We have been taught the wrong things. Stop picking destinations
My mentor just opened a time capsule from 20 years ago. He’d written it the week his nephew was born, a one-pager that captured goals, predictions, things he hoped would be true by the time the kid turned twenty. Sealed it. Put it away.
Last week, on his nephew’s twentieth birthday, the two of them sat down and opened it together.
Over lunch later that week, he laughed about what was inside. The job titles he’d predicted: wrong. The income numbers: wrong. The house: wrong. The car: wrong. He’d missed almost every single specific.
Then he said something that hit me like a freight-train:
“But almost everything I wrote was right directionally. I wanted more freedom. I have it. I wanted more time with the people I love. I have it. I wanted to build something I was proud of. I did. The destinations were nonsense. The directions were dead-on.”
I asked him what he’d put in his next time capsule, twenty years from now. He didn’t hesitate.
“More of and less of. That’s it. More time with the people who matter. More health. More energy. Less of the noise. Less number-chasing. The numbers were wrong last time. The specifics will likely be wrong next time, too. But I know the directions won’t be.”
That lunch reframed how I think about goal-setting.
We’ve been told for years that goals need to be specific. SMART. A number, a date, a finish line. In a stable world, that worked. The five-year plan made sense because five years from now looked roughly like today.
The world doesn’t sit still anymore. In 1965, the average company on the S&P 500 stayed on the list for 33 years. Today it’s around 15. About half of today’s S&P 500 will be replaced over the next ten years, and the CEOs I’m talking to in tech think that pace is still accelerating.
The role you’re chasing might not exist in five years. The company you’d kill to work at might be gone. The city you want to move to might be a different city by the time you arrive. The destinations we set today are guesses about a future that won’t exist by the time we get there.
Direction is a different animal. More freedom. More health. More mastery. More time with people you love. Those don’t go obsolete. Those don’t get acquired. Those don’t change shape when the market shifts.
Direction is durable. Destination isn’t.
Direction tells you who to become. Destination tells you where to arrive.
Direction grows with you. Destination holds you hostage to the version of you who set it.
You’ve felt this. Are you exactly where you thought you’d be ten years ago today? My guess: the specific destination is completely off, but the direction is probably pretty accurate.
The version of you who set those goals didn’t have access to what the version of you reading them now knows. That gap is going to keep widening. The faster the world moves, the bigger the gap, the more the destination drifts.
You can keep picking new destinations and missing them. Or you can stop picking destinations.
So here’s the move. Take the biggest goal you’re carrying right now and do what my mentor is doing with his next time capsule.
I call it the Time Capsule Test.
Two columns. More of (left). Less of (right).
More of the work that lights you up.
Less of the work that drains you.More of the people who energize you.
Less of the people who don’t.More of the kind of leader you want to be known for.
Less of who you fall into when you’re tired.
Then ask only one question at the end of the year: Did the left column get bigger? Did the right column get smaller? That’s the entire scorecard.
This isn’t an excuse to drift. Direction is harder than destination, not easier. It requires you to know what you actually want at the level of values, not the level of nouns. Freedom. Mastery. Connection. Health. Energy. If you can’t name what you’re moving toward without using a number or a title, you don’t have a direction yet, you have a wish.
But once you do have it? It will outlive every plan you write.
My mentor with the time capsule didn’t drift through twenty years. He chased his direction harder than most people chase their destinations. The difference was what he was chasing. The specifics were wrong. The trajectory wasn’t.
That’s the trick. The world will keep changing the destinations on you. It cannot change your direction unless you let it.
Stop picking destinations. Pick directions.
“The destinations will keep being wrong. The directions, if you pick them well, almost never are.”
PS. HERE is a podcast episode with my mentor (he hates when I call him that), Mike, if you’re interested.
Going Deeper
The research behind why this works
The instinct to set specific, measurable destinations feels rational. It’s what every productivity book, business plan, and high-performance methodology has trained us to do. But decades of research across economics, organizational psychology, and forecasting tell a consistent story: in a rapidly changing world, destinations decay quickly, get gamed easily, and rarely deliver the experience we expected when we set them. Direction is the more durable unit.
1. When a measurement becomes a target, it stops being useful.
In 1975, British economist Charles Goodhart, while studying monetary policy at the Bank of England, articulated what is now one of the most cited principles in management, education, and economics:
“When a measure becomes a target, it ceases to be a good measure.”
The mechanism is straightforward and brutal. Once a metric becomes the goal, people optimize for the metric, not for the underlying thing the metric was supposed to represent. Behavior bends. Shortcuts emerge. The number gets hit. The outcome it was tracking doesn’t.
The destinations you commit to most specifically are the ones most vulnerable to this corruption. You hit the number. You arrive at the place. And somewhere along the way, you sacrificed the thing the number was meant to track.
Goodhart’s Law has been confirmed across education (teaching to the test reduces learning), healthcare (treating to the metric distorts care), business (quarterly targets erode customer health), and even AI alignment, where “specification gaming” is now a recognized failure mode in goal-seeking systems.
Charles Goodhart, Bank of England: “Problems of Monetary Management: The U.K. Experience” (1975, formally published 1981); subsequently formalized by anthropologist Marilyn Strathern as “When a measure becomes a target, it ceases to be a good measure” (1997).
2. The world is changing faster than ever and even experts can’t predict it.
The premise underneath direction-over-destination is empirical, not philosophical. The pace of change really has accelerated, and the data is hard to argue with.
The most cited measure is corporate longevity. Innosight’s longitudinal study of the S&P 500 found that the average company tenure on the index has collapsed from 33 years in 1965 to about 15 years today, with forecasts projecting just 12 years by the end of the decade. About half of today’s S&P 500 will be replaced over the next ten years. The institutions that defined economic stability for previous generations now turn over twice as fast.
And we are not equipped to predict around that turnover. Psychologist Philip Tetlock spent more than twenty years running the largest longitudinal study of expert forecasting ever conducted. Across more than 80,000 forecasts from credentialed political scientists, economists, intelligence analysts, and journalists, long-range predictions performed only marginally better than chance. Confidence and accuracy were inversely correlated, the most certain experts tended to be the least accurate.
Combine the two findings. The world is changing faster than at any point in recorded business history, and trained experts with full information cannot predict it. The version of you setting a long-range destination has even less of a chance than they do.
Innosight: 2021 Corporate Longevity Forecast; Apollo Academy: “Average Tenure of Companies in the S&P 500 Index: 15 Years” (2026). Philip E. Tetlock, University of Pennsylvania: Expert Political Judgment: How Good Is It? How Can We Know? (2005); Superforecasting: The Art and Science of Prediction (2015), with Dan Gardner.
3. The strategies that actually work almost never play out as planned.
Henry Mintzberg, one of the most influential strategy researchers of the last fifty years, spent decades studying how strategies actually form inside real organizations. His findings overturned the strategic-planning industry.
The successful strategies were almost never the ones written down in the original plan. Mintzberg distinguished between deliberate strategy (what you set out to do) and emergent strategy (what actually formed through acting, learning, and adjusting). The most effective organizations started with a direction and let the specifics emerge from contact with reality. The ones that clung to original destinations consistently underperformed.
Direction over destination, expressed in management form: have a direction, move toward it, let the path appear.
Henry Mintzberg & James A. Waters, McGill University: “Of Strategies, Deliberate and Emergent,” Strategic Management Journal (1985); The Rise and Fall of Strategic Planning (1994).
4. Direction-style goals make people happier than destination-style goals, even when the destinations are hit.
There’s a fork in the goal-setting literature most people never hear about. Psychologists Edward Deci, Richard Ryan, and Tim Kasser have spent decades studying the difference between intrinsic goals (oriented toward growth, connection, mastery, and contribution = directions) and extrinsic goals (oriented toward wealth, image, fame, and status = destinations).
The findings, replicated across hundreds of studies and dozens of countries: people who orient their lives around intrinsic, direction-style goals report substantially higher well-being, lower anxiety, and stronger relationships than people who orient around extrinsic, destination-style ones.
And here’s the part that bites. The effect holds even when the extrinsic goals are achieved. Hitting the number doesn’t deliver the feeling. Reaching the title doesn’t pay off the way you expected. The direction was always the prize. The destination was a proxy you mistook for the thing itself.
Edward Deci & Richard Ryan, University of Rochester: Self-Determination Theory: Basic Psychological Needs in Motivation, Development, and Wellness (Guilford Press, 2017); Tim Kasser, Knox College: The High Price of Materialism (MIT Press, 2002).
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