Failing Forward – What Does It Mean To Fail Forward In The Real World?

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I’m a big fan of the concept of failing forward. So much so that my wife gets tired of hearing me say that I make more mistakes before noon than most people will make this month…but it’s true so I keep saying it. It’s a fact that I do more stuff than most people, I take more right-sized risks than most people, and because of that, I fail more than most people. However, I always fail forward.

If you have the heart of an entrepreneur and dreams of starting your own business, then you too must lean into the idea of failing forward. Failing will happen, but those fails don’t have to be major setbacks, instead, they are opportunities to move forward toward your ultimate success.

“Right-Sized Risk” is a risk you chose to take because you know the consequences of failing are acceptable compared to the potential success and even the potential learnings associated with failing. Mastering right-sized risk is essential to learning to fail forward.


The Meaning Of Failing Forward

Failing forward means that a person embraces failing as stepping stones to future success. To fail forward means that you have chosen to value every failure for the lessons learned and then apply those lessons in future efforts, even if those efforts might also result in failure. When you are failing forward, each failure moves you closer to ultimate success.

To be clear, embracing the idea of failing forward does not mean that you are striving to fail. It doesn’t even mean that you enjoy failing.

It does mean that you understand that failure is part of the journey to success and that you won’t let the fear of failing stop you from taking right-sized risks.

Likewise, it means that you will not allow the pain and embarrassment of actually failing to be the end of your journey to success.

I want to tell you the same thing that I tell my kids about failing.

Facts About Failing

  1. You will sometimes fail.
  2. The more you do, the more you will fail. You will also succeed.
  3. You will learn more from the times you fail than from the times you succeed.
  4. Mastering a new skill takes 20,000 repetitions of practice. Success is a skill, and failing is the practice you need to master success.
  5. Expect success, but also expect to fail along the way.
  6. Prepare for the worst potential outcome, but plan for the greatest possible success.
  7. Failing does not make you a failure. The only thing that can make you a failure is never succeeding. Failure is the absence of success, not the presence of some fails.
Image by Gerd Altmann from Pixabay

In a bit, we’re going to dig into how to actually prepare to fail forward, but first, let’s make sure that we fully understand the concept of failing forward.

The Origin Of Failing Forward

At this point, countless business coaches have talked about failing forward in spoken word and countless books. And while I expect that the idea is as old as humanity, the specific phrase came into the mainstream in the year 2000.

In 2000, John C. Maxwell published the book “Failing Forward: Turning Mistakes Into Stepping Stones for Success” This was the first appearance of the phrase “Failing Forward”. While the idea of failing forward had appeared in countless other business books, having it on the cover of this best-selling business book brought the idea to the forefront.

In this book, Mr. Maxwell, advances the idea that the only universal difference between average people and successful people is their perception of failing and their response to inevitable failing.

He argues that most people fear failing and consider themselves to be a failure when they have failed. This means that they spend their entire life avoiding failing, which means that the average person never learns from failing and therefore never achieves the success they dream of.

Without embracing failing forward, your only response to failing is to define yourself as a failure and fail backward.

While this book was originally published in 2000, with revisions it remains a modern business book that should be on the bookshelf (or virtual bookshelf) of everyone who aspires to be self-employed or build a business. If you haven’t read it yet, get it today. { Click Here to see the Failing Forward book on Amazon. >>> }

John C. Maxwell’s most famous quote about failing forward is “Fail early, fail often, but always fail forward.” This quote comes from his book “Failing Forward: Turning Mistakes Into Stepping Stones for Success” which was published in the year 2000.

However, this isn’t the only famous quote about failing forward.

“Because in life, the question is not if you will have problems, but how you are going to deal with them. Stop failing backward and start failing forward!”

John C. Maxwell

Failing Forward Quotes

The idea of failing forward has been espoused by countless successful people because it’s a damn good idea. Below I’ve captured some of my favorite quotes about failing forward in hopes that you’ll find some wisdom to apply to your own journey to success.

1. “Achievers are given multiple reasons to believe they are failures. But in spite of that, they persevere. The average for entrepreneurs is 3.8 failures before they finally make it in business.” – John C Maxwell

2. “In life, the question is not if you will have problems, but how you are going to deal with your problems. If the possibility of failure were erased, what would you attempt to achieve?” – John C Maxwell

3. “Many of life’s failures are people who didn’t realize how close they were to success when they gave up.”  – Thomas Edison

4. “Recognize that you will spend much of your life making mistakes. If you can take action and keep making mistakes, you gain experience.” – John C Maxwell

5. “A mistake is only an error. It becomes a mistake when you fail to rectify it.” John Lennon

6. “When achievers fail, they see it as a momentary event, not a lifelong epidemic.” – John C Maxwell

7. “I have not failed. I have found 10,000 ways that don’t work.” – Thomas Edison

8. “Failure happens all the time. It happens every day in practice. What makes you better is how you react to it.” – Mia Hamm

9. “The more you do, the more you fail. The more you fail, the more you learn. The more you learn, the better you get.” – John C. Maxwell

10. “Try again. Fail again. Fail better.” – Samuel Beckett

11. “It is impossible to live without failing at something unless you live so cautiously that you might as well not have lived at all, in which case you have failed by default.” – J.K. Rowling

12. “Fail early, fail often, but always fail forward.” – John Maxwell

13. “Failing Does Not Make You A Failure.” – Stacey Davis

I know there are countless other inspiring quotes about failing better, but let’s not just focus on what other people have done.

Instead, let’s focus on how you can fail better while building the knowledge and skills you are going to need to be wildly successful in the future…we call that failing forward.

Photo by Andrea Piacquadio from Pexels

How To Fail Forward – 10 Tips To Fail Better To Success

These tips are not only going to help you come to terms with failing, but help you gain the best possible learning from each misstep you make on your journey to success.

1. Prepare For The Worst, Plan For The Best

The potential for failing is much less scary when you define that nightmare and come to terms with the idea that you can live with failing…if you have to.

This means taking an honest look at what failing in this project looks like and how you would deal with that challenge. If it doesn’t destroy you, then you just need a plan to overcome the setback of a failed project. You also need a plan for dealing with potential success.

This also means analyzing what failure looks like. Is it really losing everything you put into the project, or could you resale some of the invested assets to make the worst-case scenario a loss of 30% or 70%?

Plan before you start a new project.

2. Right-Size Your Risk – Start Small

The scale of a project that we can easily withstand failing does change over time. With more success, you can handle larger fails without destroying your present success or future potential.

When you are starting out, limit the resources you put into a new project to those that you can overcome losing if the project were to fail.

To be clear, I’m not recommending that you only risk what you can painlessly lose. Instead, I’m recommending that you only risk what you could lose without destroying your life. The fear of pain makes us work harder, longer, and hopefully smarter.

Start small, and with each success, your risk for the next project will grow. In time, your right-sized risk will dwarf the one you started with.

3. Identify Potential Obstacles

From personal experience, I can guarantee that being blindsided by failing honestly makes failing way harder. Do everything in your power to avoid surprising causes of failed projects.

When you plan a new project, spend a chunk of time brainstorming to create a list of the potential obstacles to success. Don’t be shy about making a huge list, starting with the most basic potential obstacles and progressing to the most complex.

For example, every list of potential obstacles that I make starts with “I don’t follow through”. I know that if I don’t follow through on a project, it does not just have the potential to fail, but it is certainly guaranteed to fail. I include this specific potential obstacle every time I make a new list because this is a list of potential obstacles, not guaranteed obstacles.

This list serves as a cautionary tale to help me stay vigilant and avoid the vast majority of those potential obstacles. Fewer obstacles mean less chance of failing and a greater chance of success.

Where do you get your list of potential obstacles? From your past failings. You can make a better list of potential obstacles by continually failing forward.

4. Learn From Other’s Failings

Not all potential obstacles need to come from your own life lessons. You can borrow the failings of others to fail forward. That’s just failing forward faster.

5. Budget In Life & Business

This is tied to Tip #2 – Starting small and budgeting well will make inevitable fails much less scary and damaging.

To right-size the risks you choose to take, you need a crystal clear picture of your financial reality. You must know how much you need to live and simply refuse to put those resources at risk.

After a lifetime of being self-employed, you might think I’ve ‘risked it all’ again and again.

I have not risked it all…ever.

I am by nature a cautious person, and even though I gave up the safety net of working for others decades ago, I never risked it all. While I take risks every day of my life, those are measured risks based on my budget for both life and business.

But this isn’t the one-right-way.

There are countless old-and-tired stories about the billionaire who risked everything to achieve success. Some of those stories are true and many are BS, but if we’re honest with ourselves, they are all kind of sexy.

However, for every billionaire success story, there are dozens of destroyed life stories that you will never hear. Everyone fails. Some people risk everything and get lucky that their fails didn’t hit at the wrong time or in the wrong way.

Most of the people who risked everything lost everything when they failed.

Most millionaires and billionaires failed forward; growing slowly and steadily while never risking more than they could afford to lose.

More importantly, almost all of your quiet and unassuming millionaires-next-door (and you have those neighbors whether you know it or not) have built their wealth through measured fails.

6. Debt Is Slavery – Save For Your Next Project

Yes, some people leverage their way into a rocket shot to success. Borrowing way more than they could ever pay back if their inevitable failings hit at the wrong time or in the wrong way.

That is not a risk I’m willing to take with my family’s future.

Now if you are young and single, maybe you want to take that risk (see Tip #2 Right-Sizing Risk), but I’d strongly advise against it. I have so many friends who end up working for someone else just to keep up on their debt payments with little or no time and energy remaining to start their own dream.

Debt is slavery…avoid it as such.

This includes debt for car loans. I promise you, paid-for beaters (i.e. an ugly and old car…at least that’s what our family calls them) drive better than fancy piles of debt that leave you lying awake at night worrying about your next car payment.

Image by Tumisu from Pixabay

7. Find A Mentor

This is related to tip #4 – Learn From Other’s Failings, but it’s the supercharged version of that failing forward tip.

You honestly can learn from others’ failings by just reading the news or participating in online forums. However, if you have a mentor who is on the same path you are following but is just ahead of you on that path, it’s a game-changer.

Not only will you learn from their fails, but you’ll also be able to learn how they addressed those fails and what they’d have done differently with the perfect clarity of hindsight.

This is invaluable (some would say supercharging) and will help you succeed more often and reach your goals much sooner.

One of these days I’m going to write an article about how to find a business mentor, if you want me to put this towards the top of my priority list, please let me know in the comments below or signup for to hear more from me in my weekly emails.

8. Reskill Yourself

I absolutely believe that an entrepreneur should have a broad base of real skills.

You don’t need to be a master of any of the skills that it takes to start, grow, and run your business, but you do need to have enough of the skill to be able to know if someone you hire can do the job and is doing the job well.

If you are hiring someone to do something you know nothing about, it’s really easy to mess up that hire.

So get busy and hit YouTube to learn the basics of what your business needs. This might be learning WordPress, honing your writing skills, learning basic graphic design, photography, website maintenance, social media scheduling, etc..

These skills are things that you can do, not things that you know.

Every new skill you add makes you better equipped to avoid or mitigate the inevitable fails of having a team working on your business.

Learn More About The Small Business Startup Plan

9. Educate Yourself

Educating yourself is all about the things that you know, not the things that you can do. Your goal should be to know as much as possible about as many topics as possible.

I’m not suggesting going back to college, I’m suggesting that you learn every day of your life.

When I’m out on deliveries, I’m listening to podcasts. I’m a big fan of podcasts from the following topics:

  • News
  • Investing
  • Business
  • Online Business
  • History

I also listen to business and history books on Audible by Amazon.

Don’t waste your days when you could be learning.

10. Celebrate Your Victories, No Matter How Small

Failing is inevitable. However, as long as your failing forward, successes are also inevitable.

It’s easy to focus on the fails, so make it a habit to celebrate your successes. These little victories are the things that keep you moving forward.

11. Strive To Be A Realist

Don’t define success so grandiosely that you can never achieve it.

When dreaming, you should aim for dreams that are big but realistic. Defining success in your life as living in a mansion on mars is probably going to lead to failure (a lack of success). However, defining success as living in a nice home on the lake while working from home is a goal that you can fail forward to achieve.

You can always revise your definition of success as you crush your first goals.

12. Define Yourself By Your Successes

I’m feeling a little bad that I seem to keep beating on the idea of failing often, but I guess this article is about failing forward so it makes sense that there is a lot of discussion about failing often.

If you are doing hard things, you will fail. You will fail often. You will sometimes fail spectacularly.

Do not let those fails become how you define yourself.

When you are talking about yourself, always start with and focus on your successes. Save your fails for those who seek you as a mentor.

Define yourself by your successes.

Image by Sasin Tipchai from Pixabay

13. Share Your Wealth

In this case, I’m not talking about giving money away (though that feels good too). Instead, I’m talking about sharing your knowledge, skills, experiences, and fails with people who are on the same path that you’re on but just further back on the path.

In time, you should be a mentor to other aspiring entrepreneurs.

By sharing your wealth, you will change lives and make the world a better place.

Oh, and when you have succeeded, share your financial wealth as well. We give locally and directly to those in need when we can. It feels good to know we can help change a family’s stars.

14. Remember That Failing Does Not Make You A Failure

Throughout this article, I’ve strived to not use the word ‘failure’, and it’s been hard. In our culture, it seems that we focus on failure.

We tend to define failure as the act of failing, but that is not a true definition of failure.

A better definition of failure is a lack of success.

That means that no one can be a failure until they’ve breathed their last breath. Success is always possible as long as you’re failing forward.

Image by Sasin Tipchai from Pixabay

Fail Often And Fail Spectacularly

Everyone fails.

Some people fail more than others. But why?

Is it that smart people fail less than average people?

Is it that rich people fail less than poor people?

Educated less than uneducated?

No. It’s none of those things.

Everyone fails and the only reason that some people fail less is that they do less.

Don’t do less; do more. Do more in your personal life and your business life. Take risks and embrace the fails that will come.

All the while, remember the tips from above to failing better to success and focus on the tips about right-sizing your risks and your fails.

When you are young and without a family, maybe you can risk everything because everything is really still nothing.

Later when you have a young family, your risks have to be smaller but never let those risks entirely disappear.

And in time, you just might have the resources to take and absorb spectacular fails.

So in closing, I challenge you to risk often, fail often, and sometimes, fail spectacularly.

But, always fail forward.


I just finished an article with examples of people who have failed forward.



With over 15 years of experience starting, running, and growing home-based food businesses, Stacey is the #1 home-based food business coach in America. Stacey is the author of the Advantage Meals: By The Numbers Book.

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