The Case for Personal Moonshots
Opt in to audacious goals.
I sat in my car shaking uncontrollably. Soaking wet, plastic tech t-shirt plastered against my torso. My left hand rested against the blowers, heat bringing feeling back into my fingers; the other held a baby wipe, smearing mud off my lower legs. It rippled like ochre peanut butter smeared upon thin bread.
I peeled off my wet clothes and, for a moment, leaned forward half-naked in the drivers seat, head bent against the wheel. I listened with my eyes closed as the rain pattered against the car, the wind blowing off the Sierra Nevada foothills in wave-like crescendos.
I’d finished the Way Too Cool 50K a few minutes earlier. And in 20 hours I would toe the line for the Napa Marathon with the goal of completing a trail 50K and road marathon in a single weekend. Or to complete the “Frogs to Grapes Challenge”, as my friend Rebecca Murillo pithily labeled it. (Cool is famous for offering frog-shaped cupcakes at the finish line.)
I’m not quite sure why exactly I decided to do this, to run a trail 50K as hard as I could the day before trying to race a road marathon as fast as possible. Getting to a Cool finish line healthy had been a longtime goal. But adding Napa into the mix wasn’t the plan until early-January. A few training buddies were planning to run it and I thought, “What the hell? Why not. It’s there to do, right?”
So, I did it. I scarfed down two protein bars and grabbed a burrito from the soggy finish line in Cool. Munching contentedly, I listened to Cher on the drive back from the canyons east of Sacramento.
The next morning, I rose before 4:00am and carpooled up to Napa with some That’s Fine Track Club teammates. Fashionably late, we caught the last shuttle bus to the start.
Things felt ok for the first 15 miles and then… they didn’t. Each step became painful, sharp pain through my quads. It began to shower and the temps dropped.
I pulled out my bag of mental tricks, honed from many a tough race: focusing on the next chunk of pavement ahead, compartmentalizing the remaining ten miles into two-mile segments, reframing the wind and the rain as personal antagonists and channeling my anger to keeping my arms pumping. A lifetime of little tactics I’ve learned to keep an ever-so human aggregation of sinew, muscle, and bone moving forward.
I finished. And for that short moment of wonder it felt amazing, like sunshine in my lungs. I’d done this silly and hard thing I’d set out to do. And in that immediate aftermath there’s nothing finer.
And then life kept moving on, as it always does.
Recently, I was feeling feeling tired and a bit depressed about a project that wasn’t going well. Fishing around, I watched a video edit of President John F. Kennedy’s 1961 speech at Rice University announcing the United States’ attempt to land a human being on the moon.
You’ve almost certainly heard parts of it. It’s a powerful piece of presidential rhetoric—a speech about the audacity of the human spirit and our innate willingness to take on bold and difficult ventures. It is a speech of unabashed nationalist optimism, almost shocking to hear in our era of progressive pessimism and reactionary culture war.
“But why some say, the moon? Why choose this as our goal?” Kennedy asked. The answer is, why do anything hard? Why climb a mountain or fly across the Atlantic or free solo El Capitan? Why run a half marathon or learn how to ride a horse? Because it’s hard.
“We choose to go to the moon in this decade and do the other things, not because they are easy, but because they are hard, because that goal will serve to organize and measure the best of our energies and skills.”
Trying to do difficult things is, according to Kennedy, worthy in and of itself. And it also forces us to marshal and dedicate our energy in purposive ways. It unifies disparate people and provides spillover effects like stronger institutions, better health (economic, physical, mental), and social resilience. It forces us to question our current direction and continually take stock of how we’re progressing. And it helps us learn about ourselves, both collectively and individually—our strengths and our areas of opportunity.
I learned from Frogs to Grapes that while running is lower in my priorities at the moment—family, career, and writing are weighted higher right now—it doesn’t mean I can’t still aim for goals that push my boundaries. Even if personal bests are out of reach, we can still set goals that motivate and maintain the qualities and objectives that we value.
So here’s wishing you best of luck in your own moonshots. Thanks for reading.
If you’re interested, here are a few thoughts about setting audacious goals:
Keep it feasible. JFK gave the moonshot speech when the United States had already achieved the basic science, technology, and institutional structures to make the attempt possible. It just required the marshaling of state power to coordinate these latent resources. Take stock of your current circumstances. To use a running example, if the furthest you’ve ever run is 6 miles, that’s awesome. And with 3-5 months of training, you can likely complete a half-marathon if that would be meaningful to you. But a full marathon will take more time. Be audacious, but don’t be unrealistic.
Make a plan. Break up your prep into cycles and benchmarks that build toward the goal. There’s a million resources and coaches out there, so plan to plan. 5-6 hours of upfront planning pays dividends: you’ll have a sense of direction, a record of your approach for future reference, and you’ll spend less time each week wondering what you need to do and more time actually doing it.
Start small, think big. Don’t let the size of an idea keep you from starting. Any number of productivity coaches or creativity gurus will say that consistent, steady effort, however small, is the most important element to reaching a goal. So avoid thinking that because your goal is audacious, your prep should be too. Lower the barrier of entry. Keep every instance of work approachable and doable. For example, since the pandemic, my working hours have morphed such that I often have early morning and night meetings. This makes it very difficult for me to rally for longer, more intensive morning workouts. But I can almost always rally for a 30-minute shakeout from my apartment. Is running a chunk of my mileage in slow, 4-mile jogs the Platonic ideal for competitive running. Nope. Is it better than not running those miles at all? Absolutely.
Failure is an option. We overly moralize quitting and failing at goals. But except in the rarest of circumstances, it’s ok to fall short or to drop a project. Life circumstances change. We might have bad luck. Or we just miss. Sometimes it’s a matter of growth and shifting priorities. The author Oliver Burkeman recently referred to these as “life tasks,” what life demands of us that helps direct our path and pushes us, in counter-instinctual ways, forward in new directions. Even when we quit or change course, we’ve almost always gained some experience and knowledge. Effort is almost never wasted; it’s just waiting for new opportunities to be re-envisioned and redeployed.
Weekly run
Breakfast Club meets every Thursday for an 8-mile run:
When and Where: 6:30am at Lake Temescal in Oakland, CA
Pace: ~7:00 to 7:40 pace with a few hundred feet of climbing
Notes from the infield
Quick splits around the interwebs.
Watch
Stanford squeaks the DMR. Razorback Lauren Gregory dropped the hammer at the NCAA Indoor Champs Distance Medley, coming oh-so-close until she ran out of tartan. Keep an eye on Gregory, who is competitive in events from 1500 to 10K, but also won the US Mountain Running champs last summer. Read a recap of this race and the rest of the champs in Alison Wade’s Fast Women report. (Twitter)
Cringiest TV scene of all time. Yes, that cringe. (Twitter)
Read
The Dubious Rise of Imposter Syndrome. The concept has become both ubiquitous and sharply critiqued as masking deeper inequalities and being specific to certain privileged experiences. (New Yorker)
Ode to the Oakland Greyhound Station. Back in 2010, I had a large package shipped from the east coast in the berth of Greyhound bus (the bus line offered a parcel service until 2022). When I picked it up at the Oakland station, I was startled by the terminal’s striking dome rotunda over its waiting room. A venerable and egalitarian piece of transportation infrastructure, the bus station is now shuttered but for the occasional bandit EDM rave. (Oaklandside)
Wear
Brooks Catamount V2 Review. Trailrunner’s first look at the new Catamount gave me both trepidation and hope. The first iteration of Brooks’ offroad all-rounder is my go-to for hard trail efforts with enough cushion for an ultra, while staying nimble enough for shorter trail race. I’m a wee bit worried about the plate tech they’ve inserted into the new version as well as the adjusted outsole lugs. One could grind over road, mud, or hardpacked trail with the OG Catamount and I hope that crossover ride is maintained. $170.
Near Earth Distance Running Sock. I’ve been rotating through a few of these understated socks and have found they hold up well for both long-intensity tempo runs on asphalt and mixed terrain trail stuff. Their made in Italy but aren’t priced much higher than the stuff churned out by authoritarian states across the Pacific. Oaklanders can pick up a pair at Renegade Running. $24.
Tweets of the week
Parting thought
“Throw up in your typewriter every morning, clean up every noon.”
- Ray Bradbury










Hey Sam. Knowing that super runners like yourself are human too and that you experience challenges along the way and have other priorities besides running makes me feel better and gives me the encouragement I need to get back to running when life gets in the way as I set audacious goals.
Thanks for keeping it real!
✊🏼
Sam, huge congrats on your back-to-back. But you're so modest, I had to look up your times. 3:38 for a top 10 finish at WTC in those insane muddy conditions, then 2:41 at Napa. Whoa! That is crazy fast. I know back-to-backs are special challenges, in many ways harder than doubling the distance at a single event. It's hard physically & mentally to give your all on Day 1 when you know what you face the next day. I also admire your versatility, to do trail ultra then speedy road. Nice work, especially in the rain and cold! I have a back-to-back on calendar this summer, the Silverton Alpine + Kendall Mountain on the second week of July. The back-to-back I really want to do, but can't this year, is the Sawatch 50/50, two 50Ks--one runnable, one high alpine--in late September. You should check it out!