How do successful people know when to give up and move on

“Part of being a winner is knowing when enough is enough. Sometimes you have to give up the fight and walk away, and move on to something that’s more productive.” — Donald Trump


Should you give up when you fail at something?  Maybe!  That is really the truthful answer.

There are many types of failure in many aspects of our lives.  We may fail at relationships, academic pursuits, or in our careers and business endeavors.  I could speak to each of those areas but let me generalize a few insights that will help you learn to recognize and learn from failure.

Research has shown that that 70 percent of us fail to achieve the goals they we have set for ourselves.  This tells me that failure is inevitable.  But most of us don’t need research to tell us this.  We feel it and we have lived it.
Deciding when to give up or press on is one of the feedback mechanism that failure offers you.  Failure may inform you to make a critical change in your path that may lead to the success you have been seeking. On the other hand, failure might be indicating that you are on the wrong course and you need to pivot form your current path and go in a completely different direction.  If you don’t head this feedback you might spend year’s picking up the pieces from a cascade of failures.
Failure should be our teacher, not our undertaker. Failure is delay, not defeat. It is a temporary detour, not a dead end. Failure is something we can avoid only by saying nothing, doing nothing, and being nothing.” – Denis Waitley

Darius Foroux wrote this profound observation about failure and giving up.

Most of us believe that it’s wrong to quit. That it’s for losers. And that quitting equals failure.

The ‘never quit’ attitude is a good thing. Especially when we pursue hard things. I don’t think you should ever quit just because you can’t handle something.

However, quitting is also a smart strategy. Sometimes quitting is even the better option.

Seth Godin wrote a book about quitting. It’s called The Dip. And it’s very good. He says:

“Persistent people are able to visualize the idea of light at the end of the tunnel when others can’t see it. At the same time, the smartest people are realistic about not imagining light when there isn’t any.”

Sometimes you’re in a tunnel where there is no light to be found at all. So no matter how hard you work and persistent you are, you will never achieve anything.

Dead end jobs, businesses, projects, relationships, behavior. We’ve all been there.


If failure is such a great teacher why aren’t we learning?

Unlike a real teacher who has you in a captive setting, failure is more like a tutor that only shows up to teach you something if you ask for help and if you spend the energy to learn the lesson.
Here are four reasons why we fail.  We fail for reasons:
  • That are self-evident
  • That are unknown
  • That you mislabel
  • You recognize but do not take action upon

I have had rich life experiences and I have failed for all of these reasons. In retrospect, if I could fully comprehend and calculate the full measure of my failures back then, maybe I could have recognized the path forward and changed a few outcomes?

Self-evident failures

Having the wrong attitude, the wrong knowledge, and a lack of skills are self-evident attributes that are contributing factors to most failure.  Lacking one of these attributes is somewhat self-evident why you failed.  You didn’t study of the test, you didn’t prepare for the meeting, and you said the wrong thing.  All failures that you created if you are brave enough to acknowledge them.

Even though some of these failures are self-evident to the rational mind, they may not be that evident to us when we are in the middle of them and looking at failure through the prism of emotion.

Unknown reasons for failure

It is also possible that you are doing all the right things but for some reason success doesn’t flow in your direction.  At that moment and perhaps for years later why you failed can seem like a mystery.  Sadly without examination those failures can lay dormant and remain a mystery. I would submit that while some reasons will remain a mystery, many reasons for failure can be unearthed and examined to help you learn from them.
If you’re in a spiral of failure but don’t know why it is probably because you are not appreciating their value and you are not learning from them.  The good thing about a failure is that it doesn’t have an expiration date.  You can learn from them long after their initial impact.  I further propose that if you go deep enough and become accountable for your life those failures of the past will make sense to you and the mystery will be solved.

Mislabeled failures

More damaging to your soul is when failures are mislabeled.  We can call this blame.  When you think you are doing everything right, but you later find out you were wrong this can be a sobering moment.  For a multitude of bad reasons you can completely miss the point of a failure event.
Many years ago as a new product manager I was succeeding in many areas of my job, but I later came to understand I was failing in other aspects.   The general manger of my division made this comment after a group presentation:  “how can your product be successful and not sale?”  I was doing 80%of my job right but ignoring the other 20%.  At that moment I didn’t learn anything from my failure.  I didn’t dig in and learn about why my product wasn’t selling, instead I blamed my sales team for lack of sales.  My failures were both mislabeled and simultaneously recognized by me but I failed to take corrective action.

Failures that you don’t act upon

I could see the failure.  It was in mathematical terms.  My product wasn’t selling. However, the failure didn’t teach my anything because I was unwilling to learn. It is important to note that recognizing failure is only the start of gaining value from that analysis.  In my example, if I would recognized my failure I may have stopped short by saying to myself “Yeah my product is not selling and I don’t understand 20% of my job.  I’m stupid. The end.”  I think, even for the self-conscious and for the seekers of success, we often just let a failure like this have that level impact.  We deflect, we set a new goal and move on.  We don’t seek to understand if our attitude, knowledge, or skills are contributing factor to our failure.
What I should have done is recognize my failure and then created a learning strategy that would have helped me understand what is missing from my tool kit as a product manager.
If a failure is going to help you become more, become better, or become successful you need to not only recognize that you failed, but I need that experience to inform your strategy or system for becoming better.
In hindsight I should have said is:  “Wow I need to own this, I need to learn more about product marketing and software development and what it takes to keep a product healthy.  If I learn this now I’ll be in a better place in my career later and I’ll place myself in the crosshair of luck/ opportunity.”
However, my initial reaction is somewhat typical. I was not rational, but emotional and I just cracked that experience up to – wow my boss is a jerk – and tried to pick up my self-esteem.
So don’t do that!  Be smarter than me.

What should you learn from your failures?

The story arch here is that this failure was so profound and its impact so deep that it has taken me over 6 years to place that experience within a learning framework, which has helped me pivot and truly learn from that failure.  I recommend that you avoid letting a failure taint you for years as it did me.  There is a difference between learning from your failures and using what you learned to make a change. If I had a system then, like I have now, I would have known how to react, how to process that event, and how to move forward in a more positive manner.
In John C. Maxwell’s book Failing Forward, he illustrates this point by relating a story about John James Audubon, who we know now as the founder of the Audubon society.
In the early 1800’s Audubon was involved in several trading and manufacturing business that all failed.  Some of these were simply bad timing.  For example he started a trading business with England right before the war of 1812. That of course devastated his prospects.  What Audubon was good at was hunting and drawing.  In fact he used his artistry as a meager part of his income for most of his adult life before he became published.
In 1826, now at the age of 41, Audubon was able to publish his book and found great success in those endeavors.

In contrast let’s take a look at Richard Branson.   Branson is a billionaire, an entrepreneurs and viewed as an overall model for success.  But his track record shows that he fails perhaps as much as he succeeds.  Most of his Virgin product lines have failed while other have succeeded.  Branson, I submit, knew when to quit and when to stick with the right investment or business.  His failures didn’t inform him to change careers, rather they confirmed his overall direction.  He pushed forward and in most respects he is successful.


If your goal is to become a successful entrepreneur and the failures of companies on long the way fits within your system as you keep learning and perfecting your skills than you are well aligned with Branson and everything might work out for you.

If you were not well suited for business and you’re more like an Audubon, then failure should inform you that you need to change your course and do what you’re good at, which is what Audubon did and then he became a success.

In her article “Strategies for Learning from Failure” Amy C. Edmondson said “Once a failure has been detected, it’s essential to go beyond the obvious and superficial reasons for it to understand the root causes. This requires the discipline—better yet, the enthusiasm—to use sophisticated analysis to ensure that the right lessons are learned and the right remedies are employed.”

One of the keys to know if you are on the right track or if your plan is wrong is by taking this simple litmus test when failure occurs.  Is your failure today the result of a long string of bad decisions or is the failure of today isolated to the events of the day?  I think success comes to those who can interpret, categorize and segregate failures so that they don’t cripple their dreams.

No matter the type of failure, try not to fail, but if you must fail, fail the best way you can. Don’t try to avoid all risk, but set yourself up so that you can pivot from your mistakes. If failure paralyzes your momentum you need to recognize what failure is trying to teach you and then move in a purposeful direction.

The real trick is to be able to learn and learn rapidly form your failures.  If you have created a system for success (whatever that might mean to you) it is much easier to learn and pivot from a failure.

If you don’t have a system that helps you react and process a failure events you can get stuck, and in doing so, you don’t move toward anything productive.  You simply let the dark tar of failure simmer in your soul.

If failure is inevitable then success is contingent upon your perceptions, actions and recovery from a failure.  From that informed point of view you can rationally build a learning strategy to change your attitude, update your skills or knowledge.


most-interesting-man-in-the-world_I LEARN

Learn more:  Read my new book The Value of Failure.

Shane Lester is the Author of the new book: The Value of Failure

“This book will change everything you thought you knew about failure.”


Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s