Why The Undertaker Should Stay Retired, and When You Should Call it Quits

Last night was Monday Night Raw’s 25th anniversary special. One of the things that kept fans on edge for months was the announced return of The Undertaker.

Was he retired or wasn’t he? Was he going to have a showdown with John Cena or not? These questions were what Robert Cialdini would call attention magnetizers heading into the show. We wound up not getting any answers. The segment felt like Undertaker and WWE still didn’t know what they wanted to do.

If the goal of a message isn’t to confuse its audience, this segment failed. It was bullshit. Except for the opening segment with Stone Cold Steve Austin, the entire show was.

But if there is one silver lining, it’s that Undertaker isn’t yet coming back for another match. That’s as it should be. He should stay retired.

Why The Undertaker Should Stay Retired

All of his matches since 2013 have been bad. He looks more and more like a broken down old man in the ring each year.

He’s also missed many opportunities that would have been perfect for him to bow out gracefully. 2012 was the best time, as it saw the excellent Hell in a Cell match at WrestleMania 28 that was being billed as “the end of an era.” The image of Undertaker, Triple H, and Shawn Michaels walking out together after the brutal match became an instant icon, and Undertaker’s victory that night saw him go to a nice, round, psychologically satisfying 20-0 in his WrestleMania undefeated streak.

But Undertaker stayed. His decline became precipitous afterward. In 2014, he lost the thing that defined him most, his WrestleMania streak, to Brock Lesnar, and followed it up with pitiful performances in 2015, 2016, and 2017.

With each new match, Undertaker is slowly and steadily overwriting the cherished memories his fans have of him with newer, darker ones. He’s becoming an object to be pitied rather than respected.

The saddest thing is, he signaled 15 years ago that he knew there would come a time like this and that he didn’t want to be there for it.

Unfortunately, we reached the point of “you should have seen him when” years ago. 2018 Undertaker should listen to 2003 Undertaker.

When is it Time to Call it Quits?

There are two times to stop doing something. The first is if it’s not working. That’s the easier one. Scott Adams has a chapter on this in How to Fail at Almost Everything and Still Win Big if you’re confused about when something isn’t working.

But what happens if something is working? Retiring will be much harder. How do you retire from something that’s gone so well? The Undertaker is one of the best ever in his field. We can forgive him for not having retired earlier, even if it was the wrong decision.


Ironically, he also had the right answer. The time to retire is just before you’re in danger of being seen as past your prime. Undertaker’s peers like Mick Foley, Stone Cold Steve Austin, and Shawn Michaels, are good examples of this. They all got out when they still had gas in the tank…but not a whole lot. As a result, we didn’t see them run on fumes, so we have nothing but good memories of them.

Athletes in other sports, like Mariano Rivera and Derek Jeter, are other examples.

This dynamic isn’t limited to sports. George Washington’s decision to retire after two terms was as much about leaving while his reputation was still intact after a difficult second term which threatened to crack it.

It also applies to Vince McMahon himself, who has lost his creative talents in recent years. He’s not what he was in his prime and it shows on each episode of his programming. His lazy creative patterns this decade has dented his legacy among his company’s fans.

Staying long past your prime guarantees you’ll be seen as less than what you were. The comparisons will be sad. Undertaker has gone from The Phenom of yesteryear into the broken down old man of today. He looked terrible at WrestleMania 33 and it was sad to watch. Another match would just be a repeat.

This is the risk you take in overstaying your welcome. You need to know when to retire. Since you’re reading this, it’s not a question you’ll have to ponder soon, but you should think about it.

Now, how do you know when you’ve passed your prime?

Sometimes it’s just not obvious. You need to rely on people close to you to tell you, as The Undertaker said. But people are usually nice and want to avoid confrontation, so you need something else.

Undertaker RAW 25

Take this with a grain of salt, since I’ve not experienced it yet, but in studying contemporary and historical figures, I’ve found a clue.

You’re past your prime when the things that you influence the least are consistently better than the things you have direct involvement in.

Vince McMahon is a perfect example. NXT, WWE’s developmental brand, is consistently regarded by fans as the company’s superior show. Vince isn’t involved in it. It’s run by his son-in-law, Triple H.

Henry Ford is another one. Though the Model T was revolutionary, it lasted long past obsolescence and competitors were passing it by. It took quite a bit of prompting from his son, Edsel, for him to finally end its production and move on to more modern cars.

Pay attention to the quality of the things you’re producing and compare them to earlier iterations. If you’re in an organization, pay attention to the things directly influenced by you versus things less so.

If you’d been hitting a stride for a long time but notice a decline, it might be time for you to retire, so that your legacy remains intact.

To learn more about recency memory bias, which should strongly influence your decisions on retirement, read Stumped.