not pursued the EMBA at that time, spent less time on it, focusing on graduating, not excelling (I received recognition for being in the top 10% of my graduating class), or taken steps to defer the program until I could properly focus on it. There would have been some "yes" and "no" decisions to consider along the way!
CVS: True to Their Calling
My version is tiny by comparison, but the feeling is similar to stories like CVS deciding to stop selling cigarettes back in 2014. Their purpose was helping people on the path to better health, yet they were still profiting from tobacco. On the finite scoreboard it made no sense—they walked away from a couple billion dollars in annual revenue and took heat from analysts. But they chose to align fully with their Just Cause instead. Saying no to easy money so the longer game could advance more honestly took real courage.
Measuring the Cost
That kind of choice didn’t always feel brave in the moment. It mostly felt like extra work and a fair bit of uncertainty. Some mornings I sit with my coffee wondering if I should have waited until the company asked or until the timing looked cleaner. The assignments pulled on time I could spend with the family, sleeping in, exercising, or just recovering from the week. Yet when I look at why I started—to get better at helping others Aim Up—it still feels like the right yes at the right time for the longer game.
One of the quieter parts of this bravery is that it doesn’t stay private. Kids notice when you’re stretching yourself for something bigger than the next paycheck or promotion. Colleagues sometimes pick up on it when you talk about investing in growth even when no one required it. It becomes a small example that it’s okay to say yes to things that serve a purpose beyond the immediate scoreboard, and no to waiting for perfect conditions. I’m not trying to be anyone’s hero here. I’m just trying to show up consistently enough that the people around me feel a little more permission to do the same in their own lives.
The Courage to Keep Aiming Up!
None of us wake up with unlimited courage. It builds the same way most things do: through small, repeatable choices when the pressure is real. We’ve talked about this before in the series on habits – atomic habits. They’re “atomic” because they’re small, like an atom, not because they’re nuclear-explosion level! They’re nothing flashy. It’s saying yes to a study block. It’s saying no to an extra commitment that would dilute the energy I need for the things that actually matter to my Just Cause. Sometimes it yes to an impulsive activity, because you just need some fun; or it could be a “no” because the opportunity cost against your Just Cause is just too great.
Will we get it right all the time? Certainly not. And that’s fine. We can learn from it. The point isn’t perfection — it’s practicing the muscle of measuring yes and no against the infinite view instead of the short-term noise.
If you’re facing your own version of this right now — a training opportunity, a promotion conversation, or any commitment that pulls on your time and energy — try running it through that same filter. Does it clearly serve the bigger purpose you’re playing for, or is it mostly feeding a finite scoreboard? One small micro-challenge this week can make the next decision feel a little less heavy.
Leadership, courage, and bravery, and Aiming Up! I am going to keep using those words, but we’ll be sure to stay on the same page! Thanks for joining the conversation and keep Aiming Up!
