To Grit with Grace: Lessons of a Lifetime
By Randy Kaufman with research assistance from Dustin Lowman
As a woman working in the male-dominated financial industry since the mid-1980s, I have had my share of challenges and letdowns, both professional and personal. Through all of these experiences I have learned that the key to a long and successful career is learning to manage these challenges with grit and a dose or two of grace (which I learned from my elegant mother). The following ten lessons demonstrate the delicate balance of these essential attributes I believe are helpful for a woman to survive and thrive in any career.
Otto Von Bismarck once said, “Only a fool learns from his own mistakes. The wise man learns from the mistakes of others.” I have always taken this quote to heart and tried my best to be wise in this sense. It is my hope that by providing you with some of my lessons learned, you can aspire to the same wisdom.
1. Accept that you live in a man’s world, then get past it
This is difficult. Professional women of all types face a common, multifaceted balance: wanting to fit in, to be liked, to be one of the guys, to be able to be feminine and yourself, to not be too sensitive, to be tough without being perceived as bitchy or arrogant, to know when someone is just giving you a compliment rather than harassing you, to know when someone is harassing you, to know when to take certain comments or looks, to know when not to, to know how to complain, to know when to smile, and to know when to move on.
If I had a universal, magic-bullet solution to equanimity in the face of this challenge, I would share it. Unfortunately, I do not. This balance is individual for each and every woman out there. However, my advice is this: Get grit to find that balance and grace to get through it.
As Elizabeth Gilbert saiid, “The women whom I love and admire for their strength and grace did not get that way because shit worked out. They got that way because shit went wrong, and they handled it. They handled it in a thousand different ways on a thousand different days, but they handled it. These women are my superheroes.”
2. We have nothing to fear but fear itself
Over the course of my life, I’ve had many doubts and fears, and I still do. When I was applying to colleges, I was told I would never get into my top choice of Middlebury, as no previous graduate of Croton Harmon High School had attended the prestigious school. I proved them wrong. A few years later, when I applied to law school, I was told I would not get into one of the top three. Again, I proved them wrong. This perseverance in the face of fear eventually led me to Paul Weiss, one of the top law firms in the country. On I went from there.
If I had listened to my doubters, I wouldn’t have dreamed as big as I did, and I likely wouldn’t have had nearly as much success. But I never let fear of failure get in the way of what I really wanted and what I knew I could do. As Robert F Kennedy said, “Only those who dare to fail greatly can ever achieve greatly.”
3. Embrace uncertainty
All of life is uncertain, yet we have to make committed, definite choices. Jason Zweig, one of my favorite writers, defines certainty as “an imaginary state of clarity and predictability in economic and geopolitical affairs that all investors say is indispensable, even though it doesn’t exist — never has, and never will.” We can make lists with advantages and disadvantages. These are helpful, but not dispositive.
The Aristotelian pizza test, something I learned from a professor of philosophy in college, has guided me through many hard decisions. When I could not decide between two fine law schools, he told me to put my lists away and to stop splitting hairs. His advice was for me to pick the school closest to the best pizza. I chose the University of Chicago, of course. This pizza test was also instrumental when I was choosing between many top law firms. I chose the one closest to Saks Fifth Avenue because as many of you know, Saks is my own little deep dish pizza!
Sometimes you have to ski down the black diamond run under a rock, hoping that no more rocks lie ahead. Sometimes you just have to take a deep breath and trust that it will all be okay. I became an investment banker with a gut sense that Wall Street would be a good career for me, but I really had no clue. In all honesty, when I started out, I didn’t understand the difference between investment banking and investment management. But why let that stop me?
I eventually moved from mergers & acquisitions (something I was familiar with from my time in law but found quite boring) to emerging markets (which was certainly unfamiliar to me) and eventually to structured derivatives (a true alien beast). I didn’t even know what a derivative was — let alone an ISDA — but I was confident that I could learn it. Then, in 1998, someone asked me to run a planning group for high net worth individuals at the Bank of Boston. I laughed and said I was honored, but uniquely unqualified for this job. My colleague said it seemed to her that if I graduated from University of Chicago law school, worked at Paul Weiss, and ran a structured derivatives desk, then I would be able to figure this out too. To my surprise, and great relief, she was right. It wasn’t easy, of course, and if I had dwelled too much on the uncertainty, I would have been scared out of my mind.
4. Whatever else — be confident
One of the biggest things holding women back is our lack of confidence. This was true when I was a young lawyer, and sadly, it’s still true today. A New York Times article, “Why Girls Beat Boys at School and Lose to Them at the Office,” by Lisa Damour, posits that the very habits that propel girls to the top of their classes hold them back in the workforce. Journalists Katty Kay and Claire Shipman found that “a shortage of competence is less likely to be an obstacle than a shortage of confidence … Overqualified and over-prepared, too many women still hold back. Women feel confident only when they are perfect.” This is a feeling I know all too well.
One typical morning when I was at Paul Weiss, I went into my supervisor Eileen’s office, bleary-eyed and groggy, having spent much of the previous night researching an esoteric tax code section. I entered her big fancy office exhausted, slumped over, and mumbling how the answer could be this, or could be that. She stood tall over me and scowled. Her shoulder pads loomed as she told me to get out of her office and to come back when I had 50% of the confidence of the male associates who did half the work. All of my research went down the tubes — it didn't matter! This made me realize that no matter what, I needed to gain confidence to succeed in this man’s world. Eileen became a dear friend, and she remains so to this day. She’s the most important mentor I’ve ever had. I channel her often and be will forever be indebted to her for this moment of tough love.
5. Fake it till you make it
If you don’t have the confidence you desire, fake it until you do. Perhaps your quest for confidence entails getting a speech coach or image consultant. Maybe it means meditating on what confidence means to you. Lack of confidence in ourselves and our abilities is the single biggest factor responsible for women not getting ahead.
There are simple ways to appear more confident than you feel. To start, always pay attention to how you hold yourself in a room full of people. Check your posture, speak up and observe how your words resonate, adjusting as needed if you don’t get the response you’re looking for. This is what I call becoming a chameleon communicator.
I promise, more people notice your confidence — real or performed — than you think. If you appear insecure and incompetent, people will often take advantage of you. By displaying your insecurities, you are revealing your weaknesses — you might as well just paint a giant target on your forehead.
6. Give it up — you can’t control what you can’t control
It took many decades to realize this life-changing pearl of wisdom: There is only one thing you can truly control, and that is how you behave. You cannot change your partners, spouses, clients or colleagues, so don’t try. As for the markets and taxes, ha! Sure, you can and should always try to influence people for the better by pushing them to become the best versions of themselves. But accepting people for who they are is the first step of letting go of your urge to control them and their actions. This is as true for bosses and co-workers as it is for lovers and life partners.
7. Read great books, and think about thinking
I was an avid reader as a young girl, but unfortunately, I stopped for many years while I was pursuing my career. Compound interest (what Albert Einstein calls the eighth wonder of the world) pales in comparison to the compounding of knowledge. When Warren Buffett was once asked about the key to success, he pointed to a stack of nearby books and said, “Read 500 pages like this every day. That’s how knowledge works. It builds up, like compound interest. All of you can do it, but I guarantee not many of you will do it.”
In 2007, a dear friend changed my life. He gave me a book — Fooled by Randomness by Nassim Nicholas Taleb Just like that, I rediscovered my love of reading and eventually engaged in a thorough study of behavioral finance and psychology. This helped me understand myself, and why I did so many things that seemed to make no sense. In the end, it turns out, we’re only human.
This study validated my view that the “rational man” I studied in college was a myth, pure and simple. It helped me understand other types of people as well. This is a personal study that continues to this day. Other important readings for me have been history, historical fiction, positive psychology and memoirs, especially about people who have endured difficult times. I continue to keep up with the Farnam Street Blog which is committed to helping readers think about thinking. It’s brilliant! For more great reads on this topic, see my behavioral finance book list.
8. There is only one true failure: Giving up
I was raised by a father who had grown up in a Brooklyn tenement, and was then drafted to fight in Nazi Germany. He taught me about resilience and tenacity. Little did I know that years after my father was gone, I would repeatedly call on his example, and use it to overcome my own challenges.
I had lived a charmed life until my late forties. In 2008, I was slammed with what I call “the trifecta of devastation”: my business closed, I was diagnosed with cancer, and I got divorced. There were times when I could not imagine making it out alive. I took solace in endless weekends of hiding in bed under the covers, reading as much as I could, and finding inspiration from those who had suffered far worse fates than I could ever imagine. (You can find many of these books on our Grit with Grace book list.)
It took a lot of time and far more courage than I knew I possessed as well as support from friends and family to not give up. I channeled Frank Sinatra (and Obama) by picking myself up, dusting myself off and getting back to work instead of letting myself wallow in misery, which surely would have led to true failure. To read more quotes about failing from the likes of Charles Dickens, FDR, and Andrew Carnegie, visit my quote list.
9. Never underestimate the power of a social network
In my early career, I thought hard work alone would get me ahead. I had hard work nailed — it came naturally to me. Especially for women, whose lack confidence, as we’ve seen, compels them to work harder. Alas, sadly for so many women, hard work isn’t the issue. I figured that was all I needed. How wrong I was! Remember, this is a man’s world. Success is more about showing up (thank you Woody Allen), connections, how you comport yourself, and luck.
In 2011, I was connected with an amazing job opportunity through a partner at Paul Weiss, with whom I had not spoken since 1988. I had emailed all of my electronic contacts explaining that I was leaving Boston and was unsure of my next move. That resulted in him connecting me with a Private Equity partner who eventually wanted to hire me. I had never known that Stuart thought particularly highly of me. By keeping him on my contact list, he remembered me over 20 years later. By the way, I was offered many more jobs in that era, all of them obtained through long-standing connections.
Building a social network is all about how you consistently carry yourself. You never know who’s watching, especially in this era of social media.
10. Grit
I have saved the best, and my favorite, for last: Grit. It’s the backbone of all the above lessons I have learned. Grit means having resilience and tenacity. It means enduring everything that comes your way, knowing you will come out the other side a stronger, better person. Study after study concludes that the one attribute all successful people have is not intelligence, not kindness, not empathy and not risk-taking. It is so simple, yet so rare to find. It’s grit.
I hope some of these pearls of wisdom resonate with some of my readers. With gratitude for all I have and all I have learned, I have grown by acting with grit (always) and grace (when I can muster it).
As always, if anything in this article sparked your interest, please don't hesitate to reach out!
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