James R. Stewart

Principles

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In my journey as a product manager and, more fundamentally, as a person, I've come to realize that I hold certain principles. Truths about life, working effectively in the workplace, and building products. Like most others, I hold these subconsciously most of the time. Every so often, I'll find myself in a situation and these principles will re-surface themselves in my mind. This essay is my attempt to articulate these principles, exploring their importance and their personal significance to me.

This list is dynamic and will evolve as I do. It's open to changes as I learn and grow.

How I decide

Seek truth, not compromise (source)

In every team, company, or organization, conflict is a natural part of working together. When faced with conflict, we typically encounter two paths: seeking compromise or seeking truth. Opting for compromise is often the path of least resistance. Jeff Bezos illustrates this: "Take you back in time 10,000 years, and you're in a small village. If you go along to get along, you can survive, you can procreate." He goes on, "If you are the village truth-teller, you might get clubbed to death in the middle of the night." This exemplifies the inherent challenge in truth-telling – it's against our natural instincts for harmony and survival. Yet, embracing truth is crucial in creating a culture of openness and integrity within the teams I lead. It's about facing reality head-on, not shying away from it or reshaping it to fit our desires. I firmly believe that confronting the truth, despite its difficulties, is fundamental to achieving meaningful progress and building genuine, dynamic team relationships.

There are no solutions, only tradeoffs (Thomas Sowell)

Every decision I've made at work looked like a solution at the time. It wasn't. It was a trade. Ship sooner and you take on risk. Add a feature and the product gets harder to use. Hire the senior person and you lose the scrappy one. So I've stopped asking "what's the right answer?" and started asking "what are we giving up, and are we okay with that?" When nobody in the room can name the cost of a decision, it usually means nobody has looked for it yet.

If it's not a "Hell yeah!", it's a no (source)

The easiest framework for decision-making. If you are ever met with a high-stakes decision — be it personal, professional, or otherwise — ask yourself: is this a "HELL YEAH!"? If there's any hesitation that stops it from being a resounding yes, then it's a no. This approach is like the Net Promoter Score (NPS) used for products, where only those consistently rated 9 or above are truly considered exceptional. By applying this 'Hell Yeah!' framework, I ensure that my efforts are dedicated to pursuits that genuinely matter and resonate with me. It helps me maintain a laser focus, leading to a more meaningful and satisfying life. This is my personal NPS framework for life.

How I work

Fall in love with the process (James Clear)

James Clear says you don't rise to the level of your goals; you fall to the level of your systems. Nick Saban built a dynasty on the same idea. His teams were taught to ignore the scoreboard and win the next play. Goals are good for picking a direction. They're bad for getting you there, because everyone in the race has the same goal. What separates people is what they do on an ordinary Tuesday. The Zen version is older and shorter: chop wood, carry water. I keep relearning it.

Calculation is miscalculation (The Inner Game of Tennis)

Tim Gallwey noticed that his tennis students played worse the harder they thought. He described two selves. Self 1 is the voice in your head that calculates, judges, and corrects. Self 2 is the part of you that already knows how to hit the ball. Every time Self 1 steps in, it gets in the way. Calculation is miscalculation. I see it most in big moments, like a hard conversation or a pitch. The more I try to compute my way through, the worse it goes. The work happens beforehand. In the moment, the job is to trust it.

How I grow

What got you here won't get you there (Marshall Goldsmith)

The habits that make you good at one job often get in the way of the next. At startups I was rewarded for doing everything myself. At a big company that same instinct makes you the bottleneck. The hard part is that old habits don't feel like weaknesses. They feel like the reason you got here. Every time I change roles, I ask which of my strengths just turned into a liability.

Chase the person ten years ahead (Matthew McConaughey)

When Matthew McConaughey won his Oscar, he said his hero is himself, ten years from now. He picked that hero at fifteen. Every decade, the hero moves another ten years out. He'll never catch him, and that's the point. I like this better than most advice about role models. It turns an ordinary day into a question: is this setting up the person I want to be in ten years? Usually the answer is in small things. What I read. Who I spend time with. Whether I go for the run.

A genius is the one most like himself (Thelonious Monk)

Earlier in my career, I spent a lot of effort trying to seem smart. I worked on how I presented myself and how I framed my ideas, all to impress people. I had it backwards. What works is saying what I think, the way I'd naturally say it. When I stop performing and just sound like James, I do better. Ten times out of ten.

How I live

This is water (David Foster Wallace)

Two young fish swim past an older fish, who says, "Morning, boys. How's the water?" A little later one turns to the other: "What the hell is water?" The most important parts of your life are the ones you've stopped noticing: your assumptions, your habits, the people you see every day. Wallace's point is that paying attention is a choice you have to keep making, usually when you're tired and stuck in a checkout line. It's the hardest principle on this list, because it never stays done.

Build cathedrals, don't lay bricks (source)

As a product leader, my role is to set a compelling product vision, embodying the principle of "Build cathedrals, not just lay bricks." It's crucial for me to ensure that every team member sees beyond the day-to-day tasks to the grand vision we're constructing together. I strive to make everyone aware that they are not just laying bricks, but are integral in building an awe-inspiring catheral. My responsibility is to keep this vision clear and present in all our efforts, ensuring that each action contributes to our magnificent end goal. This approach not only enhances our work but also fuels motivation and a sense of purpose within the team.

Man in the Arena (source)

This quote from Theodore Roosevelt powerfully captures the mindset I aspire to in work and life. It's about setting audacious goals, taking risks despite critics, and finding fulfillment in the journey - win or lose. It stands as the guiding principle I strive to embody in my life — so much so, that it's permanently embedded in the source code of my website. To me, "the man in the arena" represents courage - the courage to create, build publicly, and push limits. It's less about outcomes than the grit required to attempt great things. This quote drives me to take that first step and pour my energy into efforts that deeply matter, whether or not they succeed. If I had to choose one guiding principle, this would be it.

To be continued…