What Happens After You Crack The Glass Ceiling

As Hillary Clinton makes history, we’re hearing a lot about women breaking through the glass ceiling. Less is said about what awaits on the other side. It’s not always pretty.

Erin Callan knows.

An ambitious Harvard grad born in Queens, Callan started out as a tax attorney for elite law firm Simpson Thacher, before jumping to Lehman Brothers and working her way to chief financial officer in 2007, becoming the first woman ever to sit on the investment bank’s executive committee.

Before her steep fall from grace, she was considered perhaps the most powerful woman on Wall Street, dubbed an “alpha female ” by at least one investing magazine . 

Callan’s trip to the top serves as a cautionary tale as more women move into the male-dominated corridors of power. 

Callan spent years putting in extreme work hours, always prioritizing her career over her personal life, sacrificing boyfriends, time with family, her marriage. And, crucially, not thinking much about the fact that she was pulling ahead in an industry notoriously hostile toward, and devoid of, women.

The now 50-year-old former banker recounts all this with regret in a book released this spring, Full Circle: A memoir of leaning in too far and the journey back. 

“I could’ve achieved comparable success without being so maniacal about it,” she told The Huffington Post recently.

The book also offers a remarkably candid window into what it’s like for the very few women who ascend to the top in banking.

When Callan got there, she found herself caught in a male-dominated labyrinth, constantly reminded she was “different,” she said. She was told she asked too many questions in meetings remember she was the chief financial officer. The impeccably stylish executive was told that her outfits were “distracting” to her (adult) male colleagues on the executive committee. Portfolio magazine wanted to do a photo shoot in a hotel room with Callan in an evening gown. There was a lot of talk about her shoes .

Of course of all this was soon eclipsed by the financial crisis. Callan’s downfall was widely reported in the business press. Here’s a 2008 CNBC interview with Callan as her firm was melting down: 

When the mortgage meltdown hit Lehman, Callan was sent out to represent her firm. Meanwhile the guys in charge especially former Lehman chairman and CEO Dick Fuld laid low, essentially throwing her over the glass cliff in what sure looked like an attempt to save himself.

Many years later, Callan writes in her new book, Fuld apologized for this. Callan even gave him a heads-up two days before her book published so he wouldn’t be “surprised,” she told HuffPost. When he finally read it, Fuld called to compliment her. “He said I did a great job,” she said.

Callan resigned in 2008, essentially taking the fall for the firm’s decline. That didn’t work. Lehman went under. The economy cratered.

Without the career that she had devoted her life to, Callan went under, too. A new job at Credit Suisse fell apart quickly after she couldn’t bring herself to work anymore. She overdosed on sleeping pills. Landed in a hospital room. Recovered. Found love. Remarried. Resolved to change her ways. She and her husband went through several rounds of fertility treatments and had a baby.

These days Callan is retired. She splits her time between homes in Shelter Island, New York, and Florida. She and her husband, Anthony Montella, a retired New York City firefighter, are raising a daughter. 

Callan, now Callan Montella, was 15 minutes late to our interview, not because of a client meeting, but because she was adjusting to her 17-month-old daughter’s changing nap schedule. Maggie’s making the move from two naps a day to one.

HuffPost talked to Callan about her personal experiences at Lehman, the painful lessons she learned and what it’s like to retire from Wall Street in your 40s to devote yourself to your husband and baby. (Those looking for an accounting of the financial crisis and Lehman’s role in it should stop reading.)

Early on you didn’t give much thought to how you were one of the few women in the room. When did you start to realize how potent your gender had become?

As I started my career, right away it became apparent to me that women weren’t equal at the highest level. My [law firm starting] class was 50-50 men and women, but when you looked at partner population there was only a handful of women. I was cognizant of that, [but] I didn’t want gender to be part of anything. That was unrealistic. I tried to separate out an aspect of my identity. And trying to ignore it and pretend it doesn’t exist isn’t a healthy way to operate.

When I got to Lehman, I started to see it was a positive. Ninety-nine percent of the people in the room were men, so I felt it was an advantage to be a woman because the clients didn’t forget me.

Once I was in the C-suite, I wasn’t just some woman running a business. Now it became something a lot of other people kept pointing out. I can’t say I was a big fan of that. I think the people around me focused on it. 

When you were CFO, Lehman’s then-President Joe Gregory pulled you aside and told you the way you dressed was too provocative. That seems incredible to me.

Things like that would really blindside me. It was not in my nature to think about those differences. I was a very competent, talented banker. I’m in the room and I got questions to ask. I was really thrown by that. I didn’t even consider those kinds of things. I was too much the other way. But if it’s the reality, it’s the reality. Somehow it was having an impact. I said, ‘I don’t want to have that impact,’ as opposed to saying, ‘Screw you, are you kidding me?’  

Meanwhile, you were being photographed for The Wall Street Journal and other places wearing all these great outfits.  

I know. I did have nice clothes. To me it was a perk of working so hard and making a lot of money. I do take responsibility for the media stuff where I was really left on my own. I wish I had controlled it. I wasn’t wise about those types of things.

Do you think your work-life balance got pulled out of whack, in part, because the work piece was in so many ways easier?

Real life is a lot messier than work. Everyone has their work dramas. But on the whole, I think the incentives and rewards are clearer. Nobody does a 360 review with you in your relationship or gives you a compensation speech. 

I started to see, I know I can work very well and when I do there’s a lot of positive feedback and rewards, that feels like a good place to put my energy. In my personal life, every ounce I put, the less rewarding it got.

That works when everything goes great. Eventually something will happen ... you can see what happened with me. I had nothing else.

Do you think men in finance were making the same choices avoiding family, putting everything into work, that you were making? Do you think the fallout for them is similar?

Absolutely. I can’t say every single person. Certainly a majority of the more senior people. There definitely was a culture of working as much as possible. That was a key part of my success. Culturally being in the office, working constantly were all considered very good things. Nothing unique about that to anyone’s gender.

Do you have any advice for young women today?

Pay attention to the little things you’re doing that might be undermining what’s important to you. I didn’t wake up one day and say, ‘I don’t want a baby or I don’t want to have a great marriage.’

It doesn’t seem like a big deal to work an extra hour but over time it becomes your new normal and it becomes acceptable. It’s a slow erosion of your priorities.

These are things that seep in over time without you noticing. You do these little things that eat away at the other important things. 

This interview has been edited and condensed for clarity.