There’s a popular meme that floats around the internet every few months. It shows two images side by side. On the left: a straight, clean, smooth arrow drawn from Point A to Point B. The caption reads: “What we think success looks like.” On the right: a line that loops, swirls, dips underwater, climbs a cliff, falls in a hole, gets tangled in itself, and eventually, after chaos, makes its way to the other side. That caption reads: “What success actually looks like.”
Everyone laughs because they recognize the truth. Everyone shares it because they feel seen. And yet everyone still secretly plans and expects life to look like the left-hand image.
That’s worth talking about.
Because in the real world (in business, in projects, in entrepreneurship, in military operations, in relationships, and in personal growth) things almost never go according to plan. And that’s not a sign of poor planning. It’s a sign that reality exists.
The mission never unfolds in a sterile environment. The enemy gets a vote. The market gets a vote. Your children get a vote (as I write this today, my middle son is packing to leave home tomorrow for the next chapter of his life). Your own biology gets a vote. Hell, sometimes the weather gets the deciding vote.
We draw straight lines because they’re comforting. They soothe the anxious mind. They give us a false sense of control. They make the future feel predictable, which is a nice feeling right up until the part where life walks in and throws a wrench into our perfect Gantt chart.
Humans are hardwired for certainty. There’s an evolutionary reason for that. Certainty keeps you alive. Certainty keeps you safe. Certainty keeps you sane. The problem is: certainty also creates unrealistic expectations.
The straight line tells us that if I follow the plan, everything will go as expected. If I do A, I will get B. If I line everything up, nothing will deviate.
But here’s the part we don’t like to admit: We don’t just plan for success. We fantasize about it.
The plan becomes a movie in our heads; directed, produced, and starring us. And in that movie, the plot points are convenient, obstacles are minimal, and the soundtrack swells at all the right moments. Then the movie meets reality, and the first plot twist feels like betrayal.
But it isn’t betrayal. It’s life.
Here’s where people get this wrong: When I say reality doesn’t follow plans, some interpret that as “planning is pointless.” That’s nonsense.
Planning is essential. Planning is preparation. Planning is leadership. Planning forces you to make decisions ahead of time when you are calm, objective, and not yet under pressure. Planning allows you to identify risk, allocate resources, and align people.
But the purpose of planning is NOT to predict the future with divine accuracy.
The purpose of planning is to improve your ability to adapt when the future doesn’t cooperate.
In Special Forces, we used to say: “The plan is nothing. The planning is everything.” That wasn’t cynicism, it was wisdom. The value of planning is the mental models, shared understanding, and contingencies it gives you once the situation inevitably changes.
Because situations change. Markets move. Competitors pivot. People leave. Budgets get slashed. Customers ghost you. Timelines slip. Supply chains jam. Regulators regulate. And sometimes (just to keep things interesting) everything goes wrong at once.
If the only tool in your toolbox is “do the original plan harder,” you’re not leading. You’re hoping. And hope is neither a strategy nor a valid course of action.
There’s a psychological phenomenon at play here, and it’s worth naming: The gap between expectation and reality is where disappointment lives.
When you expect the straight line, reality feels unfair. When you expect the squiggly line, reality feels normal. What separates resilient people from fragile people isn’t their intelligence, their planning skill, or their experience… It’s their relationship to uncertainty.
Some people collapse under uncertainty. Some people fear uncertainty. Some people freeze in uncertainty. And some people (the rare ones) build capacity for uncertainty.
Capacity is what allows you to keep your head in the fight when the world refuses to cooperate.
We teach planning everywhere: Schools teach it. Corporations teach it. Business books teach it. Certifications teach it. Consultants teach it. Even militaries (some of the most chaotic organizations on the planet) obsess over planning.
But very few institutions teach adaptability. Because adaptability is uncomfortable. Adaptability requires humility. Adaptability forces you to give up the fantasy of control and accept what actually is.
Adaptability is the gap between “This isn’t how it was supposed to go,” and “This is how it is, so here’s what we’ll do.”
That shift sounds simple. It isn’t. It’s a skill built through exposure to volatility and reflection on mistakes.
One of the most important muscles you can build is the ability to re-plan quickly without emotional meltdown.
There are four steps professionals go through when reality deviates from the chart:
Recognize the deviation. Not after it’s catastrophic, as soon as it becomes reality.
Admit the deviation. This seems obvious, but denial is the enemy of adaptation. Pride kills more projects than incompetence.
Reassess the situation. What changed, why, and what resources remain?
Communicate the changes. Leaders who adapt but fail to communicate aren’t leaders; they’re lone wolves.
Notice what isn’t on that list: “Emotionally beat yourself up about it.”
Yet that’s where many people waste precious time… Stuck in regret, embarrassment, or frustration that the plan didn’t unfold perfectly.
I’ve been in situations (both overseas and in business) where the original plan was invalid within the first five minutes. Not wrong. Not suboptimal. Literally impossible. At that moment, no one cares how elegant your PowerPoint was. No one cares that the Gantt chart was color-coded. No one cares how long you spent building the plan. The only question that matters is: What now?
Adaptability without communication creates confusion. Communication without adaptability creates rigidity. You need both. Most leaders make one of these two mistakes when deviating from plans:
Mistake #1: They don’t tell anyone. They assume people can “see what’s happening.” They assume people will “just adapt.” They assume people understand the new goal. They assume alignment. But assumption is a form of negligence.
Mistake #2: They over-explain and under-direct. They narrate instead of lead. They drown teams in context but fail to make the call.
Communication during deviation should be concise, directive, and time-aware: What changed? Why it changed? What we’re doing now? What success now looks like? What support is needed from whom?
The faster you install alignment, the faster you regain momentum.
Here’s an uncomfortable truth: Most people struggle with deviation because deviation feels like failure.
When the plan changes, they interpret it emotionally: “We messed up.” “We should have known.” “We weren’t prepared.” “This makes me look bad.” “Now people will judge us.”
Emotionally mature leaders don’t attach their identity to their plan. They attach their identity to their ability to execute in reality. This distinction matters because confidence built on correctness is fragile. Confidence built on competence is durable.
Competence is what allows you to say: “We planned well. Reality changed. Now we adjust.” No drama. No shame. No panic. Just execution.
Here’s the part where we turn philosophy into practicality. Adaptability is not talent. It’s not “just who you are.” It’s a set of habits and mental models that anyone can build.
Here are seven ways to build adaptability:
Expect Variation. If the only acceptable outcome is “things go exactly as planned,” you will be disappointed every day of your life. Expecting deviation makes you resilient. Demanding perfection makes you brittle.
Run Pre-Mortems: Before executing, ask: “If this fails, where is it most likely to break?” Then either reinforce those joints or build contingencies around them. This simple exercise converts unknowns into knowns.
Shorten Feedback Loops: Speed matters in adaptation. The faster you realize something isn’t working, the cheaper it is to fix. Slow feedback destroys good ideas.
Remove Ego from Execution: Ego clings to the original plan. Ego resents correction. Ego fights reality. Professionals don’t ask, “How do I protect my pride?” They ask, “How do we win given the current situation?”
Normalize Re-Planning: The more often you say, “New information, new decision,” the less shocking the adaptation becomes. Professionals re-plan. Amateurs stubbornly persist.
Build Systems, Not Scripts: Systems are resilient. Scripts are fragile. If your strategy requires the world to behave a certain way, you don’t have a strategy; you have a fantasy.
Communicate Early, Not After the Explosion: Most leaders wait too long to communicate deviation. They wait until stakeholders ask hard questions. They wait until customers complain. They wait until the problem is undeniable. Communicate early. Communicate honestly. Communicate concisely. You earn trust by narrating the reality, not defending the fantasy.
Leadership isn’t proven when things are smooth. Smooth is easy. Smooth is where average performers can masquerade as high performers.
Leadership is revealed in the squiggle: in the chaos, the ambiguity, the re-planning, the deviation, the part of the mission where the map no longer matches the terrain.
The leaders who thrive are not those with the best straight-line plan. They are the ones who: Stay composed. Stay aligned. Stay communicative. Stay adaptable. Stay accountable. Stay in motion.
Motion beats perfection. Reality beats fantasy. Execution beats intention.
The straight line was never the point. The point is the destination.
No one gives you medals for having the cleanest plan. No customer pays you for the elegance of your Gantt chart. No investor funds you because your roadmap was free of risk.
They care about one thing: Did you get there?
The path will curve. The path will detour. The path will double back. The path will frustrate you. The path will humble you. The path will surprise you.
But the path will make you better… If you let it.
The more you learn to stop resisting reality and start partnering with it, the straighter the squiggly line will feel.
The truth is this: Life was never straight. It only looked that way in your imagination.
Reality is the squiggle. Leadership is navigating it. Success is reaching the other side anyway.
Stay adaptable. Stay communicative. Stay in the fight.
