It’s Never Too Late

When we are early in our careers, our knowledge of what our working (and non-working) lives can look like is limited. We lack context.

If your mother was a freelance graphic designer, you’ll be more aware of what it is like to work for yourself than, say, the person with two parents who had a “traditional” corporate 9-to-5. If your father was a powerful CEO, you have a better idea of what it takes to climb the ladder (and the costs and benefits of doing so). Steph Curry has natural talent, but surely having the context of his dad playing 16 years in the NBA helped him realize what was possible. 

As we advance in our careers, we meet different kinds of people. We cross paths with different sectors of the economy. We gain an awareness of what is possible. 

When I talk to people about taking sabbaticals, they sometimes lament that they “missed their window” or that they’re too deep into their careers to press pause. On the contrary, the bigger the contextual gap between when you started your career and where you are now, the more helpful a sabbatical can be.

Taking a sabbatical later in your career means you are more aware of what is possible. Whether you want to change course or hop back into your previous career, your cumulative connections and talents make it possible.

Sure it’s difficult to press pause mid-career with “more to lose” and more to manage. But we’ve seen already that you can take your entire family on sabbatical. You can do it as an entrepreneur (see below). You can leave a promotion on the table.

The more career experience you have, the more fruitful your break will be.