#2 – How to Fail Your Way to Success

Share This Post

#2 - How to Fail Your Way to Success

Today we are going to talk about success and what it really takes to achieve it. I am sure you have heard motivational quotes about how you have to “fail forward” or “fail your way to success,” but I am not confident it has ever been properly broken down for you. It has taken me decades to fully comprehend this concept, and the objective of this blog is to help you do the same.

At first glance, the concept does not make any sense. Why would failure lead to success? Isn’t the point of success not to fail? Aren’t failures and successes opposites? How does this actually work? More importantly, why does it work that way? Let’s dive more deeply into this and answer these questions.

I would like you to imagine two people in a gym. One person is crushing the free weights and looking good. They are wearing the perfect gym outfit and making it look easy. They are doing the same exercises they have always done and choosing dumbbells well within their current capabilities. They are enjoying the workout and emanating self-confidence.

Now, imagine a second person on the struggle bus. They are pushing their limits with a new workout variation they have never tried. They are sweating profusely and doing more weight than they can comfortably handle. They are wrestling internally with their deepest fears and do not look very confident. They are breathing heavily and are uncertain they will be able to complete the workout.

Looking at the present moment only, most people would assume person one is more confident, athletic, and capable. However, looking from the lens of trajectory rather than the present moment, that is simply not true. It is actually person two who will be far more capable in the long run.

On our podcast, Next Level University, I often say “The struggle bus leads to greatness and the party bus leads to mediocrity.” In the example I just gave, person one is on the party bus, and person two is on the struggle bus. To take it one step farther, I say “Micro Success for Macro Failure is the party bus” and “Micro Failure for Macro Success is the struggle bus.”

Micro Success for Macro Failure focuses on looking and feeling good in the moment at the expense of long-term growth. Micro Failure for Macro Success focuses on embracing discomfort, embarrassment, and failure in the moment, to maximize your long-term potential. Both cycles usually run in the background without our conscious awareness, and it is important for you to become aware of which cycle you are running, or perhaps more importantly, which cycle is running you.

The Full Break Down


As you can see in Figure 1 above, both cycles have eight distinct steps. Let’s break them down one-by-one.

Step 1 — No Belief vs. Belief

If you have high belief, you are likely to try just about anything to achieve your goals. If you don’t, however, you are unlikely to try much of anything. Imagine desiring to have a new job but not believing it is possible, or having the desire to date someone you do not believe would ever be interested in you. Desire is like a car without gas. It is a start, but is not sufficient by itself. Desire only translates into tangible action if there is enough belief in the “gas tank” first.

To fill up the “tank” and take action, three beliefs are required. You must believe 1) it is possible, 2) it is possible for you, and 3) it will be worth it. Imagine you want to start a podcast, but have a deep fear of judgment and low self-belief. You believe it is possible, but not necessarily worth it. You have never felt good enough, and even if you did, you are not sure it is worth risking the judgment you may receive. Given these factors, what are the chances you will actually start a podcast?

Now imagine you have high belief. You are scared, but genuinely believe it will be worth it. Since your belief is high, you cannot live with the idea of not trying. You would rather try and fail rather than live with “what if?” You are petrified of failure and criticism too, but are convinced you can succeed if you stay focused.

When broken down like that, it is easy to see why so many people do not achieve their dreams. Why would someone pay a painful price today for a promise that is so uncertain? This is why so many people give up before they even start. It is an inner game. All great things start with believing in something no one else can see yet, and that is where you need to begin.

To put this into action, think about what you want to accomplish, and ask yourself the following three questions:

  • On a scale of 0 to 10, how much do I believe this is possible?

  • On a scale of 0 to 10, how much do I believe this is possible for me?

  • On a scale of 0 to 10, how much do I believe this will be worth it?

Once complete, add up your ratings and divide by three, then multiply that number by 10. This will give you a percentage that represents your chances of achieving your objective with your current level of self-belief.

For example, if you gave yourself a nine, eight, and 10, you have a 90 percent chance of achieving your goal.

I broke down the math for you as follows:

9 + 8 + 10 = 27

27 / 3 = 9

9 x 10 = 90%

What is your percentage? Calculate it now before moving on.

Step 2 — No Try vs. Try

This is where the rubber meets the road. Now that you have enough belief, it is time to give what you are looking to accomplish a try. The question to ask yourself is, “What is the next best action to take to maximize my probability of success?” This is where reverse engineering comes into play.

For example, if your goal is to become a successful podcaster, perhaps you will start by recording the first episode. If your goal is to become a successful author, perhaps you will start with writing the first chapter. If your goal is to become a doctor, perhaps you will apply to medical school. This is the step where your belief will be tested. This is where the gap between talking the talk and walking the walk reveals itself. I have often said, “the distance between what you say and what you do is your ego.” Here are a couple guidelines to help you take the first step.

First, do not try things just to try things. Make sure that what you are trying is part of a larger strategy that maximizes your chances for success. People tend to romanticize carefree wandering, but carefully contemplated chess moves are far more likely to succeed. Think of that friend who is a lot of fun but also kind of a mess. Now think of a friend who is a little less fun but more calculated and responsible. Who is more likely to achieve their goals?

Second, try things within your challenge-skills sweet spot. If you are new in the gym, do not try to benchpress 225 pounds. On the other side of the coin, if you have been weight training for a decade, do not stay at 10 pounds forever. In scenario one, you will injure yourself. In scenario two, you will get bored and will not improve.

Lastly, always air on the side of massive action. Nothing grows on the fence. While choosing your next move wisely is critical, taking consistent, messy action is more important. Messy action will trump waiting around for a better idea any day of the week.

Step 3 — No Failure vs. Failure

This step is about failing forward and why it is so important. First, it is important to note that no one enjoys failure. Failure, rejection, and disappointment are not enjoyable experiences. They are, however, a necessary prerequisite to being successful in any endeavor. After reading this blog, my hope is not that you will enjoy failure, as that is not real or helpful. Rather, I hope you will embrace failure more after gaining a more comprehensive understanding of its long-term benefits. If you have belief and try (steps 1 and 2), you will fail at least some of the time. That is inevitable.

Imagine you are at bat and strike out or get a C on a test. Imagine applying to college and not getting in or trying out for varsity but only making JV. In this context, those are considered “failures” because you did not achieve your desired outcome. However, those are not the types of failures on which this blog focuses.

Those types of failures are obvious and rarely overlooked, and people generally understand them. My focus in this blog is on the less obvious Micro Failures that happen every day. For example, you ask a friend to go to the movies with you, but they already have plans, or you try completing a task in one hour and it takes two. Perhaps you skip a workout, overeat, or arrive five minutes late to a meeting. Maybe you say something embarrassing at work or ask a “dumb” question.

Those are the Micro Failures I am talking about. The death of 1,000 cuts that get us when we do not even realize it. Any one single Micro Failure seems inconsequential, but over time, they slowly accumulate and erode our self-esteem and self-confidence. If not handled with care and consciousness, the pain, rejection, sadness, and failure eventually reach a tipping point. The pain and self-doubt become too great, so instead of aiming higher, focusing on growth, and achieving our dreams, we slowly stop believing in ourselves. We start taking fewer risks and aim just a little lower. In a last-ditch effort to hang on to what little self-esteem we have left, before we know it, what we thought would preserve and protect us, eventually becomes the very shell that keeps us small.

Let’s look at an example of two people. Person one tries to complete 10 critical tasks in a single workday. Person two struggles with self-confidence and failure, so they only put three easy to-do’s on their list. Person one works hard all day and completes only six of the 10 essential tasks. They are slightly demoralized and wrestling with their self-worth. Person two, however, completed all three easy tasks and feels accomplished. The philosophical questions are “who failed” and “who is more successful”? But, what if instead, we ask “who is more likely to be successful in the long run?”

This seems overly simplistic, but it happens every day. Having coached everyone from beginners to world-class multi-millionaires at the top of their industry, the truth has become self-evident. Some of the most productive, well-developed, and successful people I know, rarely, if ever, actually feel great about their day-to-day productivity. It is an interesting duality because the opposite is often true with some of the laziest people I know. Ironically, those are often the very same people who feel the best about themselves. However, it is rooted in ego, not merit.

Step 4 — No Pain vs. Pain

This is where the uncomfortable part comes into play. I will never forget when I first started dating my beautiful girlfriend, Emilia. She is highly growth oriented, so I asked, “Is it possible to grow without challenge?” She quickly responded, “No.” I followed up with, “Is it possible to have a challenge without pain?” She quickly responded again, “No.” Lastly, I asked, “Why is it then, that we are all avoiding the one thing that is actually best for us?” She knew the last question was rhetorical.

I tell that story because Emilia is incredible at taking action and changing her behavior. Still, I know that would not be the case if she was not honest with herself about pain being a necessary part of the process. In this section, I want you to ask yourself, “What is my relationship with pain?” If you would prefer, you can also change the word “pain” to “discomfort.” Both are pretty interchangeable in this context.

That said, we have all heard motivational quotes like, “Nothing grows in the comfort zone” or “No pain, no gain.” Intuitively, we know this to be true. We get it. We know we cannot have an incredible body without challenging workouts or a multi-million dollar income without hard work. I often joke about how everyone hates the StairMaster, but do we fully comprehend pain’s part in the process of behavioral change?

According to Merriam-Webster, pain is “A localized or generalized unpleasant bodily sensation or complex of sensations that cause mild to severe physical discomfort or emotional distress.”

Everyone understands the obvious downsides of pain. We have all felt it and it is not pleasant. So what are its benefits? What if there is an upside to this? To advocate for the upside, I would like to frame pain as a catalyst. Just like a spark can ignite a fire to keep you warm, pain can be the spark to ignite positive change.

Have you ever waited until the last minute to get a haircut or finally cleaned your house right before your parents came over to visit? Perhaps you consistently went to the gym just a few months before your wedding or started watching what you ate only after the doctor said you were at risk of becoming overweight. Unfortunately, pain is the unsung hero in all of these instances. Whenever you are putting off doing something you know is best for you, pain starts to accumulate. Eventually, it reaches a critical tipping point where action is finally taken to alleviate the pain.

So, why did you not take action sooner? The answer is quite simple: the pain of not taking action finally surpassed the pain of taking action. In simple terms, the pain of procrastination finally became significant enough to take the action.

In the case of the haircut, the pain of long hair finally became more significant than the pain of getting it cut. Maybe you had a big date and did not want to look bad. Maybe school photos were coming up or there was a big meeting at work. Either way, something finally tipped the scale in favor of you taking action. In other words, the pain became great enough.

We do not always realize it, but pain has a positive place in our life. Without it, minimal action is taken. When we feel hungry, it is painful, so we know to eat. When we get sick, it is painful, so we know to rest. When we sprain our ankle, it is painful, so we know to take extra special care of it.

In the Micro Failure for Macro Success cycle, pain is inevitable. Belief causes us to try new things and unavoidable failures cause pain. That pain catalyzes one of two responses. We either contemplate how to improve, or we stop trying altogether, and that is where the Micro Success for Macro Failure cycle starts to take over. In that cycle, short-term pain is avoided by not trying at all, which brings us to our next step, contemplation.

Step 5 — No Contemplation vs. Contemplation

If you stay in the cycle of Micro Failure for Macro Success, contemplation is where all of the gold is. This is where learning really takes place, but it is usually done behind the scenes with only close relationships, which is why it is so often overlooked. Still, this step is where knowledge, experience, and reflection collide into a higher awareness that can pay dividends for a lifetime.

For example, I have done thousands of podcast episodes, and I cannot think of a single one that is perfect. There is no such thing. Perfection is a fictitious ceiling that does not exist. There is always room for improvement, no matter how good you become at something. Some episodes go better than others, and the long-term trendline is definitely up, but there is always some pain and contemplation every time.

I often contemplate several questions after a podcast episode: What went wrong? What happened there? How did that happen? Why did that happen? What am I missing? What went well? What didn’t go well? What can I do better next time? Was the topic good? Do you think that resonated with our listeners? Was that story relevant? Did I tell the story well? Did I communicate well? Will our listeners take something valuable from it? etc., etc. This is the heart of why failure is so useful.

I will never forget when a client specifically asked me to train her to become an undeniable coach. She wanted to become world-class and asked me to teach her how to coach like me. I was flattered, but what I told her was simple:

“If you want to become world-class, you have zero wiggle room. You can never rest on your abilities. Most people celebrate when they succeed and contemplate when they fail. Win or lose, succeed or fail, I contemplate. I constantly ask myself questions to ensure I have the deepest possible holistic understanding of how and why things work. This is an infinite game that never ends. This is a mountain that has no summit. There will never be a point where you know enough or have honed your skills enough. I know it sounds exhausting, and it is, but it will be well worth it in the long run.”

Remember, contemplation is often the unseen bridge between experience and the deeper understanding you need to unlock the vault of your dreams. It is not fun or sexy, but it is accurate, and that is why this step is so important and cannot be overlooked if you want to succeed.

Step 6 — No New Awareness vs. New Awareness

To explain this step, imagine there are two young women playing a high school basketball game. They are on the same team and it is championship night. One player dreams of playing in college and the scouts are watching. The other player does not intend to play or even go to college, and this is the last game of her career. Both players show up and do their best, but the one not intending to go to college actually performs better.

The game is now over, and unfortunately, they lost the championship. Both players feel good about their effort, but only one feels good about her performance. In fact, the non-college-bound player is actually relieved it is finally over, as she is ready to move on.

The college-bound athlete, however, is distraught. She gave it everything she had and still lost the championship. How did this happen? She knows she still has a long basketball career ahead of her, so she is deeply concerned about figuring out what went wrong. Instead of partying with her friends that night, she asks the coach if she can review the film. This is her contemplation phase.

While reviewing the film, she has a lightbulb moment. “Holy crap!” she says out loud. “The other team was using a tricky double-team tactic every time I touched the ball… that is why we lost.”

But here is the kicker. Every time they double-teamed her, they left another player wide open who also happens to be a great shooter. Instead of passing the ball around the court to the always-open player for an open shot, she constantly tried to fight through the double team. “Wow… I will never make that mistake again,” she says to herself.

Now, imagine she is playing in college and being scouted to play in the WNBA. The stakes are higher and there is a lot more on the line. This time, when an opponent uses that same double-team tactic, she recognizes it, and knows to find the open shooter.

That is the power of contemplation. What was once a massively painful “failure” transformed into a far larger and more meaningful success later, but only because she had the will to go back to the drawing board when it hurt the most.

In this part of the process, curiosity is everything. When failure, pain, and disappointment happen, you must stay insanely curious about what happened and why. Perhaps even more importantly, you must realize that answers rarely come easily. Those lightbulb moments are hard to come by, and you often have to dig for hours, days, or weeks to get the gold.

Have you ever seen the meme on the internet of a diamond miner digging underground? It shows two men digging and written at the top is “The difference between success and failure.” On the bottom, it shows a miner who gives up just inches away from the diamonds he cannot yet see. On the top, it shows a diamond miner who continues to stick with it long enough to get the payoff. That is what contemplation is like.


Figure 2 – Diamond Miner

New awareness is like a diamond, but it will only be treated like one if you understand its value and have the goals that require you to seek it. Remember, only one basketball player rewatched the film to improve for next time. Was that player naturally more curious and contemplative, or did she have a bigger reason to get better? I leave it for you to decide.

Step 7 — No Better Decisions vs. Better Decisions

Once you have contemplated and gained new awareness, you are ready to make better decisions. This is where the fruits of failure, pain, and contemplation manifest into long-term positive outcomes. Before we go any further, it is essential to unpack what decisions are, and why they are so important.

So, what is a decision? More importantly, what is an intelligent decision, and how do we know if we are making “good” or “bad” decisions? This is an interesting philosophical construct I have contemplated for decades. Have you ever heard someone say, “that person is so amazing” or “they always do the right thing”? While those are kind words, and often justified in positively recognizing someone’s value, they never seemed fully accurate to me.

No one “always does the right thing.” What even is the right thing? What does that mean? The “right thing” is entirely subjective. What is right and wrong is a spectrum, and it all depends on the objective, context, and circumstance. For example, killing is wrong, yes? Of course. But what if someone is attacking your children? What if it is in genuine self-defense? My point here is that the rabbit hole goes deep when it comes to decision making.

Personally, I love what Aristotle wrote about doing the “right thing.” He argues that doing the “right thing” is actually doing the right thing, in the right way, in the right amount, at the right time, with the right people, and for the right reason. Do you see how challenging this can be to discern?

This is why all decisions are built on awareness. Put another way, the quality of your decisions can only ever be as optimal as the quality of your awareness. Imagine a car mechanic building an iPhone or a computer engineer fixing a car. Both could figure it out eventually, but neither would be able to make “intelligent decisions” compared to the other in the opposite circumstance.

In other words, a decision is a choice you make either consciously or unconsciously that you believe will maximize the probability of getting a specific outcome. For example, getting to class early increases the likelihood you will get a good seat. Being on time at work increases the likelihood you will keep your job or get promoted. Exercising regularly increases the likelihood you will stay fit and healthy.

We all make decisions every day, but how intentionally and effectively we make those decisions is predicated on our level of awareness at the time. For example, we do not expect an infant to do calculus or a 40-year-old to suck their thumb. Why? Because those decisions are not in alignment with the person’s level of awareness at the time. We do not expect a toddler to build a multi-million dollar business or a skyscraper. Why? Because they do not yet have the awareness necessary to make effective decisions to accomplish that. We can, however, accept that they can build a house out of their colored blocks.

The bottom line is this: your ability to get better results is predicated on your ability to make better decisions, which brings us to our last step in the cycle.

Step 8 — No Better Results vs. Better Results

This is it. We made it. This is the moment we have all been waiting for: results. This is where the hard work of Micro Failure for Macro Success pays off, and where the truth of Micro Success for Macro Failure finally reveals itself.

Imagine an Olympic athlete who invested four years training vigorously, failing forward, and learning from it, finally getting his or her chance to compete at the highest level. Now imagine the opposite. Imagine a former Olympic gold medalist, once the best in the world, slowly letting themself go for four years, never trying anything new or challenging themself, and finally looking in the mirror only to realize they have become overweight.

This happens all around us all the time. Seemingly overnight successes and seemingly overnight failures are everywhere, but none of those “overnights” are the entire story. That famous couple did not suddenly hate each other and get divorced, and that wildly rich and famous local band you listen to, did not get famous overnight. All Macro Successes and Macro Failures, in reality, were a slow accumulation of tiny Micro Successes and Micro Failures, compounded over time, that made the difference. Maybe that married couple slowly stopped showing affection and appreciation, or maybe that local band continued playing, getting better, and booking bigger venues for years before they “popped off.”

I do not know all the details of these scenarios, of course, but I do know none of it happened overnight. In my line of work, coaching and consulting with people and businesses all over the world, it has become very evident that what most people perceive as overnight successes are actually just overnight awarenesses. In other words, most of the journey simply went unnoticed. The real work was always behind the scenes and beneath the radar for months, years, or even decades before most people found out about their “overnight success.”

Coming Full Circle

So here we are at the end, only to begin again back where we started with no belief versus belief. If you refer to Figure 1 at the beginning of the blog, you will notice something interesting: both cycles are self-reinforcing. They are what most people refer to as a self-fulfilling prophecy. In other words, when you are operating with a fixed mindset (Micro Success for Macro Failure), you do not get any better results, and have even less belief your next time around. When you operate with a growth mindset (Micro Failure for Macro Success), however, the opposite is true. If you stick with it long enough, you will eventually get far better results and reinforce your belief.

So around and around we go, either failing forward, learning, getting better results, and believing in ourselves even more, or trying hard to look and feel good now at the expense of our own long-term growth and fulfillment. Even at this moment, as I complete this blog, I am failing forward. It is not perfect. Every sentence is another Micro Failure I had to slowly work through, edit, and re-edit.

And now there are only two questions left to ask.

Will these Micro Failures accumulate into Macro Success, and perhaps more importantly, after reading this, are you going to join me on this never-ending journey of failing your way to success?

The decision is yours.

Sign up to get the latest blogs

More To Explore

Next Level Blog

#2 – How to Fail Your Way to Success

I’ll never forget when my business partner had the courage to ask what I was doing differently in my coaching. It was 2020, and we were in the podcast studio nearing the height of Covid. We’d been growing NLU together for 4 years, and he was starting to see a significant transformation in the people I coached. He was a coach, too, less confident but eager to grow and improve.

Next Level Blog

#3 – How to Express Uncomfortable Truths

I’ll never forget when my beautiful girlfriend Emilia taught me the concept of The Truth Dial. She was trying to help me become a more impactful leader, and she gave me hard feedback I’ll never forget. She said, “Alan, you’ve been conditioned to suppress your truth to protect others from their insecurities, but you can’t lead or help others grow without the courage to express uncomfortable things.”