Stop Jumping Without a Parachute

"If I had an hour to solve a problem, I would spend fifty-five minutes defining it and five minutes solving it." ~Attributed to Albert Einstein (unverified)

Jumping Without a Parachute

A founder recently told me his inter-company accounting process should be "XYZ."

I had to remind him that A-W come first.

His frustration was immediate. Why was I slowing this down? Why was I overcomplicating something straightforward? Why couldn't we just implement the solution?

What was the solution? "Just move the money from account A to B and make a note of that on a spreadsheet. We can figure out the rest later."

Later. That word should terrify you. Because "later" in startup time means years. And "figure out the rest" means untangling a disaster while trying to raise money, pass audits, or explain to investors why your books are held together with spreadsheet notes and hope.

Trying to do XYZ before A-W is like jumping out of a plane without a parachute. But what he was proposing wasn't even XYZ. It was jumping out of a plane, making a note that you should probably get a parachute, and planning to "figure out the landing later."

You're not taking a calculated risk. You're not being bold. You're not moving fast and breaking things. You're just dead. The outcome isn't uncertain. It's guaranteed. The only variable is how long it takes you to realize you're falling.

He wasn't picking a solution that was risky or aggressive. He was picking something that would create years of cleanup work, destroy any chance of clean financials, and guarantee failure of any audit or due diligence. Inter-company accounting requires entity structure, chart of accounts, transaction classification, basic bookkeeping systems. Without those, "move money and make a note" isn't a process. It's just creating a pile of problems you'll have to solve later when the stakes are higher and the mess is deeper.

You don't get to spell words until you have letters. You don't get to XYZ without A-W first. You don't get to land safely by making a note that you jumped without a parachute and figuring out the rest later.

He thought he was defining the problem and proposing a pragmatic solution. He'd actually just decided to jump without checking if he had a parachute, while assuring everyone he'd "figure out the landing later." And when I pointed out he was about to step out of a plane with nothing but gravity and a spreadsheet, it didn't feel like I was saving his life. It felt like I was being difficult, overly cautious, opposed to action.

But I wasn't slowing him down. I was preventing him from creating a disaster that would haunt the company for years. The solution without the process is no solution at all. It's just you, falling, holding a spreadsheet with notes about how you should have built a parachute, wondering why nobody told you that "later" never comes.

This is what happens when you skip the 55 minutes of definition. You think you're being decisive, moving fast, making progress. What you're actually doing is jumping out of planes with spreadsheets instead of parachutes and calling it efficiency.

The Captain's Real Work

In my previous article, Are You an Imposter, I wrote about CEOs who abandon the bridge to work in the engine room. The ship hits the iceberg because nobody's watching where it's going.

But here's what I didn't fully explore: What is the captain actually doing on the bridge?

Most people think the captain's job is decisive action. Making calls. Giving orders. Steering through crisis.

That's the five minutes.

The real work, the work that determines whether the ship survives, is the 55 minutes that come before any of that. The captain's actual job is seeing clearly before deciding anything.

The captain who spots the iceberg five miles out doesn't need frantic maneuvering. Slight course correction, executed calmly, and the crisis never happens. The captain who only sees the iceberg when it's fifty yards away? Now you need heroics, and heroics often fail.

Sun Tzu understood this 2,500 years ago: "Every battle is won before it is fought."

The general who wins isn't the one who makes brilliant tactical decisions in the heat of combat. The general who wins is the one who understands the terrain, the enemy, the weather, the supply lines, his own forces so thoroughly that by the time combat begins, the outcome is already determined.

Einstein (allegedly) said the same thing about problems: spend 55 minutes defining them, five minutes solving them.

Different domains. Same principle. The work isn't in the doing, it's in the seeing. And most people get this completely backward.

The False Urgency

We're addicted to action.

"Move fast and break things." "Bias for action." "Don't overthink it." "Just ship something." "Fail fast." "Ready, Fire, Aim."

These aren't strategies. They're permission slips to skip the hard work of understanding what you're actually trying to accomplish.

And here's the irony: most people never read past the title of "Ready, Fire, Aim." They see those three words and think it means skip ready, just fire. They think it's permission to act without thinking, to shoot without aiming, to jump without a parachute and call it decisive leadership.

But that's not what the book says at all. Michael Masterson's entire point is about the sequence of business growth stages and when different approaches apply. Early stage (up to $1M) needs rapid iteration because you're discovering what works. But even then, you don't skip "ready", you just shorten it. You aim quickly, you fire, you adjust based on what happens.

What you don't do is fire without any aim at all and hope you hit something.

The founder who wants to "move money and make notes" isn't following Ready, Fire, Aim. He's following Fire, Fire, Fire and hoping he eventually hits a target he never identified. That's not iteration. That's not learning. That's not bias for action. That's just chaos with a business book title attached to it.

The culture celebrates visible motion. The meeting where decisions get made. The code that gets shipped. The campaign that launches. Action feels productive. Action looks decisive. Action gets rewarded.

But here's what nobody wants to admit: most action is wasted because it's solving the wrong problem.

You ship a feature customers don't want. You launch a campaign targeting the wrong pain point. You hire for a role that shouldn't exist. You implement a process that creates more problems than it solves. You optimize something that doesn't matter.

And because you skipped the 55 minutes of definition, you don't realize any of this until you've burned months or years pursuing the wrong solution.

The founder wanting to jump to XYZ wasn't unique. He's every entrepreneur who thinks planning is procrastination, who mistakes motion for progress, who confuses activity with accomplishment. He read the title "Ready, Fire, Aim" and thought it meant fire without ready.

He felt the pressure to do something, so he picked something to do. The fact that it was the wrong something, solving the wrong problem, in the wrong sequence, with a parachute full of holes? That's a later problem. At least he was moving forward.

Except he wasn't moving forward. He was falling, confidently, in the wrong direction, with a book title as his justification.

What Definition Actually Looks Like

So what are you doing in those 55 minutes?

You're asking why.

Not "what's the problem." That's surface level. That's where the founder started: "We need an inter-company accounting process." Fine. But why do you need it? And why that specific process? And why now?

Keep drilling down:

First why: "We need inter-company accounting to track transactions between entities."

Second why: "Because we're growing and need clearer visibility into cross-entity financials."

Third why: "Because investors want to understand how value flows through the organization."

Fourth why: "Because we're preparing for a funding round and need to demonstrate financial sophistication."

Now we're getting somewhere. The problem isn't "implement process XYZ." The problem is "demonstrate financial sophistication to investors." Those require completely different solutions.

Process XYZ might be the right eventual answer. But maybe what you actually need first is clean books. Or clear entity structure. Or proper documentation of existing transactions. Or a CFO who can speak investor language. Or fifteen other things that must exist before process XYZ makes any sense.

This is what proper definition reveals. Not just what you're solving, but why you're solving it, which surfaces what must be true for your solution to work. Which shows you whether you have a parachute before you jump.

When They Jump Anyway

Here's what actually happens when founders ignore the 55 minutes and jump without a parachute:

Month 1: They start "the solution." Someone moves money between accounts. Someone makes a note in a spreadsheet. It feels productive. It's fast. It's simple. Nobody realizes they're falling yet because the ground is still far away. The spreadsheet has a few entries. Everything seems manageable.

Month 3: The spreadsheet has dozens of entries now. Some transactions got noted, some didn't. Different people used different formats. Some notes say "transferred for project X" and some say "moved money" and some just have dollar amounts with no context. But it's fine. They'll clean it up later.

Month 6: The spreadsheet is chaos. Hundreds of transactions. Multiple versions floating around because different people have different copies. Inconsistent entries. Missing dates. Unclear purposes. Some transactions that nobody remembers making. But they're busy growing the business. They'll fix it later.

Month 12: The investor meeting is next month. They need clean financials. Now they need to reconstruct a year of inter-company transactions from spreadsheet notes that were never meant to be the actual system. They hire someone to untangle it. That person quits after two weeks because it's impossible to know what actually happened. The notes don't match the transactions. The transactions don't match the accounts. The accounts don't match reality.

Month 14: They're trying to prepare for due diligence. The investors want to understand how money flows through the entities. The spreadsheet - actually multiple contradictory spreadsheets now - says things that don't match bank statements. There's no entity structure. No proper classification. No audit trail. Just notes that made sense at the time to people who no longer work there or can't remember what they meant.

Month 18-24: Two options. Either they halt growth to spend six months having expensive accountants reconstruct what should have been built correctly from the start, or they go into fundraising/due diligence with financial records held together by hope and spreadsheet notes. Most choose option two. Most fail due diligence. Those who don't fail immediately carry the mess forward, where it gets worse, more expensive, and eventually fatal anyway.

The founder who wanted to "just move money and make a note" is now two years behind, hundreds of thousands of dollars poorer from trying to untangle the mess, has lost investor confidence, missed funding rounds, and still doesn't have working inter-company accounting. All because "we'll figure out the rest later."

Later arrived. It brought accountants, auditors, investors, and an impossible mess.

The 55 minutes would have prevented all of this. But 55 minutes felt slow. "Move money and make a note" felt decisive and pragmatic.

Now they're falling, watching the ground rush up, holding a spreadsheet with hundreds of notes about transactions they can't reconstruct, still waiting for "later" to turn into a solution instead of a disaster.

The Wrong System Is Worse Than No System

Here's what makes the "move money and make notes" approach even more catastrophic: the wrong system is just as bad as no system. Actually, it's worse.

The wrong system is like having a parachute with a giant hole in it.

You jumped. You pulled the cord. Something deployed. For a few seconds, it feels like you did the right thing. You have a parachute! You're slowing down! Then you look up and realize the canopy is shredded. You're still falling, just slightly slower, with the added psychological torture of thinking you were safe.

No parachute means you know you're falling. Everyone understands the problem. When you jump, you know immediately this is wrong and you need a different plan. It's honest. It's clear. The problem is obvious.

No system means you know you have a problem. Everyone understands there's a gap. When investors ask about inter-company accounting, you say "we don't have that yet" and they know exactly what that means. It's honest. It's addressable. You can build it correctly from scratch.

The wrong system gives you the illusion of having solved the problem while actually making it worse. You're moving money. You're making notes. You're "tracking" transactions. It looks like you have a process. It feels like you're being responsible. Leadership thinks the problem is handled.

You pulled the cord. Something deployed. You must be safe.

But you don't have a system. You have a mess that's masquerading as a system. You don't have a parachute. You have shredded fabric that's creating the illusion of safety while you continue falling. And that mess is actively making things worse every day:

Every transaction that gets "noted" in the wrong format becomes one more thing to untangle later. Every inconsistent entry becomes one more mystery to solve. Every missing detail becomes one more hole in your financial records. Every day the wrong system runs, it's generating garbage that someone will have to sort through, reconstruct, or explain.

No system means you have zero garbage to clean up. The wrong system means you're creating mountains of it while thinking you're being productive. No parachute means you know you're falling. A parachute with holes means you think you're safe until you hit the ground wondering why slowing down didn't help.

And here's the worst part: the wrong system creates false confidence. Leadership thinks they've handled it. "We have a process for inter-company accounting." No, you have a spreadsheet with notes. "We have a parachute." No, you have shredded fabric attached to your back. But because everyone believes the problem is solved, nobody's building the actual solution. The wrong system doesn't just fail to solve the problem - it prevents you from solving it by making you think you already did.

When the audit comes, when due diligence starts, when investors want to understand your financials, you're in a worse position than if you'd done nothing. At least with nothing, you can say "we haven't built this yet." With the wrong system, you have to explain why your "process" produces financial records that don't make sense, can't be audited, and don't match reality. At least knowing you have no parachute lets you prepare for impact. Thinking you have one and discovering it's shredded at 1,000 feet? That's when people panic.

You can build a real system on top of nothing. You cannot build a real system on top of garbage. You have to remove the garbage first. Which means the wrong system doesn't just fail, it costs you twice. Once to create the mess, and once to clean it up before you can build what you should have built in the first place.

You can pack a parachute onto nothing. You cannot pack a good parachute onto shredded fabric. You have to cut away the bad one first, while you're falling, before you can deploy something that works.

The founder's "solution" wasn't just inadequate. It was actively destructive. Every day it ran would make the eventual fix more expensive, more time-consuming, and more likely to fail. The wrong system is worse than no system because it creates work, destroys value, and prevents the real solution from being built. The parachute with holes is worse than no parachute because it creates false confidence, wastes your altitude, and gives you less time to find a real solution.

The 55 minutes would have revealed this. It would have shown that "move money and make notes" isn't a stepping stone to a real solution, it's an obstacle to building one. It would have shown that a parachute with holes in it doesn't slow your fall enough to matter - it just makes you think you're safe while you die.

Every solution has prerequisites. Invisible dependencies that must exist before your solution can function. Not "should exist for best results." Must exist for the solution to be possible at all.

Every parachute has prerequisites too. The plane. The altitude. The training. The packing. Skip any of them and jumping stops being skydiving and starts being suicide.

The founder wanting inter-company accounting at step XYZ wasn't missing nice-to-haves. He was missing the actual alphabet:

• Entity structure (A)
• Chart of accounts (B)
• Transaction classification (C)
• Basic bookkeeping systems (D)
• Through probably W

Those aren't bureaucratic obstacles. They're the parachute. Without them, XYZ is just you falling and calling it flying. You can document your process all you want. You can hold planning meetings. You can create detailed implementation timelines. But you're still falling, and documentation doesn't slow your descent.

Process XYZ doesn't work poorly without the foundation. Process XYZ doesn't work at all. It's not a solution that's risky or suboptimal. It's not a solution. It's just gravity doing what gravity does.

This happens everywhere, and it's always fatal:

The startup that wants to scale sales before product-market fit. You're not taking a risk. You're trying to multiply zero. You can hire all the salespeople you want. They have nothing to sell that people actually want to buy. That's not aggressive growth strategy. That's jumping without a parachute and expecting enthusiasm to slow your fall.

The company that wants to implement advanced analytics before they have clean data. You're not building sophisticated insights. You're building elaborate visualizations of garbage. The dashboards will look impressive and tell you nothing useful. That's not data-driven decision making. That's jumping without a parachute and calling the falling "progress toward landing."

The entrepreneur who wants to optimize conversion rates before they understand what customers actually need. You're not improving efficiency. You're making it easier for people to buy something they don't want, which just means they'll discover faster that you built the wrong thing. That's not conversion optimization. That's jumping without a parachute and being proud that you're falling faster than competitors.

In every case, someone skipped the 55 minutes. They had a problem (or thought they did), picked a solution (usually whatever they'd heard about recently), and jumped without checking for a parachute.

They're not building on weak foundation. They're building on air. And air doesn't hold weight, no matter how confidently you step onto it.

The Stonecutter's Wisdom

Joshua Medcalf tells the story of the stonecutter in "Pound the Stone":

"When nothing seems to help, I go and look at a stonecutter hammering away at his rock perhaps a hundred times without as much as a crack showing in it. Yet at the hundred and first blow it will split in two, and I know it was not that blow that did it, but all that had gone before."

The first hundred blows look like failure. No visible progress. No apparent impact. Just the same motion, repeated, with nothing to show for it.

Then the rock splits.

People watching only see blow 101. They think that's when the work happened. They celebrate the final strike, the moment of dramatic success. They miss the hundred invisible blows that made it possible.

But here's what the stonecutter knows: blow 101 didn't split the rock. Blows 1 through 100 split the rock. That final strike just revealed what all the previous work had already accomplished.

The 55 minutes of definition are those first hundred strikes. They don't feel productive because nothing is splitting. There's no immediate result. No visible progress. You're just asking questions, drilling down, challenging assumptions, mapping dependencies. It looks like you're wasting time.

But you're not wasting time. You're doing all the actual work. Every question you ask, every assumption you challenge, every dependency you map, that's another strike weakening the stone. The problem is becoming clear. The prerequisites are revealing themselves. The right solution is becoming inevitable.

The five minutes of solution, that's blow 101. It splits the rock. It looks impressive. It feels decisive. But it only works because of the 99 strikes that came before.

And here's what most people miss: there is no shame in letting people watch the 100 strikes. There is actually great honor in that.

The stonecutter doesn't hide while he strikes the stone. He doesn't pretend the first 99 blows don't matter. He doesn't rush to blow 101 because the audience is getting impatient. He strikes the stone, methodically, transparently, letting everyone see the real work being done even when nothing appears to be happening.

That's leadership. That's integrity. That's the confidence to do the work that matters even when it doesn't look impressive.

The founder who rushes to "move money and make notes" because 55 minutes of definition looks unproductive? He's ashamed of the 100 strikes. He thinks showing real work makes him look slow or indecisive. So he jumps to blow 101 without the first hundred, holds up his shredded parachute, and wonders why everyone's losing confidence.

The founder who takes the 55 minutes, who asks why five times, who maps prerequisites, who builds A-W before attempting XYZ? He's the stonecutter. He's letting his team, his investors, his board watch him strike the stone. He's showing them the real work. And when blow 101 splits the rock, everyone understands why it worked because they watched the foundation being built.

There's no shame in doing the work that matters, even when it takes time, even when nothing appears to be happening, even when people are watching and wondering why the rock isn't splitting yet.

The shame is in pretending you can skip the work and jumping without a parachute while calling it decisive leadership.

The founder wanting to jump to XYZ was trying to split the rock with blow 101. No foundation. No preparation. Just swinging at solid stone and expecting it to crack because he's swinging hard.

Skip those first hundred blows and hammer away at blow 101 all day long. The rock won't split. You'll just be making noise, wasting energy, and wondering why nothing works despite all your effort.

When You're Already Moving

Here's what I always hear: "But I don't have 55 minutes. The ship is already in motion. I can't stop everything to do a comprehensive analysis."

Fair. You're not always starting from a blank slate. Sometimes you inherit a mess. Sometimes you're fixing problems in flight. Sometimes you genuinely don't have the luxury of starting over.

But even then, especially then, you need some version of those 55 minutes.

You don't need to stop the ship to figure out where it's going. But you do need to stop long enough to look at the map, check your instruments, and verify you're not sailing directly into disaster.

The captain who says "we're moving too fast to navigate" is heading for the rocks. The founder who says "we're too busy to understand our problems" is building on quicksand. The entrepreneur who says "we don't have time to plan" is guaranteeing they'll waste far more time later.

You always have time to ask why. You might not have time for a comprehensive strategic review. But you have time to ask "what problem does this solve" and "what has to be true for this to work."

Even five minutes of definition is better than zero. Even asking why once is better than never asking at all.

"But I Can't Afford To Do It Right"

Further, the objection I hear most often when founders resist the 55 minutes: "I don't have the money to build this properly. I'll do it quick and dirty now, then fix it later when we have cash flow."

This sounds pragmatic. It sounds like smart bootstrapping. It sounds like the scrappy founder making do with limited resources.

It's actually the most expensive decision you can make.

Let's do the actual math on the accounting example:

Doing it right from the start:

• Hire competent bookkeeper or fractional CFO: $2,000-5,000/month
• Proper accounting software and setup: $500-2,000 one-time
• Time investment to set up correctly: 10-20 hours
• Total first year: $25,000-$65,000
• Result: Clean books, audit-ready financials, investor confidence

Doing it wrong "temporarily":

• Spreadsheet notes and moving money: $0/month (feels free!)
• First 12 months: $0 (winning!)
• Month 13: Realize you need to raise money or pass audit
• Hire expensive accountants to reconstruct: $50,000-150,000
• Time investment to untangle the mess: 100-300 hours
• Delayed fundraising/deals while you fix: Opportunity cost $200,000-500,000+
• Actual cost: $250,000-650,000+
• Result: Months of stress, damaged investor confidence, possibly unrecoverable mess

You didn't save money. You spent 10-20x more while destroying credibility and missing opportunities.

But it gets worse. The "I can't afford it" thinking assumes you'll have more money later to fix it. That's backward. You have less ability to fix it later because:

The mess compounds: Every day you run the wrong system, you generate more garbage to untangle. Month 6 is cheaper to fix than month 12. Month 12 is cheaper than month 24. The longer you wait, the more expensive it gets.

The stakes get higher: When you're small, wrong accounting is a problem. When you're trying to raise Series A, wrong accounting kills the deal. The bigger you get, the more catastrophic the mess becomes.

You lose negotiating power: When you need clean books right now for due diligence, accountants know you're desperate. They charge accordingly. When you're planning ahead, you have options.

The opportunity cost multiplies: Early stage, messy books slow you down. Growth stage, messy books prevent fundraising entirely. The bigger the opportunity you're missing, the more expensive the wrong system becomes.

The Real Bootstrap Move

Here's what actual smart bootstrapping looks like:

Spend the money on prerequisites, not solutions.

You can't afford a fancy inter-company accounting system? Fine. Don't build one yet. But you can afford basic proper bookkeeping. You can afford to set up entity structure correctly. You can afford to classify transactions properly from day one.

That's not the expensive part. The expensive part is implementing sophisticated processes on top of that foundation. So don't do that yet. Build the foundation (A-W), skip the fancy house (XYZ) until you have cash flow.

What you cannot afford is to skip the foundation and build the house anyway using spreadsheet notes and hope. That's not bootstrapping. That's creating a disaster and calling it scrappy.

The founder wanting to "just move money and make notes" wasn't trying to save money. He was trying to spend money (on moving money around) without spending money on doing it correctly. That's not thrift. That's false economy.

False economy is buying the cheap parachute with holes because you can't afford the good one. Real economy is not jumping until you can afford a parachute that works.

When You Actually Can't Afford It

Sometimes you genuinely cannot afford to build the full solution. The money truly isn't there. What do you do?

You wait.

You don't try to outsmart the system. You don't build XYZ on spreadsheet notes. You don't jump with a parachute that has holes. You wait until you have the resources to do it right, or you find a different path that doesn't require what you can't afford yet.

This is where the 55 minutes saves you. Because proper definition reveals what you actually need versus what you think you need. Maybe you don't need inter-company accounting yet at all. Maybe you need to restructure so you don't have inter-company transactions. Maybe you need to stay smaller longer. Maybe you need to find a fractional CFO who can set this up correctly for $3K instead of trying to do it yourself for "free" and creating a $300K problem.

The 55 minutes shows you the real options. The five-minute solution misses them all because you never asked why you need this, what must exist first, or whether there's a different path entirely.

The Expensive "Free" Solution

Every founder who tries to outsmart the system with "we'll do it cheap now and fix it later" discovers the same truth:

Free is the most expensive option.

The spreadsheet notes are free. The reconstruction is $150K. The wrong system costs nothing to implement. The cleanup costs everything. The parachute with holes is cheaper than the real one. The funeral is more expensive than both.

You cannot afford to skip the 55 minutes. You cannot afford to skip the prerequisites. You cannot afford to do it wrong first.

What you also cannot afford is to do it at all if you can't do it right. Sometimes the answer is "not yet." Sometimes the answer is "find a different path." Sometimes the answer is "we need to solve the cash flow problem before we can solve this problem."

But the answer is never "do it wrong and fix it later." Because later costs 10-20x more, assumes you survive long enough to get there, and often arrives at the worst possible moment when you can least afford the distraction.

The 55 minutes of definition shows you this. It shows you the real cost of the wrong solution. It shows you whether you can actually afford to do this at all. It shows you alternative paths you didn't see when you were rushing to implement.

That's why founders who "don't have time" for 55 minutes are actually the ones who most need it. Because they're about to make the most expensive mistake possible while thinking they're saving money.

The Pattern in Every Domain

This isn't just business advice. This is physics.

The general who scouts the battlefield doesn't need brilliant tactics during battle. The problem-solver who understands root causes doesn't need complex solutions. The captain who sees icebergs from miles away doesn't need heroic crisis management.

The chess master doesn't make brilliant moves. The chess master sees fifteen moves ahead and makes the obvious move that creates inevitable advantage.

The master strategist doesn't fight battles. The master strategist positions forces so that victory is assured before engagement.

The expert problem-solver doesn't find clever solutions. The expert problem-solver defines problems so clearly that solutions become self-evident.

In every domain, at every level, the pattern is the same: the work is in the seeing, not the doing. The 55 minutes of definition matter more than the five minutes of solution.

Because if you see clearly, solving is trivial. But if you see poorly, no amount of brilliant execution saves you.

The Cost of Skipping Definition

Let's be specific about what happens when you skip the 55 minutes:

You solve the wrong problem and call it innovation. You've built something nobody needs, but you shipped fast, so you feel accomplished.

You solve the right problem badly because you didn't understand the constraints. Your solution works in theory but fails in practice because you missed critical dependencies.

You solve the right problem correctly but at the wrong time. You've built step XYZ when steps A-W don't exist yet, so your perfect solution sits unused because it can't function without prerequisites.

You solve the problem for the wrong reason and create new problems downstream. You implemented what was asked for without understanding why it was needed, so you've optimized one thing while breaking three others.

In every case, you're moving. You're taking action. You look decisive. Your team thinks you're being a leader. And you're wasting spectacular amounts of time, energy, and resources because you didn't spend 55 minutes understanding what you were actually trying to accomplish.

Foundation or House. Pick One.

Here's what founders don't understand about skipping prerequisites: you cannot build a foundation under an existing house.

You can try. People do try. They build the house first because building houses is exciting. Framing goes up fast. You can see progress. Walls appear. A roof goes on. It looks like a real accomplishment.

Building a foundation? That's boring. It's slow. It's underground where nobody can see it. It doesn't feel like progress. So they skip it. They build on dirt and convince themselves it'll be fine.

Then the storm comes.

Not might come. Will come. Because storms always come. Market shifts. Competitive pressure. Scaling challenges. Regulatory changes. Economic downturns. The normal weather patterns of business.

And the house falls.

Because it had no foundation.

I wrote about this before in Built Right or Rebuilt Twice: doing things right the first time is always cheaper than building wrong and fixing later. The mathematics are brutal: a 15% savings upfront becomes a 200-300% penalty when you account for rework, lost opportunities, and the cascade of failures that weak foundations create.

Now you have two options, both terrible:

Option 1: Try to build a foundation under the existing house. This is nearly impossible. The house is in the way. You can't excavate properly. You can't pour correctly. You're trying to retrofit something that should have been built first. It's exponentially more expensive, takes far longer, and usually fails anyway because you're trying to support weight while simultaneously building support structure. Most houses collapse during this process.

Option 2: Tear the house down and start over. Now you've wasted all the time, money, and effort that went into building the house. The framing you were so proud of? Trash. The walls that went up so quickly? Gone. Everything you built, all that visible progress, has to be destroyed so you can do what you should have done first: build the foundation.

The founder wanting to jump to XYZ accounting process isn't even at the "building house on dirt" stage yet. He's trying to build a house in midair. The inter-company accounting process is the elaborate framing he wants to put up. But without entity structure, chart of accounts, basic bookkeeping systems - without A through W - there's literally nothing to attach it to. XYZ cannot exist without the alphabet that precedes it.

He's not taking a risk. He's not making a bold move. He's trying to do something that's physically impossible and getting frustrated when someone points out that alphabets work in order.

When the storm comes (and it will come in the form of an audit, investor due diligence, scaling complexity, or regulatory scrutiny), he won't have an accounting process that fails. He'll have no accounting process at all, just pieces of XYZ scattered around with no A-W to connect them to.

The 55 minutes of definition would have revealed this. It would have shown that you cannot spell without letters. It would have shown that A-W must come first not because it's best practice, but because that's how sequences work. It would have mapped what must exist before XYZ becomes possible.

But that felt slow. It felt like overthinking. It felt like delay.

So now he's looking at months or years of building A-W first anyway, plus all the wasted time trying to implement XYZ on nothing, plus the organizational confusion created by attempting the impossible and calling it a strategy.

The Math Is Brutal

Building foundation first, then house: 100 units of effort, one time.

Building house first, then trying to add foundation: 250+ units of effort, massive risk of failure, probable need to start over anyway.

Building house first, having it fall, tearing it down, then building foundation and house correctly: 300+ units of effort, all the original time and money wasted.

The 55 minutes aren't slow. The 55 minutes are the only efficient path. Everything else is just expensive learning.

And here's what makes this particularly brutal: almost every founder tries to build the house first. Almost all of them fail for the same reason. And almost none of them see it coming because they skipped the 55 minutes that would have revealed the pattern.

The founder with his XYZ accounting process would have discovered this six months in, after burning time and money implementing something that couldn't function because the foundation didn't exist. Then he'd either have to rip it out and start over (wasting everything) or build the foundation under the existing structure (making everything harder and more expensive).

Or he could spend 55 minutes now understanding what has to come first.

The Discipline Nobody Wants

Here's the uncomfortable truth: spending 55 minutes on definition feels unproductive.

You're not shipping anything. You're not making decisions. You're not checking boxes. You're just asking questions. Challenging assumptions. Mapping dependencies. Exploring possibilities.

To everyone watching, you're just standing there hammering at solid rock. No cracks. No progress. No results. Just the same questions, over and over, with nothing to show for it.

It doesn't feel like leadership. It feels like overthinking. It doesn't feel like progress. It feels like analysis paralysis. It doesn't feel like decisive action. It feels like hesitation.

This is why most people skip it. Because in the moment, it feels like you're wasting time. The pressure to "do something" is enormous. Your team wants direction. Your investors want progress. Your competitors are moving. Your own brain is screaming at you to stop thinking and start doing.

Everyone wants you to swing blow 101 right now. Nobody wants to watch you strike the stone a hundred times with nothing happening.

But this is precisely when you most need those first hundred strikes. When everything is urgent and everyone wants action, that's when proper definition becomes most valuable. Because that's when the cost of skipping straight to blow 101 becomes catastrophic. That's when swinging at solid stone wastes the most time, energy, and resources.

The discipline is forcing yourself to slow down when every instinct says speed up. It's asking why when everyone wants what. It's mapping prerequisites when everyone wants to jump to solutions. It's delivering strike after invisible strike while everyone around you wonders why the rock isn't splitting yet.

It's recognizing that the captain's job isn't heroic maneuvering around icebergs. The captain's job is seeing icebergs five miles out and adjusting course calmly.

That adjustment, that slight course correction made with full information and clear understanding, that's the five minutes. That's blow 101. But only if you spent 55 minutes striking the stone first. Only if you did the invisible work that makes the final strike inevitable.

What This Looks Like in Practice

Proper definition isn't abstract philosophy. It's concrete practice.

Before implementing any solution, map the prerequisites. What has to exist for this to work? What has to be true? If you can't answer that, you're not ready to build.

Ask why at least three times. The first answer is usually surface level. The second answer starts getting real. The third answer reveals the actual problem you're solving.

Challenge your own assumptions. You think you know what the problem is. But what if you're wrong? What if the problem you're seeing is actually a symptom of something deeper?

Look for what's invisible. The most important constraints, dependencies, and prerequisites are usually the ones nobody mentions because everyone assumes they're obvious. Make them explicit.

Test your understanding by explaining it to someone else. If you can't articulate the problem clearly to someone who wasn't in your head, you don't understand it yet.

Verify you're solving causes, not symptoms. The symptom is "we need inter-company accounting." The cause is "investors need to understand our financial structure." Solve the cause, not the symptom.

This isn't complicated. But it requires discipline. The discipline to resist the pressure to act immediately. The discipline to ask uncomfortable questions. The discipline to say "we're not ready to solve this yet because we don't understand it yet."

The Real Constraint

The constraint is never time. The constraint is discipline.

You have time to ask why. You have time to map prerequisites. You have time to challenge assumptions. What you don't have is the discipline to do it when everything in you wants to just pick a solution and start moving.

The founder didn't lack time for those 55 minutes. He lacked the discipline to spend them. It felt like delay. It felt like overthinking. It felt like I was blocking progress.

But I wasn't blocking progress. I was preventing waste. The 55 minutes feel slow. The six months spent building the wrong thing is actually slow.

The 55 minutes feel unproductive. The years spent solving problems that keep coming back because you never addressed root causes is actually unproductive.

The 55 minutes feel like hesitation. Confidently sprinting in the wrong direction is actual hesitation, just disguised as decisiveness.

The Iceberg Doesn't Care

In my previous article, I ended with this: "The iceberg doesn't care that you're working hard. It doesn't care that you're good at what you do. The iceberg only cares whether there's someone on the bridge."

Now I'll add this: being on the bridge isn't enough. You need to be looking at the right things.

The captain who's on the bridge but staring at the deck isn't better than the captain in the engine room. The founder who's making strategic decisions without understanding what problems they're solving isn't better than the founder stuck in execution.

The iceberg doesn't care that you're on the bridge. The iceberg only cares whether you saw it coming.

And you only see it coming if you spend 55 minutes looking at where you're going instead of five minutes frantically reacting to what's immediately in front of you.

The Choice, Again

You can spend 55 minutes defining the problem and five minutes solving it.

Or you can spend five minutes picking a solution and six months discovering you jumped without a parachute.

You can ask why until you understand root causes.

Or you can solve symptoms repeatedly while gravity accelerates your fall.

You can map prerequisites and build foundation before house.

Or you can build in midair and act surprised when nothing holds.

You can check for a parachute before you jump.

Or you can step into nothing and call it decisive action.

The founder wanted to move fast. I wasn't stopping him. I was pointing out that A-W come before XYZ, that parachutes come before jumping, that you cannot defy physics by being confident about it.

That's not caution. That's reality. That's the 55 minutes that show you the difference between skydiving and falling to your death.

The question isn't whether you have time for those 55 minutes. The question is whether you can afford to jump without them.

Most people don't realize they can't until they're already falling. And by then, all the confidence in the world won't slow your descent.

The ship needs a captain on the bridge. But the captain on the bridge needs to be looking at the right things. Spend the 55 minutes. Define the problem. Check for the parachute. Then the five minutes of solution becomes obvious.

The iceberg is still out there. The only question is whether you'll see it in time.