An Oscar-Winning Retirement

Molly asked if it would bother me if she had the Oscars on TV in our room while I drifted off to sleep. I couldn’t think of a more sleep-inducing television experience than a bunch of self-congratulatory Hollywood communists patting each other on the back and giving shout-outs to their middle school drama teacher who believed in them when no one else did. So I was happy to oblige that request.

I did slightly wake up about an hour later when she started yelling “WHAT IS HAPPENING RIGHT NOW??” But I was still more interested in sleeping, so I just rolled back over and didn’t think anything of it.

When I woke up the next morning, Twitter was ablaze with a bunch of jokes that I didn’t understand. After I finally saw the footage, the jokes started to make sense.

If you somehow haven’t seen the glorious awkwardness of the moment, you can check it out here.

As it turned out, the producers of something called La La Land spent about two minutes basking in the glory of their “Best Picture” victory before the red carpet got pulled out from under them and they had to cede the stage to the rightful winners, the producers of something called Moonlight. They handled it with as much dignity and class as anyone could have asked for, but you know that it felt like a punch in the gut.

Unfortunately, I’ve seen retirement pan out roughly the same way for people who didn’t do adequate planning.

It usually looks something like this…

You announce to everyone at work that you’re retiring. Some are jealous of you, others are genuinely happy for you, some seem to be outwardly happy but are actually jealous and don’t want you to know it. But there’s a lot of uproar and cake and congratulatory Hallmark cards and then you ride off into the sunset. The trophy is yours.

Maybe a year goes by. Or it could be several years. But then you start hearing this little whisper in the back of your head that says, “Hey bud, unless you die a lot sooner than you’re planning to, you’re going to run out of money.”

“But I had almost a million dollars,” you say. “Isn’t that plenty?”

So you go on for another few months and the whisper turns into a much louder voice.

So you go to visit a financial advisor. You talk about how much you don’t miss your job and the trip you took to Europe and the 14-pound catfish that you caught. And then the conversation turns to your portfolio and you discover that the whisper-turned-shout was actually right all along…you’re going to run out of money.

You’re now faced with a choice. You can either significantly reduce the quality of your lifestyle for your remaining years, or you can go back to work.

And now you find yourself in the same boat as the La La Land producers—you’re giving back your retirement trophy that you only got to hold for a couple of minutes before somebody came along and told you that you didn’t actually win. You try to handle it with dignity and class, but there’s no denying that it’s a gut punch.

Imagine how things would have been different if Warren Beatty had been handed the correct envelope and he’d simply read Moonlight as the winner from the very beginning. Sure, the La La Land guys would have been disappointed that they didn’t win, but they wouldn’t have had to endure the pain of having that momentary taste of euphoria only to have it yanked away moments later.

Now, imagine if you’d started working with a competent planner and constructed a well-conceived retirement plan a few years before you actually retired. You would have discovered that you actually couldn’t retire at the age you were planning, and while you would have been disappointed, at least you found out in advance. So you continue working for an extra couple of years, nobody else knows any different, and then you can enjoy the lifestyle that you wanted…instead of enjoying it temporarily only to have it taken away later.

The bottom line is that I’m constantly amazed by the number of people who waltz off into retirement without a real understanding of whether or not they’re retiring at the right time, or any inkling of how much they can legitimately spend each year once they no longer have a paycheck.

So just be sure you’re holding the right envelope. It’s much better for everyone that way.