Home > Spotlight > Project Sweet Spot > A Fascinating Tale of Sex, Punk Rock And Finally Solving The Money Thing: Meet Author, Speaker And Coach Jen Sincero

Yes, I realize the headline for this article may seem sensationalized, yet it’s an actual reflection of the path taken by my latest guest on the Project Sweet Spot Interview Series: best-selling (and highly entertaining) author, speaker and coach, Jen Sincero. Her story has some real golden nuggets for you – especially if you’re still challenged by the whole money thing, yet want to be in your Sweet Spot doing good in the world.

I had the great fortune of taking Jen’s Write Your Book Proposal In A Week bootcamp last year – an intense, laser-focus-and-get-it-done, totally fun experience – and instantly recognized her as a Sweet Spot entrepreneur that I wanted to showcase and share with others. Check out the short version of her bio, then and now…

THEN: Jen worked for CBS Records as a copywriter while also playing in a punk rock band, wrote her first semi-autobiographical book called Don’t Sleep With Your Drummer (optioned by both HBO and Oxygen TV networks), experimented with being a lesbian which led to her second book, a national best-seller called The Straight Girls’ Guide To Sleeping With Chicks, and evolved into her next career as a ‘sexpert,’ including teaching and speaking gigs all over the US, a nationally syndicated sex column, and regular features on national TV, radio and print media, including The Howard Stern Show.

Cool, right? Not entirely. It turns out that while Jen was doing all this hip stuff, she was constantly BROKE. Chronically, painfully broke.

After getting sick of hearing herself complain about the money issue, she finally realized it was time to make a serious change:

“One of the main things I did was plunking down a crap-load of money for me at the time to work with a coach. Man, it was inconceivable how much money I paid. It was more than I paid for all of my cars put together. It’s sort of my big line, but it really was. It was unheard of. And, of course, the second I paid it, I had a full-on breakdown panic attack about “What have I done?” But that was a pretty big defining moment – was investing in myself in a way that was completely uncomfortable and crazy.

That’s really what I focused on was money for me, and learning how to make it. It’s like anything else. If you’re not making money, you need to learn how to make money. Why do you think that you don’t need to learn that? We have no problem taking classes for other stuff that we don’t learn in school, getting expert advice, but somehow we decide that we’re just going to figure out how to make money if we work really hard. And it’s like, if you’re not, perhaps you should change it up and maybe hire somebody who’s going to help you.

…And I want to say, once I signed up for coaching, I tripled my income in the first couple of months…I ended up using my bestseller status as an author and all of my writing skills that I’d used to then make crap-loads of money.”

Fast forward to NOW: Jen is a thriving author, speaker and coach who teaches people how to “Write your damn book!” and/or how to make changes in other aspects of their lives where they want to fulfill a dream. As she likes to say, “Live Your Damn Life Already!”

She recently delivered a talk at the TEDx conference in Scottsdale called “Freefalling Into The Strong, Hairy Arms Of Uncertainty,” and just landed a book deal for her next book in the self-help genre, the working title for which is You Are a Badass, Now Start Acting Like One:  How to Stop Doubting Your Greatness and Live Large and In Charge (I love that title!). Jen is travelling the world for an indefinite period of time because she can (her entire business is conducted using the computer and a phone and she can run it from anywhere), and is currently looking for the right place to start writing the new book because she refuses to be in anything but a sundress as she writes (would you expect anything less from a true badass?).

Why do we need to intentionally learn about money? Because most of us were never properly schooled in it, and typically pick up all kinds of subconscious beliefs about it from the people around us that we may not even realize. Jen has noticed some common themes:

I think one of the biggest things for most people is shame around asking for money, and about raising your rates, that you’re a greedy, disgusting person. You know there’s so much in our culture about money is bad. People do such disgusting things for money in our world that we equate wanting money and making money with “Now I am one of those disgusting people.” Getting over that is a big one, huge one. I like luxurious things. I drive a fancy car. It’s fun! I like having a nice car. It beats the hell out of having my roof leak on me in a rainstorm. It’s like “I’m okay with it now. I’m totally okay with it.”

But for so long I was the writer. I was the punk rocker. I was so in-your-face anti-establishment. It’s like not so fun anymore and not worth it. It was getting over my identity crisis around it, and I think a lot of people have a big identity crisis around being the kind of person who makes money, especially if you’re a coach or a healer or an artist. Like there’s a big thing that comes with that. These are the people who need to be making money. Artists and healers and coaches need to have a lot of money because they’re going to do such great things with it in this world. Please people, get over it. It’s so time.”

You can listen to my entire interview with Jen here, in which we talk more about getting over the money thing, how she handled losing some people in her life as a result of her success, and which practices keep her grounded and focused on what really matters.

Being in your Sweet Spot means financial well-being and self-sufficiency. It doesn’t mean making a specific amount of money, it means being able to generate the level of income that supports the lifestyle that’s right for you. It’s going to be different for each person, and requires an honest self-assessment and level of self-awareness that does not include what anyone else thinks you should do or have. It likely means learning some new things, and breaking down some false and seriously limiting beliefs. It’s all part of the journey, and well worth it – because you’ll do more good in this world as a financially healthy badass than a broke one.