The Power of Being an Outsider at Work

By Sallie Krawcheck

Last week, I had the opportunity to be part of the Masters of Scale Summit in San Francisco. (No, I didn’t see Prince Harry. Darn it.)

My session was on “How to Think Like an Outsider.” I shared the stage with Tope Awotona, the CEO of Calendly, and Shellye Archambeau, former CEO of Metricstream. The idea behind the panel was that being an outsider — and thus avoiding the echo chamber of the insiders — can be a strength. 

Here’s what I shared: That I knew all the way back when — when I looked up and realized that I was the senior woman in my investment banking division at the age of 26 (!)  — that my chances of career success on Wall Street by doing-things-the-way-they-were-always-done were probably next to nothing. 

Instead, in my next jobs — as a research analyst, as a Director of Research, as a business manager — I decided I would take the same information and data that others had and see if I could see something different in the data, to paint a different picture with it. In other words, to be a natural contrarian. 

For example, for the first financial company I followed as a research analyst: Other research analysts saw a company that was growing its loans very quickly. I, by picking apart the stats on loan quality, saw a company that was growing its loans very quickly by making loans others wouldn’t. So while others were bullish on the company, my first research report pointed out the underlying credit deterioration on it. I called the report “Whoa, Nellie.” 

Same information; different interpretations. (Happily for me — not happily for the company — I turned out to be right.) 

Same with Ellevest. Financial service companies have long understood that women don’t invest as much as men do. They have looked at this stat and have concluded that women are more risk averse than men. We looked at that stat and hypothesized that the financial industry hasn’t been serving women well. 

Same information; different interpretations. (And I’m feeling like I’m right on this one, too.)

So harnessing my outsider status has been a key factor in my career. 

Oh, also hard work, a ridiculous amount of persistence, good luck, no toxic boss, a great spouse, a healthy dose of insecurity, thick skin, the right mentors at the right times, being in the right place at the right time, and no crushing family obligations. Those, too. But my outsider status? I continue to lean on that.

Sallie Krawcheck Signature


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Sallie Krawcheck

Sallie Krawcheck is the Founder & CEO of Ellevest.