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Emotional Defeat: How Your Ventures, Projects & Dreams Die

Published or Updated On: 
February 3, 2023

A couple of years ago, I learned a lesson while trying to remove a TV mounted in my living room. The TV was 20+ years old and about 75lbs, one of the first generation plasmas from Pioneer. Once upon a time, it was state of the art. Now it was a a dusty relic. The TV was mounted in a way that made it exceedingly difficult to get at, and of the 20 screws holding it in place, around half of them were stripped. I'm not the most handy but I'm pretty good at figuring things out, so I gave it a shot. Over the course of a couple of days, I made a mess of our living room trying to get it out.

There was a distinct point in time where, after watching a 3rd YouTube how-to video and going to the hardware store for 2nd time to get a different tool, I hit a point where I felt like it was hopeless. I couldn't get the damn thing out! I’d put in a lot of effort at this point, but nothing I had tried was working. I didn’t know what else to do. I thought to myself “I can’t do it!” as I plopped down onto the floor, feeling frustrated, annoyed and defeated.

I sat there for a while considering my situation. Despite these bad feels, I knew this basic home improvement project was obviously possible. It was just a matter of getting the screws out. I recognized that even though it feels hopeless, if I keep trying, I’ll likely make progress. And so despite feeling low, I mustered the energy to keep trying. A little more persistence was all that was needed, and over the course of just 15 more minutes, I went from “I can’t” to “I did”. My sense of defeat had completely vanished & now I was laughing at myself for almost giving up on a project that was so clearly possible.

I later realized that this experience was a condensed version of an arc I’ve had with much bigger, harder projects: Try, Fail, Repeat ➡️ Feel Defeated ➡️ Pivot, Persist, or Give Up.

What struck me with this TV project was that I almost chose Give Up, despite success being just around the corner. That point where I felt defeated was a critical time, and it’s the focus of this blog post.

😔 Emotional Defeat

  • 🏳️ Feeling defeated is an emotion — you feel like you can’t succeed, like your odds are hopeless. It’s characterized by low energy, frustration, doubt and despair. It becomes hard to summon the willpower to keep going. For the rest of this post, I will refer to this as emotional defeat.

If you're trying to do something hard, such as starting a business or becoming a best selling author, at some point along the way you're guaranteed to experience emotional defeat. The path to doing hard things is, by definition, laden with big obstacles, setbacks and uncertainty. This makes emotional defeat an important concept to understand. It strikes when you've put in a lot of effort, haven't seen results, and are no longer confident about what to do.

Emotional defeat matters because it’s a time at which your ventures, projects & dreams can die. ☠️ As the graphic above shows, when you hit the Feel Defeated juncture, one path forward is to Give Up. To make matters worse, Giving Up usually feels like the default path. Why keep trying if what you're doing isn't working? All of this makes emotional defeat a consequential place to be, and I think most people are not aware that this is how things die.

This sentiment was captured well by Bonobos founder Andy Dunn*. While describing the many failures & few successes of the brand, he said something along the lines of “companies don’t die when they hit life expectancy, they die when founders give up”.

The risk when you hit emotional defeat is that you might give up too early, based on a lack of success, when success is very possible with some persistence or a pivot. Success could be just a few unopened doors down from where you are now. 🚪 You might be 6 customer conversations away from your big “a-ha” moment that turns everything around, 2 manuscript revisions from the one that will give you the book deal, 1 marketing channel experiment from a growth explosion. Or 15 minutes from getting that damn TV off the wall.

This point highlights the value of persistence, and indeed persistence is often all that’s needed. Doing hard things can require a shocking amount of work and resilience, often far more than we initially expect. This has been true for virtually every hard thing I’ve tried to do, whether I succeeded or not. A mismanagement of expectations can easily lead to a feeling of defeat.

In trying to get this blog going, I have arrived at Feel Defeated multiple times: frustration with how much effort it has taken to get better at writing, despair from how apparently easy it is for other bloggers to crank out outstanding material, and doubt about if this is a worthwhile thing to be doing at all. And because I’m still fairly early on, I think persistence is the answer.

Persistence is a much lauded virtue, and probably the most popular advice given to someone trying to do a hard thing: “Just keep at it.” But this isn’t always good advice. While it’s true that you’ll never get what you want if you give up, an overemphasis on persistence can lead to a lot of wasted time.

🔂 Futile Persistence

You may arrive at Feel Defeated because you misunderstood how much effort it would take to get what you want. In that case, persistence is a good prescription. However, you may also have arrived at Feel Defeated because your strategy sucks. In that case, persistence is going to waste a lot of time.

Author Chip Heath said it well in his book Decisive: “At some point, the virtue of being persistent becomes the vice of denying reality.”

If you focus too much on being emotionally resilient & persisting, you can miss the feedback signals that your approach isn’t going to work. ⚠️

You can think of Try, Fail, Repeat as a feedback loop from reality. When you arrive at Feel Defeated, it’s your job to decide why you’re there. 

🤔 Was this a mismanagement of expectations? 

🔁 Or is this feedback on the effectiveness of your strategy? 

🧰 How to Use This

If you start towards your hard goal knowing that somewhere along the way, you'll feel emotionally defeated, that can be a big advantage. It gives you the opportunity to ready yourself in advance.

Moreover, if you understand that it's how things die, and therefore a risky place to be, you can also use that to your advantage.

When you hit the juncture of Feel Defeated, the first thing to do is get some distance from the project. If you’re all emotionally wound up, it’s hard to make objective evaluations. Sometimes getting distance means taking an afternoon, other times it means a full week (or more) of being totally unplugged. You can decide what’s right for you based on how defeated you feel & how important the project is.

Once that’s done, the next thing to do is examine your strategy. Here are some simple questions to ask yourself:

1️⃣ What evidence do you have that your strategy will work?

2️⃣ How much feedback has reality given you on your strategy? How many doors have you opened?

  • If not much, you probably just need to persist.
  • If you’ve gotten a lot of feedback, compare that against the evidence you have that your strategy will work. 

3️⃣ Do you need to persist or pivot?

4️⃣ Are your expectations well managed?

Go forth and do hard things, my friends!

*hat tip to my business partner Emery for sharing this

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