Special Sunday Edition: 12 Thoughts On Running (And Leading Teams & Building Products)

A little exception to the norms of our monthly Implications newsletters, but I wanted to share some realizations while running that I think are relevant for building teams and products as well.

Hope this finds all of my fellow Implications enthusiasts well. This one is a bit of a deviation from our normal Implications routine, but hey it’s August. In a week or so, you’ll get edition #9 of Implications which will explore humanity’s declining tolerance for friction and a set of seemingly wild concepts today that may pierce our daily lexicon over the coming decade (excited about this one). As for running…

About six years ago I started running. I was never a good athlete, and never particularly enjoyed running. But I started running a couple miles at a time, then three, then four to five daily, and this activity has brought much more to my life than I ever expected. Aside from the energy and health benefits, running has influenced how I live, lead, and make things. A recent chat with a few friends prompted this summary of what I’ve learned thus far. I hope these realizations prove helpful and perhaps encourage you…to run, whatever your running equivalent is.

(1) Don’t judge because the context you’re missing is everything. As a naturally competitive person, it is tempting to pace myself with other runners I encounter, and you’re liable to judge those you swiftly pass along the way. But such judgment is misleading, as you have no idea when they started or their previous pace. For all you know they’re the world’s greatest runner on a recovery day. Ultimately you learn, don’t judge anyone at a single point in their journey because chances are you are missing context and will be wrong. Simply respect that they’re running. Same applies when you lap someone and are inclined to feel great about yourself. Truth is, you have no idea and any story you tell yourself is likely a false story. This insight has changed the way I view press, cancel culture, and take-down pieces — they’re all moment-in-time judgments and lack context. The noise of inaccurate snap judgements will mislead you in work and life. When you generalize people you marginalize the potential of people. I also challenge myself to be less of a “thin slice” evaluator of talent and avoid the “Fundamental Attribution Error” (described by HBR as “an individual’s tendency to attribute another’s actions to their character or personality, while attributing their behavior to external situational factors outside of their control.”) Everyone is engulfed in their own drama, with a unique series of challenges to overcome. You’re in a lane unique to you, with its own conditions. Stay humble, don’t judge, and focus on beating yourself at your own game.

(2) When you’re forced to unplug, your mind is forced to wander. Our phones, schedules, and constant connection to the world as it happens is a tremendous burden on the spontaneity of our imagination. Even Uber rides and airplane flights have become windows for productivity at the expense of just thinking. At this point, the only two places I am forced to unplug and let my mind wander are the shower and…while running. The endorphins released while running, paired with the forced period of disconnection, are a godsend for me. I challenge my plans and contemplate my projects, I think of UX tweaks in products, I brew new articles to write, I develop tactics to close deals…and if I didn’t have this window of thinking imposed on me, I’d likely just be responding to more emails and slacks and and… In the modern era, we desperately need forced windows of non-stimulation and can no longer rely on circumstance. Find something in your life that forces you to regularly disconnect, do it regularly, and open the aperture of your free-flowing imagination.

(3) The pause between idea and action has a bounty we seldom reap. Wait for it. I have a lot of ideas while running, and I get obsessed with just trying to remember them but I never let myself stop mid-run to write them down. Partly because that would be a pathetically seductive excuse to take a break. But mostly because, if I let these ideas continue to brew they actually get better. Turns out, the time and distance between when you have an idea (and feel tempted to stop and capture it) and when you wait until you finish your run is a golden period of polish that doesn’t exist in the normal real-time sitting state world. That space in between is both a period of natural selection and iteration that supernaturally extends your blue sky state at a moment when endorphins are running high. On many occasions in my life, a good idea became a great idea (or a properly discarded idea) during this period. Which all begs to question: should we be careful not to capture actions too quickly in our everyday life at the expense of sticking with a creative process long enough to let ideas build on each other? My friend Sahil, while reviewing a draft of this piece, reminded me of the Viktor Frankl quote, “Between stimulus and response, there is a space. In that space is our power to choose our response.” Should we bake in a “wait for it” period upon every major decision in life? Keep running when you’re tempted to stop, and come to appreciate the polish period in between.

(4) Catch your subconscious acts that enable excuses. A few years ago I had the tendency of needing to pause mid run to tie a shoe. For some reason I kept forgetting to tie my shoes with two knots on the longest runs, often forcing me to stop along the way. At some point I suspected that this may be my subconscious “out” and, by identifying the likelihood of it being an excuse, I no longer forget the double knot. We all have a powerful subconscious set of forces that cater to our fears or laziness, and step one is observing and detecting what these might be across all parts of our lives.

(5) Build your tough-love inner-coach: I’ll often whisper to myself towards the end of a hard run, “Come on, give me another sprint…another mile, you can rest later.” This “inner coach” voice has developed over recent years. It celebrates a good run and calls me out when I’m sloppy. When running around the Central Park reservoir, there is a certain stretch I call “the straight shot.” When I reach this point about two miles into my morning run when I am in NYC, my inner coach reminds me to sprint it from start to finish. Doesn’t matter if I’m on a recovery run, feeling under the weather, or exhausted. I do it to remind myself that I always can despite the circumstances, and my inner coach won’t let me get away with an excuse. I’ve come to realize this inner voice is what keeps us honest with ourselves and performant across many parts of our life. All too often we think that, if nobody else notices a short-cut we take, that we can get away with it. But your inner coach cannot be fooled. Your inner coach stubbornly remembers everything. And the self-reliance, strength, and commitment to raw truth that result from empowering and respecting your inner coach makes you better. Develop this inner coach persona in your head. And pay attention to your terrain for anything that can be merchandised to yourself (and team) as a moment of challenge like my “straight shot” around the reservoir and tuck these sprints in.

(6) Overcoming personal challenges develops self-efficacy — a form of transferable confidence. The muscle memory of overcoming a personal challenge in one part of your life (like running) is surprisingly transferrable to other parts of your life. Why? Because you’re proving to yourself that “a faster time” or “a better quarter” (whatever the challenge) is always possible. The confidence gained from the breakthrough, like a form of muscle memory, is surprisingly context agnostic. You develop this strong sense of transferrable self-efficacy, what is known in psychology as “an individual’s belief in his or her capacity to execute behaviors necessary to produce specific performance attainments.” As you realize what you can accomplish in one area, you become more confident in both that and other areas. When you hire people, this is an important trait to look for. Asking about past challenges and how they have influenced more recent challenges can help you asses self-efficacy.

(7) Overrun your milestones by a margin of safety. The legendary investor Seth Klarman is best known for his investment principle “Margin of Safety” and book by the same name. In short, Klarman’s book is mostly about avoiding loss by investing with a series of precautions to stay disciplined, avoid fads, and tactics to protect yourself from large losses in a volatile market. For some reason, I have adopted these principles for other parts of my life, always trying to slightly exceed milestones for safe measure. In my world of running this means always slightly over-running what the watch says or whatever gamified goal I mentally adopted to make it a good run. I never want to fall under the reported mileage on my watch or the goals I unwaveringly set for myself. When I do, the possibility of falling short or missing a window to get a product JUST RIGHT ruminates in my mind. I can’t escape it. In product, perhaps this translates into how you set your goals and OKRs, and the level of assurance you seek before shipping. After all, the finish line is ultimately customer delight, not just shipping. I’m on the record as critical of the traditional MVP model because I don’t think you should ship the thing that differentiates your product without extra polish. You should execute your ideas and perform your craft with a margin of safety to ensure excellence.

(8) Your performance is advanced when you run with people who push you. A couple summers ago when my friend Sahil came to visit with his family, he joined me for a run. At the time I was averaging a bit over an 8 minute mile for 3–5 mile runs. Sahil was a college athlete but said he didn’t run often and was happy with a 8–8:30/mile pace. But as we ran, got lost in conversation, and paced each other, we accelerated each others’ times and ended with 3 miles at less than a 7:30/mile pace. You can see a good example of a normal run at the time (on the left) compared to a (probably leisure for him!) Sahil Bloom run (one the right) below. Can you guess which run left me with an evening of ankle pain? But the experience emphasized the benefits of running alongside people that push you, and the compounding returns of team work. A good team is a classic 1+1=3 type of situation, you make each other better. I am reminded of all the adages around hiring people smarter than you, surrounding yourself with people you admire, etc. This is why. Your pace (and your potential) goes up when those around you not only raise the bar but pace you to reach it.

(9) Running uphill or through bad weather are where times are beaten and races are won. Uphill is the hardest terrain — both in running as well as bold projects of all kinds. Startups (and innovation within large companies) feel like running uphill. Why? Because you’re working amidst ambiguity, uncertainty, anxiety, and fear. But great founders always remind their teams: whatever you find difficult to do becomes differentiating for your product and your company’s future moat. Those especially difficult periods, where it feels like you’re running uphill against the laws of gravity, are the periods of truly material and differentiating progress. When I face an upward slope and my legs start feel the strain, I try to keep the same pace uphill. I remind myself that this is the opportunity to be better. Similarly, I have come to enjoy running in bad weather. It’s less crowded, but there’s an extra sensation of hustle knowing you’re one of the few still training and making progress. This was the same sensation I felt during our five bootstrapping years of Behance — and periods of being underestimated at Adobe — whenever my team faced a dose of hardship with a product, a re-platforming, or in the economy but doubled-down nonetheless. Doing the hard thing makes you more rare because few people do, and doing so gives you an extra dose of much deserved and surprisingly transferable confidence.

(10) When you consider the challenge you’re facing as a journey, you enjoy it far more. I hate the treadmill. I find it harder. Even without nature’s sporadic inclines and with a more controlled pace and the omnipresence of metrics, it is harder for me because I don’t genuinely feel the rush of progress from running TO something nor the distraction of mother nature. A run needs to feel like a journey to me, with a start and finish and surprises along the way. In my book The Messy Middle I talk at length about the necessity of merchandising progress to teams in order to drive more progress. Progress begets progress, which is why celebrating milestones and team culture in the form of stories and surprises that become folklore are critical. This is the stuff that keeps a team together long enough to figure it out. Without these elements of adventure, building a company or any other bold project feels like you’re on a treadmill and will be harder.

(11) Goals are effective even if they’re entirely arbitrary. Any runner knows that pushing yourself to sprint to an arbitrary marker on the road is an effective way of improving your average pace over time. This is the mental art (not science) of hustle that I’ve found so valuable as an entrepreneur, often pushing myself to “just send ten more customer emails before bed” or “do one more run-through of that strategy document” and other sprints that, over time, vastly accelerated my team’s pace of execution. Similarly, our team’s shipping cadence always included somewhat arbitrary “shipping seasons” that were associated with arbitrary launch dates or board meetings that we would spring to make. While some folks (especially engineers) would challenge the reasoning for these dates, they were important and increased our average speed. One of my most disappointing runs in recent memory was 2.97 miles. Disappointing for an obvious reason: A clear mile marker will forever remain unreached. You can rest assured that will never happen again.

(12) To measure or not to measure, that is the question. It all comes down to intrinsic reward and adhering to your truth. I usually pace myself with metrics, challenging myself to stay under a particular number of minutes per mile or keep running for an amount of time. But the consequence is that I’m liable to become metrics dependent, where I need numbers to feel progress. This is effective but unhealthy for longer-term pursuits void of metrics as well as those less quantifiable but equally important goals in work and life. I’ve always told myself, given my experience in the ramifications of “coin-operated” people and companies, that I would aspire to transcend this need. Well, I’ve come to believe that we all need metrics to drive breakthrough performance, but you can, in fact, be creative with them. A “No Metrics” run is very similar to a startup or bold project void of any clear near-term payoffs. At such moments (where I forget my Apple Watch, or it dies on me) my desire to run only comes from within. Do I end up running better or worse, faster or slower than usual? Am I more motivated or less motivated without this source of truth? And what is the equivalent of forgetting your watch in real life? I have come to see the life equivalent as making progress in your passion without anyone noticing - without any external accolades, yet still feeling great about it. Pushing yourself and achieving a personal best without anyone needing to know about it is an important form of mental exercise in itself.

Hope some of these relate or prompt your own perspective.
Sending my best, -scott