Culturally clueless (Or: 'the big break')

In which I interview celebrity fitness trainer Jillian Michaels and have to admit, like 10 things about myself. Also: 7 other things worth a click.

I did an interview with Jillian Michaels yesterday. Between you and me, I didn’t know much about her beforehand.

I knew she was famous for being on The Biggest Loser, but since I never watched that show, I didn’t really know why. If you’d held a gun to my head, I would have said I thought she lost a lot of weight on the program and made a career out of it.

Basically, she was filed on a mental index card in my head next to Carrie Underwood. Or maybe I mean Kelly Clarkson.

Turns out, and maybe you knew this, she was one of the trainers on the show. These days, she has a fitness app with more than 3 million downloads. (Our talk was for a short feature I was asked to write.)

In my line of work, I often find myself interviewing people who are way more famous than I ever will be. (Next up: Sandra Boynton. That will be fun.)

In fact, I think that without a doubt, the best thing about what I do is that I get to meet and interview great people.

  • Well, that and just writing: I do really like writing.

  • Oh, and also: the experience of what happens when you write something, and you put it out there, and sometimes it resonates with dozens or hundreds or thousands or occasionally even millions of people.

  • That's quite a rush. Plus, sometimes (not always, but enough) the money isn’t bad either...

All right, I guess my point is that I can’t settle on the single best thing about what I do. But I like it most of the time, and it’s all possible due to one single “big break.”

That would be when I got out of the Army JAG Corps and immediately got hired by Bob Woodward at The Washington Post.

  • Well, either that or afterward, when I got a couple of book deals that made me feel like a “real” professional writer …

  • Or else, it's when I started having real success with and some of my other writing, or some of the work I did at the company behind Scary Mommy.

  • Or maybe you should go back to when I was graduating from college in the middle of a recession, and I got my first job writing professionally...

Forget it. There’s no point in trying to name just one.

I think a lot of us probably have similar experiences in our professional lives.

You know that you’ve had big breaks—inflection points—but when you go back and try to deconstruct the whole thing, it’s harder than you might think to point to just one moment.

What you thought was the starting point wasn’t, because you realize that an earlier moment made that later turning point possible.

And one before that, and so on. I mean: heck, we were all born on Planet Earth, and that’s a pretty nice break to begin with.

Since I had Michaels on the phone, I asked her about exactly this. What was her “big break?”

The obvious one, she agreed, was being cast on The Biggest Loser. It gave her a platform and a megaphone to the point that even culturally clueless people like me sorta/kinda knew who she was.

“But arguably,” she said, “I would tell you the one that facilitated that opportunity was even more important.”

It starts when she was 28 years old, and working as a physical therapy aide and trainer, helping to build other people’s sports medicine practices in Los Angeles. It hit her that since she and a colleague were the ones bringing the clients in.

“We could do this ourselves,” she said. “We could own the business and have a physical therapist and a chiropractor on staff.”

It took about two years. One key was convincing some of her clients to put up the startup cash: to “literally give me $10,000 each. … And my collateral was—if I can't pay you—if I lose the money, I'll train you for free.”

How cool is that? Raising money for a business is amazing, but raising the money from your own clients is super-validating. My hat is off.

“I think without that, The Biggest Loser would have been like, ‘Yeah, I dunno,’” she told me. “I think having my clients give me that opportunity and invest in me allowed me to open my business. And I got from there to The Biggest Loser.”

Hey, tomorrow is Friday, and we haven't done a real, honest-to-goodness comment thread in a while.

Let me know if you think this would be a good one. I’ll work up a better prompt, but we’ll ask people to share what they consider to have been their "big break." (And if they’re still waiting for it, what do they think it will look like?)

Oh, I like this one. (Just to underline this: it’s for tomorrow, not today. I know the UX isn’t 100 percent clear on this all the time.)

But I think it’s working out best for these when I give everyone a hint about the topic, then we wait 24 hours and have the discussion the next day.

Wildly counterintuitive, but I like the results.

There you go: Another thing I like about doing this kind of thing professionally.

Question: the number-1 complaint I’m getting lately is that people don’t like when I link to sites behind paywalls. Let me know if that’s an issue for you. (You can just reply to this email or hit me at

I have an idea to address it … but it would require a bit of work. So I’d like to know how many people are bothered by it first. Thanks.

7 other things worth a click

  1. If you work for Microsoft in Seattle, work from home. (Microsoft)

  2. The IRS is trying to collect $9 billion in taxes from Facebook. (Adweek)

  3. Former Uber exec ordered to pay $179 million to Uber; he immediately files for bankruptcy (which is his right!) (The Washington Post)

  4. Apple and Netflix back out of SXSW over Coronavirus fears. (Axios)

  5. How hard is it not to touch your face? So hard that a public health official couldn't tell people not to touch their faces without touching her face. (Buzzfeed News)

  6. Cyberstalker of Parkland victims' families gets five years in prison. (CNN)

  7. Let’s just all feel good about Mark Hamill helping a young girl who was born without an arm get a R2D2-themed prosthetic (and throw in tickets to Disney). (CNN)

Photo credit: Gage Skidmore. Ideas and feedback actively solicited. If you haven’t subscribed, please do so! (You can also just send an email to

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