Ready by Moving

I wish I could say I handled every misadventure there with grace, but the truth is I once tried to buy breakfast with the wrong currency and ended up with a handful of lottery tickets instead of coffee. There was a moment where I just stood there, clutching these tickets and wondering what they even promised, realizing how far off the mark my expectations had landed. I still have one tucked away in a desk drawer. Most days, it makes me laugh—the kind of mistake you only make when you’re deep in unfamiliar territory, figuring out the rules by doing.

There’s a direct line connecting that off-script travel decision to the way I approach engineering and AI work. If you’ve spent any time building in high-ambiguity spaces, you know what I mean. The specs are rarely perfect. Nobody’s sure what’s around the bend, and often, momentum stalls because we wait for the kind of certainty that never shows up on time.

It’s tempting to think that predictable, fully-mapped projects are what sharpen your skill. But most of my biggest growth moments started with no plan, just a hunch, some discomfort, and the belief I’d figure it out. Movement in those moments—shipping a thin slice, pushing through uncertainty, choosing a step you know you can reverse—produces readiness, not the other way around. That pattern shows up everywhere.

It shows up in early product demos, risky architectural bets, and even team moves that felt premature until feedback made them clearer. When you act in ambiguity, the path doesn’t firm up first. You build it by walking. If you want to lead in this kind of environment, being comfortable with not knowing is what speeds up everything that matters.

Teams Stall Waiting for Certainty

You’ve probably seen this play out. Teams freeze instead of choosing to ship without perfect specs, holding out for a roadmap that anticipates every bump. It feels responsible, like things will go smoother if you hold for more clarity. But clarity isn’t a prerequisite for action. Most of the time, it’s just a stall.

Why do we hesitate? There’s the fear of rework, of looking careless, of having to explain a zigzag later. There’s a real concern for quality, too. But ambiguity isn’t a flaw in the plan. It’s the day-to-day reality in high-trust engineering work. I didn’t always see it that way. Early on, uncertainty made me tense up, like it was a sign I was about to mess up. Over time, I realized ambiguity is a muscle. The more you use it, the more you adapt. You don’t get braver staring at the map. You build it by taking steps in the fog.

Here’s the hidden cost. Every day you stall is a day you delay the feedback that shows you what actually matters. That waiting? It compounds.

One way to break the cycle is simple. Optimize for reversible decisions and short feedback loops. Most moves you mull over aren’t one-way doors—they’re reversible, just like Bezos’ “two-way doors” model of decisions. So go ship that thin slice now and learn. It’s rarely as risky as it feels. You get clarity one actionable bet at a time.

Movement Produces Readiness

Here’s the core of what I wish I’d learned sooner. In engineering and AI, momentum gives you the clarity you keep waiting for. You don’t need to be ready before you act. A bias toward action creates readiness, not the other way around.

What makes this work? Simple. Feedback compresses uncertainty. When you take a small, deliberate swing—even if you’re just guessing—you unlock crucial signals about whether the design holds up, what’s technically feasible, and what customers actually care about. It’s no accident—the Build–Measure–Learn loop runs on speed because getting feedback faster is what unlocks actual customer development. I’ve watched excessive planning drain weeks from projects, only to have a two-hour hack reveal the blind spot everyone missed. Every experiment is a flashlight into the fog.

Six months ago, I found myself watching a project stall for weeks as everyone waited for more user stories to be written up. The moment we dropped a thin prototype in front of users, everything sped up—the issues jumped out, the debates got sharper, and suddenly the next steps were obvious. There’s a pattern here I still haven’t broken: I know fast feedback is key, but I’m always tempted to wait for more information than I probably need. Doing it the messy way, with limited prep, still makes me uncomfortable.

I could wax poetic about precision, but if I’m honest? Over-prepping has burned me more times than I can count. Military drills scrapped mid-exercise, software sprints that landed behind schedule anyway. Naivety gets a bad rap, but sometimes the naive start is momentum in disguise. A first attempt, no matter how imperfect, beats another day lost “getting ready.”

Pause and breathe. You don’t need heroics. Just choose one small move, then get it out the door.

Worried about quality? You should be, and that’s why thin slices aren’t reckless. Set guardrails. Feature flags let you ship safely, test harnesses catch regressions early, and shadow mode means you monitor impact before anyone’s affected. These aren’t afterthoughts; they make experimentation safe and feedback useful.

Every ambiguous step forward compounds. That’s how you become the engineer people trust when no roadmap will ever be enough.

Lead Engineering Teams Under Uncertainty: Leading Through Ambiguity

I’ve learned to staff teams with engineers who excel at leading through ambiguity when specs are sketchy and deadlines are serious, because real progress depends on that kind of temperament. It’s less about bravado, more about staying present when the floor shifts beneath you. Over time, I started to value people who treat fuzzy requirements as normal, not as signs that something’s gone wrong.

The trick is to design an environment that rewards learning velocity—where the pace of useful feedback matters more than the illusion of control. If you tie recognition to momentum in uncertainty, you reframe ambiguity as fuel, not friction. There’s a quiet pride in saying, “We moved the needle with half the map missing,” and after a few cycles, that pride becomes habit.

This is why I keep very specific rituals in place. Every day, my teams check in on a “reversible next step”—what’s the smallest thing we can do now that we won’t regret later? There’s always a public log that shows our learning, no matter how rough, so progress is visible even when outcomes aren’t. And for the few moves that really can’t be undone—a one-way door—we raise the flag and escalate. These signals aren’t bureaucratic. They’re the scaffolding for trust. That’s why I trust engineers who thrive in ambiguity.

When someone worries that taking two days to prototype will slow us down, I point out the opposite. A 48-hour spike often saves entire weeks. Spinning your wheels building the wrong thing eats far more time than tossing out a rough draft for early feedback. I wish more folks made this a habit—ship something visible, get a reaction, then course-correct on real not imagined problems.

“Are we just going to build the wrong thing?” I get that concern a lot, especially from folks newer to high-ambiguity fields. But this is where nearby feedback comes in. Baked-in user touchpoints, evaluation harnesses, and shadow launches mean every thin slice sharpens the target as you go. You learn by shipping—not by guessing. The correction happens at the edge, not in the planning doc. That feedback loop is our north star, and it’s why betting on movement is safer than betting on getting things right the first time.

When you lead engineering teams under uncertainty, that’s what sustains momentum without sacrificing quality or trust. You hire for composure, design for learning speed, and build feedback into every layer. When the path isn’t clear, your job is to keep the wheels turning and make sure your people feel confident doing it. That’s how you lead teams, and yourself, into places no perfect spec ever could.

Ship the Thin Slice When the Path’s Unclear

I keep coming back to that Costa Rica weekend, years ago—a bus I didn’t mean to catch, no plan, no rehearsed Spanish, just a string of small, uncertain choices. What stuck wasn’t the beach or the awkward introductions, but the lesson: when you move, you create the context for figuring things out. Standing still never taught me how to pitch a tent or carve a place in a group.

It’s not the only time action beat waiting for certainty. I signed up for the military without really knowing what I was stepping into. Most decisions before then were mapped out, boxed in. This one was a leap, and I only understood what I was capable of by keeping my feet moving—the unknown didn’t shrink, but my own competence grew to meet it. One-way tickets, leaving stable jobs, saying yes to messy early-stage work: each time, movement transformed ambiguity into adaptability. It’s the one leadership trait I trust most—seeing someone dive when the outcome’s not guaranteed.

So pick one ambiguous problem on your desk right now. Name the smallest, reversible next step you can ship in the next 24 hours. Don’t overthink—just get one slice moving.

This is how you lead in uncertainty in a zero-to-one environment. Readiness is produced by movement, not by stockpiling answers. Take the thin slice, ship it calmly, learn from the first wave of feedback, and let the next move reveal itself. You’ll build the map by walking—one step at a time.