How Failure And Divorce Were Essential To This Finance Luminary's Success

 
Catch Krawcheck at the Girlboss Rally NYC.

Catch Krawcheck at the Girlboss Rally NYC.

The Failure Chronicles: Out of college, everything came crashing down around Ellevest founder and CEO Sallie Krawcheck and she was forced to reconsider a career in media. Here's how she pulled herself through.

It was the early 90s when I got out of college, and I decided to go to business school. I’d been working as an investment banker, and I hated it—the endless cycle of working on deals, flying around on planes, the swinging dicks. 

Business school was a means of pivoting my career into something new, though really, what I wanted was to work in media. I’d had an internship over the summer after my first year, but I didn’t get the full-time job, so I went into my second year of business school more determined than ever to get a job in media. 

And then one day, there it was: I had my dream job at Disney in my grasp. I’d actually sent them a cold letter, which usually never gets a response, but this one did. I went through a series of interviews with them, becoming more and more excited, and all the while I was getting offers to come back to investment banking. But I turned them down—forget about the bird in the hand versus two in the bush; I was going for it. 

And what do you know, the job offer came in. But it was in California, and my then-husband and I lived in New York. And he would not at all entertain the idea of moving to California. 

We were on vacation at the beach at the time, renting a little beach shack with a porch. I remember we were sunbathing when the call came. When I came back out, I laid down on the beach and threw my arm over my eyes, and I sobbed and sobbed and sobbed.

I ended up going back to those investment banking job offers and asking if any of them were still available. I took one of those jobs. But I saw it was a huge failure. I spent two years of hard work, lots of money, and so much energy to get out of investment banking, only to end up back there.

And then there’s the second part to this story: I discovered my husband was having an affair. In fact, he’d been having an affair while I was going through talks with Disney. I told him it would have been super helpful if he’d told me he’d been unfaithful while I was giving up my dream career to stay with him in New York.

Again, I sobbed and sobbed and sobbed and sobbed. I dropped down to 108 pounds, which is not a good look on me. On my first day of work back in investment banking, I had to leave in between orientation meetings in order to lose my lunch any place it would come out of my body. I’d tried so hard to make my life better and propel my career, but there I was, vomiting in the bathroom at a job I desperately did not want, while my marriage was disintegrating. 

It felt like everything was over. I stayed in that job for a year and I hated every minute of it, and I didn’t start to recover until I quit. It took me three years to regain that weight. 

Epilogue to an epic fail

But eventually, I got remarried and had a baby. And there was this moment when I was standing in my kitchen one day, a new stay-at-home mom, and it hit me, what I wanted my job to be: A self-taught equity research analyst—the dream of so many young women!

That role had some of the characteristics of investment banking, but with much more creative freedom and much more personal responsibility, and landing that job took some time. Every firm on Wall Street rejected me, with one exception: Sanford Bernstein. But within a couple of years, I went from one of my lowest points to being the number-one ranked analyst in my industry.

It changed everything. I loved it. I was intellectually engaged, I was curious. I jumped out bed in the morning because I couldn't wait to go learn more. At the same time, I had an infant at home, and I was fully engaged with someone who was fully engaged with me.

I was exhausted, of course, but I was living the fullest life I could possibly imagine. That one step to be a research analyst led to me becoming director of research, and the strategy we chose when I was director of research led me to being on the cover of Fortune Magazine as “the last honest analyst.”

It didn't mean everything was perfect—not by any means. I was in a new marriage that had its ups and downs as we were figuring each other out, but from a career perspective, well, thank goodness I didn't get that Disney job. Thank goodness I went through all that, because it set me on the trajectory I’m still on. 

Failure (and success) is a squiggly line

I went on to run wealth management company Smith Barney (which I had no right to run) and then to be the CFO of Citigroup. And I went through failures there, too. When I got fired from those jobs, it was because I was doing the right thing for clients. But by actually failing and spinning out of these companies, it put the onus on me to decide what I was going to do.

Society somehow gives us this message that success is a straight line—that this happened, and then this happened, and then this happened and then, by God, I was a billionaire! But there are at least a hundred opportunities to be successful every day; you just need to be out there, playing in traffic. 

Success requires having self-knowledge, and not only being ready for opportunities, but proactively making opportunities and kicking up dust. If you only have one or two things go right, you can have a brilliant career.

Too many people tell the “so-and-so called me, and that was that” version of the story, but the phone doesn't just ring. Things happened because you make them happen. Don't forget that.

As told to: Deena Drewis
Photos: Courtesy