How to Execute The Dreaded Career Pivot, from a lawyer who knows

No New York cast of characters is complete without the high-powered lawyer, and Shiela Davidson, the Executive Vice President and Chief Legal Officer at New York Life with over 30 years of practice under her belt, more than fits the bill. But what happens when a lawyer doesn’t want to work in a law firm? Well, if she didn’t know what to do, at least she knew where to be. With a career that took her from Wall Street to one of the most gorgeous buildings in New York, Sheila Davidson offers career and life insights that will get you exactly where you need to be. Even if you don’t know where that is yet.

Boucherie is one of those old-world New York restaurants where the chairs never rock, the tables are always clean, and the waiters’ shirts are so stiffly ironed, you could break a nail on their collars. It absolutely ranks as one of the many places in the city that bleed history. It is, therefore, absolutely appropriate to sit down with one Sheila Davidson, a connoisseur of all things big apple. On her recommendation and reservation, I’m seated at a corner table against the windowed wall that frames Park Avenue and she joins me not a minute later. We both decide against wine at noon but indulge in Sheila’s favorite off-the-menu item which she describes in detail to the waiter. Once the business of what to eat was handled, we got on to the fun part.

Where did your New York story begin?

My New York story began in New Jersey. I grew up in Cliffton, NJ. You could see the Empire State Building. You could see the World Trade Center going up. We used to come in all the time. Go to the Village, walk around Washington Square Park. I always knew that I would live there. The only question back then was: how do I get there? And what I say now is: I got through the tunnel and I’m never going back. 

So you knew you were going to be here, did you know what you were going to do?

I moved here after law school, and I had the choice of two jobs because I didn’t want to work in a law firm, which is a very unusual thing for a lawyer. I didn’t like law school, I didn’t like the people I went to law school with. It was very competitive, I had never been in that kind of environment before. I’m a lifelong learner, I love to learn. I didn’t like the competitive aspect of law school as a first-generation college graduate. I got there and all these people are from Ivy League schools, and “We can’t tell you that” or they’re hiding this book— I just didn’t like it and I thought, “Why would I ever want to work with them?” They’re all going to law firms, so I didn’t want to do that. 

For something that’s usually such a linear path, that little caveat must’ve thrown some fun surprises your way.

I knew I could work for the SCC in Washington because I had interned there while I was in college, or I could work, not in a law firm, but for Shearson Lehman American Express. It was all one company at that time. So I moved into the city in 1987, after spending six miserable months living with my mother and commuting into the city. The job that I had, I was humbly overqualified for, but I learned a lot. I was answering customer complaints about a big brokerage firm. And what I discovered a few months into it was that I didn’t like the behavior that I’m defending, and I felt like I didn’t have enough grounding to do it. I didn’t have enough critical thinking skills to do that. So I found a new job that was basically— think of cops and the DA. Now, it was civil, but I was kind of like the DA and the “cops” were the examiners that developed cases about fraud on Wall Street. All different kinds of cases, all different kinds of people. And all these cases were tried in front of really executive people on Wall Street, that’s who judged them. So I got to see how the Wall Street folks lived— one of them was one of the Madoff brothers—

Oh my god—

Yeah, I knew Peter Madoff from that job. Very interesting. And his brother, he was involved too, but Bernie I didn’t know as well. He always seemed like he was standing back from the crowd, Peter was a much more vivacious, fun kind of guy. But they’re all fun personalities in this, and they’re very successful— very successful executives. And it didn’t have anything to do really with the law, it was just the way that they thought about how to manage a company, manage the risks within a company and the different styles in which they did that, how they judged people, how they judged behavior. It was a huge learning experience for me. But I did that for about four or so years. My dad died my senior year of college, my mom died while I was in that job and I had massive student loans, and I wasn’t making that much money. So I thought: “All right, it’s time to make some money.” But I still didn’t want to work for a law firm. So I answered an ad in the New York Times, in the Sunday times where they used to have a help wanted section, and your fingers would get dirty looking at it. I answered an ad for a job as a broker-dealer lawyer for New York Life insurance. Do you know that New York Life Building?

Of course!

Well, at the time, New York Life’s ads were “We’re large, dull, and conservative. Reassuring in times like this, isn’t it?” And I felt like “Yes it is! Yes, that is very reassuring!” I had just spent four years bringing cases against people who were behaving badly on Wall Street, so now I want to go work there, I want to wear a white hat. So I did. And I don’t know if you’ve been to the building, but it’s amazing. Built in the 1920s, vaulted ceilings, it’s called the cathedral of life insurance. It’s magical. It’s everything that you think New York is from old movies. I worked in there and thought, “This’ll do.” I still work on the floor where I was first interviewed by the general council, which is all— I mean all of the woodwork and the rugs are preserved from the 1920s. It’s so old New York, you feel like Edith Wharton is in the room next door. And I’ve worked there for 30 years, almost 31. 

If it’s good enough for Edith Wharton, it’s good enough for me. What was your social life like in the city?

When I first moved in, I lived with a friend from college. She wasn’t my best friend, but she was still a good friend, and all my other friends were already all set up here because they didn’t go to law school. So I lived with her and her sister on 87th and Columbus when that had just been re-gentrified and it was a new building. And I thought that was the coolest thing in the world, even though after a while you realize you don’t want a roommate anymore.

We all get to that point.
 

Right, but I wasn’t quite there yet because I figured I hadn’t had a roommate in New York. But that’s how I can tell you how many old bars and restaurants are still here because I always loved the city and I love the history of the city and I love learning about the city, I love watching old movies about the city. But then, my roommate’s older sister got married, we needed a new roommate. And there was no Craig’s List or anything so we found a friend of a friend. But we found this roommate from Boston, she was much older than we were because at the time I was 24, maybe 25. She was like 32 which seemed like a vast difference. She was a character. She would talk in this squeaky voice and say “I don’t know what you’re doin’, you’re just sitting around hemmin’ and hawin’.” But anyway, that’s my New York Story— is that what you want? 

I just want whatever you’ll tell me. Usually, people start with the classic: “I got to the city and had no idea what I was doing,” which is comforting to those of us who’ve just gotten out of school.

Ah, well we always called it Freshman year of life, Sophomore year of life. But I can tell you so many stories about my friends at that age— I remember my friend, Kitty, she would complain like, “You know, I fucking hate American Express. They’re so mean. Like I’m gonna pay you. Every frigging month, they call me!” 

It’s so lovely how little things change. 

What I tell my kids is that your twenties are so spectacular in terms of your social life, but they’re also so damn scary.  You work hard and you’re not always happy, but that’s where you’re learning your basic life skills, your work skills. When I had my first job in college, I didn’t even know how to answer the phone. So I think that sustains my son as he slaves away at an investment bank. 

Fear is probably the main emotion in most of my friends. I think it gets easier when you get a group of 20-somethings together. Strength in numbers.

In a law firm, you meet a lot of people your age— not so much in the jobs that I had. But virtually all my friends from college lived in New York, so it was all of them and their boyfriends and their work friends and then the weddings start. 

Ah, the weddings.

But it was a lot of fun. A lot of good weekends.

Any good nights you remember from your 20’s?

‘Couple I don’t.

Even Better.

A few nights started at Caliente Cab Company.

Oh, a classic. That cab looks very different after a margarita.

Well, I won’t say anything more about Caliente Cab Company, but this: I’ve never had tequila again. 

You filled your lifetime quota of tequila.

Absolutely. But there were other parties. I had some guy friends from college and then they lived with some friends of theirs from work and they had a loft over in the flower district, and they used to have great parties there. I’m having these flashbacks of places I’ve been to parties…

Hit me.

One of them was in 24 5th Ave, all the way at the top. It was my friend Cheryl from college,  and her boss, Barry, and this woman she had met, Julia, who was an artist. And the woman who lived in the apartment of the party was Julia’s sister. And they were both British by way of Austria— fantastic accents. And the apartment— Alexandra and James’ apartment, was very Mediterranean, it had a lot of archways, and balconies and this huge roof terrace. I was only there once but I’ll never forget it. 

Sounds like it.

And then the other one, you know I don’t remember who’s an apartment it was, but I do know that it was in Tudor City and it had these beautiful huge, high windows that looked out over midtown. 

I’d give my left arm for an apartment like that.

No, you just have to find yourself a way to get in. Some of the apartments I saw… You know, a friend’s daughter came by to visit, she lives in LA. She came to my apartment and she was taking pictures out the window and everything, saying “I didn’t know there were New York apartments like this.” 

The best part of social life in New York is getting to see beautiful apartments. 

But then your network just sort of expands. Barry ended up becoming one of my closest friends. We had kids at the same time, and our apartments were a ten-minute walk away from each other. And she met her husband in union square, at Cafe Luna. She is a Jewish girl from Milwaukee who was really into astrology, she worked in advertising. He is a shortlisted potential Nobelist, a brain surgeon from Austria. 

Speaking of parks, I know you’re on the board for Madison Square Park. How did that happen?

Well, for me with Madison Square Park, it’s New York Life’s backyard. When I started working there, I started working there in 1991, and that park was a needle-park, the lawns were dust bowls and the pathways were blacktop, but all broken up. Not safe at night. If it was dark you couldn’t walk through it. But we would still walk through it around lunch. One time, I saw a ten-dollar bill on the ground and I went to pick it up, and a squirrel ran across and took it.

That is not where I thought that was going. 

But that’s how bad it was, even the squirrels were stealing. So New York Life, along with Danny Myer who was at the time coming up with the concept for 11 Madison, Credit Swiss, and Met Life got together and said, “If we’re going to renovate this park, it’s not going to be a one and done, we’ll have to endow it.” And it was endowed for programing (art, music, and children’s programs), horticulture, and safety and facilities and that sort of thing. So New York Life had a board seat early on, and the guy who had the board start was retiring. And I lived right nearby so that was my park. So I got it and I’ve been on that board for a long time as the arts program has developed. And that is not a particular passion of mine, but it did let me go to the Venice Biennale. 

I’ve heard that’s quite a ticket.

The first night, we had the fancy dinner at Cipriani in Venice and that next night it was a private cocktail party at the Guggenheim. And we were just allowed to wander through there. 

And all of that from just wanting to help the city a little bit.

And it was another place to meet people. I met Danny Myer, the woman who did the curation for the event, and all these people in real estate and that broadens your social life too. 

When you’re meeting all these interesting New York people, is there something they all have in common?

The people who do that sort of thing love the city. Love the city. And want to give back. And even if they’re brash or too arty for my taste, there’s that commonality, and they’re all decent souls. 

There go those grumpy New Yorkers stereotypes.

I’m always very defensive about New Yorkers. We aren’t mean. We’re always willing to help, to give directions. Just don’t stand in the middle of the street with your M&M’s shirt and your white sneakers. That’s all we ask.

With all your New York expertise, do you have any advice to offer the 20-somethings in the city?

General advice? It doesn’t make sense to have some big life plan in your twenties. You’ve gotta open yourself to possibilities.

Do you take risks on opportunities that you might not like or do you take a risk on opportunities you might not get?

This is a career talk that I give a lot to young women—

Guilty.

— which is three principles: work hard, be kind, take risks. Particularly for women, I mean you know the old song: you ask a man if he’s ready for the job and he’s forty percent ready, he’ll say “Yes, I am.” You ask a woman who’s 95% ready for the job the same question and she’ll say “I couldn’t possibly.” And that’s just something women have to overcome. So for me, earlier in my career, when I started at New York Life, I knew that I could do this, it was something I’d done, I started doing it, I was good at it. And then a year into it they started asking, well now we’d also like you to do this. And I’m thinking, I can’t do that, I only learned how to do this. And they’re saying “No, no you can do this, it’s just an extension.” So I did that. And that went on, but I always needed someone there to push me, and I try to tell young women that they should try to push themselves. Or push your friends. Because they need another voice to tell them “Yes, you can do this.” And as you get older and you do know what you’re doing, it’s your responsibility to go to the next generation of 20-year-olds and pull them up.