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You will fail 95% of the time, and that’s a Good Thing™

Credit: amboo who?

Credit: amboo who?

A short time ago, I wrote about how the best way to get better at headlines is to write a lot of headlines. It cited a slideshow by Upworthy and how they have editors write twenty-five titles for each content piece they want to share.

There were a lot of nuggets in that slideshow but there was one that stood out for me, in part because there was no emphasis on it – check out slide #15.

Here it is:

Failure is expected


It gives you an idea of their success rate.

If you do the math backwards, with 5 posts being 0.3%, then they’ve put up close to 1,700 posts as of the slideshow’s creation.

933 posts don’t reach 10,000 views and 1583 posts don’t reach 100,000.

That’s a lot of grinding (and luck!) to get to the 5 superstars.

And this is after they already identified awesome stuff and put it through the Upworthy machine.

Remember, they hand-pick what they want to share (they don’t create anything) and they have an entire team trained in the ways of viral magic.

Failure should not only be expected, it should be embraced because it gets you one step closer to success.

Your skill is undeveloped

Ira Glass is the host of This American Life, a weekly radio show in which they tell stories about, well, American life.

He’s a great storyteller and he did an interview with about storytelling back in 2009 (here’s part one). There is one quote in that interview that sticks out for me, and a lot of people. Here it is, beautifully stylized by David Shiyang Liu, with a transcript below:

Transcript: Nobody tells this to people who are beginners, I wish someone told me.

All of us who do creative work, we get into it because we have good taste. But there is this gap. For the first couple years you make stuff, it’s just not that good.

It’s trying to be good, it has potential, but it’s not.

But your taste, the thing that got you into the game, is still killer. And your taste is why your work disappoints you. A lot of people never get past this phase, they quit.

Most people I know who do interesting, creative work went through years of this. We know our work doesn’t have this special thing that we want it to have. We all go through this.

And if you are just starting out or you are still in this phase, you gotta know its normal and the most important thing you can do is do a lot of work.

Put yourself on a deadline so that every week you will finish one story.

It is only by going through a volume of work that you will close that gap, and your work will be as good as your ambitions. And I took longer to figure out how to do this than anyone I’ve ever met. It’s gonna take awhile.

It’s normal to take awhile.

You’ve just gotta fight your way through. OK?

The lesson? Your ability to judge your work, your taste, will be disgusted by what you produce. But in order to get better at it, to get better at anything, you need to practice.

To get better, you need to do the work. Day in and day out, you need to grind.

You need to put out 25 headlines. You need to fail often and learn from it, not have it get you down.

Then, one day, you’ll look back and realize you’ve built something great.

But that only happens if you start now and keep grinding.

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In 2005, I founded a personal finance blog ( that became successful enough that I quit my career as a software developer in the defense industry. It is my goal to share everything I learned so that you can do the same - build an online business that let's you pursue your passion.

15 responses to “You will fail 95% of the time, and that’s a Good Thing™”

  1. Mark Ross says:

    More than a thousand posts just to achieve that amount of traffic? Wow.

  2. “You need to fail often and learn from it, not have it get you down.” I could not agree more Jim! I think all too often we run from failure and practice, when it actuality we need to learn all we can from it. I’ve found that the most profitable lessons generally come through failure and practice – of course, it took me getting older (and hopefully wiser 🙂 ) to realize that.

    • Jim says:

      I believe age has helped me understand that failing is to be expected, since you’re progressively trying harder and harder things. When you’re in school, it’s fairly regimented and often taught to the lowest common denominator. There’s a schedule you are put on based on expectations. Once you leave the structure of schooling, you can go at your own speed and you are likely to be far more aggressive on your own.

  3. Joe says:

    I didn’t have right attitude about failure when I was young. I just didn’t understand how much you can learn from it. It’s natural to avoid failure. It’s much more difficult to embrace it especially when you’re young. Now, I know to keep pushing and improving.

  4. I just wrote today about my past failures. Only these failures have allowed me to achieve success. I had to learn from the mistakes and keep on grinding. If I stopped because failure got me down, then I don’t know where I would be now.

  5. I’m finally learning this so this post couldn’t have come at a better time. Thanks for the reminder Jim.

  6. Steve says:

    I’ve seen this Slideshare before and was also amazed at the number of posts Upworthy has had that have done very little traffic wise. I was even more blown away when I saw how much work they were putting into each headline. That is simply amazing, because like you said, they don’t create the content, they simply curate it and their job then is to get shares based on their headlines. Studying the headlines and what makes them work so well could be a good way to spend a few hours.

    • Jim says:

      One of the risks of studying it too much is that it can be formulaic. The problem with formulaic is that it works now but eventually people will get immune to it. There are only so many times I’ll click on something that’s “shockingly simple” or whose response “I won’t believe.” You recognize it for what it is, an enticing headline, and sometimes the content behind it doesn’t deliver 100% (even at 95% it’s not enough).

  7. David Spell says:

    Wow. This is timely for me to find this. Granted, I’ve only just begun, but a total lack of traffic is not what I was expecting. This encourages me to keep trying. Thank you!

    • Jim says:

      You need to get out there and share your craft with the world, just publishing a blog doesn’t guarantee success (unfortunately).

      • David Spell says:

        Yes, I’m realizing that. It also takes time to learn how to do that (share with the world), apparently. 🙂 I guess that’s part of the fun!

        • Jim says:

          It will take time to find the best place to share your work, different sites are good for different things. The fun is in experimentation and maybe finding a few gems others don’t know about.

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