How to avoid a successful life

[Editor’s Note: This is another guest post from the excellent Tyler Watkins. You can check out his work on how to live a better life at]

In the late 1960s, psychologist Walter Mischel at Stanford University conducted a series of experiments on delayed gratification collectively known as the Stanford marshmallow experiment.

In these studies, a child was offered a choice. Get one marshmallow right now. Or wait for a short period of time (15 minutes) and get two marshmallows.

Decades later, in follow-up studies, the researchers found that children who had been able to wait longer for the preferred reward tended to have better life outcomes, as measured by SAT scores, educational attainment, body mass index (BMI), and other life measures.

Dr. Mischel’s studies had apparently shown us the key to success.

Delayed gratification was a major difference between society’s successful people and its unsuccessful, marshmallow-eating pleasure chasers.

Long-term planning, goal setting, and sacrifice, we’d be taught, were of paramount importance to a successful life.

Society would ask us to dream big. To focus our attention on the future.

“What do you want to be when you grow up?”

“Where do you see yourself in 10 years?”

“What do you want to have? To be? To do?”

The Problems with Success

Delayed gratification is a powerful tool. It’s very hard for me to write this article and talk trash it.

Delayed gratification got me through university. It got me six-pack abs. And it got me hundreds of thousands of dollars.

And I still believe it’s nice to have two marshmallows to eat, instead of one. It’s smart to plan for retirement and put money away for a rainy day. prioritizing your education today to gain skills for tomorrow is a constant necessity in life.

But when we use delayed gratification and  general “success orientation” as a way of life it screws us in several critical ways.

I’ll summarize each here and explore in detail below.

  1. We’re fooled into thinking of life as a series of desired outcomes rather than a series of lived moments. We chase a horizon that we can never reach. We feel perpetually incomplete and treat life like a video game where the goal is to constantly level up until we die.
  2. We assume a level of control over the world that we simply don’t have. We live as if we know when we’ll die, we fail to appreciate what the world gives us, and we miss out on all kinds of random opportunities that come up along the way.
  3. We focus blindly on outcomes/ destinations and overly identify with both our failures and achievements. Rather than focusing on and celebrating what’s truly important, our day-to-day actions.
  4. We get caught up chasing goals that adhere to society’s or someone else’s agenda rather than focusing on what’s truly important to us. We never really find our own unique path which focuses on the lived moments that make us truly come alive.

The 1st Problem with Success Orientation: Life as a Video Game

With success orientation, life gets viewed as an 80-year chunk of time where we try to achieve as much as possible while avoiding getting killed until the end.

We set and accomplish goals one after the other.

Life’s a video game where we complete one “level of success”, feel good for a moment, then immediately begin working on the next level.

Society will always let us know what level we’re on. The game’s leaderboard is displayed at every moment.

We’re told as an absolute minimum the “successful person” is expected to complete these levels:

Get Good Grades -> Get into a Good University -> Get a Job -> Develop Some Advanced Industry Skills -> Earn Upper-Middle Class Money -> Buy a House -> Raise a Family ->

After which you get to…

Retire -> Play with your Grandkids -> Die

There are alternative paths and advanced bonus levels like buying a Land Rover, making a million dollars, or becoming an executive manager. But these don’t change the essence of the game.

The game is about delaying life. We sacrifice our todays to chase goals of our future years.

We probably have an ultimate goal in our minds…

  • A high enough level on the leaderboard
  • That house, that family, that job title, that cool million in the bank

and tell ourselves that one day when we reach it…

  • We’ll be complete, be happy
  • We won’t have to level up anymore
  • And we’ll be ready to live

But our ultimate goal is an illusion. The game doesn’t work that way.

What really happens when we reach our ultimate goal is that we’ll be happy for a moment, a week, a month, then we create a new goal.

A life of delayed gratification is an addiction. It was originally supposed to be a tool to build a brighter tomorrow but it becomes the only way of life we know.

It’s the price of success.

Eventually, We run out of time. Be it tomorrow or 50 years from now, it doesn’t matter. The game is eventually over and we never actually lived.

We face the final boss battle with the Grim Reaper. No matter what success level we completed in the game there’s no way to survive, and no reset button.

The 2nd Problem with Success Orientation: The World Doesn’t Care About Your Plans

A friend of mine had plans. We worked together in the oil and gas industry and every Saturday afternoon we’d sit in the office working and chatting about the future.

He didn’t like his job. The long hours, the time away from his family, the meaninglessness of the tasks.

But he had a plan. This job was a stepping stone. He was getting skills and saving money. He would eventually do something different where he’d work less and have more time for his family.

Then he got on a helicopter and it landed in the ocean.

This was a harsh reminder that the world really doesn’t care about our plans.

And when we think about how small of a role we play in this infinite extent of space and time, why should it?

We’re tiny. We’re smaller than specs of sand. We have about the same amount of control as a drop of water in the ocean being pulled by currents and crashed around in waves.

Whether we’ll die tomorrow or in 50 years is not certain. What is guaranteed though is that some unexpected things will happen to us along the way. Life will be random. Plans will get interrupted.

Does that mean planning is pointless?

Should we stop setting goals because maybe our helicopter will go down tomorrow?

Is the answer for us all to become monks and sit around smiling and waiting for death?

Some advocates of eastern philosophy might recommend this but I don’t think so.

I think we can live in alignment with the randomness of the world. Not waiting for retirement to live, but also not drowning ourselves in immediate pleasures because today could be our last.

The problem with success orientation is that it assumes a predictive power of the future that we simply don’t have. It asks us to plan our lives as if we already had all of the answers. And when life interrupts those plans (assuming we’re still alive) we decide to get upset.

But life’s randomness doesn’t know whether it’s being an inconvenience or a blessing. It just is. It’s our option to choose the interpretation.

Use life’s craziness as information to update our plans and actions. To pivot our lives in new directions.

Think about the best things that have happened in your life. Were they not at least partially made up of random encounters, events, and actions?

I took a 5-day vacation to Brazil and found my new home for the next 5 years. A friend started training martial arts, got motivated to quit his job teaching medicine and leave the United States. That journey led him to meet his current wife and build a new career. Another friend was introduced to a bitcoin early adopter in 2011 and decided to spend 4 months with him in Chile, sleeping on his couch. He turned $20,000 into $1 million.

Who ever heard of cryptocurrency before now?

Cryptocurrency || Engineering and Leadership

Success orientation asks us to make a plan, put our head down and go after it. To eliminate as much risk and randomness as possible. Treating life as a series of problems to be handled while ignoring opportunities to pivot.

It’s impossible to predict when our own helicopter will go down.

But while we’re here it’s our choice. We can embrace the randomness of life and appreciate each moment.

We can interpret chance as opportunity. We can ride the wave and pivot on one opportunity after another, ending up in places we had no idea existed and building a unique life that gains from the ever-present randomness of the world… while we have the chance.

The 3rd Problem with Success Orientation: Why SMART Goals are Stupid

If you’ve ever worked in a company you’ve probably heard of SMART goals.

SMART Goals || Engineering and Leadership

You’ve probably had a performance review or end-of-year evaluation where the results of these goals were analyzed.

And in most cases, no matter what happened during the course of the year,you were evaluated against the projected outcomes.

I’m not a fan of excuses. I think that we do a lot better when we take more responsibility than we realistically should for the outcomes of our work (especially negative outcomes).

But we have to admit that sometimes we over identify with outcomes as well – both good and bad. We tend to get too high with the highs and too low with the lows.

A lot of times that big sale we made had more to do with the client’s affinity to a certain technology than our stellar sales skills. And that top-notch recruit we lost had more to do with his personal agenda than our offering.

Success orientation asks us to focus on outcomes. But when we focus on fixed outcome goals we neglect to pay proper attention to the only thing that’s truly important: our daily actions.

We let the goal become the goal rather than focusing on the reason for the goal and the daily actions that go into it.

Out of Greek antiquity was born an ancient school of philosophy known as stoicism. Used historically by emperors such as Marcus Aurelius, and today by business leaders and professional sports franchises such as the New England Patriots, stoicism is largely considered the go-to operating manual for thriving in complex and high stress environments.

The stoics didn’t get lost dreaming about future outcomes. They were very focused on living in the present moment.

They separated the world in to two categories. That which we control: our actions, intentions and demeanor. That which we don’t control: everything else.

Their goals were based only on that which they control. They set action-based process goals.

Everything outside of their control, which includes all outcomes, were categorized only as a preferred or dispreferred indifference.

Stoic Goal Example:

If a Stoic desired a raise at work, it wouldn’t be his goal. It’d only be his preference. Instead, his goal would reflect what’s within his control. Namely, to work his ass off every day, to study his company’s needs and align his actions to try and maximize the benefit he brings to the company.

He does everything he can to point himself in the direction of his preference. But ultimately, the outcome is dependent on other factors that are outside of his control. Like the budget for raises, industry trends, his boss’s personal tastes, etc.

Whether he gets the raise or not, when it’s time for him to self-reflect he will judge himself only by the actions he took (or didn’t take) and decisions he made during the process. Not the outcome.

In complex situations, it doesn’t make sense to set outcome goals. Rather, it makes more sense to set process goals aimed at temporarily preferred outcomes. Preferred outcomes that we’re willing to change as new information becomes available. This is more in alignment with how the real-world actually works. And that new information might come from the outside world or it might be an insight we make during our daily actions.

For example. I may have a preferred outcome to become a famous rockstar. I realize that I’ll need about 10,000 hours of practice on the guitar to get there. After my first month of putting in 20 hours a week on the guitar I realize that I hate practicing. Guess what: it’s time to find a new preferred outcome.

We always need to remember that life is composed of daily actions. Life is too short to spend significant time working on a preferred outcome which is composed of daily actions we don’t want to be doing.

Comparison of Process vs Outcome Goals

Goals comparison || Engineering and Leadership

Side note on Excuses: The world being full of randomness doesn’t mean we get to make excuses. We still can and should use intelligent planning to try and mitigate/ prevent disruptions. We still can and should accept pain and discomfort to power through obstacles. If it’s raining outside that doesn’t mean the universe is telling you to not go to gym. Get your lazy ass off the couch and go. But as we look at more complex, longer term goals like “having a meaningful career” or “having a great relationship” we need to be willing to update our preferences and align our actions with the real world. The journey becomes very important and the “outcome” needs to become more flexible.

How to set process based goals.

  1. Start with Why: What’s your Dogma/Purpose?
  2. Define the What: This would traditionally be the outcome goal that relates to the overall purpose. Use SMART here if you like and define your temporarily preferred outcome.
  3. Define the How: What actions need to be executed on a daily/ weekly basis to point you in the direction of your preferred outcome. Do you actually want to do these actions every day? Is this the life you want to live? If not, rethink your Why and What.
  4. Review regularly: Evaluate the progress made from your How (daily actions) as well as the continued relevance of your What and Why. Adjust each as needed.

Transitioning from Success Orientation to Self-Actualization

Success orientation tells us to treat life like a video game, assume we have perfect vision, and control our way to the top.

Deep down we know that life isn’t a competition.

Orienting your life towards success is not a natural or fulfilling way to live.

But it’s still very attractive.

It’s attractive because it’s safe. It’s well-accepted. Everyone else is doing it. People look up to you when you have success.

Success orientation frees us from the responsibility of making our own choices, and carving our own paths.

Success orientation frees us from our biggest fear. Our fear of freedom.

In 1951, shortly after Hitler had convinced a nation of Nazis to band together and exterminate every man, woman, and child Jew, Eric Hoffer wrote, The True Believer. It’s a timeless explanation on why people will do the stupidest shit imaginable as long as everybody else is doing it. He wrote extensively about how “group think” solves our anxiety and why we actually don’t want freedom…

Freedom aggravates at least as much as it alleviates frustration. Freedom of choice places the whole blame of failure on the shoulders of the individual. And as freedom encourages a multiplicity of attempts, it unavoidably multiplies failure.

If we choose self-actualization over success orientation, we will screw up. And it will be our fault. Not the system’s. Not our company’s. Not the economy’s. Ours.

We won’t be able to cry and say, “I did everything I was supposed to do. Why didn’t it work out?”

We’ll be to blame.

That’s scary.

However, if we can overcome this fear to be wrong, to screw up our lives, to go against the judgement of others, we can do something better.

  • We can live a life based on self-mastery, with a focus on action.
  • We can listen to our instincts. Do work that makes us feel alive.
  • We can build a unique path where the journey itself is the reward. We can take pride in what we actually control, namely our decisions, demeanor, and actions, and leave the objective results to the world to decide.
  • We can take in new information and stimuli as they come to better shape our decisions and actions. And live a life one day at a time, learning, growing, doing, and enjoying.

Step by step, year by year, skill by skill, we do it.

This is an antifragile life.

This is self-actualization.

Some Practical Tips as well as Traps to Avoid

The “Success Life” comes with a few traps that can keep us on a path we don’t want to be on for a long time. Here I’ll quickly discuss a few ways I’ve used and seen used over the years to help avoid these traps.

  1. Always consider the path and not just the potential outcome.

Always ask, “Even if this doesn’t work out how I planned, will I be happy to have walked the path?” All outcomes are uncertain. Choose paths you’ll be happy to have walked either way.

  1. Get yourself in a position where you have “F**k you” money.

The ancients considered people in debt to be slaves. Avoid debt at all costs. I’ve seen people get personally destroyed and forced into years of soul crushing labor because they bought houses and cars they couldn’t afford. Life is too short.

Try to save until you have at least 12 months of living expenses in cash or assets you can liquidate easily. This doesn’t have to be a large sum of money if we drop our living expenses to a reasonable level by not buying all the crap we don’t need.

The difficulty is almost always that we want too much, not that we make too little.

  1. If you need to use delayed gratification, keep it quick and to the point.

Get very clear about it. How much time are you going to spend pursuing this thing? What is the exact outcome you’re going after? When will you walk away? Remember that your helicopter could go down tomorrow.

  1. Find real mentors.

You wouldn’t take financial advice from the homeless, or diet advice from the obese.

Who’s living a life that you don’t want? Avoid their advice.

Who inspires you? Take their advice.

Look at people further down the path your headed and ask if that’s still a direction you’re interested in pointing yourself.

  1. Avoid overspecializing if possible.

Industries are getting overturned, and positions becoming obsolete faster than ever.

Don’t spend time learning niche skills you don’t enjoy. Learn a variety of robust skills that interest you, and get ready to embrace chaos. Build foundational skills that can transfer between industries. For example, crucial conversation skills and sales.

  1. Follow your gut

Every good thing that’s happened to me has come from following my gut. I don’t know why.


This article was tough for me to write. I’ve been indoctrinated with a success orientation since childhood and have been obsessed with achieving goals and being successful as long as I can remember.

I don’t really know if there’s a perfect way to live. I think we all need to find our own. But that’s the point. The journey is our own. Not some pre-defined definition of what we should aspire to.

I’ve been on my own journey for a couple of years now and for anyone else who’s doing something similar or wants to talk about it, hit me up with an email any time at

And if you’d like to subscribe to the site where I talk about experiments, practices, and philosophies related to building a meaningful life, visit

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