109 - Building for the Future: Investment in Loss (Part 2 of 2)


career design

Last week I asked a question. What do you look for in a hire for your early-stage startup, for your less-than-30-member unit, or for your tiny 0-to-1 unit? We explored ex-Meta and ex-CZI operator Molly Graham’s J-Curve. I promised to share one other way of sussing out critical early hires.

Before we dive in, here are the highlights of this piece:

  1. The earliest hires in your fledgling startup or business unit will have to frequently take on new challenges and experience a lot of failure. You can offer them psychological safety but there’s a kind of pre-permission they need to grant themselves to expand their minds and develop their capacities to take on challenges.
  2. Investment in loss is not resisting the urge to look good in early skirmishes during the learning process. It is actively seeking out painful encounters because we believe on the other side of such self-punishment is the possibility for growth. Growth comes at the point of resistance. The more we struggle, the more we stand to learn.
  3. Doing new things and sucking at them is hard enough. But doing so when being watched is ten times harder.
  4. Tolerance for discomfort is a good barometer for future success. The good ones tolerate discomfort better. The best actively look for / create discomfort.
  5. Deliberate practice is one way of creating discomfort. Test yourself every day, regardless of how you feel.

Josh Waitzkin is a former chess prodigy.

When Waitzkin was nine, a book about him came out. It was called Searching for Bobby Fischer, after Bobby Fischer whom some believe to be the greatest chess player ever. The book sold enough copies to be made into a movie of the same name. That brought loads of attention to a teenaged Waitzkin and, paired with a coach who tried to change his natural style of attacking chess, he lost his way. Chess became a chore. He gave it up.

This is the point where most prodigious life arcs would return to normalcy. Not Waitzkin. This was the start of his remarkable learning journey to becoming a world champion martial artist, a bestselling book author, and a highly sought-after coach to the best from the finance and sports worlds.

So, what does polymath Waitzkin have for us? Waitzkin is a conceptual learner. He’s able to break down a new pursuit (a martial art, a sport, any discipline) into its key concepts and work on each to reach an expert-level proficiency. He also tends to do all of this in a very short time. And he seems particularly good at applying principles from one discipline to others, further turbocharging his learning process.

Among the learning strategies Waitzkin applies across disciplines, there’s one that strikes close to your business challenge of finding the right hire for your fledgling setup. That principle is called investment in loss.

The desire to look good while learning

Picture this. Waitzkin is learning how to foil. Foiling is a water sport where you’re standing on a surfboard and holding on to a wing. The surfboard itself is elevated above the surface of the water, on a two-and-a-half-feet mast, so you’re propelled frictionless at high speeds.

>>>>> gd2md-html alert: inline image link here (to images/image48.jpg). Store image on your image server and adjust path/filename/extension if necessary.
(Back to top)(Next alert)


Foiling is a kinesthetic skill, the very opposite of chess in which Waitzkin achieved expert status. How does Waitzkin teach himself to foil? He creates a set of conditions conducive to repetitive failing and learning.

_So zooming out for a moment, the way I think about taking on these arts, it’s understanding what are the component parts and doing lots of reps in them so that you’re comfortable with them, then putting them all together. So my learning process won’t look great in the first couple of days or couple of weeks. And I’m not concerned about that. _

Working for a startup or a small set-up puts you right up close to all the component parts of building a product or running a business. You’re getting multiple shots at figuring things out—think of them as waves—and you’re getting quick feedback from each.

But you’re in the weeds. You’re making a ton of mistakes and feeling stupid all the time. It’s un-sexy and disorienting because you’ve not done something as hard or failed so badly. At this point, you may say, this life sucks! and try and optimize for your immediate state (get an easier role or get a cushier job and restore your confidence).

This is a kind of reaction Waitzkin sees around him among foiling learners:

I think that a lot of what’s happening in surf culture and foil culture is people have these Instagram accounts, and they’re always posting videos of what they’re doing, and they have to look cool.

Take a cursory tour of social media and such signaling catches the eye. It is common to find those with intermediate-level proficiency overstating the depth of their experience with well-curated stories. It’s hard to shake off the immediate public gratification that comes with it.

So, the reason Waitzkin learns so quickly and thoroughly is because he’s willing to look stupid?

I mean, embracing looking absurd in certain moments is a very interesting hack to what others might not be taking advantage of in the learning process. I mean, I went over hundreds and hundreds of boils on the eFoil and learned how to absorb them.

Say you’re proficient at performance marketing. You know how to set up campaigns where you pay Google to bring you traffic. But say there aren’t dollars to spare. Could you solve the discovery problem leading to long-term demand without burning cash all the way? Trying something new—brand marketing?—may mean failing. It may mean having to own bleak numbers for multiple quarters.

At this point the desire to look good steps in. For someone un-invested in loss, a few failures may usher in an occasion (weekly reviews?) to put up a stirring defense. ‘Because we’re spending too little money’ or ‘I told you, our website is a mess.’

Offering ready reasons exudes certainty. Whereas a simple ‘I don’t know’ or ‘let me find out’ would convey doubt. What comes with certainty? The appearance of confidence. What else? An aversion to learning. You’re no longer invested in this loss-making endeavor called learning.

How can one get out of this pit of certainty?

Learning not to resist (when you are being watched or have been successful already)

If a big strong guy comes into a martial arts studio and someone pushes him, he wants to resist and push the guy back to prove that he is a big strong guy.

This is Waitzkin from his book The Art of Learning. He’s talking about Tai Chi but it may be about a situation at work.

Sometimes, a new hire, like the performance marketer I presented before you, comes full of preconceived notions about how things should be and looks to change things up without understanding the ecosystem that the problem is a product of. To such a hire, those who came before were idiots. Unfortunately, this curious phenomenon isn’t limited to those starting out. It is known to happen across the spectrum.

Learning not to resist is hardest when you’re being watched and you’ve been successful publicly in the past.

_The problem is that he isn’t learning anything by doing this. In order to grow, he needs to give up his current mindset. He needs to lose to win. _

Waitzkin is advocating perspective-taking. He’s calling for anyone in a new role to submit to understanding the new reality of that role before rushing to employ their pre-existing mental models. Those models or heuristics may have helped them previously in getting things done faster or better but that doesn’t guarantee a similar outcome now when the underlying reality may have changed.

As Waitzkin notes, It gets harder to give up the ego as we rack up notches in our career.

It’s very interesting to observe who the top competitors pick out when they’re five rounds into the sparring sessions and they’re completely gassed. The ones who are on the steepest growth curve look for the hardest guy there, the one who will beat them up or who might beat them up. While others will look for someone they can take a break on.

Investment in loss is giving yourself to the learning process. Whether you’re being watched and whether you’ve been successful, it is about giving up your default problem-solving methods so that you allow yourself to pick up new ones.

But why is it so hard? Why do seasoned professionals choose to exploit that same bag of tricks over exploring a new one? Why are they in such a rush to affirm their competence?

‘I used to have a Beginner’s Mind. All I have now is the Knower’s Syndrome.’

A friend of mine who works closely with entrepreneurs outlined his vision for his venture studio. He was clear that it is the youth who will make a telling difference. He was clear that if he has to err, he would err on the side of investing in youth. Youth as operators, youth as entrepreneurs in residence.

The middle-aged me was taken aback. I thought it was ageist. But the more I thought, the easier it became to get over this crimp. The problem is not age. It is something that age brings in us.

When learning a physical skill, it is natural for our bodies to stiffen up, to resist.

When learning a mental skill, the same thing happens. The mind stiffens up, resists absorbing new perspectives.

During moments of stress, which doing anything new is, it is natural to retreat into what we know. To revert to old habits. To defend our views.

The older we get, the more we have to lose. It gets harder to not resist, and to release instead. We get hard and defensive. We have the Knower’s Syndrome. ‘Knower’s Syndrome,’ in the words of community builder April Maclean, ‘is what happens when we’ve decided we already know the answers and close ourselves to other possibilities...’

But take yourself back a decade, or two? The resistance has not built up yet. You're open to being thrown around. You're soft and receptive. Beginner’s Mind?

If you can let the years not make you hard and defensive, you have not aged at all. If you can let time make you more receptive, you have learned by unlearning.

The problem is not age. It is what comes with it. It is what you let in with age.

The ones hungriest for growth will look for chaos, will beg for a challenge, will not wait to be told, will walk into a gunfight. They will invest in loss. Like this 19-year-old.

The fork in the road: give yourself to the process of learning or be safe

Most founders of early-stage startups would hire for slope than for y intercept. And little gives away slope as clearly as the willingness to take on big responsibilities and run the risk of making a fool of oneself.

Kat Cole, COO of Athletic Greens, faced a fork in the road at age nineteen. In her words…

I was presented with the opportunity to start traveling internationally to open franchises. And I was only 19 years old, and I had never been on a plane, and I did not have a passport. And I’d only been out of the state of Florida a couple times for sports competitions, like to Tennessee, and I’d never opened a restaurant, yet I was asked, “Are you willing to be a part of the international training team to leave in 45 days to go open the first ever Hooter’s restaurant in Sydney, Australia?”

And so the fork in the road was, I can either say, “I’ve never opened a restaurant. I can’t legally exit the country. I’ve never been on a plane. I’m not sure how to do what you’re doing, so sorry, I can’t.” That’s one path. Or the other path, which is say yes, and then figure out very quickly how to solve for what I didn’t have to the best of my ability, which is the path that I took. I said yes. They said, “Great.” They put me on the list. I then bought my first ever plane ticket to Miami, brought my paperwork, stood in line, had my passport expedited so I could legally exit the country, and then read and talked to people and did all the research I could on preparing for a new store opening, and then did my best to learn on the job once I went, and it literally changed the trajectory of my career.

I first heard Cole’s initiation story a few years ago and I make it a point to go back to it in times of my own urge for certainty. Why? Because Cole’s decision to invest in loss took her down a painful learning path almost immediately. This is a snippet from issue #97:

_When a 19-year-old Cole led Hooters to one of its first international outlet openings in Buenos Aires, she found the kitchen staff up in arms. In the beef capital of the world, the franchise used ribeye (a substandard cut of meat), flat top grills (considered inferior to an open flame), and served baked beans as sides (considered poor man’s food in Argentina). The whole thing smelled of cultural blindness. The franchise had pushed through identical standards (same kitchen equipment, cut of meat, sides) in a culture that was anything but. _

At this point, Cole could have taken the easy way out. She could have thrown the rulebook at the problem. But she chose to learn about the local culture and she chose to take a stance on a consequential decision. She got a ton of heat from higher-ups in the corporate office who had to redo their budgets because of the menu and equipment upgrade but that taught her a valuable lesson in dealing with forks in the road that she continues to carry well into her illustrious career.

What to look for in people?

‘When you get in situations where you have to make big hiring decisions on little direct evidence,’ I wrote last week, ‘go looking for broader patterns: What’s their relationship with discomfort? Where does their confidence come from—not having been tested or having survived an examination?’

It is rare for such behavioral patterns to shine through from a CV or even over an interview the applicant has rehearsed for. Yet, much more mundane moments offer incisive tells.

Impatience while standing on line at the buffet might betray a problem sitting with tension. It’s amazing how much you can learn about someone when they get caught in the rain! Some will run with their hands over their heads, others will smile and take a deep breath while enjoying the wind. What does this say about one’s relationship to discomfort? The reaction to surprise? The need for control?

While searching for tells in everyday situations can offer deep insight into people’s personality, in a post-COVID world even the mundane can be mysterious. I, for one, haven’t physically been with a candidate in an interview room for over three years.

This is where I like the hiring approach of Dr. Thomas Zurbuchen, ex-NASA head of science missions. He doesn’t search for tells so much as put on the table what he (and his hiring team) fishes out about the applicant.

It is standard practice for Dr. Z to say to the candidate before making an offer:

I have good and bad news for you. Good news is you’re the best candidate in this whole thing. We did a detailed assessment of your strengths and weaknesses and let me tell you all the things that were particularly important and defining why you’re the best person. Here’s the bad news though. You have weaknesses. Here’s the weaknesses we’ve found and we identified and they’re here. These are the things and I want you to know, first of all, we’re hiring you with all these weaknesses. You’re going to notice everybody has weaknesses here. You will be one of them. My full expectation is in the first year I want to see how you adjust your leadership team to offset your weaknesses.

Such an approach is perhaps best suited to leadership hires, yet by bringing forward the first performance appraisal to the time of hiring, founders and operators can clarify expectations upfront. Contrast the revelatory power of this interaction with the usual practice of fishing for support from references curated by the applicant or trusting the highlights reel on a CV.

In a scene from The Last Dance, a Netflix documentary on Michael Jordan and The Chicago Bulls’ dynasty, a reporter catches Jordan in the lobby of a hotel during the ‘92 Barcelona Olympics:

‘Michael, game on the line, who would take the last shot?’

Jordan pulls his brow together, wondering if there’s more to the clear-as-a-bell question, before saying, ‘Me! That’s a dumb question.’

Arrogance aside, it reveals Jordan’s deep desire to put his reputation on the line. Every time he demands the ball with the game on the line, he owns up to the possibility of defeat. But in doing so, he also meets the challenge in full.

As it turns out, Waitzkin is a Michael Jordan fan. These words from his book capture the essence of investing in loss.

What made him the greatest was not perfection, but a willingness to put himself on the line as a way of life. Did he suffer all those nights when he sent twenty thousand Bulls fans home heartbroken? Of course. But he was willing to look bad on the road to basketball immortality.

Ultimately, losses may be painful in the moment, but false, easy wins are painful for life. When we invest in loss, we invest for the long-term.

Enjoying the article?

Check out our free ebooks and companion resources to aid your learning and development!

Explore Ebooks

Articles Categorised with the same tags