Creating A Masterpiece By Failing Forward

Here’s a guest post from Ryan at Planting Dollars.  I was intrigued by one of his comments of “failing forward” (not falling forward) and asked him if he’d be interested in writing a guest post about the topic.  Please enjoy and visit his site afterwards.  He has my envy of living in Hawaii and pursuing his dream of being a shark photographer!  Best, Sam

Have you ever noticed that some of the most successful people in the world seem to just naturally fit in their role? It’s as if they’ve been perfectly sculpted to be the best actor, businessman, or even blogger.

I have a secret to tell you… It’s because of their previous experiences… The one’s you didn’t see before they became wildly and unbelievably successful. These people are actually the biggest failures in the world! But shhhhh, I didn’t tell you that…

Don’t believe me? I want you to try something… The next time you talk to a successful person simply ask them this question:

“What failures have you experienced on your journey towards being where you are today?”

They’ll probably talk your ear off for hours and you’ll begin to realize this: They’ve just swung the bat of life a few more times and eventually hit one out of the park.


Think of your failures as the strike of chisel. Each chisel strike adds a little more depth and a hint of uniqueness to the block of marble your live started as. Each new experience and failure is a lesson in life that teaches you something. Now, if you decide to not take risks, to be complacent, avoid new experiences, and ideas your life will not change much. You’ll still be just a hunk of un-sculpted marble waiting, just waiting, for someone to come along and call you a masterpiece.

But if you take risks and fail, and fail you will, you’ll be chiseled into greater and greater detail until finally, you’ve become a masterpiece. A masterpiece that you’ve made yourself. Through failing forward.


Dive In! Just Jump! Feet first, eyes wide open!

If there’s something you’re curious about, simply try it. You’re going to suck at it, I guarantee it. In fact, you’re going to look like an absolute moron, but you know what? Who cares? You’re still alive so just laugh about it, get up, brush yourself off, send me an email about how horrible it was then go try again. You should be excited to fail forward because you’ll be learning new things, constantly growing, and becoming step by step closer to your very own version of success! How is that not exciting?


There’s a big difference here. Einstein said it best when he said:

“Insanity is doing the same thing over and over again and expecting different results.”

If you’re not constantly failing forward, you’re probably not aware you’re failing at all. Be honest with yourself, see the signs, take a step back, and swallow your pride. If you’re not happy, if you’re not growing, if you’re not trying new things, you’re probably failing. Once you’ve realized you’ve failed there’s only one question you need to ask yourself to fail forward:

“Why did I fail?”

Was it because you didn’t try hard enough, was it because the other person was better prepared, was it because you were going in the wrong direction, was it because you’re overweight and frankly, she doesn’t dig fat guys? It could be any number of reasons, but ask this question to yourself, and more importantly, ask it from other people who’ve seen you fail. They’ll often give you priceless feedback that you can learn from.


A One Way Ticket to Hawaii from Wisconsin: That’s what I bought two months ago when I took a risk and decided to follow my passion of scuba diving. I rolled the dice of chance to follow a dream without regrets. Turns out I didn’t have anything to be scared of. I snorkel in my free time, still work off my debt, and landed a job in a field I enjoy M-F, 40 hours a week. Meanwhile back home they’re getting snowed on! I think this might not even be a failure, but if it was… It would’ve been me failing forward…

This guest blog post. I’ve never written a guest blog post before. Especially not for a blog ranked in the Alexa top 100,000. This is intimidating and odds are, it’ll fail. But here I am, jumping, throwing my self out there so you can tell me how crappy this article is, but yet how I can improve it (hint hint… comments much appreciated). However, tomorrow I’ll know that I did something completely new, something that’s scary, and something that made me grow.


I challenge you to do the same, to leap, to jump, to try something new.  Once you’ve failed, realize that by doing so you’ve just become a little bit more chiseled and one step closer to becoming your very own masterpiece.

Ryan is a recent college graduate who blogs about personal finance, financial freedom, nomadic living, and following your passions.  One of my favorite articles of his is “How To Live In Honolulu for Less Than $1,000 A Month”!

Readers, how have you “failed forward”, and what have you learned from the experience?

I tried to teach my wife how to surf yesterday and failed forward.  She told me to leave her alone when I tried giving her a push a couple times when the waves came.  I was annoyed she didn’t want my help, because the iddy biddy waves weren’t big enough for her to catch on her own.  However, I knew she’d figure this out eventually, so I left her alone, not wanting to fight.  Besides, I think she was nervous, wanted to acclimate on her own, and felt bad “wasting” my time.

When I returned 20 minutes later, she was exhausted and realized she needed some help.  On one of the very last attempts, I gave her a push, and she stood up for a good 20 yards!  Success!  Sometimes she’s stubborn when it comes to learning new things as many of us are.  I feel that each time she pushes me away and fails, she realizes that I’m only trying to help.  This is my small story of failing forward towards better communication and understanding as a couple.  What’s yours?  Sam

Sam started Financial Samurai in 2009 during the depths of the financial crisis as a way to make sense of chaos. After 13 years working on Wall Street, Sam decided to retire in 2012 to utilize everything he learned in business school to focus on online entrepreneurship. Sam focuses on helping readers build more income in real estate, investing, entrepreneurship, and alternative investments in order to achieve financial independence sooner, rather than later.

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  1. Gordie says

    Thanks Ryan,
    I haven’t heard the term failing forward before. I love it.

    Also, there’s now way this post is a failure. It reached me. Count that as a small success. :)
    .-= Gordie´s last blog ..Look, Mom! My Blog’s Sprouting Pubes! =-.

  2. says

    After working in a risk-evasive organization for years, I can tell you avoiding failure is the single biggest cause of failure. We had three editors and one writer. (Should give you an idea of just how risk sensitive we were.)
    Anyhow. Great guest post. I do envy the weather in Hawaii, but I tell you what, I have little chance of being chewed up by a Tiger shark in Pennsylvania. So there.
    .-= Matt S.´s last blog ..Hacking Your New Year’s Personal Finance Resolutions =-.

  3. says

    Good job, Ryan. Excellent article. When I was playing Bill Nye the Science Guy in my previous job I told about 5,000 kids over a 4 year period to rethink their definition of failure as not something to be afraid of but something to be expected. The only way to get better at anything is try it and learn from your failures. I used Thomas Edison as an example and the story goes he was asked how it felt to finally succeed at developing a working light bulb after so many failures and his response was they weren’t failures, he just learned how not to build a light bulb. He would document what worked and didn’t work and move on to the next iteration.

    One of my favorite quotes is by Henry Ford: “One who fears limits his activities. Failure is only the opportunity to more intelligently begin again.”

    I “fail forward” all the time. I’ve made lots of mistakes with my blog, in my job, finances, personal relationships, etc., and I try to chalk it up to experience and move on. I think the key is to admit to the mistakes quickly, let everyone know what you’re doing to prevent it from happening again, and try something different. The alternative is to stagnate and never get anywhere in your life and that doesn’t seem like living to me.
    .-= David @ MBA briefs´s last blog ..How to analyze stocks like a pro – part 2 =-.

  4. Joel says

    A really interesting perspective. It takes a certain zen perspective to concentrate only on the activity at-hand, and not the potential ramifications. If Ryan had said, “I could move to Hawaii, but what if I don’t find a job? What if I end up slinging burgers? What if…” That thought alone would have likely paralyzed him.
    .-= Joel´s last blog ..The We Seed Philosophy: Easy Enough for a 14-Year-Old =-.

  5. Minority Fortune says

    Great concept! Failing is so often looked at as the end. As discussed in this post, it’s an experience that pushes you closer to success. Think about how hard toddlers struggle to walk, but with each fall, they get back up and try again. That’s the spirit that we should all have when we fail in something. Failing forward is a great way to look at it as it turns something deemed so negative into something positive.
    .-= Minority Fortune´s last blog ..Building The New Las Vegas in Asia =-.

  6. Jesse says


    Great article – definitely not a failure! Really like the phrase and plan to reference it (giving credit of course).

    I recently returned from one of my own “failures” – took a job with a firm who focused on projects in the Turks & Caicos Islands. Not quite the Indiana Jones adventure, still have plenty of stories.

    Ralph Waldo Emerson said something to the effect of, “Life is a series of experiments. The more experiments the better”.

    Failure has such a negative connotation when really what we are doing is extending ourselves beyond what we’re currently capable of or already know. When you push your own limits by diving into the unknown, failure is almost guaranteed.

    As you highlight, growth and development come from consistent failure (and learning from). Ironically, the more random things you try, explore, and learn – the better you will likely become in your passions since so much of life is inter-connected. Some of my own personal finance beliefs have been derived from unrelated interests like running and traveling.

    And hey, if all else “fails”, at least you’ll always be “that guy” everyone wants to talk to at dinner parties.

  7. says

    I love the post. Even with all the ‘how-to’ books and manuals you will not succeed at something until you jump with both feet in. A book can only tell you so many to-do’s and not-to-do’s, but every situation is different for each person. And you won’t tell what is good or bad until you… again…. jump with both feet in.

    BTW, I commend your wife for trying. Surfing is a hard thing to do. :)
    .-= Money Funk´s last blog ..2010 New Year’s Resolutions =-.

  8. says

    @Money Funk
    Will tell my wife you said so! :) Gotta say, surfing is the LOWEST return on effort fun thing to do! Paddle, paddle, paddle, wait 5 minutes for the perfect wave, miss it, paddle, paddle, paddle. Rest cuz ur delts are burning, paddle paddle, stand, ride for 5 seconds, fall, paddle paddle. OK, lunch time!

    C’yall in 5 hours. Gonna go battle the ex ATP tennis player who wiped me out earlier this week!

  9. says

    @Matt S.
    You’ve got me there, hopefully failing forward with sharks doesn’t incur losing my life! Knock on wood… However, if there are any rivers in Pennsylvania that lead to the Atlantic (I don’t know this offhand as I’m geographically challenged) I’d be weary of those fresh water swimming and most dangerous bull sharks!

    haha, prepare the “lazer” – your comment made me laugh.

    @David @ MBA briefs
    I was actually thinking of using that exact quote in this post. I think Edison illustrated how we should look at failure very well and it’s amazing how much he accomplished which is proof why you should constantly be seeking failure. I haven’t heard that particular quote from Ford though, so thank you for sharing it. I agree with you about being stagnate. If you’re not moving forward, you’re going backwards.

    Agreed, being stuck to me is worse than failing a million times over, plus it’s so incredibly boring!

    I’ve never thought about it that way. I was motivated more by the fear of having regrets than the fear of failure, so in a way fear can be worked to your advantage. I like the idea of being in a zen like state though, haha, although I have not learned anything, yet, about that topic so maybe I just got lucky. I suppose even if I ended up flipping burgers, I would have learned something new in the process, which is incredibly fun for me. Maybe I would have learned how to be a master griller who could down the road use that for entertaining guests?
    .-= Ryan @ Planting Dollars´s last blog ..5 Reasons Grocery Carts are Evil =-.

  10. says

    @Minority Fortune
    I like how you linked it to toddlers beginning to walk… I wonder at what point that desire to constantly challenge ourselves leaves us due to fear. Maybe when we’re picked on in grade school, get pimples in high school, or aren’t the athlete in college?

    Feel free to use the term, I’m sure it’s been used in the past somewhere else as well so no worries at all. Turks and Caicos…? Have you gone yet, and what did you think? Are there lots of sharks there???

    I think you bring up a great point in that we learn from everything we do, since everything is interconnected. I remember Steve Jobs talking about just that in a commencement speech where he mentions how he sat in a bunch of classes just for fun after dropping out of college… one of those classes was calligraphy which inspired him to create a visually appealing computer company when he was older… Apple…. I think the same can be done in our own lives and I like to think of it as creating a hybrid career or business. Mixing and matching things we enjoy into something that fits exactly who we are and what we enjoy.

    @Money Funk
    Oh my gosh I’ve read so many of those books already, and although I learned a lot of concepts from them, it’s not nearly as valuable as just doing something. From that same angle I value my college education, but would be more interested in what a person has done with their life and in their spare time than what vocabulary words and theories they memorized for an exam. Life doesn’t have a grade.

    Thank you for the compliment, better late than never right? That’s also a great post you’ve got going on today over at your site ;)
    .-= Ryan @ Planting Dollars´s last blog ..5 Reasons Grocery Carts are Evil =-.

  11. says

    What a great term “failing forward,” and I can truly appreciate it. The only way you can ever know if something will work, is to try it. Kind of like taking a leap of faith (wait, did you say that in the end?)

    P.S. to Sam- I want to comment on the surfing, many years ago on a visit to Hawaii, I tried surfing. It was really hard! Kudos to your wife who stood on the board for 20 ft. I could never get myself to stand up. But at least I tried.
    .-= Little House´s last blog ..Incredible Credit Scores! =-.

  12. Tracy says

    Sharks with laser beams on their heads? Those are the worst, for sure! I love the idea of “failing forward” My blog was inspired by failures and through it I am learning more and more ways to risk failure while having a blast and interacting with a whole new world of people and ideas. I can almost feel my brain cells expanding…or maybe that’s dementia or an anuerysm or something…whatever, it’s fun.

    I think our culture teaches us to reach for an ideal without appreciating the journey and the images of this invariably picture the trappings of success without much discussion of the price paid to achieve it. We are an instant everything society and if we aren’t careful life will leave us in the dust wondering where the time went. Be happy that you get this at such a young age. I ran away from a career in the middle to teach skiing for two years. I came back eventually, but I don’t regret a single moment of my adventure.

  13. says

    Failing forward is a great way to help yourself get over your fears, and you may just realize it was all in your head.

    Sometimes, you just have to do it and ignore the (well-meaning) naysayers.

    With that being said, I’d also be careful to have SOME money saved up for whatever you plan on doing.

    It’s nice to be impulsive and all about your dreams, but the reality is that you are taking a bit of a risk, so do it the smart and calculated way.
    .-= FB @´s last blog ..Fun Final Year End in Review: Budget & Blog =-.

  14. says

    @FB @
    Agreed – blindly failing forward seems a bit pointless. Having an idea of what you’d like to do is what you’re taking the gamble on, and the goal of course isn’t failure, but success. I heard a great quote that simply said: “success lies on the other side of fear,” so I think overcoming fears is one of the key elements in any successful life.

    Personally I saved up for a year so I could take my risk, so it wasn’t much of a risk at all because I had saved enough. People who live paycheck to paycheck in their hometown I feel live at a higher risk than I do. I knew worse case scenario I would be waiting tables, but still shooting for my goal and being able to live within my means, and I was okay with that.

    Living a frugal life so you can achieve your larger dreams is what’s most appealing. When collection agencies are calling you because you can’t pay for your big house, sports car, and boat and you have too much pride to take any job out there to pay the bills you’re not failing forward… you’re failing period. Frugality allows you the freedom to follow passions without the weight of consumerism, which is… fabulous!
    .-= Ryan @ Planting Dollars´s last blog ..Thank You Samurai and Cash Money Life =-.

  15. Charlie says

    great post! I like the concept of chiseling away to a masterpiece. I like the mentality of trying new things without being afraid of making a fool of yourself and messing up. Surfing sounds like fun to me even if it does take time to get a good wave. Wish I lived near a warm ocean to try it out and practice enough to get good at it. Definitely takes guts to get out there in the first place so props to you and your wife for giving it a go!

  16. says

    Great article! I came across the “Failing Forward” term from a Maxwell book before but your article definitely explains it better and in a very engaging way at that. I like it.

    I remember writing a similar story before when I tried to ride my bike for the first time. I failed and failed and failed many times but eventually I learned to steer it the right way. There was only one problem – I didn’t know how to stop the bike. So I had to “fail” again by intentionally turning the bike over – which got me several scratches on my arm…and yes, I also learned to stop the bike the right way after a couple more scratches. More power to you! =)
    .-= Rich Money Habits´s last blog ..A Look Back on my Financial Journey in 2009 =-.

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