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5 Ways to Fail Successfully

Photo by Robert Bejil
If you are making mistakes, then you are making new things, trying new things, learning, living, pushing yourself, changing yourself, changing your world. You’re doing things you’ve never done before, and more importantly, you’re Doing Something … Whatever it is you’re scared of doing, do it. Make your mistakes next year and forever. ~Neil Gaiman

There’s a story about a ceramics teacher who, at the beginning of the quarter, divided his class up into two groups. The first group was told that their grade would be based solely on the quantity of their work and the second group, on quality.

At the end of the quarter, contrary to what one would think, it was the first group that received the higher marks. Why? Because every day they churned out pot after pot, trying out new things and quickly learning from their mistakes.

On the other hand, the second group was so hyper-focused on creating that one theoretical perfect pot —planning and analyzing every little piece — that in the end, they had little to show for their efforts.

Most of us are very much like that second group of students — obsessed with getting things right. We’re taught it as kids in school: Wrong answers mean bad grades, mistakes being the difference between winning and losing.

We’re programmed to pursue the straight As, the top college and the high paying job, developing in us a sensitivity to criticism and judgment.

Then we become afraid to try new and unfamiliar things (often the things that actually matter to us), concluding that we’re not smart, strong or good enough to be successful at it.

I’m the first to admit that I put off writing my blog — the one I’ve fantasized about starting for years — because I lacked the expertise, time, network and writing chops I thought I needed. I was afraid of falling flat on my face.

I still am. Every day I have to put great effort into looking at my work through a scientific lens — as a constant feedback loop of writing, sharing, learning and iterating — and not as an attack on my identity.

So how do we undo our years of programming and find this “fail forward” mindset?

1. Acknowledge the Fear

For the most part, we don’t much think about our motivations behind what we think, say or do. We rarely get into the weeds to unearth what it is we’re really feeling.

We have to ask better questions. What are we afraid of? Fear that people will hate your script? That you don’t have the qualifications to get the job? That people will think your blog is a waste of time?

2. Do Something New & Uncomfortable

This is an exercise in getting accustomed to taking action, making mistakes, getting used to discomfort and reminding yourself quickly and often that mistakes are not things to be avoided.

Success is preceded by lots of messy failures, terrible ideas, bad art and botched efforts. So go take a salsa class or an improv class. Talk to a stranger. Draw a self-portrait and share it on Facebook.

Try a language learning program. Learn the ukulele. Be bad at something.

3. Be Curious

Curiosity provides energy and excitement. It gives us the power to experiment and grow. Kids explore all the time and it’s wonderful to watch.

Sadly, we don’t try very many new things, and we are the first to talk ourselves out of exciting ideas and opportunities because of all the “shoulds” in our lives.

Next time an interesting idea pops into your head, spend an hour exploring it just for fun.

4. Test the Waters

The reality is, most of us are not in a position to drop everything and set off on our own personal hero’s journey. We have jobs, obligations and mouths to feed.

So don’t look at it as this massive goal. Instead, approach it as a series of small steps — actions that you can start today.

Want to write a novel? Sit down and write for 30 minutes.

Want to be a veterinarian? Volunteer at an animal hospital once a week. Interview a practicing veterinarian on life on the job. Read a book on basic animal biology.

Go ahead and explore the things you think you might want to pursue.

5. Don’t Give Up

I saved the most obvious for last, only because we hear a variation of it every day. Failure is not a dead end street.

Yes, it stinks and it hurts and makes us question our intelligence and abilities. But if you can learn from it, keep moving and creating every day to find and do what you love, you will get better.

Success begins in the mind. I remind myself of this every time I sit down to write, share a new blog post or ask for help. I know that my blog isn’t perfect. I’m certain that parts of it are downright bad.

But I know that if I keep showing up every day to put words and sentences together the best way I know how, my blog will upgrade from “decent” to “good” to “really good” until it becomes my something great.

And that is something worth chasing.

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About the author

Rosanna Casper is on a quest to improve health, energy and performance, each month immersing herself in a new project for the mind, the body and the home. A mom of two living in California, Rosanna is obsessed with nutrition, fitness, productivity hacks, reading and creating food art as a way to make healthy eating fun for kids. Join her on her journey at her blog,

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8 thoughts on 5 Ways to Fail Successfully

  1. Hi Rosanna. Thanks for sharing this post. We as human beings have a tendency to want to avoid things due to fear. Some deep primal instinct makes us want to keep safe (even from non-existent or imagined dangers!).

    And by the way, your blog is lovely! Some very interesting posts, and I too need to put ‘getting healthy and finding more energy’ on my list of priorities! :) One thing I have started doing, is going for a 30 min – 1 hr walk every day (or almost every day – I try!), and for the same reason you decided to – to get some movement into my sedentary day. Being a freelance writer, I spend a lot of time sitting in front of a computer, and then at night sitting watching TV or some equally sedentary activity! So since NY’s eve, I have been out walking in the evening. And I find it clears the mind a bit and I am enjoying it.

    Thanks again for an inspiring post.

  2. Talya

    Thank you for this. I am one who fails everyday and still keeps going.

  3. I recently started a blog much similar to yours in the past two months. I was in depressed before I started my blog It’s a whole new arena for me. I was a negative Nancy because nothing seemed to go right and I’m even harder on myself because of my craving for self actualisation. I want to share the stage with Oprah and share the stage and let the world know that children are our now and our future. I am a believer that mothers who are the bringer of spirit/ soul into this world should live a life of ideals. Harness that power for our sons and daughters can leave in a world where children do not need to take up arms to get their next bread or eat at the crumbs of the master’s table. Let’s share in the knowledge of love, light and abundance. There is no difference between you or I there is no individual problem. It’s a human problem and we are all collectively responsible for the livelyhood of our Earth.
    The thought of me going through the pressures of going online and making a mark seems worth it. Even if I only have 1 subscriber.

  4. Your title caught me off guard. How would one fail successfully? Is that not an oxymoron? While that is true, what you’ve done is very clever. And you’re spot on too, if you never fail then you never learn how to do it better the next time. This is a great article, and I love how you’ve made it real and down to earth, so we can all do it.

  5. Yes, getting out of your comfort zone is always the beginning for something potentially new and wonderful. And yes… failing… I’m good at that one. But on the up side… It has always been a prerequisite for any worthwhile success.
    Thanks for your insight.
    Bill Peak

  6. HI, thanks for this great post, it is such a good reminder for all of us, taking the risk and being uncomfortable at times would definitely help us improve and grow more productively. Failures has always been a stepping stone to success if we only learn from our mistakes. Thanks for sharing.

  7. Both the book and the workbook promise to help those who need a direction in their lives. The synopsis is well written.The comments included are all praises for it, so it may be safe to recommend.

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