How Jen Reinvented Self Help

Jen Sincero

FOR TEN YEARS OR SO in the 90s, I co-owned and edited Psychology Today. There, I dutifully made a bi-weekly pilgrimage to the Barnes and Noble super store on 18th St. and 5th Ave. I went there for story ideas.

On the ground floor, I would behold the burgeoning self-help section, an emerging bull market of books on personal improvement. They were all very serious.

The hot new stock issues – the books of the week – got their very own rack. Editorial market research on display was oracular – in the dawn of Oprah, the evangelist. It was all very serious. In fact, I confess now to feeling that genre a little embarrassing, even tedious. How many times could you read about how to be happy in seven steps? Honestly, I haven’t read one psychology book since leaving New York. While on my self-imposed exile from self-help, Jen appeared on the scene.

She is a pioneer, perhaps the entrepreneur who re-invented the self-help genre. Psychology is out; self-help is old, heavy, ponderous…too much brain focus.

Why did Jen’s Badass books make the New York Times Best Sellers list and stay there? How was her different way of giving help accessible and fun? Something about her did not love the way self-help was presented. She realized that self-help was dreary and humorless, often dryly academic. The writing was stilted. Her delivery, instead, has aspects of a stand-up comic. Line after line of hilarious, dead-on observation – an expedition in addressing your problems and having fun while changing for the better. Her deceptively radical approach has spawned a whole cottage industry of writers.

In person with her, you feel free and light.

You went to a psychic about your hip pain.

Yeah, that was a weird psychic. He said I had a bad ass. That was not a good reading.

I’ve had good psychic readings before. The funny thing about those words is I never used them in my real life when I was coming up with the title of my book. I had a friend who had a website called, Hey Little Badass. And I was like, oh, that’s such a cute title, so it sort of brought the word into my radar. Just being open to using a word that isn’t comfortable or doing something that isn’t comfortable can wind up being the perfect thing. Like deep down in your deepest, we’ve all got that little fire in us. I just wanted to point it out to people.

As challenging as writing is for me – because it really is – I’m not one of those people who has to write or I don’t feel good. It’s a bit of a struggle, but I’ve always just sort of come naturally to it. I’ve just always had a pretty clear writing voice.

Your voice is wry and self-deprecating. It has a combination of Western psychology and Eastern thought.

When I came up with the idea to write the book, I’d read a billion self-help books. And honestly, they were so helpful. I really am so grateful for all the people who wrote all of those books. But I was like, where’s the cursing? Where’s the entertainment? Where’s the fun? I read them and they changed my life, but I was sort of like, God, how many more people could we reach? I am more snarky; this stuff is for the woo-woo crowd.

I come from a funny family where your value is basically placed on how funny you are. I have three siblings and it was like a writer’s room where we’re all trying to warm up each other. I was raised to communicate through humor. And I also think if things are funny and if there’s a good story, I certainly absorb information way better than if it’s dry and just facts.

Coming from a funny family, I definitely wanted to reach a new crowd. That’s sort of how that happened.

Talk about that, where you came from.

I think how you perceive reality is based on what your parents told you. And theirs is based on what their parents told them. So the first step is breaking your patterns, waking up to what you’ve been buying into as reality and questioning it, and being like, well, is money hard to make? Do I have to work hard to make money? Are relationships hard? What have you been taking for granted as the truth that’s not making your life good? That’s where you start.

It’s so obvious and so profound at the same time. I had a friend who had duh tattooed on her arm, because it’s like every aha moment is like, well, duh! Don’t worry, be happy. You have to really grok it. You can hear something a million times before the light bulb goes on.

So it’s questioning the beliefs that you were taught by your family. If you were raised by somebody who hated their job, who found money hard to make, who was grumbly about it, who acted like rich people sucked, it affects you. Your parents are like your gods creating your world, and you buy into what they’re telling you. Even if in your conscious mind you’re like, my mom’s an idiot, deep down in your fiber that really was what you were taking in.

And then once you start questioning, well, I’ve been broke my whole life, or, I’ve had rotten relationships my whole life, that’s a good sign that you might want to look at some of the things that you are buying into as the truth in your subconscious, because that’s where all the stuff lies that you need to unravel.

That’s what inspired me to write it in the first place because I really didn’t think it was possible at all. I was living in a garage in my 40s, and I was just like, seriously, this is the best I can do? I had a pretty fun life, but I was always scraping by and always so broke and really felt like people with money were a different species. And it was just completely impossible for me. I felt like if I could do that, I had to tell other people. It was almost like, look at this cool thing I figured out. It actually worked for me, the impossible case.

You also talk about getting out of your comfort space, what does that mean?

I prefer to call it the familiarity zone because a comfort zone is usually not that comfortable. Take an abusive relationship, for example – it’s familiar to people, and this is why they stay in it, even though it’s not comfortable. It’s familiar, and humans hate the unknown. We’re terrified of things that aren’t familiar.

A lot of people will stay in living situations and relationships and jobs that they don’t like at all, but it’s more familiar and more comfortable than taking a risk and putting yourself out there into the unknown. You have to be willing to be uncomfortable to change your life.

And if you’re really gonna make a big fat change in your life, if you’re not scared, you’re doing something wrong. There has to be a sort of terrorcitement – terror and excitement. Re-frame that fear as good, as opposed to coming up with excuses why you can’t do it.

Part of the power of your message is that you can make fun of the little dark points in people’s lives. That you can take ordinary disappointments and turn them into jokes.

If you’re a sense of humor kind of person, making fun of it makes it light. Somebody else’s opinion of you is none of your business, really. I don’t know about you, but the older I get, the less of a crap I give about what other people think of me. What a great gift of aging that I didn’t know about! The energy it takes to deal with other people’s BS, the energy to people-please all the time.

Here’s the thing: when somebody jabs you, you realize there’s somebody else who would applaud you for the same thing you’re getting a jab for. So it has actually nothing to do with you and everything to do with them.

Are your readers more women than men?

Yes, I think because it’s more socially acceptable for women to be introspective. I do have a lot of men clients and readers, but definitely way more women.

I also think that women are more socially adept and more comfortable sharing their feelings. Honesty is something that’s harder for men. It’s just the social structuring.

Do you still do coaching?

I don’t love the one-on-one coaching anymore, but I do a lot of group coaching, which is pure joy.

What brought a girl from Westchester to Santa Fe?

There are a lot of New Yorkers here. It’s funny. All I know is I went to a college in Colorado and it broke me open to the West. Then one time I came on a road trip to New Mexico and the second I stepped foot here, I was like, Oh, this is where I’m from.

There was just such a deep resonance with New Mexico. I moved to Albuquerque in the 90s and loved it. There’s something about the light here. Just because the earth is red.

Albuquerque and Santa Fe haven’t always had a perfect relationship.

Which is so silly. People are ridiculous. And listen, Albuquerque’s got one of the best music scenes. I moved there from New York City and I was in a band and I was like, I’m from New York City, a much better music scene. But people here were the nicest. If your drummer was sick, five other drummers would just sit in for you. Albuquerque is the nicest, most unpretentious place I’ve ever lived.

How did being in a band inform what you do today?

There is a certain attitude when you’re in a rock band that probably is expressed in my You Are a Badass books. It’s edgy, irreverent.

I mean, my band sucked. I worked at a record company in the marketing department, and so did my bass player. And neither one of us had ever picked up an instrument, but we got far for people who really had no idea what the hell they were doing. We would just go out there and have fun. There’s a playfulness to it. And I think there might be that playfulness in You Are a Badass.

In your books, you have these hilarious names for things. Were you ever a copywriter?

I wrote ad copy at that record company.

You learned to say snarky, sarcastic things in five words or less.

Yeah, Ozzy Osbourne rips your head off with this new album…


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