Something can look simple from the outside, but the experience often turns out a little different than expected.

Take riding in a Waymo. You open the app, summon a driverless car, and hop in. Sounds straightforward enough.

But then you have to figure out which car is yours when it arrives & what the exact pick-up location is, how to unlock it, and how to navigate the ride. None of it is difficult, but it’s something you only learn by doing.

The same is true of retirement…you can spend years thinking about it. You can read books, run financial projections, and imagine mornings on the golf course, extended travel, and no more meetings.

But what will it actually feel like on a Monday morning when you have nowhere to be? Will you enjoy the freedom, or miss the structure, people, and challenges of work?

Until you experience retirement, you won’t really know the answers. Which is why I’m an advocate for phased retirement.

Rather than moving directly from full-time work to no work, phased retirement lets you gradually implement your transition. You might reduce your hours, take on consulting work, or slowly step away from certain responsibilities.

The real benefit is that it gives you a chance to test your assumptions. You may discover that a three-day workweek suits you perfectly, or that you miss parts of your career more than expected. Either way, you learn something valuable before making a permanent change.

Think of it as a test drive. You wouldn’t buy a car without getting behind the wheel. Why approach one of life’s biggest transitions any differently?

Retirement isn’t just a financial milestone. It’s a different way of living. If you can phase it, you can experience it before fully committing, and that may be the most valuable retirement planning of all.