How to Fail Your Way to Success


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

At first glance, it doesn’t 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?

Imagine two people in a gym. One person’s crushing the free weights and looking good. They’re wearing the perfect gym outfit and making it look easy. They’re doing the same exercises they’ve always done and choosing dumbbells well within their current capabilities. They’re enjoying the workout and emanating self-confidence.

Now imagine a second person on the struggle bus. They’re pushing their limits with a new workout variation they’ve never tried before. They’re sweating profusely and doing more weight than they can comfortably handle. They’re wrestling internally with their deepest fears and don’t look very confident. They’re sweating profusely, breathing heavily, and uncertain they’ll 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’s simply not true. It’s person two who will be far more capable in the long run.

On our podcast, Next Level University, I’ve often said that the struggle bus leads to greatness, and the party bus leads to mediocrity. In this example, the party bus is person one, and the struggle bus is person two. “Micro Success for Macro Failure” is the party bus, and “Micro Failure for Macro Success” is the struggle bus.

Micro Success for Macro Failure is focused on looking and feeling good in the moment but at the expense of long-term growth. Micro Failure for Macro Success is focused on embracing discomfort, embarrassment, and failure in the moment to maximize your long-term potential. Unfortunately, both cycles usually run in the background without our conscious awareness…

Which cycle are you running, or perhaps more importantly, which cycle is running you?

The Full Break Down

As you can see from the cover image, 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’re likely to try just about anything to achieve your goals. If you don’t, however, you’re unlikely to try much of anything. Imagine wanting a new job but not believing it’s possible or wanting to date someone you don’t believe would ever be interested. Desire is like a car without gas. It’s a start, but it’s not sufficient by itself. Desire only translates into tangible action if there’s enough belief in the tank first.

Three beliefs are required before any action is taken. No matter what you’re trying to accomplish, you must first believe it’s possible, possible for you, and that it’ll be worth it. Imagine you want to start a podcast but have a deep fear of judgment. You believe it’s possible but not necessarily worth it. You’ve never felt good enough, and even if you did, you’re not sure it’s worth risking judgment. Given these factors, what are the chances you’ll start a podcast?

Now imagine someone with high belief. They’re scared but genuinely believe it’ll be worth it. Since their belief is high, they cannot live with the idea of not trying. They’d rather try and fail than live with “What if?”. They’re petrified of failure and criticism too, but they’re convinced they can succeed if they stay focused.

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

For Step 1, think about what you want to accomplish and ask yourself the following three questions:

  • From 0 to 10, how much do I believe this is possible?
  • From 0 to 10, how much do I believe this is possible for me?
  • From 0 to 10, how much do I believe this will be worth it?

Once complete, add up your ratings and divide by 3. Then multiply that number by 10. This represents your chances of achieving your objective with your current level of belief.

For example, if you gave yourself a 9, 8, and 10, you have a 90% chance of achieving your goal.

I broke the math down for you below:

9 + 8 + 10 = 27

27 / 3 = 9

9 x 10 = 90%

What’s your percentage?

Please calculate it now before moving to the next section.

Step 2 — No Try Vs. Try

This is where the rubber meets the road. Now that you have enough belief, it’s time to give what you’re looking to accomplish a try. The question is, “What is the best next action to take that maximizes your probability of success?” This is where reverse engineering comes in.

For example, if your goal is to become a successful podcaster, perhaps you’ll try recording the first episode. If your goal is to become a successful author, perhaps you’ll try writing the first chapter. If your goal is to become a doctor, perhaps you’ll apply to medical school. Remember, this is the step where your belief will be tested. This is where the gap between talking and walking reveals itself.

I’ve often said that the distance between what you say and what you do is your ego. Here are a couple of guidelines to help.

First, don’t just try things to try things. Make sure what you’re 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’s a lot of fun but also kind of a mess. Now think of a friend who’s a little less fun but more calculated and responsible. Who’s more likely to achieve their goals?

Second, try things within your challenge-skills sweet spot. If you’re new in the gym, don’t try bench pressing 225 pounds. Similarly, however, if you’ve been weight training for a decade, don’t stay at 10 pounds forever. In scenario one, you’ll injure yourself. In scenario two, you’ll get bored and won’t improve.

Lastly, always air on the side of massive action. Nothing grows on the fence. While choosing your next moves wisely is critical, taking consistent messy action is more important. Massive messy action trumps waiting around for a better idea every day of the week.

Step 3 — No Failure Vs. Failure

This step is about failing forward and why it’s so important. First, it’s 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 this article, my hope is not that you’ll enjoy failure. That’s not real or even helpful, but rather that you’ll embrace it 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’s inevitable. Imagine you’re 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 didn’t achieve your desired outcome; however, those aren’t the failures this article is interested in.

Those types of failure are obvious and rarely overlooked. People generally understand those, but what about those less obvious Micro Failures that happen every day? For example, you ask a friend to the movies, but they’ve got plans, or you try completing a task in 1 hour that takes 2. Perhaps you skip a workout, overeat, or arrive 5 minutes late to a meeting. Maybe you say something embarrassing at work or ask a “dumb” question.

Those are the Micro Failures I’m talking about. The death of 1,000 cuts that get us when we don’t 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’ve got left, before we know it, what we thought would preserve and protect us eventually becomes the very shell that keeps us small.

Imagine 2 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 3 easy to-do’s on their list. Person one works hard all day and completes only 6 of the 10 essential tasks. They’re slightly demoralized and wrestling with their self-worth. Person two, however, completed all 3 easy tasks and feels accomplished. The philosophical questions are, who “failed”? Who’s more successful? Better yet, who’s likely to be more 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’s 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, but it’s rooted in ego, not merit.

Step 4 — No Pain Vs. Pain

This is where the uncomfortable part comes in. I’ll never forget when I first started dating my beautiful girlfriend, Emilia. She’s 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’re all avoiding the one thing that’s actually best for us?” She knew that the last question was rhetorical.

I tell that story because Emilia is incredible at taking action and changing her behavior. Still, I know that wouldn’t be the case if she wasn’t so 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 to pain?” If you’d like, you can also change the word pain to discomfort. Both are pretty interchangeable in this context.

That said, we’ve 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 can’t have an incredible body without challenging workouts or a multi-million dollar income without hard work. I often joke about how everyone hates the stair master, but do we fully comprehend pain’s part in the process of behavior 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’ve all felt it, and it’s not pleasant. What are its benefits, though? What if there’s an upside to this? To advocate for the upside, I’d like to frame “pain” as a catalyst. Just like a spark can ignite a fire to keep you warm, pain can be the spark that ignites 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? Or perhaps you’ve been consistent in the gym only a few months before your wedding or started watching what you eat only after the doctor said you’re at risk of being overweight. Unfortunately, pain is the unsung hero in these instances. Whenever you’re putting off doing something you know is best for you, pain starts to accumulate. Eventually, it reaches a critical mass or tipping point where action is finally taken.

Why didn’t you do it sooner, though? Because the pain of not taking action finally surpassed the pain of taking action. In simple terms, the pain of procrastination finally got significant enough.

In the case of the haircut, the pain of long hair finally got more significant than the pain of getting it cut. Maybe you had a big date and didn’t 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 don’t always realize it, but pain has a positive place in our life. Without it, minimal action would ever be taken. When we feel hungry, it’s painful, so we know to go eat. When we get sick, it’s painful, so we know to rest. When we sprain our ankle, it’s 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 stop trying altogether, and that’s 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 first cycle, Micro Failure for Macro Success, contemplation is where all of the gold is. This is where learning really takes place, but it’s usually done behind the scenes with only close relationships, which is why it’s 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’ve done thousands of podcast episodes, and I can’t think of a single one that’s perfect. There’s no such thing. Perfection is a fictitious ceiling that doesn’t exist. There’s 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’s always some pain and contemplation every time.

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 it 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’ll 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, fail or succeed, 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’ll be well worth it in the long run.”

To close out this section, remember that contemplation is often the unseen bridge between experience and the deeper understanding you need to unlock the vault of your dreams. It isn’t fun or sexy, but it is accurate, and that’s 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 2 young women playing a high school basketball game. They’re both on the same team, and it’s championship night. One player dreams of playing in college, and the scouts are watching. Another doesn’t 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’s over now, and unfortunately, they lost the championship. Both players feel good about their effort, but only one feels good about their performance. In fact, the non-college-bound player is actually relieved it’s finally over. She’s 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’s 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 light bulb moment. “Holy crap!” she says out loud. “The other team was using a tricky double-team tactic every time I touched the ball… That’s why we lost.”

But here’s 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’ll never make that mistake again,” she says to herself.

Now imagine she’s playing in college, and another opponent uses that same tactic. Now she’s at the collegiate level, and the stakes are higher. Now she’s being scouted to play in the WNBA, and there’s a lot more on the line. However, this time, she recognizes the double team and knows to find the open shooter.

That’s 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 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 easy. Those light bulb 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 that meme on the internet of a diamond miner digging underground? It’s double-sided, and written at the top is “The difference between success and failure.” On the left, it shows a miner who gives up just inches away from the diamonds they can’t see yet. On the right side, it shows a diamond miner who stuck with it long enough to get the payoff. That’s what contemplation’s like.

No alt text provided for this image
Figure 2 – The 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 just 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’ve contemplated and gained new awareness, now you’re ready to make better decisions. This is where the fruits of pain, failure, and contemplation manifest into long-term positive outcomes. Before we go any further, it’s essential to unpack decisions, what they are, and why they’re so important.

What is a decision? More importantly, what is an intelligent decision, and how do we know if we’re making “good” or “bad” decisions? This is an interesting philosophical construct that I’ve 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 is the right thing? What does that even mean? Here’s where it gets tricky. The “right thing” is entirely subjective. What’s 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’s attacking your children? What if it’s 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 get a good seat. Being on time at work increases the chances you keep your job or get promoted. Exercising regularly increases the chances you’ll 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 don’t 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 don’t expect an infant to build a multi-million dollar business or build a skyscraper. Why? Because they don’t yet have the awareness necessary to make effective decisions. We can, however, except that they can build a house out of their colored blocks.

Bottom line… Your ability to get better results is predicated on your ability to make better decisions, and that 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’ve 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 4 years training vigorously, failing forward, and learning from it, finally getting his or her chance to compete at the highest level. Or how about the opposite? Now let’s imagine a once Olympic gold medalist, once best in the world, slowly letting themselves go for 4 years, never really trying anything new or challenging themselves, finally looking in the mirror and realizing they’ve become overweight…

We see this all around us. We see seemingly overnight successes and seemingly overnight failures everywhere, but none of that is the entire story. That famous couple didn’t suddenly hate each other and get divorced, and that wildly rich and famous local band you used to listen to didn’t get famous overnight. Like all major Macro Successes and Macro Failures, in reality, it was a slow accumulation of tiny Micro Failures and Micro Successes 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 don’t know… What I do know, however, is that it did not happen overnight. In my line of work coaching and consulting with people and businesses all over the world, it’s become self-evident that what most people perceive as overnight successes are actually just overnight awarenesses. In other words, most of the journey just 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 quote-unquote overnight success.

Coming Full Circle

So here we are at the end, only to begin again back where we started, no belief versus belief. If you refer to the image above, you’ll notice something peculiar. Both cycles are self-reinforcing. They are what most people refer to as a self-fulfilling prophecy. In other words, when you’re running cycle 1, Micro Success for Macro Failure, you don’t get any better results, and therefore, you have even less belief in your next go-around. In cycle 2, Micro Failure for Macro Success, the opposite is true. If you stick with it long enough, you’ll eventually get far better results, which will ultimately re-enforce 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’s not perfect. Every sentence is another Micro Failure that I had to slowly work through, edit, and re-edit.

And now there are only two questions left to ask.

One, 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.

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