This painful, terrible, amazing exercise forced me to become a better designer

Flash back to 2010, and I’m giving a workshop to a room full of entrepreneurs who want to learn copywriting. We were on the subject of headlines. I’d given them the basics, and now, to make sure they “got it”, I had them each write a headline of their own.

The room was silent except for the tapping and scribbling of pens. Then, some pens hit the table, and I looked around to see smiling faces. These people were proud of what they’d written.

“Okay, now that everyone is done, here’s what I want you to do next. Pick your pen back up. Read over your headline one more time. Now cross it out.”

I got wide eyes and gasps.

“Cross it out? My beautiful headline?” their eyes said.

“Cross it out,” I said. “Now, pick your pens back up and do it again. Write another headline.”

I had them do this 5 more times. And each time, I had to pull teeth to get them to do it.

And it’s understandable. When you really put effort into something, attachment to that creation is a natural side-effect.

It’s your baby.

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Who wants to cross out their baby?

But this exercise was teaching them more than they realized (I’ll explain that in a bit). And every time they wrote a new headline for the same product / service, it got better.

When I took this same exercise I’d developed, and used it for design, the results were truly amazing.

I learned most of what I know about design from my partner, Louisa (my partner both in business and in life). She’s a truly outstanding designer, and she’s always painfully honest.

Although writing is my true craft, design has always pulled me in. Over the years I’ve kept trying at it, creating designs, and bringing them to Lou for feedback.

And… her first glance would usually let me know I’d done a terrible job. But she always had constructive feedback that I took in like grass in the sun.

Over the years I’ve gotten better. Now, Lou even uses many of my designs as a starting point, and they become the end-products we give to our clients. Of course, she takes them to a level I’ll probably never be able to – but that’s alright. The fact that she sees something in them in the first place shows me how far I’ve come.

And many of my other designs we actually do use and ship. Particularly with typography and text formatting.

But it was this exercise that accelerated my learning. Here’s how:


This exercise teaches you that you can always do better. When you create something that you think is amazing, and you throw it in the trash, it’s a statement to yourself and the universe that says,

“Wait till you see what’s next.”

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Because the truth is, the moment you create something, your skills evolve beyond it. You really can do better the next time.


Every time you design, you innovate. And those innovations become embedded into your style. By creating, deleting, creating, deleting… you accelerate that process.

Each time, you challenge yourself to innovate. And then you throw it out. And then you innovate. And then you throw it out.

But while the design is deleted – the innovations are not. They’re a part of you forever.


You learn how to detach from your work, and give it more “space”. You learn how to take away a lot of the pressure that comes with design and blocks creativity.

After all, if it’s no big deal to scrap a design, suddenly the design isn’t this big, scary monster. It’s something you could easily throw away and do all over again.

You learn that the design isn’t what counts. It’s your skill and artistic soul that matter. That’s where your design comes from, and that’s why you get paid for what you do.

You learn that you’re truly capable of creating great things, no matter what. And that feeling is truly priceless.

Have thoughts or comments? I’d love to hear them.

Just post them in the comments on this post. And who knows? Maybe we can even start a conversation.

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Millo Articles by David Tendrich

David Tendrich is the co-head of creative agency Unexpected Ways, as well as the co-founder of Reliable PSD: the first-ever PSD to HTML & PSD to Wordpress service run by designers, for designers. He co-runs his companies from Portland, Oregon with his lovely wife and biz partner, Lou Levit.
Read more from David.

  1. Henry Alvarez says:

    This article is incredible. I’m only a freshman in high school and I’ve kept doing this with my designs and they keep getting better and better. I have been receiving comments for my designs by major graphic design companies and professionals. It’s amazing what this exercise did for me. I’m gonna be a pro designer one day thanks to you!

  2. Russ Clow says:

    This is all well and good until you’re not being paid by the hour and you’ve got a tight deadline to hit! 😉

  3. No matter how perfect you think your design is, there’s always room for improvement, being it a small color change or a different font size. Your exercise is brilliant, it helps you see the work from a different point of view. Knowing to accept and to actually learn from the feedback you get is vital as it helps you mature as a designer.

  4. April Greer says:


    So I gasped at the mere suggestion of tossing several hours’ worth of work. I’m still reeling, and I kind of want to kick you in the shins.

    But you’re spot on. I think this is why it’s so important to come up with 3 initial design concepts no matter how in love you are with the first (or second) one. It forces you to approach at a new angle. It forces you to trust yourself that you’ve got another great idea inside your brain.

    And maybe most importantly, it forces you to accept that your idea isn’t the only “perfect” solution out there.

    Thanks for the great post!


    1. David Tendrich says:

      Haha, I know the feeling. If it makes you feel any better, the soccer field the other day left me bruised in a lot more places than my shins :-\

  5. Great article and great advice. I remember an artist/professor I had back in college that told us we should take all of our paintings from class, put them in a pile and burn them. Everyone freaked out until he explained that we could and would go on to create more and better art in the future.

    Your article reminded me of that lesson.

  6. Sahm Seera says:

    So true.
    Every time someone comment on my work positively, then I see work of someone else.
    I always feel what is so good about my work, the other guy’s work is better.
    And I never get satisfied with my own work even when it got selected for display multiple times.

    Now I know how to terminate that terrible feeling.
    Thanks for this article.

  7. May I say, this sounds scary. A lot. I see the point, though. It makes you be the best you can be and it doesn’t allow you to settle with “as it is”. It pushes you to improve. I’ve never done it but I’ll definitely give it a try (and hopefully won’t shed a tear). Thanks for sharing, David!

    1. David Tendrich says:

      Whenever something scares the crap out of me deep down in my gut, I know it’s my next step 😉

      Best of luck, would love to hear how it goes!

      1. April Greer says:

        Hear, hear! That gut check means it resonates.

        Then it’s just about stepping up to the plate and doing what needs to be done.

  8. Your Creative Junkie says:

    Nice post David!
    It reveals the pain we need to go through to arrive at something special, something authentic. I essentially do this with my logo designs. I’ll sketch out up to 50 concepts over a 2 to 3 day period, then let it sit a day. Go back and pick the most promising ideas to present to the client for feedback. Here’s a link to some of the sketch work I’ve done to finally get to a solution that works –
    Thanks again for articulating the pain and the glory designers go through… well done sir!
    – Vincent

  9. emileezer says:

    I had a boss who could never articulate what he did or didn’t like about a design. If he didnt like something he would call it “butt ugly” and have me start over.

    So I would do it over. And over. And eventually, he would approve a final. The final almost always was similar to the original concept, but much more refined, and definitely better.

    It kind of stings to hear that something is “butt ugly” but I eventually figured out it was his way of saying it wasnt exactly quite right. It made me better as a designer, and better about taking feedback. It’s nothing to hear “well, it’s nice but….” after years of very harsh words.

    1. David Tendrich says:

      Sounds like emotional boot camp lol. That’s so cool that you can look back on it fondly though and see a lesson. Sounds like it was well worth it 🙂

      Thanks for sharing your story,

  10. Victor Brown says:

    Your so right! The idea may be perfect from the start yet the execution and process are ongoing…

  11. Danielle Zuckerman says:

    This is a great article and a wonderful reminder of the true creative process.
    This is why artists have sketchbooks, so that we can try out, and cross out, all sorts of designs and ideas before truly revealing our BEST.

    Thanks for sharing!

    1. David Tendrich says:

      Hey Danielle,

      That’s true… but this exercise actually is about revealing your best, and then saying to heck with it 😉


  12. Alex Rodriguez says:

    Great read, I separated my worth from my design sometime back and it truly helped me become a better designer and business owner. Design something you love, look at it and appreciate it, torch the files and start over. You will become fearless and unattached to your designs, you can now pitch with confidence and understand feedback in a way that improves your ability to work with clients instead of for or against clients.

    Great read.

    1. David Tendrich says:

      Loved your comment, Alex. Thank you for sharing 🙂

      By the way, great pics on your “coming soon” site.


  13. That is such great advice!! I used to always fall in love with my first design and that is the worst thing you can do, especially when the client asks for other input.

    1. David Tendrich says:

      Haha yes, and they always, always have changes, don’t they…


  14. Good post. Absolutely right about not wanting “cross out” your baby. But you make an excellent point about the value of creating and deleting. Good read – thanks!

    1. David Tendrich says:

      Yes, it’s very difficult. Even to this day, and I’m not sure how many times I’ve gone through these steps. But I think dealing with that pain is maybe just part of the process.


  15. Hi David, this excercise is truly amazing, I have always try to avoid experiencing the power of repetition, but being a pro drummer as taught me that every thing you do productively and seamlessly is all thanks to the power of repetition. Thank you for consciously bringing this excercise to attention again. Maxwell

    1. David Tendrich says:

      Maxwell, that is so awesome, my friend.

      Thanks so much for sharing,

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