Imagining Success Versus Anticipating Failure

Imagining Success Versus Anticipating Failure

I am guilty of not spending enough time planning what to do when things don’t work out the way I want. I have written in the past about the importance of planning for failure and adversity, but like many others, I find it hard to do and hard to get myself to sit down and think seriously about how my plans and projects may fail. Planning for resilience is incredibly important, but so many of us never get around to it. Daniel Kahneman in Thinking Fast and Slow, helps us understand why we fail to plan for failure.

 

He writes, “The successful execution of a plan is specific and easy to imagine when one tries to forecast the outcome of a project. In contrast, the alternative of failure is diffuse, because there are innumerable ways for things to go wrong.”

 

Recently, I have written a lot about the fact that our minds understand the world not by accumulating facts, understanding data, and analyzing nuanced information, but by constructing coherent narratives. The less we know and the more simplistic the information we work with, the more coherent our narratives of the world can be. When we have less uncertainty, our narrative flows more easily, feels more believable, and is more comforting to our mind. When we descend into the particular, examine complexity, and weigh competing and conflicting information, we have to balance substantial cognitive dissonance with our prior beliefs, our desired outcomes, and our expectations. This is hard and uncomfortable work, and as Kahneman points out, a problem when we try to anticipate failures and roadblocks.

 

It is easy to project forward how our perfect plan will be executed. It is much harder to identify how different potential failure points can interact and bring the whole thing crashing down. For large and complex systems and processes, there can be so many obstacles that this process can feel entirely overwhelming and disconnected from reality. Nevertheless, it is important that we get outside of our comfortable narrative of success and at least examine a few of the most likely mistakes and obstacles that we can anticipate. Any time that we spend planning ways to get the ship back on course if something goes wrong will pay off in the future when things do go wrong. Its not easy because it is mentally challenging and nebulous, but if we can get ourselves to focus on the likelihood of failure rather than the certainty of success, we will have a better chance of getting to where we want to be and overcoming the obstacles we will face along the way.
Thinking Forward to Prepare for Obstacles

Thinking Forward to Prepare for Obstacles

A useful technique I learned for overcoming obstacles is to think ahead to the challenges you are likely to face and how you can overcome those challenges. If you only think ahead to the success you will have and picture a perfect life once you reach your goal, you will be less likely to actually achieve the success you desire than if you think about the challenges that lie ahead. However, dwelling on only the hard parts and obstacles can also be unhealthy. The key is to look ahead not to the obstacles themselves, but to how you will overcome them.

 

When you think about things that can go wrong in your life, you should picture yourself  getting through those obstacles. You should be realistic and specific in thinking things through. “I might encounter X, and if that happens, then I know I can do Y and ultimately be successful or at least manage a reasonable level of comfort.” If you start your plan for how you will overcome those obstacles, you will be more likely to persevere when the going gets tough. If you only think about how nice it will be once you have reached your goal, then you will be unprepared for the obstacles that you will face along your journey.

 

While this is a much more healthy way to think about the future, it is not the most common way for us to think. Most of us anticipate the things that can go wrong, but never get to the next step of thinking through the ways in which we can prepare for and overcome the problems we fear. What we usually end up doing is living in dread of the troubles ahead.

 

In Letters From a Stoic, Seneca writes, “Why, indeed, is it necessary to summon trouble—which must be endured soon enough when it has once arrived, or to anticipate trouble and ruin the present through fear of the future? It is foolish to be unhappy now because you may be unhappy at some future time.”

 

Seneca recognized the dangers of living in dread. If we think ahead to the future and only worry about what negative things we may face, then we turn our present moment, which might be quite peaceful and enjoyable, into a negative space consumed by the thing we hope doesn’t happen. Seneca encourages us to be more present and grounded in the current moment. I would argue that looking ahead and thinking of how we can overcome obstacles and truly understanding how we can adjust to and adapt to these challenges can help us be more confident in ourselves, and help us ultimately live with a greater sense of presence. It will also help us prepare for those times when we do face the obstacles we are afraid of.
The Value of Difficulties

The Value of Difficulties

“For our powers can never inspire in us implicit faith in ourselves except when many difficulties have confronted us on this side and on that, and have occasionally even come to close quarters with us,” writes Seneca in Letters from a Stoic.

 

In the quote above, Seneca writes that we can never develop a legitimate sense of self-confidence if we never face difficulties and challenges. If our lives are free from real obstacles and if we never face any real struggles, then we will never be prepared to step up  to take on greater challenges. Growth and preparation for large and important moments in life comes from the struggles we wish we could have avoided along the way.

 

Seneca continues, “It is only in this way that the true spirit can be tested – the spirit that will never consent to come under the jurisdiction of things external to ourselves.”

 

By learning from mistakes, overcoming obstacles, and finding strength during difficult times, we begin to be able to step back and become more objective in how we view ourselves and the situations in which we find ourselves. Wild successes and crushing failures lose their influence on our lives when we have faced difficulties and survived. Instead of placing all our happiness in a certain outcome, instead of living with constant fear of something negative, we are able to be more calm and centered, accepting that things may not go well, but confident that we can make it to the other side in a reasonable manner if things don’t go well. In this way external pressures and outside considerations of our lives cease to have influence over how we live and how we feel from moment to moment. Only by facing obstacles, learning about ourselves, and surviving difficulties can we develop the mental fortitude to reach this level of self-confidence.
Developing Self Esteem

Developing Self-Esteem

One of the reasons I write this blog is because I believe that we need deeper conversations about minor aspects of our lives. I think we need to be more considerate about what is truly important, and we need to think more deeply about how we can remove some of the less important things, so that we spend more time engaging with what is meaningful. I want to pull out the crucial ideas within the aspects of our lives that go overlooked and that are under-discussed so that hopefully someone can have a more thoughtful conversation about these important topics.

 

One topic, which came to mind from Sam Quinones’s book Dreamland, is the development of self-esteem for adolescents. I’m not a parent, so I am sure that I am missing some important points here and I’m sure that my perspective is limited, but from my experience and observations I feel  confident to say that important conversations about meaning, value, and expectations are not taking place with adolescents. What I’m thinking about now is how parents, coaches, and people in society can help young people develop a sense of self-esteem aligned around meaningful values that help make the world a better place.

 

Quinones quotes Ed Hughes, the former executive director of The Counseling Center in Portsmouth, OH, “You only develop self-esteem one way, and that’s through accomplishment.” Quinones himself is critical of parenting in the 90’s and 2000’s writing, “Parents shielded their kids from complications and hardships, and praised them for minor accomplishments – all as they had less time for their kids.”

 

The critique that Quinones and Hughes make is that parents have gone through great lengths to give their kids everything and to try to ensure that their children are never bored, never unhappy, and never potentially harmed – either physically or mentally. The result, according to Quinones and Hughes, is that children are unprepared for real life. They lack self-esteem because any accomplishments that they have are minor, and were parent assisted or directed. Many kids did not struggle on their own, did not learn from mistakes, and were propped up with empty praise. This left them feeling bored, empty, vulnerable, and inadequate, which made drug addiction all the more likely.

 

What I hope we can do, not just as parents but as a society, is talk about real opportunities for taking meaningful actions in our lives. I hope we can back away from terrible work schedules and the pursuit of ever more money and consumer goods, and move toward a society which encourages real interaction and contribution toward involvement and engagement. This can be done starting with our youth, with the opportunities we provide them to be engaged in something meaningful, and with the conversations we have with them about what is important in life.

 

If we don’t have these conversations with our youth, if we don’t help give them opportunities to do something meaningful, then they will look to TV, celebrities, and our own actions to determine what is good and important. Often that will be the same empty vision of happiness presented in our consumer culture focused on buying products and showing off our wealth. Quinones and Hughes would likely argue that this is only going to exacerbate our loneliness, emptiness, and the potential for drug use and despair.

Temporal Landmarks

My general sense the last several years is that people are starting to sour on the idea of a new year’s resolution. People that I have talked the last few years seem to be getting away from the idea of making a big change for the upcoming year, or at least if they are planning on making a change, they are not admitting it. Generally, I have been supportive of killing off the new year’s resolution tradition, but Dan Pink’s book When challenged my thoughts on the usefulness of such resolutions.

 

I have had the mindset that people shouldn’t wait for a specific date to try to make a change in their life. I am also skeptical of trying to implement a resolution on January first, since it is immediately after the Christmas holiday in the United States and many people likely still have family hanging around, still have extra pie in the fridge, and its a cold and dark time of year. Trying to start a big change during this time, when the weather is demoralizing and you are not on track with a routine schedule, seems like a poor idea to me. As a result, at least as long back as I can really remember, I have never made any substantial new year’s resolution and I have not been one to encourage people to adopt a resolution.

 

The reality, however, is that people find it helpful to make a change when there is something that can delineate a new starting line for them. Pink describes it this way, “The first day of the year is what social scientists call a temporal landmark. Just as human beings rely on landmarks to navigate space – to get to my house, turn left at the Shell station – we also use landmarks to navigate time. Certain dates function like that Shell station. They stand out from the ceaseless and forgettable march of other days, and their prominence helps us find our way.”

 

I had not thought of navigating the space of time the way we navigate the space of the world around us. But it is accurate to say that days and time can blend together, and since we can’t control time, it can feel as though it relentlessly races forward. I have heard people in the Bay Area in California talk about the disorientating nature of their climate. The Bay Area doesn’t have pronounced seasons the way other parts of the country do. Most days are ok, and the temperature and weather doesn’t vary dramatically across the year. The passage of time feels different when you don’t really have a spring, summer, fall, and winter.

 

Using temporal landmarks helps us make sense of the passage of time and gives us a place to plant ourselves for our upcoming life pivots. Just as we might use another wall or a step to brace ourselves if we are pushing a heavy piece of furniture, a specific date can be a brace for us to push for a new habit. It can provide a reference point for how far we have moved and how successful (or not) we have been with any changes that we want to make.

 

So rather than looking down on the idea of new year’s resolutions or being unhelpful in telling people to just make the changes they want to see in their lives today, I can help encourage people to use temporal landmarks in a smart way. I can encourage people to think about the obstacles they will face and how long after their temporal marker they think they might face those obstacles. I can encourage people to think in time chunks with more temporal landmarks to navigate the time landscape they traverse as they implement new lifestyle goals.  Time landmarks are not just random and arbitrary, they are social constructs that can help establish shared meaning and goals across time and space.

Preparing for Challenges

In November of 2018 I wrote a post about planning for resiliency. Michael Bungay Stanier described the importance of planning for failure, looking ahead and anticipating obstacles, and thinking through the ways we could recover from a drastic blow to our plans. It is not easy, but preparing ourselves for hard times will make it more likely that we can successfully manage setbacks when they occur.

 

This idea seems pretty clear and while we all familiar with saving for a rainy day, there has been relatively little focus in our society on preparing ourselves for other non-financial hardships. Interestingly, the idea from Michael Bungay Stanier is not as new as I thought when I first encountered it. In Letters From a Stoic Seneca wrote, “It is precisely in times of immunity from care that the soul should toughen itself beforehand for occasions of greater stress, and it is while fortune is kind that it should fortify itself against her violence.”

 

Stoic philosophy advises us to take advantage of the times when things are going well so that we can ready ourselves for times when it all falls apart. Rather than simply relaxing and enjoying our comforts, stoicism suggests that we pause, evaluate what is truly needed to live a good life, and consider how we would move on if all our comforts were suddenly stripped from us. It asks us what could go wrong and forces us to think about how we would still move forward, a skill that is hard and gloomy, but has a lot of upside.

 

I don’t think we need to overwhelmingly focus on death, loss, and hardship. We can still enjoy our comforts and our pleasures, but at least once every day we should stop to consider what things we have, how we live our life, and what is truly important for us. By doing this, we can enjoy our hobbies, relationships, and comforts more fully. By recognizing that things could fall apart we can better appreciate what we have now. Additionally, seeing the potential obstacles before they arrive allows us to be better prepared to overcome them when we must rise to the occasion. We don’t have to be on guard at all moments nor do we need to constantly look over our shoulder for danger, but we should be prepared to work for what is important or move in the direction we want when something shows up to block our path. We will be more successful and sound if we have been considerate and acted accordingly along the way.

Be Calm Ahead of Your Obstacle

In Letters From a Stoic Seneca writes, “There are more things … likely to frighten us than there are to crush us; we suffer more often in imagination than in reality.” Our minds work really hard to keep us safe, keep us in important positions, and keep us connected so that we can succeed and so that our children and grandchildren can enjoy a high status life. Our minds are trying to help us navigate an uncertain future, but sometimes our minds go too far and we become paralyzed with a fear that is worse than the outcome we want to avoid.

 

Seneca continues, “What I advice you to do is not to be unhappy before the crisis comes; since it may be that the dangers before which you paled as if they were threatening you, will never come upon you; they certainly have not come yet.”

 

We can live our lives worrying about what will go wrong five minutes from now, five days from now, or five years from now, but we never truly know what is around the corner. Sometimes we set artificial deadlines on ourselves and sometimes those deadlines are forced upon us, but that doesn’t mean we need to live every moment of our lives up to that deadline in fear of what will happen if we don’t achieve what we intended by that date. The fear that we feel can be useful in pushing us to get stuff done and avoid procrastination, but when we notice that we can’t sleep at night because we are worried of the negative consequences of what may happen if that bad thing we fear occurs, then it is time for us to step back and refocus on our present moment. I find that it is helpful for me to look at the fears that I have and recognize that in the present moment I am fine, and to recognize that the status quo will most likely continue if I miss the deadline or if the bad thing does happen. There are plenty of things to fear, and we should build a capacity to see that we will still be able to move on with life even if some of our worst fears come true.

 

Ultimately, we know we are going to have obstacles and setbacks in our lives, but that does not mean we need to live every moment in fear of what bad thing is around the corner. We can live conservatively and save money and resources to confidently weather such challenges, but we do not need to allow negative things in our lives to cause us trauma before they have occurred. Preparing ourselves ahead of time will help mitigate the fear, but learning to accept that bad things will happen and learning to enjoy the present moment are the only ways we can truly escape from the fear of what lies ahead.

Individual Circumstances

For many of us, things in our life and our mental states begin to break down when we look around and compare ourselves to others. We can be perfectly happy on our own, enjoying our own flow of life, but when we see the neighbors buy a new car, when a friend posts vacation pictures on Facebook, and when a family member gets a promotion, we suddenly feel inadequate. Conversely, when we have overcome obstacles it is easy to look at everyone else who has not been as successful as us and look down on them, criticizing them for not being as strong as us and for not making the smart decisions that we had to make to get to where we are.

 

In my first example of comparing ourselves to others, I am referring to jealousy and envy that we can feel relative to others. Our status in the world will always be relative, which means that as someone else does better, our status relative to  that person is in a worse position. There is no global status meter ranking us all, but we unconsciously rank our status against one another all the time. It is stressful, and it is also all made up. Recognizing our status comparing impulses and choosing not to allow these impulses to drive our lives will free up our mind, our goals, and what we feel we must do to show that we are just as successful as other people in our orbit.

 

The second example from the opening paragraph of comparing ourselves to others is something I have been thinking about more recently. Once we become successful, I would argue that we have an incentive to over-hype the obstacles we faced and to make it even more challenging for other people to follow in our footsteps. If I had come from nothing and succeeded, and a hundred thousand people after me also came from nothing and found success, then my achievements would look smaller. If, however, I came from nothing and achieved great success and suddenly found myself in a rare group of individuals with very few other people able to pull themselves up by their bootstraps, then my accomplishments would look even more impressive. What I did to achieve success may not have changed, but how it is perceived will change based on how many others also become successful. We have plenty of incentives to build up our story, trump up the obstacles we had to overcome, and to then criticize those who don’t make it. We shouldn’t believe the story we tell ourselves, because it is probably and exaggeration and will likely make life unnecessarily challenging for others, just so we can hold a special place in our own minds and in the eyes of society.

 

In his book Becoming Who We Need To Be, Colin Wright writes the following, “Don’t compare your efforts to that of your peers. Everything you do should be customized for your individual circumstances.” We never know all of the challenges that another person faces. We never know what advantages another person has in life. And ultimately, for ourselves, neither of those things matter. What does matter is whether or not we are making efforts to be well-rounded individuals and whether we exist in society for ourselves or with the goal of making all of society better for everyone. Comparing ourselves to others in an attempt to monitor who is working hard, who is cheating, who deserves what they get, and who is high or low status will simply burn us out and lead to negative thinking and negative interactions with others.

A Clear Picture of Success

In 2017 I wrote a piece about an idea from Colin Wright in his book Come Back Frayed. In our lives, the primary yardstick we use to measure our success, Wright explains, is often a monetary yardstick. We look at our bank account, the funding levels of the organization we are a part of, and how much we make each pay check and determine whether our lives have value and are meaningful based on how much we make. Colin Wright was one of the first authors who helped me be aware of how frequently I judged myself and others based on income, or cues related to income (how fancy is someone’s car, what shoes does someone have, do they live in a wealthy neighborhood?).

 

Wealth and income, however, are both impacted by a number of forces beyond the control of a single individual and both people who we hold in high esteem and people who are self centered and morally questionable can become fantastically wealthy through either hard work or dumb luck. Therefore, judging someone based on wealth and income is an incomplete measure of another person. Wright was one of the first people to express this in a way that really connected with me, and I found the idea again in the writing of Ryan Holiday and Marcus Aurelius. In a long quote from Ryan Holiday’s book Ego is the Enemy, he writes,

 

“You will be unappreciated. You will be sabotaged. You will experience surprising failures. Your expectations will not be met. You will lose. You will fail.
    How do you carry on then? How do you take pride in yourself and your work? John Wooden’s advice to his players says it: Change the definition of success. “Success is peace of mind, which is a direct result of self-satisfaction in knowing you made the effort to do your best to become the best that you are capable of becoming.” “Ambition,” Marcus Aurelius reminded himself, “means tying your well-being to what other people say or do … Sanity means tying it to your own actions.””

 

We cannot expect that in our lives everything will go well and we will live up to the external yardsticks we use to define success. If we expect a certain number of followers, likes, or shares then we are deciding the value of something based on the perceptions of other people and whether something randomly becomes a hit. If we decide that we are only successful if we have enough money to buy a new Tesla, we are putting ourselves in a position where we may compromise on being a good human being in order to obtain enough money to purchase something that we think will tell people that we are valuable and successful. We give control of ourselves to other people when we live this way. Our happiness is not our own, but a yo-yo string controlled by the opinions of our social, work, and family networks.

 

Changing our definition of success to measures internal to who we are is more healthy and reasonable. Pursuing a craft, hobby, or passion for self-fulfillment is different from pursuing a goal for reasons of obtaining greater wealth, respect, and admiration from others. Those things may come from living well, but when they are a result of good work and arrive obliquely through our efforts to do our best at what is in front of us, they will be more rewarding and less tied to our definition of who we are. This can give us the opportunity to live on our own terms, content with the person and lifestyle we pursue.

The Destructive Ego – Lessons from Jefferson Davis and Napoleon

In his book Ego is the Enemy, author and super reader Ryan Holiday gives us lots of examples of the ways in which our ego can lead us astray and tear down the things we are trying to accomplish. Holiday explains that part of why the ego is dangerous is because it damages our relationships with others and doesn’t allow us to set aside trivial matters to focus on the important things in our lives. It dials in on perceived slights, seeks recognition and attention, cannot handle even the slightest criticism, and ultimately pulls us down while we try to vault to new heights.

 

As an example, while Jefferson Davis was the Secretary of War for the United States, he was engaged in correspondence with General Winfield Scott. In his book, Holiday explains that Davis, “Belligerently pestered Scott repeatedly about some trivial matter. Scott ignored it until, finally forced to address it, he wrote that he pitied Davis.” In a letter addressed to Davis Scott wrote, “Compassion is always due to an enraged imbecile who lays about him in blows which hurt only himself.” Davis was a successful politician, but he continued to attack the General in an attempt to gain leverage over him or to at least call him out on a flaw or issue. In a battle of ego, he tried to magnify the flaws of another by attacking him, and ultimately just made himself look worse. The ego likes to draw energy from outrage, to draw a line in the sand and yell that the ego is on the correct side and the offending parties are on the wrong side. The ego wants to be right and it wants to angrily shout down those who are wrong. The problem with allowing our ego to run free in this way is that it reveals how impulsive, insecure, and weak our ego truly is.

 

Holiday continues with another example of the ego ruining goals and objectives by writing the following about Napoleon, “A critic of Napoleon nailed it when remarking: “He despises the nation whose applause he seeks.” He couldn’t help but see French people as pieces to be manipulated, people he had to be better than, people who, unless they were totally, unconditionally supportive of him, were against him.” The ego wants everyone’s adulation, but it is constantly putting other people down so that it can feel superior to the rest of society. When the ego takes control of the steering wheel, we mock other people but at the same time everything we do is some type of performance or show with those same people in mind.

 

What we can take away from Davis and Napoleon is the danger that flows from our ego. When we put a great deal of importance on our own self-image and live in a way that is meant to show off and inflate who we are, we risk alienating others and alienating ourselves. The ego will pester others and put them down, but at the same time the ego will only feel validated when it receives praise from those who we put down. Its destruction of meaningful connections and relationships with others is what ultimately dooms our goals and aspirations.