Penn Jillette: how to lose 100 pounds, and keep it off (#26)

The Vegas magician lost a lot of weight fast. But how did he keep it off?

There’s losing weight, and then there’s keeping it off.

Many people lose weight—even extreme amounts of weight, even people we know— but most don’t maintain it. By the end of year one, somewhere between 50-80% of people gain weight back. By the end of year two, there’s hardly anyone left.

But some people do it. And

Penn Jillette

— the taller half of the Las Vegas magic show, Penn & Teller— is one of those exceptional people.

Being that it’s the beginning of January, and everyone and their father-in-law is trying to lose some LBs, it seemed like the perfect time to share Penn’s tale.

In his great book, Presto! How I Made Over 100 Pounds Disappear, Penn tells— in very Penn Tellerish vulgar, dramatic fashion— the entire story: How he almost died from a skyrocketing blood pressure, how he lost one hundred pounds in months, and— most importantly—how he kept that weight off (and still) years after.

And it’s the subject of today’s OGT.

How To Keep Off 100 Pounds

Jillette had been over weight for decades before he took changing seriously.

It took his brush with death, and his doctor recommending gastric bypass surgery.

I know the word fat has caused untold suffering, but it still wasn’t bad enough for me. But a doctor suggesting surgery—that made me obese. Now I had to see myself as obese. Could I shrug that off? That’s a word you can’t spin nice. There are no ‘Obese Burgers’

The doc’s stomach-sleeve prescription gave me what I needed. It gave me something I had never had … the power to go fucking crazy… not only the license but the mandate, the life-or-death imperative to be crazy.

Most articles about Penn and his transformation talk about this “crazy” weight loss.

The part where he lost nearly 100 pounds in 3 months, completely changing his diet from Las Vegas porterhouses and chocolate soufflés to a “whole food plant based” diet.¹

This obviously reads better in headlines, but the truly unique part of the Penn— and the OGT— is about how he kept it off.

As Penn writes, the weight loss was the easy part:

On December 8, 2014 I weighed 304.3 pounds, and on February 28, 2015. In eighty-two days I’d lost 74.5 pounds. That’s 0.9 pounds a motherfuckingcuntlapping day! I had lost 24.5 percent of my bodyweight in Eighty three days.

I'd accomplished the short-term goal, and it had been easy. Now I was starting the long-term goal. The hard part. I wanted to stay healthy for the rest of my life.

And the hard part, as Penn tells it, took a massive shift in perspective, values, and beliefs about food. Reading this book, you can tell the thinking Penn had before and after the change.

And the difference is striking.

Now that I think back on it, I kind of felt—I could never think this, it's too stupid— that taking care of myself was the easy way out. I felt respecting my body and my energy would make me a loser. Only wimps pay attention to their health and were careful about what they ate. Assholes would have the ask the waiter...for steamed vegetables... Tough guys would say, ‘I don't care; bring me any food you have lying around.’

This is the one part of the lifestyle change I hate: caring about what food I eat. I really hate it. It’s not hard for me to give up the food, but it’s really hard to give up the “I don’t give a fuck” part of my personality. I’ve never been a picky eater and Iv’e always prided myself on that.

Part of the shift was realizing his previous feelings were false.

I was raised in the Church of Food, and I was a believer-- yeah I was a believer.

Penn says whenever his unhealthy friends complain they want to be healthy too, and he tells them how he did it, they always say “I like food to much to eat like you.”

Penn thinks that’s BS.²

I've lost my taste for doughnuts, pizza, and bacon. I never thought it would be possible. I thought the love of grease, sweet, and salt was built in. I had a lot of just-so stories that explained it from a evolutionary standpoint. Calories and salt were scarce, and we had to look for all we could get. It doesn't seem that way now. I order organic, vegan soup at a health food store, and it's just too salty for me to finish. 

I never enjoyed eating more than I do now. I love pea soup, beans, salad, and fresh watermelon more than I ever enjoyed Kobe beef and uni. So my answer to my friends; statement is "I now like food too much to eat like you." 

Penn also changed his perspective on what being healthy meant to him.

The truth is [being unhealthy] fucked me up in every way possible. It made me less good as a performer and as a dad. It fucked me up as a husband, as a coworker, and as a human being. When I lost the hundred pounds, everything got easier and better. I lost the weight and found a kind of happiness I had forgotten I could feel....I smiled bigger, more sincerely, and more often, with less effort. I was easier to get along with. I was funnier. I was kinder.

Over a year after the weight loss, still off and not even considering changing back to how he used to eat, Penn wrote a letter to himself a decade earlier. One he thought might get to him. To make him change earlier.

In the letter to himself, in part, he wrote:

Get healthy. Your beautiful daughter Moxie just turned six months old...your life expectancy at your present weight is about another fifteen years. Remember how you couldn't stop crying for a full year after your dad died? You were forty five then. How do you think Mox and Z are going to deal with you dropping dead of fat when they're just teenagers you selfish prick?

Here's something you'll like, at first, weight loss is really hard. You need to take off in a few months what you put on in a few decades. Enjoy the difficulty. Everything you love in life, everything you're proud of, you had to work for. That's why you're proud of it. Don't believe the hype that there are easy ways to get healthy. ...All the things that make life worth living take work. Don't go on any diet that's easy and makes only small changes.

Penn, please go crazy. Obsess. Change. Have Fun. 

The OGT

The hard part of any long-term pursuit— changing your diet forever, becoming Steph Curry, building a business— is not the starting, not even getting the ball rolling, but the continuing to do for years and years. Anyone can pick up the guitar for a few months. But how many people are playing daily years later? Very few.

To lose weight, you eat less calories than you consume. Don’t worry about anything else if that’s your goal. You don’t need to, for example, workout. Penn didn’t, neither did Matt McConaughey when he lost weight for the Dallas Buyers Club.³

And don’t worry about various myths of weight loss—like carbs. Penn ate plenty of carbs. He also didn’t focus on increasing protein. He just restricted calories (he happened to do it eating whole plant foods).

The harder part was the perspective and belief and goal changes required for keeping it off. What Penn calls, “the hard part.”

What I take from Penn is exactly that—focus on the hard part.

1. Many articles are about how he ate only potatoes to lose the weight. But that was only for a week or two for a specific purpose. That purpose is what’s called a “mono diet” where you just go to one healthy food to sort of lose your taste for overly indulgent foods. And then slowly add healthy foods back.

2. From a 2020 interview with Tim Ferriss: “It is incredible how I thought that foods that I absolutely loved are now repulsive to me just because they’re out of habit.”

3. Exercise is healthy, of course. The point is don’t depend on it for weight loss.