The Myth of Owning Your Time: Why Success Rarely Buys Freedom

Be your own boss. Set your own hours. Own your time. It is one of the most repeated promises in personal finance and entrepreneurship, and according to investor and writer Nick Maggiulli, it is largely a fantasy.

His argument is simple. Leaving a job does not remove demands on your calendar, it just changes who makes them. Instead of a manager, you answer to clients, vendors and employees. A customer request lands at a bad moment. A key hire quits, sometimes alongside several colleagues, and the person who has to find replacements is you. Autonomy beats working in a job you hate, Maggiulli concedes, but your problems do not vanish when you run the show. They change shape.

The pattern also holds at the top. The more successful someone becomes, the more people want a piece of their day, and saying no gets harder. Think of a celebrity entrepreneur, a tech founder or the head of a major bank. On paper they control their calendars. In practice they answer to sponsors, regulators and shareholders.

The data points the same way. Researchers at the National Bureau of Economic Research found that in 1983 the lowest-paid fifth of workers were more likely to put in long hours than the highest-paid fifth. By 2002 that had flipped, with top earners twice as likely to work long hours. Yale Law professor Daniel Markovits made a similar case in 2019, noting that the top 1 percent now work four or five more hours a week than they did at midcentury, while the bottom 60 percent work 10 or 11 fewer.

A 2018 Harvard Business Review study of 27 CEOs, tracked for a full quarter, makes it concrete. These leaders, running companies with average revenue of about $13 billion, worked 62.5 hours a week, worked on 79 percent of weekend days and on 70 percent of vacation days.

One response is that these executives could take time off and simply choose not to. Maggiulli rejects that. Freedom you never exercise, he argues, is functionally the same as not having it. And unlike money, time cannot be passed on. Unused hours cannot be gifted to heirs.

He does not claim that employment and entrepreneurship are equivalent. Renting your time is still worse than owning it. But he suspects many founders overstate how much control they really have. The genuine option to own your time usually arrives only after years of hard work, perhaps after building and selling a business, not before.

His practical conclusion for investors and professionals is to stop chasing total control of the calendar. Decide what you actually want to spend your time on, then be willing to give it up for those things, whether that is a career, family, health or community. Maggiulli says his own time freedom shrinks each year, and he is fine with that because the commitments are ones he chose.

As he puts it, owning your time is a myth, but choosing how you do not own it is not.