The problem with glorifying failure

Why talking about failure works best in small doses as a pattern break

👋 Hey, it’s Wes. Welcome to my weekly newsletter where I share frameworks for becoming a sharper marketer, operator, and builder.

Today we’re going to cover how to talk about failure. Instead of speaking excessively about failure, it's safer to show a baseline of success, then sprinkle in occasional vulnerability. I'll be dissecting examples of founders and operators who talk about their failures effectively while showing vulnerability and maintaining their credibility.

Read time: 8 minutes

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Startup culture glorifies failure. We all know the quote from Thomas Edison: “I have not failed. I've just found 10,000 ways that won't work.” The part that’s not highlighted on this motivational poster is that Edison did eventually find a way that worked:

• He’s credited with inventing the first practical incandescent light bulb.

• He's described as America's greatest inventor.

• He has over 1,000 patents for his inventions.

In other words: He was, in fact, successful.

For a while now, there’s been well-meaning advice to “talk about your failures” that’s propped on the back of trends like building in public and as a reaction to social media acting primarily as a highlight reel. There are conferences and events about failure. But in a work setting where stakes are involved, I assert that most people are better off highlighting their successes.

Society doesn’t judge all failures equally. If society judges some failures more harshly, then from a practical perspective, we should be discerning about sharing stories of failure. So when and how should you talk about failure?

Failure should punctuate a strong track record

A rich person says, “I struggled a lot. Now, I’m here doing this cool thing.”

A broke person says, “I struggled a lot. Actually I’m still struggling.”

One makes you think, “What a rags to riches story. I’m so inspired.” The other makes you feel sad.

On the one hand, it’s true that “we don’t talk enough about failure,” but on the other hand, the media is full of successful people talking about how many times they failed. This works because they are speaking from a position of success. The stories of failure are sparingly to punctuate a baseline history of wins, to show they’ve overcome challenges, give them depth of character, and make them more relatable.

For example, Marc Randolph, cofounder of Netflix, admits he’s been wrong about many things at Netflix. Marc is an investor in my company Maven, and though I’ve only had a few interactions with him, I can attest that he’s a thoughtful, sharp, and humble person. I’m glad he’s starting to share more on LinkedIn, and that high-profile leaders are normalizing that people make mistakes and get things wrong.

The mistake would be if you’re an early stage founder and you think, “I want to mimic Marc verbatim because he’s being vulnerable, and I want to proclaim that I’m usually wrong too.” The messenger—and the messenger’s track record—matters. If you simply proclaim you’re wrong all the time, this doesn’t inspire confidence in investors, employees, or customers. It just makes you seem like you have poor instincts. At an early stage, when your product is nothing to write home about and your idea is mainly a dream, the only thing you’re selling is your instinct as a founder.

You don’t want to be vulnerable at the expense of your ultimate goal, which at work, is generally about inspiring confidence in your abilities—so your startup gets funded, so you get hired, so your manager trusts you more. It seems obvious to avoid doing something counter-productive, but since Brené Brown’s TED talk a decade ago in 2010, being vulnerable has become widely accepted as what good leaders should aim to be. In general, taking off some of the armor we all wear on a daily basis to protect our soft spots is a positive trend. But being vulnerable for the sake of getting sympathy from the internet or using business conversations as therapy, is not beneficial.

Let’s say you’re a candidate interviewing for roles. Over-emphasizing failure makes you seem like a risky hire. The hiring manager thinks, Wow, I appreciate that they shared this, but it was kind of a poor judgment call, they missed obvious signs, and the expensive mistake probably could have been avoided altogether. Maybe we should pick another candidate who has better judgment.

One day, I want to be as successful as Chrissy Teigan whose Twitter bio says “demotivational speaker.” At one point, her bio said personal assistant to babygirl Lisa, an homage to a participant in the show 90 Day Fiancé. Her location said everywhere like such as, a reference to this classic viral clip. First, I love this. I know I’ve made it when I can use dry humor in my bio and people still know who I am, or I’m so successful I don’t care either way. Until then, I will stick to something boring in my profile, like telling people what I tweet about and putting effort into giving folks a reason to follow me.

A bio that shows you DGAF is a great way to signal that you’re post-economic. This is a power move, but there is a trade-off that some people won’t get it, and you haven’t given them reasons to engage with you.

This is similar to why I don’t wear distressed oxford shoes. Can I pull it off? Or will it look like I’m wearing tired, dull shoes? The key is everything you do should feel intentional. I know my limitations, and there are simply certain styles that don’t look intentional on me. If it doesn’t look intentional, it feels a bit sad.

Failure can be perceived as a pattern match or a pattern break.

Pattern breaks are why Mark Zuckerberg can wear hoodies and open-toed sandals to work, but you and I probably shouldn’t.

We expect billionaires to wear blazers, Ferragamo belts, and Gucci horse-bit loafers. But Zuckerberg chooses to look unkempt. He chooses to emphasize a pattern break.

This pattern break works because his face is recognizable, and he’s a white man. His choice to wear tees is perceived as ironic and bold. He can talk at length about his failures because he’s richer than most people on the planet combined. For the rest of us, we still benefit from heuristics like a tailored blazer and washing our hair.

People root for underdogs, but pick favorites when stakes are on the line

There’s a phenomenon in social psychology where people tend to prefer being associated with winners rather than losers. For example, the social identity theory (Hogg, 2006) states that people are more likely to identify themselves with successful individuals or teams, as it boosts their own perceived social status.

But what about rooting for the underdog? People like supporting underdogs, but when personal stakes are involved (i.e. your own health or money will be impacted from a loss), people abandon the underdog and choose the favorite:

Scott Allison of the University of Richmond came to this conclusion in a study on people's support for all sorts of underdogs, whether in sports, business, or art. In one part of the study, participants read a scenario in which two companies competed for a contract to to test the water in Boise, Idaho.

One was a new, struggling, small company, the other a well-established, decades-old one. When asked, slightly more than half of participants said they'd root for the small one to land the contract. But when the scenario was changed so that participants were told the companies would be testing water for potential cancer-causing chemicals in their own hometowns, the results were the opposite: more than twice as many rooted for the established, reliable company to win the bid.

The conclusion Allison draws is that when we have something bigger on the line — in this case, health—our support for the underdog evaporates. Similarly, he writes, we might root for a mom-and-pop store when Walmart moves in to the neighborhood, but ultimately we make big purchases wherever it's cheaper.

Startups trying to recruit talent is a great example of this. One of a founder’s hardest and most important responsibilities is to recruit great talent—to do this, you have to convince A-players to leave higher paying jobs to take a bet on your team. They’ll only take the bet if they think that bet is going to pay off.

Startups have to tow the line between simultaneously playing up aspects that make them the underdog (because they’re clearly not Google and can’t hide this) AND playing up that they are proven, trusted, the go-to, reliable, stable, etc (elements of the favorite) so customers are willing to take a chance. If you’re the challenger, not the default, you’re already deemed risky. When in doubt, show why you're the winning team to counterbalance.

Share the failure and signal success in the same breath

If you are going to share about failure, there are a few factors to keep in mind to increase the chances that the failure will be perceived positively. For example, my Maven cofounder grew his Twitter following from being super transparent and honest about his career failures. He’s known for sharing honest behind-the-scenes stories and has talked about how he got fired from Udemy. Three threads about failure drove 70% of his first 60,000 followers on Twitter.

When you see this, your immediate instinct might be, Wow, I should write about my failure so I can grow fast too. The challenge with this thinking is the messenger talking about failure is the most important part of this working—and in this case, Gagan was writing as the cofounder of a company now worth billions. Even then, he signals his success with keywords:

• President and cofounder of a now-$2B unicorn

• Udemy is a household name in tech

• Raising $50M and mentioning Tier I investors like Greylock

This adds credibility and gives readers a reason to listen to him. If the founder of a random company wrote this, no one would care. Even if you haven’t heard of Udemy, the numbers are big ($2B, $50M), so that alone catches your eye and signals the stakes, which makes the story interesting. Therein lies the key: People want to read about your failures if they deem you a success.

If you’re talking about failure, remember to share a few points of credibility, so you give folks a reason to want to learn from you.

Here’s another viral thread about failure I saw recently about what it’s like to own and eventually close a retail business. It’s an entertaining, informative read—and you get to relish in a bit of schadenfreude. In this example, talking about failure works for Joe for a few reasons.

• Notice how he mentions that his marketing agency is making 6-figures in only 2 months. This might have been subconscious, but this thread about failure ends by mentioning the success of his other business.

• Joe signals his competence in a subtle, less on-the-nose way: His ability to tell a compelling story that hooks you from beginning to end is a sign of his capacity.

• The fact that this thread went viral in itself is social proof. It has 1,893 bookmarks and 1,711 likes. Imagine someone telling a long story of their failure—and it only getting 4 likes.

• Perhaps most importantly, Joe no longer plans to be in retail. He’s not planning to open another store, so talking about his failed store experience is less relevant to his current ventures because it’s not his core competency or main pursuit.

All over your feed, you see posts about biggest mistakes hooking in readers. But notice how these folks simultaneously share numbers that signal their current success and status. In the example below, this CEO shares that his company is currently at $20M ARR.

This founder below builds in public, but most of her posts are about insights on how to achieve what she’s achieved and lessons along her journey. She doesn’t talk about failure often, but still seems honest and open. In the event that she writes about failure (below), she writes with specificity and insight, which indirectly signals her competence—a less capable person wouldn’t have written such a thoughtful post. The most interesting part for people learning from your failures is feeling less alone (which happens by virtue of you mentioning a failure at all, even if it’s one line) and learning what you learned the hard way—so focus on unpacking lessons that might serve others. Plus, she wrote from a position of this being a scar, not an open wound, which we’ll talk about next.

Share when the failure is a scar, not an open wound

Timing matters. Are you on the other side of the darkness—or still in it? I love how Glennon Doyle talks about scars versus open wounds:

Well, we have to choose carefully where we do our truth-telling. One thing I remind people is something my friend, Nadia Bolz-Weber, told me: If you're going to share widely-make sure you're sharing from your scars, not your open wounds. Love Warrior is intensely personal, but it's not a diary. I started turning it into a memoir two years after it all happened, and I had enough distance to look at all of it somewhat objectively. I wrote the book and rewrote it, and with every paragraph asked myself: How is this not just about me, but about the reader? About all of us? How can I turn my personal story into something universal? I sifted through my own pain and mined it for gold to share with others. When we truth-tell widely in real time, it's alarming to people because it can feel more like a cry for help than an act of service. You have to be still with your pain before you can offer it up and use it to serve and connect with people you don't know.

If you’re still in the midst of struggle, talking about your failure can look like a cry for help. And most companies don’t want to hire a content marketer or product manager who seems like they’re in the middle of crisis.

To be clear, I’m not saying you should avoid failure. Failing vs talking about failure are different—the latter is meta. There’s a difference between giving yourself permission to fail (which I fully support) versus talking about every failure in a 1:1 ratio (which you should use your judgment for). Instead, I want you to realize there are plenty of other types of stories you could share—like your spiky point of view rooted in your area of expertise, or stories where you teach your audience something they don’t already know.

The underlying point is if you see someone you admire doing X, don’t blindly do X because it might not work given your situation. If they’re talking about failure, don’t blindly talk about your failures. And if you do want to talk about failure, consider how folks may perceive it, so you can make an informed decision about what’s most advantageous for you.

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Thanks for being here,
Wes Kao