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The Obstacle Is The Way

January 8, 2023

The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph


Every obstacle is unique to each of us. But the responses they elicit are the same: Fear. Frustration. Confusion. Helplessness. Depression. Anger.

There have been countless lessons (and books) about achieving success, but no one ever taught us how to overcome failure, how to think about obstacles, how to treat triumph over them, and so we are stuck.

Andy Grove, “Bad companies are destroyed by a crisis. Good companies survive them. Great companies are improved by them.”

All great victories, be they in politics, business, art, or seduction, involved resolving vexing problems with a potent cocktail of creativity, focus, and daring.

Great times are great softeners. Abundance can be its own obstacle, as many people can attest.

Overcoming obstacles is a discipline of three critical steps. It begins with how we look at our specific problems, our attitude or approach; Then the energy and creativity with which we actively break them down and turn them into opportunities; finally, the cultivation and maintenance of an inner will that allows us to handle defeat and difficulty.



What is perception? It’s how we see and understand what occurs around us -and what we decide those events will mean.  Our perceptions can be a source of strength or of great weakness. If we are emotional, subjective, and short sighted, we only add to our troubles. To prevent becoming overwhelmed by the world around us, we must, as the ancients practice, learn how to limit our passions and their control over our lives.

He (John D. Rockefeller) was inclined to see the opportunity in every disaster. To that we could add: he had the strength to resist temptation or excitement, no matter how seductive, no matter the situation.

For the rest of his life, the greater the chaos, the calmer Rockefeller would become, particularly when others around him were either panicked or mad with greed. He would make much of his fortune during these market fluctuations – because he could see what others could not.

You will come across obstacles in life – fair and unfair. And you will discover, time and time again, that what matters most is not what these obstacles are but how we see them, how we react to them, and whether we keep our composure.

Where one person sees a crisis, another can see opportunity. Where one is blinded by success, another sees reality with ruthless objectivity. Where one loses control of emotions, another can remain calm.

Humans are still primed to detect threats and dangers that no longer exist

There are a few things to keep in mind when faced with a seemingly insurmountable obstacle. We must try:

  • To be objective
  • To control emotions and keep an even keel
  • To choose to see the good in its situation
  • to steady our nerves
  • to ignore what disturbs or limits others
  • to place things in perspective to revert to the present moment to focus on what can be controlled


We decide what we will make of each and every situation. We decide whether we’ll break or whether we’ll resist. We decide whether we’ll ascent or reject. No one can force us to give up or to believe something that is untrue (such as, that a situation is absolutely hopeless or impossible to improve). Our perceptions are the thing that we’re in complete control of.

William Shakespeare, “Nothing either good or bad, but thinking makes it so.”

… through our perceptions of events, we are complicit in the creation – as well as the destruction – of every one of our obstacles.

Don’t forget, there are always people out there looking to get you. They want to intimidate you. Rattle you. Pressure you into making a decision before you’ve gotten all the facts. They want you thinking and acting on their terms, not yours. So, the question is, are you going to let them?

There is always a countermove, always an escape or a way through, so there is no reason to get worked up. No one said it would be easy and, of course, the stakes are high, but the path is there for those ready to take it.

When people panic, they make mistakes. They override systems. The disregard procedures, ignore rules. They deviate from the plan. They become unresponsive and stop thinking clearly. They just react – not to what they need to react to, but to the survival hormones that are coursing through their veins.

Uncertainty and fear are relieved by authority. Training is authority. It’s a release valve.

Gavin de Becker, “When you worry, ask yourself, ‘what am I choosing to not see right now?’ What important things are you missing because you choose to worry over introspection, alertness, or wisdom.”

If an emotion can’t change the condition or the situation you’re dealing with, it is likely an unhelpful emotion. Or, quite possibly, a destructive one.

We defeat emotions with logic…

The phrase “This happened, and it is bad” is actually two impressions. The first –“this happened”- is objective. The second – “it is bad”- is subjective.

How often do we see what we think there is or should be there, instead of what is actually there?

Objectivity means removing “you” – the subjective part – from the equation. Just think, what happens when we give others advice? Their problems are crystal clear to us? The solutions obvious. Something that’s present when we deal with our own obstacles is always missing when we hear other people’s problems: the baggage. With other people we can be objective.

Fear is debilitating, distracting, tiring, and often irrational.

The Greeks understood that we often choose the ominous explanation over the simple one, to our detriment. That we are scared of obstacles because our perspective is wrong – that a simple shift in perspective can change our reaction entirely.

The way we look at the world changes how we see these things. Is our perspective truly giving us perspective or is it what’s actually causing the problem? That’s the question.

Perspective has two dimensions:

  1. Context: the sense of the larger picture of the world, not just what is immediately in front of us
  2. Framing: an individual’s unique way of looking at the world, a way that interprets its events


Where the herd goes, the body follows. Perception precedes action. Right action follows the right perspective.

And what is up to us?

  • our emotions
  • our judgments
  • our creativity
  • our attitude
  • our perspective
  • our desires
  • our decisions
  • our determination


… The most harmful dragon we chase is the one that makes us think we can change things that are simply not ours to change.

… half the companies in the Fortune 500 were started during a bear market or recession.

Focus on the moment, not the monsters that may or may not be up ahead.

Focus on what is in front of you, right now. Ignore what it “represents” or it “means” or” why it happened to you.”

Our perception determines, to an incredibly large degree, what we are and are not capable of. In many ways, they determine reality itself.

An entrepreneur is someone with faith in their ability to make something where there was nothing before. To them, the idea that no one has ever done this or that is a good thing. When given an unfair task, some rightly see it as a chance to test what they’re made of – to give it all they’ve got, knowing full well how difficult it will be to win. They see it as an opportunity because it is often in that desperate nothing-to-lose state that we are our most creative.

It’s one thing to not be overwhelmed by obstacles, or discouraged or upset by them. This is something that few are able to do. But after you’ve controlled your emotions, and you can see objectively and stand steadily, the next step becomes possible: a mental flip, so you’re looking not at the obstacle but at the opportunity within it.

…Psychologists call it adversarial growth and post-traumatic growth. “That which doesn’t kill me makes me stronger” is not a cliche but a fact… The struggle against an obstacle inevitably propels the fighter to a new level of functioning. The extent of the struggle determines the extent of the growth. The obstacle is an advantage, not adversity. The enemy is any perception that prevents us from seeing this.

Problems are rarely as bad as we think…Once you see the world as it is, for what it is, you must act. The proper perception – objective, rational, ambitious, clean – isolates the obstacle and exposes it for what it is.



We forget: In life, it doesn’t matter what happens to you or where you came from. It matters what you do with what happens and what you’ve been given. And the only way you’ll do something spectacular is by using it all to your advantage.

No one is coming to save you. And if we’d like to go where we claim we want to go – to accomplish what we claim are our goals – there is only one way. And that’s to meet our problems with the right action… Therefore, we can always (and only) greet our obstacles

  • with energy
  • with persistence
  • with a coherent and deliberate process
  • with iteration and resilience
  • with pragmatism
  • with strategic vision
  • with craftiness and savvy
  • and an eye for opportunity and pivotal moments


German Field Marshall Erwin Rommel knew from history that those who attack problems in life with the most initiative and energy usually win. He was always pushing ahead, keeping the stampede on the more cautious British forces to devastating effect.

in 1878, Thomas Edison wasn’t the only person experimenting with incandescent lights. But he was the only man willing to test 6,000 different filaments – including one made from the beard hair of one of his men – inching closer each time to the one that would finally work. And, of course, he eventually found it – proving that genius often really is just persistence in disguise.

Too many people think that great victories like General Grant’s and Thomas Edison’s came from a flash of insight. That they cracked the problem with pure genius. In fact, it was the slow pressure, repeated from many different angles, the elimination of so many other more promising options, that slowly and surely churned the solution to the top of the pile. Their genius was unity of purpose, deafness to doubt, and the desire to stay at it.

Once you start attacking an obstacle, quitting is not an option. It cannot enter your head. Abandoning one path or another that might be more promising? Sure, but that’s  far cry from giving up. Once you can envision yourself quitting altogether, you might as well ring the bell. It’s done.

It’s okay to be discouraged. It’s not okay to quit. To know you want to quit but to plant your feet and keep inching closer until you take the impenetrable fortress you’ve decided to lay siege in in your own life – that’s persistence.

Stop looking for an epiphany, and start looking for weak points. Stop looking for angels, and start looking for angles. There are options. Settle in for the long haul and then try each and every possibility, and you’ll get there.

Failure really can be an asset if what you’re trying to do is improve, learn, or do something new. It’s the preceding feature of nearly all successes. There’s nothing shameful about being wrong, about changing course. Each time it happens we have new options. Problems become opportunities.

When failure does come, ask: What went wrong here? What can be improved? What am I missing?

Great entrepreneurs are:

  • never wedded to a position
  • never afraid to lose a little of their investment
  • never bitter or embarrassed
  • never out of the game for long


In the chaos of sport, as in life, process provides us a way. It says: Okay, you’ve got to do something very difficult. Don’t focus on that. Instead break it down into pieces. Simply do what you need to do right now. And do it well. And then move on to the next thing. Follow the process and not the prize.

When it comes to our actions, disorder and distraction are death. The unordered mind loses track of what’s in front of it – what matters – and gets distracted by thoughts of the future.

We want to have goals, yes, so everything we do can be in the service of something purposeful. When we know what we’re really setting out to do, the obstacles that arise tend to seem smaller, or manageable. When we don’t, each one looms larger and seems impossible. Goals help put the blips and bumps in proper proportion.

The process is about doing the right things, right now. Not worrying about what might happen later, or the results, or the whole picture.

Everything is a chance to do and be your best.

Wherever we are, whatever we’re doing and wherever we are going, we owe it to ourselves, to our art, to the world to do it well. That’s our primary duty. And our obligation. When action is a priority, vanity falls away.

How you do anything is how you can do everything. We can always act right.

We spend a lot of our time thinking about how things are supposed to be, or what the rules say we should do. Trying to get it all perfect. We tell ourselves that we’ll get started once the conditions are right, or once we’re sure we can trust this or that. When, really, it’d be better to focus on making do with what we’ve got. And focusing on results instead of pretty methods.

Pragmatism is not so much realism as flexibility. There are a lot of ways to get from point A to point B. It doesn’t have to be a straight line. It’s just got to get you where you need to go. But so many of us spend so much time looking for the perfect solution that we pass up what’s right in front of us.

Start thinking like a radical pragmatist: still ambitious, aggressive, and rooted in ideals, but also imminently practical and guided by the possible. Not on everything you would like to have, not on changing the world right at this moment, but ambitious enough to get everything you need. Don’t think small, but make the distinction between the critical and the extra.

When you’re at your wit’s end, straining with all your might, when people tell you you look like you might pop a vein… take a step back, then go around the problem. Find some leverage. Approach from what is called “the line of least expectation.”

If we’re starting from scratch and the established players have had time to build up their defenses, there is just no way we are going to beat them on their strengths. So, it’s smarter to not even try, but instead focus our limited resources elsewhere.

Being outnumbered, coming from behind, being low on funds, these don’t have to be disadvantages. They can be gifts. Assets that make us less likely to commit suicide with a head-to-head attack. These things force us to be creative, to find workarounds, to sublimate the ego and do anything to win besides challenging our enemies where they are strongest.

You don’t convince people by challenging the longest and most firmly held opinions. You find common ground and work from there. Or you look for leverage to make them listen. Or you create an alternative with so much support from other people that the opposition voluntarily abandons its views and joins your camp.

…Sometimes you overcome obstacles not by attacking them but by withdrawing and letting them attack you. You can use the actions of others against themselves instead of acting yourself.

Sometimes in your life you need to have patience – wait for temporary obstacles to fizzle out.

When we want things too badly we can be our own worst enemy. In our eagerness, we strip the very screw we want to turn and make it impossible to ever get what we want.

Adversity can harden you. Or it can loosen you up and make you better – if you let it.

External factors influence the path, but not the direction: forward.

To be physically and mentally loose takes no talent. That’s just recklessness (we want right action, not action). To be physically and mentally tight? That’s called anxiety. It doesn’t work, either. Eventually we snap. But physical looseness combined with mental restraint? That is powerful.

Rahm Emanuel, “You never want a serious crisis to go to waste. Things that we had postponed for too long, that were long-term, are now immediate and must be dealt with. A crisis provides the opportunity for us to do things that you could not do before.”

Ordinary people shy away from negative situations, just as they do with failure. They do their best to avoid trouble. What great people do is the opposite. They are their best in these situations.

Great commanders look for decision points. For it is bursts of energy directed at decisive points that break things wide open. They press and press and press and then, exactly when the situation seems hopeless – or, more likely hopelessly deadlocked – they press once more.

Perceptions can be managed. Actions can be directed. We can always think clearly, respond creatively. Look for opportunity, seize the initiative.

We have it within us to be the type of people who try to get things done, try with everything we’ve got and, whatever verdict comes in, are ready to accept it instantly and move on to whatever is next.



What is will? Will this our internal power, which can never be affected by the outside world. It is our final trump card. If action is what we do when we still have some agency over our situation, the will is what we depend on when agency has all but disappeared.

Will is fortitude and wisdom – not just about the specific obstacles but about life itself and where the obstacles we are facing fit within it. It gives us ultimate strength. As in: The strength to endure, contextualize, and derive meaning from the obstacles we cannot simply overcome.

In every situation, we can:

  • always prepare ourselves for more difficult times
  • always accept what we’re unable to change
  • always manage our expectations
  • always persevere
  • always learn to love our fate and what happens to us
  • always protect our inner self, retreat into ourselves
  • always submit to a greater, larger cause
  • always remind ourselves of our own mortality


We take weakness for granted. We assume that the way we’re born is the way we simply are, that our disadvantages are permanent. And then we atrophy from there. That’s not necessarily the best recipe for the difficulties of life.

We craft our spiritual strength through physical exercise, and our physical heartiness through mental practice.

You’ll have far better luck toughening yourself up than you ever will trying to take the teeth out of a world that is – at best – indifferent to your existence.

To be great at something takes practice. Obstacles and adversity are no different.

The path of least resistance is a terrible teacher. We can’t afford to shy away from the things that intimidate us. We don’t need to take our weaknesses for granted.

A premortem is different (than a postmortem). In it, we look to envision what could go wrong, what will go wrong, in advance, before we start. Far too many ambitious undertakings fail for preventable reasons. Far too many people don’t have a backup plan because they refuse to consider that something might not go exactly as they wish.

The only guarantee ever, is that things will go wrong. The only thing we can use to mitigate this is anticipation. Because the only variable we control completely is ourselves.

It doesn’t always feel that way but constraints in life are a good thing. Especially if we can accept them and let them direct us. They push us to places and to develop skills that we otherwise never have pursued. Would we rather have everything? Sure, but that isn’t up to us.

When the cause of our problem lies outside of us, we are better for accepting it and moving on. For ceasing to kick and fight against it and coming to terms with it. The Stoics have a beautiful name for this attitude. They call it the Art of Acquiescence. Let’s be clear, that that is not the same thing as giving up. This has nothing to do with action – this is for the things that are immune to action.

The next step after we discard our expectations and accept what happens to us, after understanding that certain things – particularly bad things – are outside our control, is this: loving whatever happens to us and facing it with unfailing cheerfulness. It is the act of turning what we must do into what we get to do.

Learning not to kick and scream about matters we can’t control is one thing. Indifference and acceptance are certainly better than disappointment or rage. Very few understand or practice that art. But it is only the first step. Better than all that is love for all that happens to us…

We don’t get to choose what happens to us, but we can always choose how we feel about it. And why on earth would you choose to feel anything but good? We can choose to render a good account of ourselves.

… there is always some good – even if only barely perceptible at first – contained within the bad.

If persistence is attempting to solve some difficult problem with dogged determination and hammering until the break occurs, then plenty of people can be said to be persistent. But perseverance is something larger. It’s the long game. It’s about what happens not just in round one but in round two and every round after – and then the fight after that and the fight after that, until the end.

Persistence is an action. Perseverance is a matter of will. One is energy. The other, endurance.

Ralph Waldo Emerson said, “with the exercise of self-trust, new powers shall appear.”

We don’t control the barriers or the people who put them there. But we control ourselves – and that is sufficient.

The desire to quit or compromise on principles suddenly feels rather selfish when we consider the people who would be affected by that decision. When it comes to obstacles and whatever reactions they provoke – boredom, hatred, frustration, or confusion – just because you feel that way, doesn’t mean everyone else does.

How can we use this situation to benefit others? How can we salvage some good out of this? If not for me, then for my family or the others on leading or those who might later find themselves in a similar situation.

Stop making it harder on yourself by thinking about I, I, I. Stop putting that dangerous “I” in front of events. I did this. I was so smart. I had that. I deserve better than this. No wonder you take losses so personally, no wonder you feel so alone. You’ve inflated your own role and importance. Start thinking: Unity over Self. We’re in this together.

Compassion is always an option. Camaraderie as well. That’s a power of the will that can never be taken away, only relinquished. Stop pretending that what you’re going through is somehow special or unfair. Whatever trouble you’re having – no matter how difficult – is not some unique misfortune picked out especially for you. It just is what it is.

Our fear of death is a looming obstacle in our lives. It shapes our decisions, our outlook, and our actions.

We forget how light our grip on life really is. Otherwise, we wouldn’t spend so much time obsessing over trivialities, or trying to become famous, make more money than we ever could spend in our lifetime, or make plans for off in the future. All of these are negated by death. All these assumptions presume that death won’t affect us or at least not when we don’t want it to. The paths of glory Thomas Gray wrote, lead to the grave.

…thinking about and being aware of our mortality creates real perspective and urgency. It doesn’t need to be depressing. Because it’s invigorating. And since this is true, we ought to make use of it. Instead of denying – or worse, fearing – our mortality, we can embrace it. Reminding ourselves each day that we will die helps us treat our time as a gift.

When you think you have successfully navigated one obstacle, another emerges. But that’s what keeps life interesting. And as you’re starting to see, that’s what creates opportunities.

Knowing that life is a marathon and not a sprint is important. Conserve your energy. Understand that each battle is only one of many that you can use to make the next one easier. More important, you must keep them all in real perspective.

Never rattled. Never frantic. Always hustling and acting with creativity. Never anything but deliberate. Never attempting to do the impossible – but everything up to that line.



Not everyone Looks at obstacles – often the same ones you and I face -and sees reason to despair. In fact, they see the opposite. They see a problem with a ready solution. They see a chance to test and improve themselves. Nothing stands in their way. Rather, everything guides them on their way.

We can see the “bad” things that happen in our lives with gratitude and not with regret because we turn them from disaster to real benefit – from defeat to victory. Fate doesn’t have to be fatalistic. It can be destiny and freedom just as easily.

First, see clearly. Next, act correctly. Finally, endure and accept the world as it is.

You are iron-spined and possess a great and powerful will. Like Abraham Lincoln, you realize that life is a trial. It will not be easy, but you are prepared to give it everything you have regardless, ready to endure persevere and inspire others.

See things for what they are. Do what we can. Endure and bear what we must. What blocked the path is now a path. What once impeded action advances action. The Obstacle is the Way.