The strategy tax

For most of my career, I believed the highest form of work was thinking without doing.

The most prestigious roles were the ones furthest from execution. Strategy consultants billing $500/hour to create PowerPoint decks they'd never implement. Corporate planners running scenario analyses for quarters before anyone shipped a feature. "Strategic" meant you were above the messy work of building things.

This wasn't just career advice. It was a status hierarchy: Thinkers at the top, doers at the bottom.

The entire enterprise software industry was built on this premise. You'd spend 18 months in "requirements gathering" and "strategic planning" before writing a single line of code. By the time you shipped, the market had already moved twice.

Then something shifted. Not gradually—suddenly, in the last five years.

The shift wasn't about tools getting easier (though they did). It was about where strategic intelligence actually comes from.

Here's what nobody told us in business school: Most strategic planning is theater.

You're trying to achieve certainty before action. Map every scenario, predict every outcome, eliminate every risk. The goal is the perfect plan—the one that accounts for everything.

But the information you actually need to make good strategic decisions only exists on the other side of execution.

I watched a founder spend six months researching "the competitive landscape" before building their product. When they finally launched, they discovered the competition they'd been worried about was solving a completely different problem. The real competitors weren't even on their analysis spreadsheet—they emerged from a different category entirely.

Six months of research. Zero useful intelligence.

Meanwhile, another founder I know built a rough prototype in three weeks and put it in front of potential customers. Within a month, she knew:

Same market. Same problem space. Wildly different strategic intelligence.

The difference? Learning velocity.

This is where most execution advice gets dangerous.

The Silicon Valley mythology says: "Move fast and break things. Ship now, fix later. Perfect is the enemy of good."

But that's not what's actually happening with successful founders.

They're not choosing speed over quality. They're choosing learning velocity over planning certainty.

This distinction matters because you're always managing competing tensions:

The old strategic playbook said: Resolve these tensions before you move. Get enough information to be certain. Wait until you have the full picture.

The new playbook recognizes: These tensions never resolve. You're always working with incomplete information. The strategic skill isn't eliminating uncertainty—it's developing the judgment to know how much certainty you actually need.

A founder building a B2B SaaS product doesn't need to know the entire market size before starting. They need to know if 10 companies have the problem they're solving. If yes, build. Learn from those 10 whether you're solving it well. That real-time intelligence beats six months of TAM analysis every time.

Here's the inversion that changes everything:

Planning didn't become less important. It became inseparable from execution.

Instead of one big strategic plan upfront, you're doing rapid, continuous planning cycles integrated with building. You plan what you can test this week. Execute. Learn. Adjust next week's plan based on real data.

Planning shifts from prediction (trying to get it perfect upfront) to adaptation (learning what matters through action).

The founders who win aren't the ones with the best initial plan. They're the ones who can extract learning from execution fastest and translate that into better strategic decisions.

This is actually MORE rigorous than traditional planning, not less. You're making decisions with real customer behavior data instead of survey responses. You're validating assumptions with actual usage patterns instead of focus group quotes.

But it feels less prestigious because you're not in "the clouds" anymore. You're in the weeds, debugging, iterating, talking to users about why they churned.

The status hierarchy inverted: The closer you are to execution, the better your strategic intelligence.

Every founder I work with asks some version of this question:

"How do I know if I'm moving too fast? What if I'm building the wrong thing?"

The honest answer: You probably are building partially wrong things. That's the point.

You're not trying to avoid mistakes through perfect upfront planning. You're trying to discover what "right" means through rapid iteration.

The strategic question isn't "Do I have enough information to be certain?"

It's "Do I have enough information to take the next intelligent step?"

Usually, you do. You just don't feel certain enough, because we've been trained that certainty is a prerequisite for action.

But certainty is often a luxury you can't afford. Markets move. Competitors ship. Customer needs evolve. By the time you're certain, the opportunity has moved.

This doesn't mean reckless action. It means disciplined experimentation with tight feedback loops.

Build the simplest version that tests your core assumption. Put it in front of real users. Learn from actual behavior, not stated preferences. Adjust. Repeat.

The clarity you're waiting for? It emerges FROM execution, not before it.

If planning is no longer the prestigious work that happens in conference rooms before execution, what is strategy?

Strategy is the discipline of learning from execution faster than your competition.

It's knowing which assumptions to test first. Building feedback loops that surface real data quickly. Having the intellectual honesty to kill ideas that aren't working. Moving resources toward what's actually creating value, not what you hoped would create value.

The founders building billion-dollar companies today aren't the ones with the most sophisticated five-year plans. They're the ones who can see patterns in real-time usage data, make decisions with partial information, and out-iterate everyone else.

This is uncomfortable for people trained in traditional strategy. It feels less rigorous, less analytical, less... prestigious.

But talk to any successful founder and they'll tell you: The most valuable strategic insights came from watching how customers actually used the product, not from the competitive analysis deck.

Execution became the primary intelligence-gathering mechanism for strategy.

The question isn't whether to plan or execute. You're always doing both.

The question is: Are you planning based on assumptions or reality?

Because reality only reveals itself when you start building.