How to Fail Well and the Similarities Between Business and Dating (I/II)

Photo by Michael Dziedzic on Unsplash
Felipe Cerón, Contributor

Felipe Cerón (MBA ’22) interviews HBS professors about their failures and what they learned from them.

How do we fail well? How do we learn from it? How do we get comfortable and move on fast? Should we share our failures?

If you are anything like me (and I would place a bet most HBS students are in this sense), you want to improve and reach the best possible version of yourself. The tough part is that lofty goals usually come with lofty failures. It is pretty inevitable unless you are some kind of superhuman.

But is it even the correct name? Failing? If the experience led you to learning, to becoming a better person, to becoming you, then why does it have such a bad connotation? Why do we run away when there is a scent of failure in the air?

We interviewed HBS professors to get their take on the matter and even got some dating advice.

On the first article of this series, we talked to Christina Wallace (MBA ’10) to get her perspective on failure from an entrepreneurial point of view. You might recognize her as the protagonist in the Quincy TEM case and from her TED talks, one on optimizing online dating (which has 2.2 million views) and another one about the future of work

Christina Wallace (MBA ’10)

Wallace is multifaceted to say the least. When it was time for her to decide on a degree she chose not to choose, majoring in math and theater, with additional concentrations in music, physics, and political science. When asked about what languages she is fluent in, she mentions English, math, and music, which led her to self describe as a human “Venn Diagram,” developing her career at the intersection of business, technology, and arts.  

From her talk about the future of work, we see the value of Venn Diagram people and how they are called to power the future and current challenges. Narrow jobs are disappearing, being replaced by creative opportunities that demand more well-rounded approaches. Nevertheless, we still tend to categorize people into boxes. Are we missing out on forcing people into boxes they do not fit? Are you putting yourself in a box? 

Wallace is now a Senior Lecturer at HBS and a coach for early-stage founders. She is also the co-creator and co-host of The Limit Does Not Exist, a podcast at the intersection of STEM and creativity. In summary, she is an entrepreneur-writer-public speaker who writes computer code and sings Gregorian chants.

How do we fail well in entrepreneurship?

It is important to distinguish types of failure. Particularly, in entrepreneurship, there are two. The first one is when you run an experiment and the learning was not what was expected. The second, and more relevant one, is when the company fails, which feels like a moral failure, or coming up short. Here is what is important to determine: Can I fail in a way that still keeps all my values and does not hurt others or minimizes their efforts? Do not focus on spinning it so you look like the good guy, focus on your values and the people you will affect. 

In general, to avoid this type of failure, always keep an eye out for how much you have to sustain your venture. This means, after paying off all your obligations, what is left? Is it safe enough? That is diligent management.

Another thing to look out for, and a prevalent characteristic of early-stage founders, is that at times they are too optimistic. This can lead to a distortion of reality and to taking unjustifiable risks. While optimism is a key trait for a successful entrepreneur, it is important to maintain one pinky toe in reality and assume your failures when you should.

What are your best tips for dealing with failure? How do you pick yourself up? Do you talk to people about it or keep it to yourself? Any rituals?

My initial reaction after being fired from Quincy was to go into myself. I was isolated and spent three weeks without talking to anyone and finished West Wing in the process. This was not the right strategy, because I didn’t have any more answers than I did before. I haven’t moved forward. Nevertheless, I did need some time to process.

My suggestion is to take the time you need, then reach out to your community and let them help you. What really helped me in that process (70 coffee chats in 40 days) was that I maintained a radical vulnerability. There is no shame in failing, so when reaching out, don’t mask it. This led me to realize that other people also have similar failures. You would be surprised. They are not that open about it until they find someone that shares the experience. 

Additionally, get as many different data points as you can and never over-index on one opinion. Sometimes the more loose the connection, the better, since they are more likely to tell you things that you had not thought about.

Finally, as a ritual, after going through my isolation period I went to an Irish wake for dead startups and took a shot of whiskey for mine.

How do we get comfortable with failure? 

When I worked at Bionic I constantly pitched deals to Fortune 500 companies. A lot of them didn’t work out. In these situations, I practiced self-reflection to figure what was my responsibility and what was out of my hands. Was I unprepared? Not listening? Did I understand the underlying motivations? I remember I had six to seven meetings with one CEO and I felt it was going great. At the last meeting, the project was dead in the water from the outset. 

Regarding things out of my hands, I ask myself, was it wrong timing? Wrong context? You need to understand which part of the failure corresponds to this category, so you don’t berate yourself with it. You would have too many bruises, and it would not be fair since not all are deserved. 

To be more comfortable with failure just fail more often. Failing is the same as any muscle, it needs to be worked. Find opportunities to do things you would probably suck at and do them! Join an improvisation club or whatever feels challenging for you. At the end you will realize that no matter how many times you screw up, life goes on.

In summary, don’t shift the blame or shoulder the blame, accept it and realize it takes practice not to be awkward or uncomfortable about it. 

How would you motivate people to be open to sharing failures? Is this a thing we should be doing?

Practice sharing with people you trust in small circles. Then you will realize how common it is, and a sense of obligation creeps up. You will benefit from the experience, and you will feel the need to help by being more open about it. A particular area that suffers from this is the fertility space, specifically miscarriages. A lot of families experience it but nobody talks about it, which could be beneficial.

Do you regret going on the path that led you to your failures? 

I don’t regret anything, it is not a useful feeling. Besides, you can learn from everything that you experienced. When I think about regret, I think that you don’t know what could have happened, so it doesn’t make sense to wonder what if.

With the things that really hurt, the ones that don’t go the way you wanted, just sit with the pain and find that silver lining. I usually think that I don’t want to repeat a situation like that, but that the ride was fun. And I am now myself because of that. A different version.

Why did you go on a one week solo trip to Maine? Do you recommend solo trips? What did you get from it?

Traveling solo is a great way to learn about failure.

I started when I was 22. I traveled to Western Europe, Central America and during my MBA I spent five weeks in East Africa, where I climbed the Kilimanjaro. I must have been to 20 countries in backpackers hostels. I knew what my first night upon arrival would look like and not much more. I made plans along the way.

It is a great way to practice failure because you are going to have setbacks. It is super uncomfortable at the beginning. Being a pale Irish girl I had a third-degree sunburn in Central America. In Zanzibar, I dealt with a big blackout and had no flashlight. I couldn’t see my own hands. These situations force you to be resilient and focus on the positives, like meeting a ton of cool people.

Maine was the summer before I turned 30. I forced myself to stay by myself since I needed to process some stuff alone. It rained, I read, journaled, hiked, ate smores, and threw a whiskey bottle at a raccoon that was stealing my smores. 

I had to work through why I had been successful in my career but not in my relationships. I had been back to back dating wrong people. I tried to apply the same problem-solving skills I used in my career to my love life, so I mapped out how I identified my potential partners and tried to understand where I was screwing up, what traits or signals did I really care about? This led me to conclude that the things I cared about were hard to identify online. Since I still wanted to go on online dates, I developed a system that would help me be more efficient, the Zero Date—one drink, one hour in which the goal is to learn if I want to have dinner with that person. I realized that I did not need a dinner’s time to realize if I wanted to see the person again. One hour was enough.

But for Zero Date to have a high chance of success you need to do some pre-work. The first part is improving the quality of the funnel. You need to understand what you are really looking for. It is the same as a sales funnel, you qualify metrics to know if the lead might turn into a deal. Determine what these metrics are for you and apply them to the funnel.

After some introspection, I realized that I was focused on winning, on whether they liked me and not if I liked them. I should have been thinking about what do I really want and what does success look like for me. If you get a one in a class but you don’t like it, does it make sense? Is it time well spent? Ask yourself, do I actually want this or is it because everyone else is doing it and it would feel great if I get the offer? Don’t win a game you don’t care about.

Do you think there’s a parallel between dating and failing and business and failing?


When someone doesn’t like me, it’s not because I’m a terrible human being. More often than not it is not about you. Getting to know you only so much, probably means that it is more about them. Never take it personally. Same as business! Stop self-flagellating, instead self-reflect, and avoid a downward spiral.

Going back to failing well, in relationships I have seen that ghosting is a thing. I feel that early on it’s ok, but doing it mid-term because you want to avoid a difficult conversation is bad because you can really hurt the other person. Failing well in a relationship is also important, don’t be a bad person. 

Your TED was in April 2018, What do you think about online dating now? Do you think it is a good thing or the traditional way is better? 

I think photo-based swiping is a terrible way to find meaningful relationships, it is more like a game than an intentional process. The mechanisms of swiping trigger the same reward as gambling does. If you are just interested in meeting a person that you will see only for the night it might be fine, but if you are interested in something more serious it could turn into another game you don’t care about.

On another note, online dating doesn’t have to suck! Just don’t treat it like a game, don’t treat it like a resume review. Use it to source and qualify leads and then go offline quickly.

Another option is the matchmaker route, which is tailored to busy young professionals and is more effective. It’s basically like having an executive headhunter connecting people for dating. It is not cheap, but they will keep their eyes open until they find you someone.

Are people moving away from traditional methods of dating? Are people scared or just too busy?

It can be hard to break through the signals-to-noise ratio, especially for young professionals in a big city. It’s hard to make time for it, everything feels so urgent and expensive. Nevertheless, I feel old school is not dead, it is harder than before, but it’s still there. For example, workplace romances still exist, because you are forced to interact multiple times in close proximity.

I think people do feel different if it is a traditional interaction because online you tend to Google and get a lot of information. This is something we grow used to, and tend to expect it, so when we don’t have it feels different.


How should we navigate it to obtain the best return with the least setbacks?

Focus on learning from yourself, what does and what does not matter. For example, I wouldn’t have met my husband if I had used my pre-Maine criteria. I would have never seen my husband’s profile because he is two years younger than me and my height (Wallace is six feet tall). After my trip, I realized that what I really cared about was the life mindset of the person and the stage of life they were in, like if we wanted the same things at the same time.

What would you say to HBS students about failure, particularly how to deal with it after it happens?

Particularly at HBS, by definition, students must have been really successful, so this implies that they haven’t experienced failure often. The downside of not failing often enough is that it can lead to feeling that a small failure is bigger than what it actually is. Given this, I would say accept right now that you will fail in business and in life, several times. Do some pre-work, ask yourself what happens when I fail, how am I gonna pick up? Who am I going to show this and allow to help me? Now when it happens, let it hurt, don’t ignore it, and don’t spin it into a story that ignores reality and prevents you from healing. Get up, take a shower, and move forward. 

All of this will make failing less shocking in that moment, because you already started on the assumption that you would fail.

If you get to your deathbed never having failed meaningfully it means that you didn’t take any real risks. It means that you missed out on opportunities. And that’s a true shame when you have the talents and the privileges that this student body has. 

Further reading on the topic recommended by Christina Wallace:

For the next article in this series, we will interview Professor Iavor Bojinov, who has some notorious insights on failing from an Academia perspective.

Felipe Cerón (MBA ’22) is a Chilean who previously worked in consulting and retail. He is a musician, and he is an avid fan of film and television. Having a laugh over a beer, getting in a challenging workout, and reading inspiring books are among his favorite pastimes. While he thinks sparkling water is the best beverage ever created, he is also currently the owner of the most luxurious home bar in SFP. He sure hopes to learn a lot about failure before finishing his MBA.