How to Succeed in Uncertain Times

The path to success is not always easy, but it has its own rewards. Consider these steps when you’re on a quest for the perfect career:
-First and foremost, figure out what type of person you are by completing an inventory of your personal strengths and weaknesses.
-Next, identify which skills that align with your personality best. If you enjoy people yet struggle with numbers or logistics view this as a challenge rather than weakness; if the opposite is true then consider using training courses to improve this skill niche!
-Once your personality profile matches up well with some area’s in their hiring process research how difficult they may be before applying for any jobs within those industries.
Lastly, create a resume tailored towards whatever industry interests you most!

Uncertainty is a part of life. It’s not easy to make decisions when you don’t know what the future holds, but it’s important that you do make them. Read more in detail here: making decisions with uncertainty.

Vintage bridge after earthquake crooked and shaken.

Kyle Eschenroeder contributed this guest article as an editor’s note.

“It is not given to human beings – fortunately for them, because life would be miserable – to foresee or forecast the development of events to any significant degree. In one phase, males seem to have been correct, while in another, they appear to have been incorrect. Then, a few years later, when the perspective of time has widened, everything takes on a new meaning. A new percentage has emerged. There is a different value scale. History wanders down the route of the past with its flickering lantern, attempting to rebuild its images and resurrect its echoes.” –William S. Churchill

Churchill observed some of history’s most colossal military defeats when he was considerably younger. There were no major conflicts in the decades before WWI. This provided enough opportunity for scholars to speculate on how new technology may be used in conflict; indeed, WWI was perhaps the most meticulously planned war in history.

Yet, right from the start, the theories began to fall apart in the face of events that could never have been predicted. The world’s most respected generals were made to appear inexperienced. Their faith in abstract planning had blinded them to the situation’s reality. Years of battle passed before they were able to accept the truth of their predicament.

These generals had no idea they were fighting in one of history’s first genuinely modern wars. More than comprehensive planning, these fights demanded the capacity to improvise.

In business, the same change is taking place right now. This summer, a slew of business books were released, all based on Eric Ries’ Lean Startup model. That is, in most circumstances, doing an experiment is less expensive than devising a strategy. Even large corporations are beginning to focus on quickly implementing a strategy on a small scale to test a concept before implementing a large-scale change.

Instead of planning and planning, poke and prod.

This has ramifications not just on a large scale in business, but also on a personal level. Twenty-year career goals are no longer viable. The number of variables in our lives has increased, and with it, the level of uncertainty in our daily lives has increased. On how to cope with this growing inconstancy, there seem to be two schools of thought:

  1. The Technophiles: These are the people who believe that you should embrace all things new. Uncertainty will be eradicated by technology. The goal is to become as integrated with machines as possible.
  2. The Paleophiles: These are the people who believe that you should reject all new ideas and instead rediscover our old human past and live in accordance with it (effectively ignoring new uncertainties). We are becoming less human as a result of technology. The goal is to disconnect from technology.

My objective is to take a more realistic look at how to cope with (and perhaps profit from) the ever-increasing unpredictability of everyday life. This isn’t a “medium” road that takes half-measures between the two points of view; rather, it’s a whole new way of thinking about things.


Uncertainty may be divided into two categories.

The first thing to realize about our unpredictably chaotic environment is that there are two kinds of uncertainty:

  1. Soft Uncertainty is a term used to describe a state of uncertainty that is This is the apprehension you have about yourself. It refers to the moral, spiritual, or philosophic ambiguities in your life, as well as the uncertainty that surrounds your decisions about what to do and how to proceed. It’s the apprehension you get before approaching your boss for a raise. It’s the apprehension you get before starting an undertaking. It’s the existential crisis’s unpredictability. It’s the sense of insecurity among generals at the commencement of WWI.
  2. Uncertainty is a difficult concept to grasp. This is an external source of uncertainty. It’s the feeling of not knowing what to expect once you ask for a raise and start your new project. It is found in the world’s probability and unpredictability. The Fates are to blame for this ambiguity. Every time, soccer mothers and economic strategists fail to address this sort of uncertainty. It’s the truth that weapons will be utilized in ways that no one could have predicted.

If we see these issues as problems, they are unsolvable.

Soft Uncertainty seems to be a solved issue at first view. Simply adopt the appropriate attitude – often that of a church, country, or political position – and you’ll be OK. However, many of us are unable to fully embrace such ideologies.

Hard Uncertainty seems to be a losing cause as well. Every time we are promised some level of scientific or economic certainty, the forecasts fail to materialize, and everything shifts.

The issue isn’t uncertainty in and of itself. The issue is that we reject it.

Perhaps discovering the solution isn’t necessary to tackle Soft Uncertainty. Perhaps the capacity to retain a contradiction in our minds securely is the better solution.

Maybe we won’t be able to regulate Hard Uncertainty. Perhaps we should position ourselves to gain from events beyond our control.

The techniques we’ll talk about below help us build our ability to deal with both sorts of uncertainty at the same time.

We shall grow confident in our uncertainties rather than arrogantly assured. Rather than claiming to be able to anticipate the future, we will be prepared for a world we could never have predicted.

“When you seek order, you get pseudo-order; when you accept randomness, you gain a degree of order and control.” Taleb, Nassim Nicholas

Some things are unchangeable.

Let us not forget that there are some aspects of life. Why Our Goals Are Best Achieved Indirectly: John Kay outlines the distinctions in Obliquity: Why Our Goals Are Best Achieved Indirectly:

“You can address issues directly if you are clear about your high-level objectives and aware enough about the systems on which they are dependent. However, objectives are often ambiguous, interactions are unexpected, complexity is high, issue descriptions are imprecise, and the environment is unknown. That’s where the concept of obliquity comes into play.”

The world isn’t completely chaotic. If you want to learn how to knot a bow tie, you may find detailed instructions here. If you want to be in shape, you already know that eating less junk food and exercising harder at the gym will get you far. Things get more complicated when you establish a company, start a love relationship, or write a book. (There are best practices for these difficult jobs, but they’ll only get you so far.)


These are the most intriguing and valuable regions; they bring the greatest challenge, and consequently the most progress, pleasure, and, ultimately, joy. It’s where you should spend your time, and it’s where the idea of obliquity comes into play. Some issues, particularly the more complicated ones, need indirect solutions and the ebb and flow of a risk and discovery cycle.

The greatest chance you have of profiting from an unpredictable environment is to be functioning inside the appropriate framework. The resources listed below will help you build that structure.

5 Uncertainty-Reducing Techniques

We’ll look at five methods for coping with uncertainty from an emotional and professional standpoint, but keep in mind that this is only for the sake of space; many of them may help you in any situation where ambiguity exists. To put it another way, it’s everywhere.

1. Stoicism: Concentrate on What You Have Control Over

When I was a day trader, I would often lose thousands of dollars on trades that I thought were accurate. The following day, I may earn thousands of dollars by making a risky deal on the spur of the moment. I would have gone bankrupt in a month if I had allowed my emotions to get entangled with these consequences.

In an uncertain environment, a wonderful outcome might result from a horrible decision, or a terrible outcome could result from a fantastic one.

The most we can do is stack the odds in our favor and then behave consistently in the direction of victory.

This is really tough since losing while doing the “correct” thing hurts much more.

Stoicism is an effective method for coping with the emotional anguish that this might bring.

Nassim Nicholas Taleb, more than any other Roman philosopher, has summed up what it means to be a contemporary Stoic:

“Stoicism is about the taming of emotions, not necessarily their removal.” It’s not about transforming people into plants. Fear is transformed into caution, suffering is transformed into knowledge, errors are transformed into initiation, and desire is transformed into endeavor in my vision of the contemporary Stoic sage.”

The only true guidebook to modern Stoicism is written by William Irvine (the Stoics didn’t bother with this, which reveals a lot about the differences between their minds and ours). In it, he discusses one of Stoicism’s most important concepts: control what you can, ignore the rest. He illustrates his point with a tennis match:

“Keep in mind that the objectives we set for ourselves are one of the few things over which we have total control. When a Stoic is concerned with matters over which he has some but not total control, such as winning a tennis match, I believe he will establish extremely specific objectives for himself. He will be especially cautious to develop internal objectives rather than external ones. Thus, his aim in tennis will be to play to the best of his abilities rather than to win a match (something external over which he has only limited control) (something internal, over which he was complete control). If he chooses this aim, he will avoid aggravation and disappointment if he loses the game: He will not have failed to achieve his aim since it was not his goal to win the match, as long as he gave it his all. His peace of mind will not be disturbed.”


It’s a lot simpler to say than it is to accomplish. Separating your emotions from external circumstances requires a lot of discipline.

What’s the best way to go about it?

Try practicing the Triad of Control whenever you feel nervous or irritated. To do so, just determine if you have absolute control, no control, or some control over any particular scenario. Then, with your whole self, concentrate on what you can manage.

At first sight, it seems that this will take away your power. It’s admitting that you don’t have complete control over everything. You will, however, notice a growing sense of control in your life after some practice. You are concerned with what you are capable of doing, rather than worrying about what-ifs and shoulding all over yourself. You establish a link with reality.

After a month or two of constant practice, you will realize that you actively seek out hardship. Take, for example, Seneca’s definition of a wise man:

“He is so far from retreating from the buffetings of circumstances or persons that he considers even damage useful, since it allows him to put himself to the test and put his virtue to the test.”

In an unpredictable world, working toward that attitude will make you a force to be reckoned with. When things change, you don’t hide; instead, you push harder. When new abilities are required, you are not frightened to learn. You aren’t scared to find possibilities when others see just turmoil.

Check out Ryan Holiday’s quick and inspiring guide to Stoicism for more information. Tim Ferriss’ favorite Seneca essay is The Obstacle is the Way, and if you want something more comprehensive, William Irvine’s A Guide to the Good Life is a good choice.

I’d recommend starting with Seneca’s Letters from a Stoic or Marcus Aurelius’ Meditations if you like original texts (which are incredibly accessible and approachable; these folks were more concerned with solving issues than appearing clever).

2. Place a lot of little bets

“People have a hard time estimating the size of tree that will develop from a seed.” –Peter Graham

In most cases, it is less expensive to test something’s validity than than waste time speculating about it.

We will utilize a blog post (investment: time) at my company, StartupBros, to measure demand for knowledge on a certain subject. We have a good sense of the sorts of postings that will be popular, but we can never be sure. We may consider creating a paid course or coaching program based on an article that receives a strong response from readers.

We start with tiny wagers (blog posts) and gradually increase our investment in those that show potential.

In a similar manner, venture capital funds work. They have no idea who will be the next Google or Facebook, so they are compelled to make a slew of modest bets, knowing that the most of them will fail.

Paul Graham, the founder of Y-Combinator, explains how this puts venture investors in an unusual position:


“It’s difficult not to fund a startup when you interview them and think, ‘They seem likely to succeed.’ And yet, at least monetarily, there is only one sort of success: they’ll either be one of the major winners or they won’t, and if they don’t, it doesn’t matter whether you finance them or not, since even if they do, the impact on your profits will be little. You could encounter several bright 19-year-olds on the same day of interviews who aren’t sure what they want to do. Their prospects of success seem to be slim. However, it is not their odds of succeeding that matter, but their chances of succeeding massively. The chances of either group succeeding large are quite tiny, but the chances of those 19-year-olds succeeding could be greater than those of the other, safer group.”

This similar strategy may be used to taking chances in our own life. Put the majority of your money into something secure while investing a tiny portion of it in high-risk, high-reward ventures.

Maintaining your day job while working on a wild startup at night is an example of this in your career.

You don’t want to put all your eggs in one basket if you’re working in a random universe. You want to be able to absorb a lot of minor losses while yet having a chance to win big.

3. Provide yourself with options

“[B]iology is seldom based on a single answer. Instead, it is prone to constantly reinventing solutions.” -Incognito’s David Eagleman

An option is something you can do but aren’t obligated to do. You are assured to be able to view a movie if you purchase a movie ticket, but you are not required to do so. You paid about $10 for that choice. If a buddy asks you to dinner, skipping the movie isn’t a huge loss. A concert ticket to see AC/DC will be significantly more costly.

Having more alternatives implies having more possible opportunities.

The ability to move freely in life is determined by the choices you make. Optionality is employed in warfare, according to Robert Greene:

“There are a lot of individuals in the world who are seeking for a secret recipe for success and power. They don’t want to think for themselves; they simply want to follow a formula. For this reason, they are drawn to the concept of strategy. In their thoughts, strategy is a set of actions that must be followed in order to achieve a goal. They seek an expert or guru to walk them through these stages. They want to know precisely what some great person has done previously, because they believe in the power of imitation. Their life movements are as robotic as their thoughts.

To stand out from the crowd, you must dispel a common misconception: the purpose of strategy is not to carry out a clever plan that unfolds in stages, but to place yourself in circumstances where you have more alternatives than your adversary. True strategy is placing oneself to be able to perform A, B, or X depending on the circumstances, rather than clutching at Option A as the sole appropriate response. That, as opposed to formulaic reasoning, is strategic depth of thought.”


The finest generals aren’t those who have the best plans; they’re those who are open to the most possibilities.

To take use of these possibilities, one must be adaptable.

Here are five things you can do right now to expand your options:

  • Learn a new skill that will help you in your career. Would you be able to find another work doing precisely what you’re doing now if your firm went bankrupt right now? If not, you’ll need to broaden your horizons. Asymmetric payoffs may result from this kind of learning since abilities typically act in tandem.
  • Begin a side business. Working on a side project is a good idea. Again, having choices is useful if everything goes wrong.
  • Spend less money. If things go well, it’s also wonderful to have choices. Money in the bank allows you to take advantage of chances, whether they be investments or a fantastic job offer that needs you to leave your current position. It’s also simpler to transfer if everything goes wrong if you have money in the bank.
  • Attend parties. Humans – both personal and professional – are often the source of opportunities. Going to parties is one of the finest methods to meet new people. I despise parties until I arrive, at which point they are always enjoyable.
  • Change your point of view. I understand. This is nonsense. But it’s also not the case. You can take use of additional possibilities if you adjust your viewpoint and become aware of them. Train yourself to recognize your opportunities and what you can do to maximize them.

4. Adaptability: Understand How to Perform Now

“The issue is that we mistakenly believe that information was lacking: if only we had known more, if only we had given it more attention.” That is, without a doubt, the incorrect strategy. The fact that we are unattuned to the current moment and insensitive to the surroundings is what leads us wrong in the first place. We’re listening to our own thoughts, responding to events in the past, and applying theories and concepts that we assimilated years ago but have nothing to do with our current circumstance. More books, ideas, and thought will only exacerbate the situation.

Understand this: the best generals and strategists stand out not because they have more information, but because they can shed their preconceived assumptions and concentrate intensively on the current moment when required.” The 33 Strategies of War, Robert Greene

“My policy is to have no policy,” Abraham Lincoln said plainly.

Remember the generals of World War I? When they joined the conflict, they had decades of theory and strategy at their disposal. All that theory became useless the moment someone made a move that wasn’t in the plan. Worse than being irrelevant, sticking to outdated plans might be dangerous.

The conflict didn’t need generals with extensive experience; rather, it required generals who could adjust to a fast changing scenario.


Today, we’re in a same tumultuous scenario. In the time it takes a college student to graduate, industries change dramatically.

If you want to be a writer, you won’t follow in the footsteps of previous authors. Writers are currently subjected to a variety of pressures. Publishing is not the same as writing. Rather of waiting for a publisher to take up your work, you may need to self-publish on Amazon.

You may be better off launching a YouTube channel than working your way up the studio structure if you want to create movies. You’ll need to adjust to the industry’s new mechanics.

Those who are seeking for work must also adjust. Looking back in time, you may have learned that having a degree (and then another) is the most effective method to get employed. Actually, you could be better off coming up with a kickass side project and flaunting it publicly.

Because the world is changing so quickly, no book (or even a blog post) can provide you with a clear route to follow. You must swiftly scan the area and behave as best you can given the circumstances.

Doing what makes sense in your individual circumstances will benefit you much more than doing what you learned you should do in a comparable scenario. Of course, there are best practices, but you won’t be able to completely benefit from the unpredictability surrounding you until you get beyond them.

The 48th rule in Robert Greene’s The 48 Laws of Power is about remaining flexible. It’s about changing into someone or something else in order to take advantage of a fresh opportunity. In evolutionary terms, he emphasizes the significance of adaptability:

“Protective armor has virtually always indicated doom in the development of organisms.” The shell, with a few exceptions, becomes a dead end for the animal encased in it; it slows the organism down, making foraging for food difficult and making it a target for fast-moving predators. Animals that take to the sea or the sky and move quickly and in an unpredictable manner are much more strong and secure.”

Just because you’ve mastered a skill set doesn’t ensure it’ll always be relevant. A well-known wedding photographer was a friend of mine. He refused to use digital cameras when they first became popular.

He became a novelty after years of defiance. For a brief period of time, he was the go-to guy for old-school film prints. After ten years, no one cared about film anymore; they just cared about amazing photographs. Now that he’s made the transition, he’s gently re-establishing his customers.

When a machine takes away your work, the greatest thing you can do is learn how to utilize it. In the sake of tradition, don’t cling to your old ways.

Castles and fortresses are often thought of as emblems of protection. We believe that if we get powerful enough, nothing will be able to hurt us. Remember the Maginot Line in France? It was a network of impregnable castles erected in response to the German invasion of WWI.


When WWII arrived, the Germans marched straight around the outside of the line, rendering it completely unusable. Instead of looking around at their present situation, the French responded to a prior assault. Instead of preparing for the future, they planned for the past. They spent a significant portion of their national budget burying their heads in the sand.

Their inability to adapt cost them even more money.

5. Accept the Unknown

“It’s also crucial to remember that in real life, no one is ‘the bad guy,’ ‘the greatest buddy,’ or ‘the whore with a golden heart; in real life, we each see ourselves as the major character, the protagonist, the big cheese; the camera is on us, baby.” You may not find it simpler to develop wonderful characters if you adopt this mindset in your work, but you will find it more difficult to produce the one-dimensional jerks that litter so much mainstream fiction.” On Writing, by Stephen King

Our attempts to confine the world in a system or notion may be harming us rather than benefiting us. Instead of attempting to discover the solution, maybe we should accept that there is none other than what we do and what is.

It’s important to remember that this applies to both our outward and psychological environments. John Kay summarizes the process of making complicated decisions as follows:

“Because we can’t, we don’t solve issues in the manner that the notion of decision science suggests.” The great statesman’s success is not to arrive at the best option the quickest, but to effectively arbitrate between opposing points of view and beliefs. According to Buffett and Soros, “the measure of financial intelligence is the ability to maneuver effectively amid irresolvable uncertainty.”

It’s the same with our inner existence. It might seem like we don’t know who we are at times. This might be manageable if we didn’t have such strong convictions about knowing who we are. That we should be able to condense our identities into a box or a phrase and offer them to everyone who is curious.

It isn’t that simple, but it is that easy. In his book The War of Art, Steven Pressfield offers a solution to this problem:

“Are you a natural-born storyteller?” Were you born to be a painter, a scientist, or a peace activist? In the end, the only way to answer the question is to take action.

It’s either do it or don’t do it.”

Allow your actions to define you, and let the words fade away (they lie anyway).

Allow yourself to accept the world’s contradictions and learn how to properly mediate between the extremes.

Let go of the desire to explain yourself, and you’ll be surprised at what you can do.

The goal is to accept — to adore — the unpredictable environment in which we find ourselves. It was Nietzsche who expressed it best:

“My recipe for human greatness is amor fati: a desire for nothing to be different, not in the future, nor in the past, not in eternity.” Not just suffer, much less hide, what is necessary—all idealism is deception in the face of what is necessary—but adore it.”


Conclusions and Next Steps

“…doing things you can’t explain is preferable than explaining things you can.” Taleb, Nassim Nicholas

There isn’t going to be any more certainty in the world. In fact, it seems like things are just going to grow more complicated.

This does not imply that we should be fearful. It does imply that we must improve our ability to work successfully in the face of uncertainty.

I suggested five particular methods for doing this:

  1. Adopt a Stoic mindset. Practice the Triad of Control in particular. Ask yourself what you can manage if you are bothered by a circumstance. Instead of focusing on the result, focus on your effort and the acts you perform. (This is, once again, simple, effective, and very tough.)
  2. Place little wagers. Consider what modest chances you may take that could pay off handsomely in the long run. Instead of focusing on the likelihood of winning, consider the size of the payout if you do.
  3. Optionality. Allow yourself to have more choices in your life. Spend less money. Attend parties. Publicize your work. Don’t make a commitment until you really have to. Get a few different deals. Put yourself in settings where you’ll be more likely to come up with favorable solutions.
  4. Adapt by being present and fluid. Take the initial move instead of reading about how to start a company. Go to the gym instead of reading about fitness. Think on what makes sense for you right now, not what the book says you should do. The scenario you’re in is unique to you; although a book or counsel may help you think things through, only you completely comprehend the circumstances.
  5. Accept Uncertainty. Uncertainty is a natural force; you can’t “fight” it; all you can do is try to exploit it. What can you do with it? Steps 1 through 4 How can you make room to start putting them into practice? Allow yourself to let go of your craving for assurance. Start to comprehend how many concepts may be accurate in the abstract, but when you put them into action, you’ll discover that there’s only one reality. You can’t and don’t have to explain everything. Indeed, if you did, something else would alter as a result. The objective is to enjoy it. Fati amor!


Accept Uncertainty. Uncertainty is a natural force; you can’t “fight” it; all you can do is try to exploit it. What can you do with it? Steps 1 through 4 How can you make room to start putting them into practice? Allow yourself to let go of your craving for assurance. Start to comprehend how many concepts may be accurate in the abstract, but when you put them into action, you’ll discover that there’s only one reality. You can’t and don’t have to explain everything. Indeed, if you did, something else would alter as a result. The objective is to enjoy it. Fati amor!

Kyle Eschenroeder is an entrepreneur and a writer. The Pocket Guide to Action: 116 Meditations on the Art of Doing is his collaboration with Art of Manliness. He sends out a letter with 5 significant ideas once a week; if you’d like to be included, go here. 



To succeed in uncertain times, one must have a strategic posture. This means that you should prepare for the worst and hope for the best.

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