When It's Time to Pack Your Parachute
A Field Guide to Corporate Aeronautics
"In theory, there is no difference between theory and practice. In practice, there is."
— Attributed to various people who learned this the hard way
Every organization has skydivers and ground crew. The skydivers make the jump decisions—when to leap, from what altitude, toward which landing zone. The ground crew packs the parachutes. If you've spent enough years in corporate life, you develop a sense for when the people making jump decisions have stopped checking weather conditions.
This essay is for the parachute packers.
The Early Warning System
The first sign isn't dramatic. It's linguistic. Someone in a conference room uses the phrase "strategic imperative" about a technology they can't define. A VP returns from a conference with a whiteboard covered in diagrams that map poorly to anything your company actually does. The annual planning deck suddenly contains a roadmap with your department's name attached to deliverables you've never heard of.
You are not consulted. You are informed.
This is the moment experienced operators recognize: the jump has been decided by people who will not be folding the chute.
The Architecture of Plausible Deniability
Modern corporate initiatives are structured like Russian nesting dolls of accountability. At the outermost layer: the bold vision, announced to shareholders and trade press. One layer in: the consultants, hired to "accelerate" the transformation with frameworks and best practices from companies that aren't yours. Another layer deeper: the steering committee, meeting monthly to review slide decks that translate "we don't know yet" into "discovery phase insights."
At the very center: you, the person who will be asked to make the parachute work using fabric and rope purchased by people who've never folded a parachute, assembled according to specifications written by people who've never jumped, inspected by people whose bonus depends on certifying it's ready.
When someone asks "can this actually work?" and is told "that's why we hired you," start packing.
The Pizza Box Test
Here's a diagnostic: When was the last time anyone senior spent an evening with the people who do the actual work? Not a town hall, not a listening tour, not an innovation workshop with sticky notes facilitated by consultants. An actual evening. Pizza. Tracing the workflow. Asking "why do we even do this step?"
If the answer is "never" or "that doesn't scale," you have learned something important about the organization's theory of expertise. They believe knowledge flows down—from strategy decks to implementation plans to your keyboard. The idea that it might flow up—from the people who know where the bodies are buried—is absent from the org chart.
A company that never does the pizza box exercise is a company that confuses announcing change with making change. They will hand you requirements written by people who've never seen the system run, timelines estimated by people who've never deployed the stack, and success metrics defined by people who won't be around to measure them.
Check your parachute straps.
The Consultant Weather System
There's a particular atmospheric pattern to doomed initiatives. It begins with clear skies: consultants arrive with frameworks, roadmaps, and reassuring precedents from other industries. They facilitate workshops. They produce deliverables. They create the illusion of momentum.
Then comes the hype front: "Based on early learnings from our successful pilot, we're scaling to production." The pilot's success was three users processing ten transactions in a controlled environment. Production is ten thousand users processing a million transactions with legacy integrations, compliance requirements, and that one XML feed from the 2003 acquisition that nobody understands but everyone fears touching.
The consultants depart on schedule, contract complete, recommendations delivered. Now comes turbulence.
You inherit the roadmap minus the budget, the timeline minus the discovery phase, the accountability minus the authority. When the initiative falters, the narrative is never "leadership made a poor decision." It's "execution didn't match the vision" or "the consultants didn't understand our unique environment."
Your job, structurally, is to be the next atmospheric layer—the one that absorbs the impact when theory meets ground. The consultants provide two services: recommendations (explicit) and insulation (implicit). You provide one: a warm body between the announcement and the aftermath.
If you are being handed a parachute packed by someone who departed three months ago, do not jump.
The Metrics That Don't Measure
Here's how you know an initiative has separated from reality: the success metrics stop corresponding to user outcomes. Instead of "reduced time from expense submission to reimbursement" you get "AI model accuracy." Instead of "fewer customer complaints" you get "agent deployment velocity." Instead of "increased revenue" you get "innovation index score."
These aren't measurements. They're incantations. They allow everyone to claim victory regardless of whether anyone's life improved. The AI model can achieve 95% accuracy while the actual process becomes slower and more frustrating. Agent deployment velocity can hit targets while agents fail 70% of their tasks in production. The innovation index can trend upward while revenue trends down.
When your organization starts measuring the theater instead of the outcomes, it has stopped trying to solve problems and started trying to survive board meetings. The parachute doesn't need to work; it needs to look like it's been inspected according to the framework recommended by the consultants who aren't jumping.
Deploy your reserve chute.
The Amnesia Economy
Every technology cycle, we forget:
- That process precedes tools
- That complexity is social, not technical
- That automation locks in assumptions
- That the people doing the work know things architects don't
- That "this time it's different" is usually wrong
We forget because forgetting is profitable—for consultants, for vendors, for executives building their "transformation leader" resume for the next role. The people who remember are dismissed as change-resistant, not visionary, insufficiently bold.
But remembering is how you recognize patterns. The current AI agent hype looks like RPA, which looked like Big Data, which looked like BPR, which looked like ERP. Different technology, same pathology: announce first, plan later, execute never, blame the executors.
If your organization has forgotten the last three cycles and is showing signs of amnesia about the current one, you're in a plane where the pilot doesn't believe in gravity.
Check for a parachute. Then check if anyone else is wearing one.
When To Pull The Cord
You don't pack a parachute after you realize the plane is going down. You pack it when:
- The people making jump decisions stop asking questions and start making announcements
- Your expertise is sought for validation, never for direction
- Timelines are set before requirements are gathered
- Success metrics measure activity instead of outcomes
- Dissent is interpreted as resistance rather than risk management
- The word "just" appears in sentences like "can't you just integrate the AI?"
- Consultants are outspending staff on the very problem staff flagged years ago
- Post-mortems from the last failed initiative are filed under "learnings" instead of "warnings"
These aren't signs the organization is doomed. They're signs that this particular jump is badly planned, and you're being assigned to a role the system needs filled but doesn't want succeeded: the person who makes the impossible work just enough that failure can be called "lessons learned for our next iteration."
What Good Flight Looks Like
Rare, but not mythical: the project that actually works.
You'll know it because it starts differently. Someone senior spends an evening with pizza and the people doing the work. They map the actual process—not the Visio diagram from the SharePoint site, but the real one, with all its unofficial workarounds and mysterious dependencies. They identify waste. They ask "why?" until the answers stop making sense. Only then do they discuss technology.
The requirements come from the people who'll use the system. The timeline accounts for integration with the thing built in 2003. The pilot is designed to encounter real operational complexity, not avoid it. When problems surface, they're treated as information, not failure. The team has authority commensurate with accountability.
Success is measured in human terms: time saved, frustration reduced, work made easier. The people doing the work can describe what improved and why it matters.
These projects don't make the trade press. No one writes case studies about competent execution. But they work. They land safely. And everyone involved learns something true about how to build things that serve the people who use them.
That's the altitude worth reaching. Everything else is theater with turbulence.
The Honest Exit
You don't have to jump. That's the thing they don't tell you in the all-hands where they announce the bold new initiative. Participation is voluntary, even when it doesn't feel that way. You can:
- Ask for the pizza box session before committing to the roadmap
- Request actual requirements instead of strategic frameworks
- Decline to own outcomes for decisions you didn't make
- Suggest the pilot prove production-readiness before scaling
- Propose the organization solve known problems before chasing new ones
- Simply say "I don't think this will work as planned" and mean it
Sometimes that leads to better planning. Sometimes it leads to being sidelined. Both outcomes are information.
The people who've been through enough cycles develop a calibrated sense for which hills are worth fighting on and which planes are best observed from the ground. They can distinguish between "challenging project that might work with the right support" and "doomed initiative that needs a warm body to absorb blame."
When you recognize the latter, you have three options:
- Stay and document everything (the "I told you so" strategy)
- Stay and make peace with theater (the "collect the paycheck" strategy)
- Update your resume (the "pack your parachute" strategy)
None of these are wrong. They're just different risk tolerances.
Epilogue: The View From The Ground
Years later, you'll read about the initiative in a case study. The language will be bloodless: "The organization's AI transformation initiative was ultimately sunset due to resource constraints and evolving strategic priorities." Nowhere will it mention the all-hands announcement, the consultant fees, the people who said it wouldn't work, or the person who was told to make it work anyway with half the budget and twice the scope.
You'll remember the pizza boxes. The sticky notes. The time you actually made something work because you started with the people doing the work and ended with technology that supported them. You'll remember that it's possible to do this well, when the people making decisions care about the same things as the people making it real.
And you'll recognize the signs earlier next time. Not cynicism—pattern recognition. Not resistance to change—resistance to performative change that consumes resources while producing nothing but the appearance of motion.
The parachute isn't for abandoning the plane. It's for surviving bad decisions made at altitude by people who confused announcing a destination with knowing how to get there.
Pack carefully. Jump thoughtfully. Land safely.
And maybe, next time, ask more questions before agreeing to board the plane.
For the ground crew, who keep showing up to fold parachutes even though nobody ever thanks them until one opens correctly. If you've packed one too many, you know who needs to read this. Pass it along.