Pressure is a privilege
Learning to love the discomfort of being in the arena
👋Hello, my friend. I’m back this week after playing in a two-day, competitive golf tournament last weekend and, no surprise, I learned a few things. Sharing that today, along with a piece of content I’ve been enjoying.
Let’s do it!
Pressure Is a Privilege 🏉️
There’s something fascinating about pressure—how it can expose us, elevate us, or unravel us completely. It’s a phenomenon I’ve been quietly studying, especially in moments when I find myself fully immersed in high-stakes, heart-pounding, situations.
One of the best laboratories I’ve found for this exploration? A golf tournament. Specifically, the annual member‑member event at our club. It’s not Augusta, but for two days every June, it might as well be. Guys in their 30s, 40s, 50s & beyond—many of us balancing work, families, and ageing bodies—come together to compete, trash talk, and test ourselves.
The high point of the event is the shootout—a playoff between the winners of each of the eight flights (each of those consisting of ~8 two-man teams) plus two wildcard teams. It's high stakes. It's where the pressure really intensifies. Everyone's wives and kids show up, lining the fairways, while the club pro announces who's up next to shoot through a megaphone. It’s as close as most of us will get to experiencing tour-style pressure.
I’ve played this tournament three times before. Each time, I’ve made the shootout. Each time, I’ve completely collapsed under the pressure. Think: “played solid all weekend, then completely forgot how to play golf as soon as all the eyes were on me.” This year, sadly, my partner and I didn’t make the shootout—but the experience brought me closer than ever to understanding something I’ve long felt but never quite articulated:
Pressure is a privilege.
Day One: Confidence Feels Good
So how did all of this go down? Let me take you through it.
On the first day, we came out strong. Of the eight teams in our flight, my partner and I finished the first day in second place—just two shots back. We were playing in the same group as the leaders, which gave it this great match‑play energy, shot for shot.
The thing that stood out? I just felt confident. Ball striking was on. Around the greens, I was in rhythm. I was feeling like hitting fairways and greens was doable, if not easy.
Feeling this confident is not always the norm for me. I’m not a low‑handicap player. Some guys in this tournament are scratch golfers. That’s not me. I can’t play 36 holes every weekend. But what I can do is show up prepared. For me, that meant playing more over the previous two months, getting out to the range, dialing in my feel, and mapping out a conservative, smart strategy for each hole.
I also adjusted my lifestyle leading into the event—dialed in nutrition, avoided alcohol, focused on rest and recovery in the week leading up to the tournament. We rode, not walked, but still—playing 18 competitive holes, in 90-degree heat, where every shot matters and every ball needs to be holed? That takes it out of you.
The payoff? Day one felt fun. Confident. Composed. Competitive.
Day Two: Confidence Can Be Fleeting
Heading into day two, I felt like I should be the one in our foursome who could put together a complete round. Our competition had played well the day before, but I thought they had a bit of luck, and I wasn't sure they could sustain it while playing their own balls for 18 holes (the first day was a mix of formats, including alternate shot).
On our second hole, I missed a 3‑foot putt that would’ve gained a stroke. Not great, but manageable. Then on our seventh hole, I chunked an approach into the water—a shot I’ve probably hit clean 9 out of 10 times. And suddenly we were four shots back. Now I’m rattled.
Next hole, both opponents go OB off the tee. We’re thinking, This is our moment. We’re gonna pick multiple shots on these guys, potentially take the lead, and not look back. But I duff two fairway bunker shots and top one in the fairway. That sent me reeling. I went from I can hit any shot, to I can’t hit anything. Completely lost my confidence.
And then the narrative started forming—the one I imagined I'd explain to people afterwards. I'm not totally sure why my mind wanted to go there, but it did: "Played great day one, fell apart day two." And we were only halfway through the round. There was still a ton of golf to play.
But then something clicked: Why am I thinking about the story I’ll tell people afterwards? Nobody actually cares. Not in a cynical way—just in a freeing way. The only person truly invested in how I did… is me. Maybe my partner. That’s it. That realization let me stop catastrophizing and start enjoying again.
And with that mental shift, my play turned around. We clawed back a few strokes. We knew we were likely out of the win, but the wildcard spots? Still within reach.
Final Push: Birdies, Chip-Offs, and a Familiar Heartbeat
With three holes left, we were heating up. A clutch net birdie on a par‑5 gave us a shot. On the final hole, we needed a net eagle to get into the shootout. It was one of the harder holes on the course, a very long par-4, so I was getting a shot, but still would need to birdie (net eagle) to get into the shootout.
I hit a solid drive but missed the fairway by a few feet. The second shot wasn’t my best and left me 100 yards from the hole in the middle of the fairway. I told my partner: I’m going to jar this to put us into the shootout. I flushed it—hit it exactly how I wanted—and it landed three feet from the cup. And then I sank the putt. Not quite net eagle, but net birdie. Pretty solid. But still left us on the outside looking in.
We thought we were completely out of it and had some lunch while the official scores were tallied up. Suddenly, we realized that our score (9 under for the weekend) tied us with two other teams competing for that final wild card spot. We were still alive! And heading to a chip-off to determine who got in. My heart instantly started racing. I recognized the feeling from previous years — and didn’t love it, to be honest.
I walked over to the range to get in a few practice shots. I was striking the ball well and felt confident. Calmed me down a bit.
Families were starting to show up and mill around. And all of the golfers—the ones still in it, and the ones eliminated already—gathered around the main putting green. Alcohol was flowing, and the atmosphere was getting rowdy. There was no shortage of hecklers. The pros explained the format: one chip per player, closest to the pin advances. Heart‑pounding stuff.
I was first to go. The pro announced me and partner’s names over the megaphone. I stepped up. Looked at where I wanted to hit it. Looked down at my ball. Had the “everyone is watching me” feeling for a split-second, but took a breath, relaxed, and swung the club. I executed the shot exactly how I wanted. Ended up maybe 10–12 feet from the hole. I was pretty happy with it. Exhale. My partner followed. Decent shot but outside of mine.
Then the next team. Both guys chipped it outside of us. They’re out. Just needed to beat one more group.
The first guy hits. It’s close to mine. The pros say they’ll need to measure. But first, his partner needs to go. A guy in his 60’s (don’t they always have the best short games?) steps up and sticks it within about 5 feet.
And just like that, we’re out.
The Real Win: Playing Inside the Pressure
Disappointing? Yes. But I walked away proud.
I felt like I had prepared myself well. I played confidently (on the first day, more of a struggle on the second). I adjusted my mindset mid‑round when things were unraveling. I hit a clutch chip under pressure. I did almost everything I could control—and as Jon Sherman reminds us, that’s all you can do in golf. And in life.
There were moments of frustration and disappointment. But also a sense of satisfaction—of being in the arena. Testing myself physically, mentally, emotionally. It felt rewarding. Also walked away with some $ for finishing second in our flight and winning a “skin” or having the lowest score on one of the holes on day 2 — that helped ease the sting of not making the shootout.
What Really Feels Rewarding?
I’ve written recently about asking myself: What do I really find rewarding? I'm pretty sure it's not drinking a bunch of alcohol just because that's supposed to be what "enjoying yourself" looks like in our culture. No, for me, I’m increasingly finding that testing myself is what I actually find rewarding. I enjoy competition—with myself and others. I enjoy doing hard things—whether I succeed or fail. And I enjoy learning how to get better each time I take on one of these feats—on the golf course, in the gym, even in the workplace.
I’ve got the golf bug at the moment, and excitedly, my 13‑year‑old son is starting to get into it more, so I may try to be on the course a bit more going forward. And maybe I’ll find another competition to get involved with.
But it's not just golf. I've already turned my attention back to strength training and recently kicked off the 4‑week "Density 2" program on Peloton. If you've got the Peloton app and set of dumbbells, I highly recommend this program. It's 3 days/week of intense weight-lifting—with reps and weights measured to ensure progress week to week. Join me in this if you’re interested — we can commiserate over being sore. And, oh my God, am I sore!
Outside of that, as I think about where else this theme of "pressure is a privilege" is applicable, I think about the workplace: about putting myself in high stakes situations, about taking on ambitious projects, about not being afraid to push myself out of my comfort zone, to keep growing and learning.
When we get to middle age, there's a tendency to get a little too comfortable—fat and happy, so to speak. We need to fight against this. To push ourselves to be uncomfortable. To be nervous. To find those situations that make our hearts pound.
That's where the growth happens. And that pressure we feel? That's actually the privilege. And when we feel it, we should recognize it, and take a moment to appreciate it, and think: Yes, this is uncomfortable. But I earned the right to feel this way. I’m not going to run from it. On the contrary, I’m going to lean into it. And, I will go a step beyond that, and actually let myself enjoy it.
That’s it for this week, my friend. But before you go, a few content recommendations.
Content Diet
Book: The Five Types of Wealth - Sahil Bloom
I’m thinking a good bit these days about prioritizing — like where do I want to spend time or money that will make me happier now and/or 10 or 20 years in the future? This book is helping me think through that a bit. Bloom proposes a framework for life choices that suggests prioritizing not just financial wealth but also social wealth, time wealth, mental wealth, and physical wealth. I took a course with Sahil a few years back and have traded some messages with him over the years. He’s had an impressive rise in his career, and I think being able to think holistically about priorities is probably a big reason why.
That’s it for this week. Thanks, as always, for reading!
Greg