4 Crushing Failures You Should Experience In Life

It’s 6am, I haven’t eaten in 12 hours, and I’m about to do high intensity intervals for an hour. I’ve done this workout 13 times in the last two weeks. I’m miserable, but I tell myself;

“that’s just how it feels to work out.”

Fast forward two weeks and I haven’t worked out again. I spent the rest of that summer eating milkshakes for lunch (no joke).

That was the first failure in my quest for fitness. There would be others (many others), but without the lessons from those failures I would never have changed.


Why Failure is Important

Failure forces you to understand yourself.

After my milkshake debacle, I learned that beating myself half to death every morning was never going to work. Surprise Surprise.

In my next fitness failure, I woke up at 7am every other day and did more moderate exercise. I still quit after two weeks; I learned that I simply can’t have a good workout before breakfast (I’m too hungry).

I’ve failed dozens of times: I failed to get a job right out of college, lost a year-long relationship, got rejected (over and over) by jobs. But without failing – without strategic failures – I would never have learned the key lessons that eventually led to success.

You can fail 20 times or 200 times. For most things, you only need one success. Strategically taking risks and failing allows you to, little by little, learn the skills that eventually make you successful.


4 Crushing Failures You SHOULD Experience

Types of Failure We Should All Experience

Of course, sometimes failure is brutal, and it feels like you’ll never recover. Those failures have the most learning potential.

These are four crushing failures that you can learn from:


1. The End of a Good Relationship

Ending a relationship can be brutal.

You cry for seemingly no reason (giant gasping sobs, not little teardrops). You reach for the phone or open Messenger, only to realize that the one person you want to talk to more than anything in the world is the only person in the world you can’t talk to.

It’s even worse when the relationship was a strong one. One of my relationships lasted a year because we had so much in common.

We had similar values, were both super into psychology and athletics, enjoyed the same TV shows and books, and even had the same favorite Disney song. But it still ended because of a difference in long-term goals, and that was my key lesson.

It’s not what anyone wants to hear, but the end of a relationship is an enormous learning opportunity. You can throw yourself into work, you can follow the famous four steps to losing weight, and you can learn what you care about most for your next relationship.

Even Wealthy Gorilla was founded after a brutal breakup. Turning your emotions from a failed relationship into long-term growth is a healthy and productive way to deal with failure.

Knowing how you act and what you want out of a relationship will help you in your next one.


2. Being Rejected From Jobs (over and over)

I didn’t have a job waiting when I graduated from college.

For the first 3 months I applied to every job under the sun, and got rejected from all of them. I had virtually no experience in the field I was applying to. I was so green that I embarrassed myself in my first interview and didn’t even know it.

If you’ve ever been unemployed, you know it sucks. You watch your savings dwindle and keep sending out resume after resume, vaguely hoping that this one will be the one that finally makes it.

After 3 months of rejections (or even worse, no response), I learned from failure and changed my approach. I started emailing and cold calling alumni and other people in my field. I took side projects to get experience.

I went to dozens of coffee meetups in the hopes of meeting the right person and learning the right thing.

I failed at this sometimes too. Plenty of people never responded to me, or didn’t want to meet up. Some were totally unhelpful – one meeting took 4 hours of travel (2 each way) and was totally fruitless.

But enough of those meetings were helpful, and I only needed to get one job. I got rejected from dozens, but I got one. I learned from the first failure and changed my approach. Now, with more experience, I won’t ever have to go through that process again.

If you’re being rejected over and over, ask why. Figure out the reasons (in my case, lack of experience and networking) and tackle them one at a time.


3. Skipping Workouts to Watch Netflix (over and over)

I’ve done this. You’ve done this. Everyone has done this.

You start the day with every intention of working out. But on your way home from work you start to have doubts:

“It’s been such a long day and I’m tired. I can make it up tomorrow.”

“I’ll just sit down for a few minutes, then change and head to the gym”

“It won’t hurt to miss this one workout”

Doubts turn into a Netflix binge, which turn into not working out. And when tomorrow comes you repeat the same process. When I was struggling, I hated that I couldn’t muster up the willpower to get fit. Honestly, I was disgusted by myself.

You can repeat this endless cycle, or you can do something about it. I learned that I get tired after work, so I started having coffee in the afternoon. I learned that I would always be tempted by my bed or comfy chair, so I brought my gym clothes to work with me.

By identifying the real causes of the problem instead of wallowing in despair, I was able to change my habits and finally start working out.


4. Failing at Something Bold

If you never try bold things you’ll never get remarkable results.

You don’t need to take enormous risks, but having little projects with the potential to evolve can lead to incredible results.

If someone asks what you do in your free time, how do they respond to your answer? Do they blandly respond; “oh that sounds nice?” Or are they intrigued, wanting to know more?

Having a bold side project helps you be more interesting, but it can also help you improve (by failing) at things without taking huge risks.

I’ve tried to start a handful of websites and blogs, but never had any success. My posts and articles disappeared into the internet, where they were read by…no one.

Through each of those failures I learned what works. I learned that people don’t always care about what I think, and that some writing belongs in a journal. I learned how to get my writing in front of people, and how to write about what they do care about.

Now I have a website that people read, and my full-time job involves producing content for websites. Without my failures, I wouldn’t have my job or an interesting side project.

Do something bold, where no one cares about the result but you. Fail at it, over and over (even if you get demoralized) – even if you don’t succeed the way you thought you would, you are guaranteed to learn.



Here’s a quick recap of the 4 crushing failures you should experience in life:

  • The end of a good relationship
  • Being rejected from jobs – over and over again
  • Skipping workouts to watch Netflix
  • Failing at something bold
  • How many of these failures have you experienced so far in life? Leave a comment below.

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