How to Succeed When the Odds Are Against You

Anita Brick: Hi, this is Anita Brick, and welcome to CareerCast at Chicago Booth to help you advance in your career. Today, we're delighted to be speaking with Polina Pompliano. And she is the founder of an amazing organization called The Profile and New Media Company that features long form profiles of successful people and companies each week. Prior to that, she spent five years at Fortune, where she wrote more than 1300 articles and earned the trust of prominent investors and entrepreneurs as the author and editor of Term Sheet.

Very favorite of people at Booth, Polina interviewed dealmakers. She talks about some of them in her book Hidden Genius. I absolutely love Hidden Genius. Even though it was a PDF, I couldn't put down because it is compelling, it is accessible and it's really, really fun and practical read. So thank you so much for writing it. Thank you so much.

Polina Pompliano: Thank you so much. I'm so excited to be here.

Anita Brick: Me too. We're very glad to have you. So let's start off. There were a lot of questions. I ran a tricky situation, so let's start with one. The person was trying to map on their process onto your process. The first question comes from an MBA student and she said, I really like your approach of framing a story full of characters whose lives put everything in context to help you remember important information. How would you advise someone to use this approach to create motivation and tenacity with one's own story during a time that is really challenging?

Polina Pompliano: Yeah, the entire book is framed around this concept of people focused learning. I learned very early on that the way that I learn is by not memorizing facts and figures and dates and historical events, but it was rather to choose a person in a historical moment and understand the things that they went through and try to empathize on a human level, because that's what would trigger my memory.

Normally, emotions trigger memories. I'm always drawn to people who have overcome somewhat incredible odds to achieve whatever pursuit they're passionate about. To do this, you know, you asked about advising you to like, create motivation, tenacity. To do this, I recommend finding people whose life trajectory looks somewhat similar to yours in the beginning, and then study how they use their circumstances to their advantage and try to extract the lessons, and not just the things that they did right or how they succeeded, but the good and the bad and the mistakes and the gritty and the things that you would not like to replicate. And then you can apply it to your own life.

The way I stumbled upon this in, I started doing this when I was 23 years old. I had just moved to New York City, and I felt really lost, and I didn't know what I wanted to do, and I was not making any money, and I was trying to figure it out. So it was like, I happened to read about entrepreneur and self-made, you know, at this point, probably billionaire, Sarah Blakely, she invented Spanx. I was reading how in her early 20s, she had these kind of dead-end jobs, and she kept telling herself, I'm in the wrong movie. I'm in the wrong movie. This is not my life.

How do I, like, start building my life the way I wanted it? I fell into a deep rabbit hole. I was listening to podcasts. She had done watching video interviews, reading books in which she was quoted, everything I could consume. That's kind of how I started extracting lessons from her life that I could then apply to my own.

If you're feeling loss, if you're in that moment of, oh my gosh, what do I do now? And it's a really challenging time. Find someone whose early life mirrors yours and then try to see how they mapped out their life. But ask yourself, like, am I willing to give up the things they've had to give up and make the same choices that led to similar results? Or will I do it another way? But I like their mentality and the way they pursued it.

Anita Brick: I like that. So here's an alum. And this alum has a couple of decades of experience. So maybe a little bit different place. And the alum said, I'm in a place right now, he said, that is so challenging. It is negatively impacted my mental health. But I'm working with a therapist on aspects of these and struggling about my next goal, because I don't really feel comfortable anymore because the last one has been crushed and wondering what would be your perspective about coming back better after a setback than if it had never happened before?

Polina Pompliano: Oh, I love this question so much because I think there's a huge misconception around failing at a goal. I think after people go through a really challenging time and let's say they fail to reach a goal they had set their mind to, they often think they're starting over. They're like, oh, I'm starting from scratch, ground zero. Now I have to build up again. But  they often forget is that in that period of “failing”, quote unquote, you've actually learned new things and you've gained new skills as a result of going through that experience.

So you actually have an advantage over the people who did not fail. What I like to tell people is that you're not actually starting over. You're now armed with all these things that you've learned, that you have the opportunity to build something bigger and better next, that you set your mind next to next. And a lot of people that I feature in the book actually take pride in that. They can start over, even if everything is taken from them, even if they've lost everything. Martha Stewart Many people forget she went to prison for insider trading. She came out, she was like, I'm going to reinvent myself and I'm going to do it bigger and better. She was more strategic. She was more humble. She she was more determined.

I often think of, again, Sara Blakely when she was growing up, her dad, they would have a family dinner and her dad would make her and her brother go around the table and share their biggest, juiciest, Meatiest failure of the week and she said that if she didn't have something to share, her dad would be genuinely disappointed because it meant that she didn’t try hard enough at something. This simple exercise redefined failure in her mind because suddenly she says failure is not an outcome. It's simply about not trying and not taking risks. So I think the way you get out of this rut is okay. I tried, thank God I failed, probably, hopefully quickly so that I can move on to the next thing and I just stay in this place.

Now that you're on to the next thing, what skills do you have that you can apply that give you an advantage over your peers that never fail?

Anita Brick: That I agree. What if, and I see this in different people that I know, whether it's inside booth or outside booth, that their family was the opposite of zeal. If you have a mistake, oh boy, that was a really bad thing. 99% of 100 is a failing grade. How do you help people get past that? Is it a matter of taking risks where you know you'll likely fail, where the impact is very small? What do you advise people to do when they've come from the opposite of Sara's family?

Polina Pompliano: As a family of immigrants. So grades were very important, school was very important. And so I did really well in school. And then when I got out and I failed at the first thing and I was like, oh my God, what? I am a perfect student. I did everything right. I think a lot of it is having to unlearn what you have learned in the past and it's really, really hard to do.

But it is like what you said, it's taking small risks every day consciously that open you up to rejection and failure and things like that, so that when the big moments come, you don't fall to your knees because you've kind of built up that muscle like it's not the end of the world. If I get rejected, you have to be very, very conscious about it.

And every day say like, what is one tiny risk I can do today to further my career or reach out to somebody? I don't know where there's potential for rejection, serendipity is always lurking. As I like to say, you never know where that's going to come from, but it could also result in rejection and failure. You just have to mentally overcome that hurdle.

Anita Brick: I have a friend who's a senior leader at a local search firm, and I had a conversation with him not that long ago, and I said, how do you view people who've had a setback in their career? And he said when he started his career in the 80s, if you had a setback, you were not going to be interviewed, you're not going to be hired.

And he said, though, that it's now the opposite. If you haven't had a setback, if you haven't had a quote unquote “failure”, you won't really be considered for very senior positions because it will happen. And like you said, if the muscle is nonexistent, you could take down the entire company. And that was a very important thing for him to share with me, because at a time where a lot of people were losing their jobs, it gave them hope.If you don't have that muscle build, yeah, it's not so good.

Polina Pompliano: That's exactly such a good example.

Anita Brick: And he had his own failure. So here's a slightly different perspective on what we've been talking about. And this isn't a an MBA student. And they said, I won't say that I'm doing something super original, but that it is different enough to be vulnerable to criticism and lots of it at times by people who have been doing the work for a long time. And they've gone well, how do I create a balance of acknowledging their perspective without losing my voice and conviction?

Anita Brick: Yeah. Well, okay. Before you start anything, you need some sort of North Star. You identify your vision and you know the things you are willing to budge on. If you start getting criticism and feedback from incumbents or the people you're trying to disrupt, in my opinion, that's a good thing.

I see it with a lot of startups. The problem is that a lot of people, they talk to their competitors and people in the industry too soon. For example, Sara Blakely, the reason Spanx was successful is because she didn't come from the fashion world. She didn't know how the stuff worked in manufacturing. All this stuff. She came into it completely naive, with fresh eyes.

And then after not telling anybody, not even family and friends about her idea for a whole year, then when she was ready to share it, she already had a patent. She was already like ready to launch a lot of outside feedback and kind of poison your idea and your originality, and it moves you back to the mean. Once you identify all the key elements, you're like, I am pretty certain of this now, you welcome criticism and feedback, because that is a gift that lets you develop a thicker skin, and you start to make sure that your idea is bulletproof against all these criticisms that will inevitably come up.

Anita Brick: I agree with you. My coach would say you need two kinds of, she would put this probably in quotes, “mentors”. At the beginning, you need people who are going to back you so that you build the routes to then how the other kind of mentors might slice and dice it. But you're okay with that, because now it is really about getting it better rather than building as possible.

So shifting gears a little, an MBA student said, my manager repeatedly tells me that I am the protagonist of my career, but I really feel like a supporting character who has been limited because of limited power and limited influence. Any advice on how to flip this would be greatly appreciated.

Polina Pompliano: That's a really interesting question because most people actually see themselves as a protagonist to a fault. So all right. So this is actually very interesting to me. But I talk about this in the book. First you have to accept that we are all the unreliable narrators of our own lives. We tell ourselves stories. In those stories we emphasize certain pieces of information, downplay others. We just store some things. We deny some things. We embellish some things.

Once you understand that your life is a story and you look at it from that perspective, I share. She's a psychotherapist, her name's Lori Gottlieb, and she has some really good advice around this. She says, okay, here's an exercise. Start with a blank sheet of paper. Write about a situation that's, you know, giving you pause or making you stressed out or something like that.

And then ask yourself the following questions. What have you been telling yourself? Who made you upset? What's the problem? And then take out another piece of paper and write about the same situation from the perspective of a different character in your life. So I think this is interesting because if you're writing as the supporting character, whose story are you in?

Who is the lead character in your story? If you're the supporting role? This exercise is really powerful because it allows you to see the holes in your story and the things that you've been telling yourself in. The beauty of it is, if you do it, you'll often find the story that you've been telling yourself that voice in your head that's been telling you that is often not your voice.

It's probably a parent or an old teacher or a colleague or somebody like that who's a voice you've kind of internalized. And if you've never updated that belief about yourself, then it sticks. And I learned this after reading the memoir of Tara Westover called Educated. In It, she's like, my whole life I held homophobic, sexist, all sorts of awful beliefs. But then I realized, hold on, these aren't actually my beliefs. This is my dad's voice. Because as a kid, you don't really question things. You just absorb like a sponge. Figure out whose story you think you're supporting character in, and then work to revise that story.

Anita Brick: I like that. So one thing that came to mind was an alum, in the book, you talk a lot about gaining wisdom from a variety of people. And she was saying, you talk about taking advice from the best, make solid choices and decisions. Well, I think this is terrific. I find that many people are not open or do not have the time to meet with me and share their wisdom. How do you advise someone to find people who would be open, or has to gain others’ wisdom, without needing to speak to them directly?

Polina Pompliano: So this is one thing that I actually have really practical advice on, because when I graduated from the University of Georgia, I really desperately wanted to move to New York City. And I didn't know anybody there, and I was just cold emailing as many people as possible. What I found is that if you're reaching out cold, this is the following framework that I found works. And also when people reach out to me, these are the emails I'm most likely to respond to.

So first, briefly comment on something that the person you're reaching out to has done that you really enjoyed. So for example, hey Paulina, you recently wrote a book that really resonated with me, something like that. Then follow it with something that you both have in common. For example, I'm also a Chicago Booth student and then ended with your ask: I'd love 15 minutes of your time to get some advice on X, and people love giving advice, especially to current students or young alums or people that have something in common in this whole thing does not have to be long. In fact, I suggest and recommend it is short and to the point because, you know, people get emails all day.

They just want something short that they can see, literally three very short paragraphs with this information. The second thing I would say is, even if you don't have access to these people, you don't have to personally know your mentors in order to learn from them. Tyler Perry, you know, the actor, director, writer, producer, he grew up really poor, and he didn't have any people who had done what he wanted to do.

But then every day that he came back from school, he would watch Oprah Winfrey. He learned a lot from her just by watching her and never having met her. So the point is that you don't need to personally know your role models. You can study the paths of those that you admire and learn from them while charting your own path. And in my case, that's how I started my newsletter, the Profile. And I just started writing about people based on information that was already out there in so many of those deep dives that I did, without ever having talked to the person, somehow got to them as a result, have been able to interview them. For example, Danny Meyer, famous restaurateur, Shake Shack lover, Madison Park. I wrote about him without ever having met him. Then he saw it, and now we're having lunch next week. So it's like, yeah, it's like things like that. You never know. My friend David Perel said. Everything you put out into the world is a vehicle for serendipity. So you never know. That newsletter you write, that podcast you put out, you never know whose eyes it might land in front of. So just put it out into the world and see what happens.

Anita Brick: I agree, I'm sure you and I could chat for hours about all of those. I like to call them coincidence. I'll just go ahead and keep things. So many people are good at that first interaction. They find someone and they talk to them, and it doesn't go anywhere because they ask the wrong questions. You talk about questions in the book. This is from a friend of CareerCast. That person said, in your book you mentioned that people are only boring if you ask the wrong questions. What advice would you have for finding the right questions to ask and avoid boring the other person?

Polina Pompliano: Oh, that's so good. If you've ever listened to Ira Glass in This American Life, the whole point of that series is to document a human being in all their flaws, quirks, ideals, beliefs, opinions, and allow the listener to kind of form an opinion about the person on their own.

And I find it fascinating because some of the questions they ask really draw out really fascinating stories and beliefs without judgment. One, that's a good reference, just to hear the types of questions asked when I talk to Humans of New York photographer Brandon Stanton, he told me that there's three questions that he uses that build intimacy in a very short period of time, because that's what he has to do.

He sees somebody sitting on a bench. He goes over. He's like, how do I build intimacy with this person quickly. He asks them, what's your biggest struggle? How has your life turned out differently than you expected it to? And what do you feel most guilty about? If you notice in all three of those questions that there's kind of a delta, there's a what you thought would happen and then what actually happened.

So in my opinion, I think the best questions trying to find the gap between expectations and reality, how that person thought things would pan out and how it actually turned out differently, and what lessons they learned from that experience. Everybody has an experience like that in their life, whether it's personal, professional business, but it's just finding those questions.

And also, I noticed that when I talk to someone, I pay attention to the subtext of what they're saying when they see something. Sure, that's great, but look at the things that they kind of downplay or the things that they try to boast about. You want to tap into that like, well, okay, wow, okay. That's interesting. You moved from another country, but you kind of like glazed over this period of your life. Tell me about that. Was that difficult for you? Whatever. So try to listen beyond just the words of what they're saying.

Anita Brick: I think that takes skill. Listening is an underrated skill, even though people talk about it all the time. And yet if we listen, we can build enduring relationships. And an alum was talking about this. He finds it challenging that relationships of all kinds, including those at work, can be challenging. How would you advise someone to keep relationships fresh and continue to view them as an important marathon, rather than as people who are easily replaced?

Polina Pompliano: Wow these are really, really good questions. So I've found that normally a high quality partnership, whether it's personal or professional, the key for longevity is to stay curious and keep each other intellectually stimulated.

The people who learn together, I find, tend to stay together, even if they work in different industries. If they can teach each other new things that's super valuable or experience something new together. I hate to keep going back to, but it's just top of mind. Sarah Blakely is married to Jesse Ensler. They have a number of kids. They've been married for a very long time, and someone once asked her about her marriage to Jesse. She said, 80% of our marriage is just ideas. They talk about ideas, they test ideas. One of them does a 100 mile race, and then the other one does something in her business, and they're able to cross-pollinate those ideas and talk about them. I think that's the key to enduring relationships.

And then the second thing that comes to mind is in the book, I talk about John Gottman. He's a psychologist and kind of like marriage counselor, therapist person. Every single day you and a partner make requests for connection, which he calls bids. Let's say your partner's a bird enthusiast, or they really enjoy something as a hobby and they tell you, hey, look at that cool bird right there. In the very act of whether you turn your head to look or not and determine and predict whether this relationship will last.

It's the idea that most people are like, oh, if I have one blowout fight with my business partner, or one blowout fight with my spouse, that's going to collapse the whole thing. The truth is, it's never just one blowout fight. Relationships often fall apart because the partners have eroded the foundation of trust by constantly disrespecting each other in small ways, not looking at the bird when the other person asks you to look at the bird, or not putting your phone down when you're talking to them. Daily small moments of respect, like those micro moments, are actually what determine the health and longevity of a relationship.

Anita Brick: It's a really good point, and if it is the professional relationships advocates, mentors, sponsors that you have, what you're just saying, correct me if I'm wrong, is that each moment you're with them, number one, you may not see them again for whatever reason, right?

In those moments, you have to pay attention to how you can share yourself, but also pay attention to that.

Polina Pompliano: Exactly. Now I was just going to say nothing is more flattering to another person than giving them the respect to pay attention to what they're saying.

Anita Brick: Right. So an alum asked a question about gratitude and your concept of hidden genius. I have a passion for observing how people treat one another well. I do pay attention to the reality around me. I like to zero in on the positive value people create. How does gratitude align with your concept of Hidden Genius?

Polina Pompliano: Gratitude is present in my everyday life. Just because I take nothing for granted. Because I also know what it's like to have nothing, and how fine of a line that is for most people. One day you have a job, then I say there's a recession, you're laid off, you don't have a job. The people who can't be satisfied with the small things and appreciating the small joys in everyday life, will never be satisfied with the big things either. So I always keep that in mind when looking at some of these, you know, successful people.

It's like, are they actually happy? Like that's an underlying question I have is I'm researching their stories. Yes. Okay. They may have succeeded in pursuing their goal, but are they actually a fulfilled happy person? Have they had a life well-lived? Because I think truly success doesn't exist in a vacuum. And everybody's going to have problems and traumatic experiences in their life. But it's all about, am I continuing to find joy in the everyday things that I'm pursuing? Otherwise, what's what's the point of doing anything?

Anita Brick: I agree. The following question is how does it sync up with Hidden Genius?

Polina Pompliano: In the conclusion, I have ten questions to help you discover your own hidden genius, and one of them is when is the last time that you bet on yourself? It implies ambition, which a lot of people confuse for never being satisfied and always wanting to reach the next goal. But in my opinion, if you have found your true hidden genius, that ambitious goal that makes you feel purpose and completely fulfilled in your life, something no one can take away from you, that's the thing that you're most grateful for, is that every day, live your work and your purpose.

Anita Brick: I love that. So do you have time for one more question? So when you think about it, what are the top three things that you would advise someone to do so they can succeed when the odds appear to be against them and actually go farther than they did before?

Polina Pompliano: Oh, okay. The first is I heard this from LinkedIn founder Reid Hoffman, and this can be applied to any area of your life, whether it's your career, a business you're starting or a personal relationship.

It's consistency, plus time equals trust. And the whole point is that when you're consistent with what you say you're going to do for a long period of time, you will earn people's trust. What many people say trust is not automatically given. And I don't think we should assume that just because we meet somebody new and we are a trustworthy person, that people should automatically trust us.

The reason that I started my newsletter, the Profile, in February of 2017 and I haven't missed a week, even though life has gotten in the way in six years that I've been doing it, I've always put in place guardrails that even if something happens and I can't write that week, I can send something in may not be the top quality, but I'm keeping my promise to my reader. Hey, you will receive this newsletter every single week for the rest of your life. But in doing that, it started. I was a free newsletter now member will be charged for it, and people were willing to back it with their dollars because they know that I've earned their trust and I'm not just going to one day stop doing it without telling me.

So consistency plus time equals trust. The second thing I would say is make sure that you tie your identity to your own name. And what I mean by that is when I graduated from UGA with a journalism degree, I had some success in college. Quote unquote “success”. I was editor in chief of my college paper. I had interned at places like USA today and CNN. All my professors were saying, oh, you've checked all the right boxes, you've done all the right things. You will 100% get a full time job. So then I started applying to jobs and quickly I lowered my bar for what I was applying to, not just that I felt really, really aimless. Not only did I not have a job, but I would go to parties. All my friends would be like, well, I work here and I work at BCG and I'm a JP Morgan. And I'd be like, well, I did all the right things, why don't I have a job? And I realized that up until that point, I had always tied my identity to something external, like a job, like an internship, like an editor at the college paper.

And suddenly all I had was my name. But I wish that I knew then what I know now, which is that you can start something under your own name. It doesn't have to be validated by an external authority, figure or institution. And in doing that, you're actually doing something you enjoy. I never thought my newsletter, The Profile, would grow to the extent that it has.

I honestly just did it as a side thing while working at Fortune, simply because I liked reading long form profiles. Never did I think I would leave my full time job to work on it 100%. Whether it's now or then. I've always kept in mind, don't hire identity around a job title, a relationship, something material like a material possession where you live because in one instant it can be taken away from you.

Yeah, I read Oprah Winfrey in her book. She said, talking to CEOs, make sure you don't tie your identity to something that you could lose in the blink of a board meeting. In one second, you're a fortune 500 CEO. The next second you're not. And that's a disaster for your self-esteem.

The final thing I'd say is be careful who you take advice from. I used to really, really respect and idolize people, mentors, professors, people like that. They meant well. The problem with meaning well is that depending on where they are at in their life and their level of ambition, they can't think bigger than what you might be thinking. When I was looking for jobs, so many people told me, oh no, you should definitely stay in Georgia and take a job at this small paper in this rural city in Georgia, because it's a job and you can always grow from there and go to like the local TV station or something.

Those weren't my aspirations. I would rather be a janitor in New York City and learn and soak up everything I can and make connections that way. Then just go and be a local reporter in Georgia. To me, it really mattered where I was, even though it didn't exactly matter what I was doing. I've learned over the years that it’s fine to seek advice, just know again, like we talked about earlier, your North Star and the things you are unwilling to budge on because I knew I would be unhappy in the first scenario. I would be very happy in a bigger city where I've. I've always loved being the small fish in a big pond. Just be careful who you surround yourself with and always take their advice with a grain of salt.

Anita Brick: I agree, I think that is very sage advice and I'll give you one more opportunity. Is there anything you didn't share with us today, or a question I didn't ask you that you were really hoping that I would know.

Polina Pompliano: These were all amazing questions. There's only one thing I'd like to add, because I think a lot of the questions are about failure and kind of succeeding in the face of all odds is somebody who has a different advantage point than a lot of people.

I was born in Bulgaria. We moved to Atlanta, Georgia when I was eight, and then for my adult life, I went to New York. So I have all these perspectives. But the one thing that I always tell people that they see as a negative thing is that the power of being underestimated cannot be overstated. I think I'm used to being an outsider, and that's given me such an advantage because I can see things for what they are and not allow judgments to really rattle me.

So, for example, when I was at Fortune and I was starting to write Term Sheet, I didn't have many connections in Silicon Valley. I didn't know many of the venture capitalists or the or the startups. So I started meeting all of them, and I just wanted to meet everybody and talk to them and see what they were hearing and kind of get a sense of the of the ecosystem.

In a lot of times, if somebody hadn't looked me up beforehand, they think Fortune magazine, they think like the people who broke the Enron story. They didn't think a 26 year old who looked like me. So when I would walk into a room, I knew that they had preconceived notions of what I would look like or I sound like, or my approach.

When they saw me, I could immediately sense like, oh, okay. They kind of like, like, oh, definitely underestimated, but just judgment. I knew I had like 30 minutes or an hour to really earn their trust. What they didn't know is that I had done so much research and I was so well prepared that when I stepped into that meeting, I asked them the right questions. I knew their business. I wasn't what they expected me to be. And I think again, like that, expectations versus reality. Some of those relationships allowed me to get scoops, allowed me to get really, really deep relationships with these people that other reporters didn't have access to because they had a superficial relationship. Knowing that you're going to be underestimated. It shouldn't be an insecurity. It should just be more fuel to achieve what you want to do.

Anita Brick: I love that, and I do think that when people are super prepared, most people don't do what you did. I would guess in a very short amount of time. Got them to pay attention. Really great. It shows in the diversity of the experiences that you share in Hidden Genius, and that you love it, that you are truly passionate about it, that makes all the difference. So I know you're super busy. I thank you for making time for us. Really, really appreciative.

Polina Pompliano: Thank you so much. These that this is one of the best, interviews I've done in a while. The questions were really, really great.

Anita Brick: I'm glad. And thank you all for listening. This is Anita Brick with CareerCast at Chicago Booth, keep advancing.