Hi. This is Dan Morrell, host of Skydeck. There's this Teddy Roosevelt quote about struggle that I came across recently that I really like. Roosevelt said, "There's never yet been a man in our history who led a life of ease whose name is worth remembering." Roosevelt said that in 1902, but it's a message that feels increasingly relevant, I think especially of Silicon Valley and its cultural acceptance of failure, which is so prevalent that there's even been conventions like FailCon based on the idea. But as much as you can gain from your struggles, it can still be hard to share those publicly. Nevertheless, we set up on Spangler lawn at Spring Reunions and asked a few brave souls to recount some of their greatest challenges and tell us what they learned from those experiences.

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David Teten, MBA 98'. I founded a company and raised $2.25 million for it, and then we shut it down. We certainly made a lot of mistakes in building out the company, but my number one piece of advice for the HBS community is that HBS offers incredible optionality and optionality declines with each year. So out of HBS, you can take almost any job and then that very rapidly declines and your career is subsequently path dependent, so I certainly didn't appreciate how much it impacts the overall trajectory of your life if you have a failure earlier on.

I am one of the few VCs who actively discourages people from becoming entrepreneurs precisely because I know the risks. I think you should not do it precipitously. There's an aphorism in our industry that CEO is the new analyst, because a lot of young people want to be startup CEOs as opposed to taking traditional entry level job, and I think that's a mistake and there's a lot of experience that you gain by working for a reputable firm and getting training, mentoring that will lower your risk of failure later on. Everyone wants to be Bill Gates and Zuckerberg, but those are the outliers. That's not the norm.

Mia Mends, class of 2003, section G. Seven years ago I discovered a company that I thought was amazing. Sodexo is a French company, Global French Company. I just fell in love with their mission and their values and their lens of the world, and their role in it as a corporate citizen. So, I was very determined to work for them. There was a job that was posted actually on the HBS website and I called the headhunter and I said, "I really want to interview for this job." Sodexo's a food service company principally. I was in financial services, and the headhunter said, "You've got zero experience," and I said, but I love this company and I think that my skills are transferable. Please let me talk to him. So he arranged the interview and I went and I, of course, I didn't get it.

I wanted it so terribly and I remember so well at the end of the interview, a couple days later, one of the woman who interviewed me was an African American woman. I'm an African American woman and she said, "I wanted this job to be yours so badly, and you're obviously smart. You're well spoken, but you lacked executive presence." And I sulked about it for a while. I internalized it. And when Sodexo called again, they invited me to come to Sao Paolo, Brazil to interview. And I fell in love again. Three months later they called and invited me to come run sales in Latin America.

I had never in sales. I needed to speak Spanish and Portuguese. I spoke in neither language, but we packed up our bags. My husband quit his job, we sold our house and we took our two children, who were at the time one and four, to Brazil. And I think about the risk they took and the risks that I took to do that job. One is I certainly think I made a better second impression, but I think that I revealed my authenticity and I revealed my vulnerability and they knew that I would not suffer in silence.

It was the hardest thing I've ever done. It changed who I was. It literally changed who I was. Learning to… operating and leading in two languages that you did not understand. I was operating from a deficit at day one and it took me a good year to feel like I could actually contribute meaningfully. But I became an introvert, so I relied on other skills. And I did leave that experience triumphant, but it just gave me a heightened sense of sensitivity and awareness for being another. I was the only black, the only American, one of two women at the executive level, and certainly the only native English speaker, and I have carried those learnings and me into my new role. I'm CEO of Sodexo's US business for one of their lines of activity. So, I think it has made me just a better, more effective, more compassionate leader.

Archie Jones, class from 1998. Post Business School for three years I worked at Parthenon Capital. I had a great start of a career there. It was a continuation of my private equity career from prior to school. And I got the idea that I would go out and find a company to buy and run, move to Atlanta with my young family and spent two years looking for the right company and spend every dollar I had and the few dollars that I didn't have.

While a wonderful experience searching for a company, it certainly was a financial hardship. I spent a couple of years working actually in the social sector. I went back to some social sector routes that had gotten planted here at HBS. Then actually got called up by one of my portfolio companies that I had led as a private equity investor and ran M&A and strategy. So that was my coming out of that.

What I found most interesting about the story is I left Parthenon Capital to go buy one company, and a few years later I'm running M&A and strategy for a public company and did 17 acquisitions around the globe. I think of it as kind of one of those best laid plans stories. Sometimes it doesn't work out exactly the way you wanted it to and it takes a circuitous route to get there, but certainly it has been a fantastic journey.

Eisha Armstrong, class of 2003. I'm thinking back to 2009, very interesting time. The company that I was working for was doing a reduction in force and was part of the group who had to decide how to reduce our workforce by 25%. That was the first time I'd ever been through a situation like that. Really hard, kind of walking around with the knowledge of who was going to lose their positions and after I got through that I had a hard time pulling myself out of it and focusing on future growth of the organization and rallying the people who were left and really started to doubt whether or not I was cut out to be in business. So when we pulled up in the summer and realized that we had to do another reduction in force I went to our Chief Operating Officer and asked if I could take a package.

My kids at the time were one and three. Obviously, I was still just kind of psychologically marred by what I'd been through and needed some time to reflect on what were my priorities and did I want to stay in the for profit environment and things like that. Thankfully he said yes, but I didn't have a plan and thought that I would just try to be a full time stay at home mom. Then I thought I would maybe do some consulting but just kind of was like a drift for about two years after that. Then my previous boss reached out and was like, "Hey, do you want to come back?" And, "How about we start something on part-time basis?"

That was great, and I went back and I was very happy. The question that I always ask myself is what would have happened if I had maybe like gone to see a counselor or had been honest with people about how I was feeling as opposed to just rushing to, I just need to leave the organization because my career suffered and I think it kind of took me out of the running, at least in that organization for being considered for a serious executive position.

I don't like to think about what woulda, coulda, shouldas. I think what I learned is that if I'm struggling, it's important to ask for help and talk about it more rather than just running away, which is kind of what I did.

Frank Lorenzo, class of 63'. As a CEO of continental airlines, and before that Texas International Airlines, we faced airline deregulation, which was of course very tough thing since we had been in a regulated business where we had a protected franchise and now we had new competition coming in, in terms of with lower costs and freedom of entry and all those things. So, the question was how do you develop a strategy that is going to give you a fighting chance in this new environment?

That's where C. Rowling Christensen, who taught the Competitive Strategy course here at Business School, which I remember it very, very well about strategic competence and trying to figure out what kind of unique competence we might have, which were essentially the kinds of things that Christensen really pushed forward in those days. And helped us develop a strategy, which ultimately ended up with Texas International, which was a company that got hit with the strategy. Because we had Southwest Airlines starting right on one side, and we had the big guys being able to come into our markets on the other side. We were the ham in the sandwich and developed a strategy where we ended up actually acquiring one of our competitors, which was Continental Airlines, merging it, and that was the current day Continental that we ended up with.

Joyce Lee, class of 2013. So I think it's as far as a professional setback goes or at least at the time it felt like a professional setback was how I navigated my career at my first company, post Business School. So I joined Anheuser - Busch. It was a really cool marketing role in global innovation, and it was a really exciting role for me because it was an opportunity for me to use business school to transition into a new industry as well as the new function.

So the experience in a lot of ways was really great. I thought as far as a professional setback goes, I think at the time I was hoping it would be the launch pad to a very comprehensive marketing experience whereby I would get to make a bunch of rotations through marketing functions and become a really well rounded, strong marketer and work with some of the world’s most iconic brands. The reality of what ended up happening was that I ended up getting deeper and deeper into my function so I started marketing innovation, but I get deeper and deeper into that space and working within innovation in a bunch of different capacities, both in the global office as well as the US owned.

On one hand, and kind of what you talk about externally to the world and on your resume and so on, an amazing learning experience. It's really helped to [inaudible] my careers in so many ways that I really appreciate. But on the other hand, especially at the time, it really felt like a professional setback because that wasn't what I wanted. And I think the other, the other component that felt frustrating about that was that it felt like a reflection of my inability to navigate my career, right? So if so sometimes you can ... I think you really can chalk things up to just bad timing, bad circumstances, whatever it is and give yourself a little bit more space. But for me, I think I struggled to navigate that more successfully in and take more ownership over how to shape my career, and looking back, I think there was real opportunity to have done it and to have done it better.

Certainly the most immediate way I think it's shaped me is in terms of how I coach my team. Right? I think about their career moves very comprehensively versus very myopically. So, instead of just taking the promotion because it was there in front of you, instead of just taking that move because your VP who you really admire, told you to do it. Let's take a step back. Think about what you want more broadly. Let's think about realistically about what the options are in front of you, and unrealistically what are you dreaming of. Understand the whole landscape, and if that, that next step still really make sense. Great. But don't just rush into it because it's right there in front of you.

My name is Seyi Owodunni, MBA 1998, section F. Well, I guess 20 years now since HBS, so there's probably been a few setbacks, but probably the most recent or challenging one was a setback of a fund that I was a partner in, that actually lost a number of key partners and hit a key man risk issue where the fund was frozen and we ended up having the whole team have to disband and a few of us were left to kind of just a rundown the fund and recover the four investments that were remaining that we hadn't exited.

That was a challenge because you felt loyalty to reach the end at a time when there wasn't much of a future for the fund. So it was a difficult time and required a lot of thinking about what I expected in my career at that stage, and was there any value in staying back to complete the task? Which is done more out of loyalty and a sense of duty rather than necessarily the best career progression plan. I think that a life has, and I think careers have challenges. There will always be setbacks. The question is how you approach it, what you take away from it.

I actually honed my exiting skills, how to really negotiate good deals, good exits out of somewhat challenging investments. I completed the four exits, which people didn't think was doable in the timeframe. So I think you take some learnings away from learning some things about yourself that you can apply beyond the setback and feeling like you did not let your investors down because when you went in and raised the funds, you've made a commitment. So even if others have left, so having that sense of duty to complete the task. And I think that is going to build you from a standpoint of when they have reference checks on you and they ask about the kind of person you are. Those types of stories are important.

Humberto Cubillos, class of 1998. On the business level I went to work for Enron, the energy giant that went bankrupt. There's many lessons, but obviously you always need to be focusing on a real business, a real cash flow. You have a responsibility for families of shareholders and all stakeholders involved. Values are the most important when you are in any organization and making sure you're doing things right, not playing with accounting books and doing things that hurt a lot of people at the end of the day.

On a personal level, I lost two children. My wife was expecting triplets. Happiness comes within. It doesn't matter what happens to you, the choices you make is the ultimate. Obviously happiness again is built from our inner strength. So those are basically one of the business level, one of the personal level. We always continue to strive.

Skydeck is produced by the External Relations department at Harvard Business School and edited by Craig McDonald. It is available at iTunes or wherever you get your favorite podcasts. For more information or to find archived episodes, visit alumni.hbs.edu/skydeck.

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