The Freedom Trap: You Spent 30 Years Buying It and Aren’t Using It

I’ve spoken with people who could take Tuesday afternoon off and simply don’t.

Nobody would fire them. The company would survive. They have enough money. There is no emergency waiting to happen if they disappear for four hours.

Yet Tuesday afternoon somehow remains unavailable.

This is one of the stranger things about success. People spend decades trying to earn autonomy and then, once they have it, continue living according to rules that were useful when they had much less choice.

No boss, but the alarm still goes off at 5:30.

Enough money, but every hour still needs an economic justification.

Control of the calendar, but very little appears on it simply because they want it there.

The cage door is wide open, but they stay inside.

The Constraints Were Useful

There is a good reason this happens.

Constraints helped create the freedom in the first place.

Deadlines mattered. Discipline mattered. Sacrificing the interesting thing for the necessary thing often mattered. There were payrolls to meet, clients to keep, people depending on you and periods when taking Tuesday afternoon off really would have been irresponsible.

Over time, these behaviors stop feeling like strategies and start feeling like reality.

Former Navy SEAL Jocko Willink has described discipline as something that creates freedom. A highly disciplined team can operate with greater autonomy because everyone understands the standards, procedures and boundaries. He also makes the less frequently repeated point that discipline can go too far. Apply enough of it and eventually creativity disappears.

That distinction interests me.

Discipline is extraordinarily useful when it serves something.

It becomes less useful when nobody stops to ask whether the thing it was serving still exists.

Solving a Problem That Changed

Arthur Brooks draws a useful distinction between complicated and complex problems.

Complicated problems may be extremely difficult, but expertise can solve them. Build the aircraft. Design the system. Work out the financing. Enough knowledge, skill and effort can eventually produce a repeatable answer.

Complex problems behave differently. The variables keep moving. Relationships are complex. So are wars. You cannot run the equation once and expect the answer to remain true. They have to be lived and continually responded to.

Building financial independence often looks more like a complicated problem.

There is a number. There are strategies. Progress can be tracked. Save, invest, build, sell, negotiate, repeat.

Then you get there and encounter a completely different question:

What should I do with this freedom?

That is complex.

There is no spreadsheet that can tell you the correct amount of work, adventure, contribution, family time, solitude or irresponsibly long lunch.

Successful people sometimes respond by treating this new question like the old one. They add structure. Goals. Metrics. Another company. Another board position. Another set of obligations.

Very quickly, freedom starts looking suspiciously like the life they worked so hard to escape.

When the Old Orders Still Feel Current

Hiroo Onoda offers an extreme example of what discipline can look like when the context disappears.

Onoda was a Japanese intelligence officer sent to Lubang Island in the Philippines during World War II and ordered to continue fighting. He remained there until 1974, almost three decades after Japan surrendered. Leaflets announcing that the war was over did not convince him. He finally stood down when his former commanding officer came to the island and formally relieved him of his orders.

His story involved real violence and loss, so comparing it directly with an entrepreneur who answers too many emails would be absurd.

The useful part of the story is narrower.

Extraordinary discipline does not contain its own stopping mechanism.

You can become remarkably good at following an instruction that is no longer relevant.

Work harder.

Keep growing.

Stay useful.

Never waste time.

Do not become complacent.

Those instructions may have helped build an extraordinary life. That does not give them permanent jurisdiction over it.

At some point, the war may actually be over.

Freedom Removes More Than Limits

There is another reason people recreate constraints: constraints provide structure.

Sebastian Junger has written about one of the paradoxes of affluent societies. As people become wealthier and more independent, they gain enormous personal freedom while becoming less dependent on community. That independence has obvious advantages, but something can be lost when fewer people genuinely need one another.

Professional life can work the same way.

A company tells you where to be. A team needs something from you. A goal determines what matters today. Even pressure can provide companionship of a sort because everyone is pushing toward the same thing.

Remove those constraints and possibility opens.

So does ambiguity.

Freedom sounds wonderful when someone else controls your time. It becomes more demanding once nobody does.

Now you have to choose.

Using the Freedom

I have some personal sympathy for this problem because I chose to use mine.

My work-life structure has allowed me to live outside the United States for decades, first in Argentina and now in the mountains of Bulgaria. I built a coaching practice that works online and does not require me to organize my life around an office. 

I spend many hours each week in the kitchen cooking and cleaning up, for example, that may seem like wasted time, but it’s very much aligned with the healthy lifestyle I want for myself and my family.  We have Concept2 machines and a full weight set with a squat rack, and walk the dog in the mountains twice a day, instead of scaling my business and hiring more coaches.

Those choices did not produce permanent clarity. That would be a suspiciously simple ending.

They did teach me something about autonomy.

Freedom becomes real when you inconvenience an old assumption with it.

You live somewhere you supposedly weren’t going to live. You protect an afternoon that could have contained another meeting. You turn down something impressive because you would rather spend the time elsewhere. You allow curiosity to influence a decision that once would have been made almost entirely by economics.

Oliver Burkeman points out in Four Thousand Weeks that having more possibilities does not create more life in which to pursue them. Choice necessarily means leaving some possibilities unused.

That can feel uncomfortable to someone who spent decades increasing their options.

But unused options are not wasted freedom.

Choosing is how freedom becomes visible.

The Permission Problem

James Hollis often returns to the question of how much of an adult life is actually chosen and how much is organized around expectations absorbed long ago.

Success does not automatically answer that question. In some ways, it can postpone it.

You become so capable of doing what is required that you rarely have to ask whether it is still required.

There may come a point when the constraint you are waiting to have removed has already disappeared.

The money is there. The authority is there. The flexibility is there.

Nobody is coming to hand you a certificate saying you may now use them.

Perhaps that is the final trap in buying freedom.

You spend thirty years earning permission.

Then discover that using it was always going to require giving permission to yourself.