Is your ladder leaning against the right wall? Six mental models for success

Defining success – craft, don’t mimic

A key component of finding meaning in life is our personal development, or what we call at Kalibra the “Grow” pillar of health. The path to finding our growth rhythm is riddled with pitfalls, and chief among them is the growth journey’s destination, or what is commonly referred to as “success”.

The phrase is often used with the implicit assumption that “success” has a universal meaning, which it does not. So, to make sure the climbing ladder is not leaning against the wrong wall, we must start with the self-discovery journey of defining success. We should base this definition on deeply personal terms rather than being borrowed from others. Otherwise, we’ll get stuck in an endless loop of chasing the next mimetic thing without stopping to think whether this is something we want to want or something society decides we should. Therefore, the first guiding principle of defining success should be: Don’t be a prisoner to someone else’s expectations.

Who cares about the endgame? We’re here for the plot twists.

One of the persistent messages from the perspectives of people who have achieved their definition of success is that it’s the byproduct of pursuing a calling greater than our ego and doing so with persistence. It’s hard to put it better than Viktor Franklin Man’s Search for Meaning:

Don’t aim at success — the more you aim at it and make it a target, the more you will miss it. For success, like happiness, cannot be pursued; it must ensue, and it only does so as the unintended side-effect of one’s dedication to a cause greater than oneself or as the by-product of one’s surrender to a person other than oneself. Happiness must happen, and the same holds for success: you must let it happen by not caring about it. I want you to listen to what your conscience commands you to do and go on to carry it out to the best of your knowledge. Then you will live to see that in the long run — in the long run, I say! — success will follow you precisely because you had forgotten to think of it.

Further to the elusiveness of targeting a specific outcome, there is the elusiveness of timing. Like wisdom and insight, success is a lagging indicator of our efforts and preparation. Two of our favourite writers, Ryan Holliday and James Clear, point out that the work laying the groundwork for success far precedes any visible results, requiring a persistent loop of working, trying, and failing, of enduring when others would give up.

Like many things in life, we can only connect the dots backwards. Shane Parrish points out the futility of looking for the miracle moment when success happens. Being too focused on the “‘I’ve arrived” timestamp is akin to being drawn to the secret ingredient we are missing to complete the recipe.

The problem is that no miracle moment, destination, or secret ingredient exists. Nature offers a great example with bamboo, which takes up to 5 years to develop its roots. To the outside observer, no visible progress has been made for years. Meanwhile, the bamboo grows below the surface, developing its seeds and storing energy. Then, all at once, it starts to grow. Years of stored energy result in exponential growth, sometimes reaching over 15 metres in weeks.

That’s how progress happens. Slowly and then all at once. Yet everyone wants the results without the process that leads to them.
If that were how life worked, the results would mean nothing, as very often, a big part of the value we perceive something to have is the price we pay, the hard work.

Armed with the bamboo wisdom that not all progress is visible, nobody rings the bell for our success, and we can only see results in the rearview mirror, we need to accept the long periods without clear markers of progress and that the daily grind is a crucial part of it. Embracing the suck of this truth will give us the wisdom required to know we’re making progress without any apparent signs of progress.

Let’s dig into how to think about the building blocks of that journey.

Mental models defining success on our terms

According to decades of psychological research, a universally accepted definition of a successful life is one in which your basic needs for food, shelter, health care, and income are met and in which you have a sense of autonomy, mastery, and belonging.

Modern society has bestowed us with a curious problem, however. As it multiplies our opportunities, it commensurately multiplies our opportunity costs, making it costlier and more difficult to commit all of our time and energy to any one thing without feeling remorse or regret. We’ve gone from looking for needles in a haystack to looking at stacks of needles that have been pre-sifted. Our brains can’t handle this burden of choice.

That’s why an internal compass is a must. Sahil Bloom points out how reading about “successful” people and thoughtlessly mimicking what success looks like actively harms our happiness, as the “cultural map of success doesn’t match the terrain of our own life.

1. Balancing the four pillars of success

One helpful framework from HBR is to think about success in terms of its four distinct components: happiness, achievement, significance (positively affecting those you care about), and legacy (helping others find future success). Winning in any one category but failing in the others will be unsatisfying. Therefore, instead of relentlessly pursuing one goal, focus on racking up victories in all areas and limit how much time you allocate to each pillar. It’s a balancing act, not a sprint to a destination.

Fast, lift, sprint, stretch, and meditate.
Build, sell, write, create, invest, and own.
Read, reflect, love, seek truth, and ignore society.
Make these habits. Say no to everything else.
Avoid debt, jail, addiction, disgrace, shortcuts, and media.
Relax. Victory is assured.

Naval Ravikant

2. “Having vs Being” Framework

Brad Stulberg contrasts “having” as defining self by possessions—job, income, house, which is fragile by nature – all of these can be lost.

Conversely, “being” defines self by core values—creativity, kindness, authenticity. The “being” framework is considerably more resilient to life’s ups and downs as these qualities are enduring and adaptable. Life becomes about being a better version of yourself, directing effort and energy toward upgrading your operating system daily, and not worrying about what your air-brushed Instagram idols are doing. You become happier, free from the shackles of false comparisons and focused on the present moment.

The “being” life philosophy requires consistent and methodical investment, with no lottery-like payoffs which can happen in the money world. It ensures constant time allocation for personal growth, emphasising the journey and protecting from the inverse “U” shaped utility of possessions, which we detail in the following mental model.

If you don’t get what you want, it’s a sign either that you did not seriously want it or that you tried to bargain over the price.
Rudyard Kipling

3. Freedom vs ownership

Not wanting something is as good as having it
Liad Shababo

Money is a tool that can be used to gain freedom, but often, it becomes a tool that curtails our freedom as it sets an ever faster beat for us to march to. The things you own can end up owning you reasonably quickly, as anyone who has bought a boat or a vacation home knows all too well.

With the caveat that most of us are in no danger of having a “too much money problem”, it is essential to realise that money turns from a reliable slave to an evil master at a much lower threshold than we intuitively guess. The responsibility of managing money or giving it away is not trivial, and focusing on what level of financial independence is the threshold to invert values and optimise for time freedom is a crucial threshold many “successful” people miss.

We look to arrange the props in our lives so that we can have free attention when all is in place one day. We already have this possibility now; however, money is frequently not the answer. Very often, it helps to think about success not as a painting (adding brush strokes) but as a statue (removing to reveal). For type A people, noticing the magic moment for transitioning from the accumulation to distribution phase is one of the biggest life challenges when defining success.

4. Insides vs outsides

“Comparison is the death of joy.”
Mark Twain

You can be anything, but you can’t be everything. When we compare ourselves to others, we often compare their airbrushed features (what we post on socials) against our average ones. It’s like being right-handed and trying to play an instrument with your left hand. The unconscious realisation that we are not better than the idealised vision of others often becomes a self-destructive, negative perception loop.

“The big question about how people behave,” says Warren Buffett, “is whether they’ve got an inner scorecard or an outer scorecard. It helps if you can be satisfied with an inner scorecard.” To make his point, Buffett often asks a simple question: Would you rather be the world’s greatest lover but have everyone think you’re the world’s worst lover? Or would you rather be the world’s worst lover but have everyone think you’re the world’s greatest lover?

The good news is that the people we hold up as heroes are just as broken as you are – rich people have rich people’s problems, famous people have famous people’s problems, and intelligent people have all sorts of issues. Elon Musk recently said that his mind is a ‘storm’ and people ‘may think they’d want to be me, but they don’t know’.

If you had a 360-degree view of the lives of those whose success you want, you’d likely not want to swap with them, as you have to take their apparent success with their private failures, fears and anxieties.

An even worse side effect of constantly benchmarking ourselves to others is that we focus our energy on mentally bringing them down instead of raising ourselves.

Finally, we forget that worrying about what others think of us is pointless, as they rarely think of us. We are all focused on our journey; others look at you like you were looking at them through a distorted lens shaped by social media and artificial expectations. When we measure our success vs. our previous selves rather than others, we’ll be more likely to support others and receive support.

The race is long, and in the end, it’s only with ourselves.

5. Trajectory vs. position

“What is the secret of success? Right decisions. How do you make the right decisions? Experience. How do you gain experience? Wrong decisions.”

Abdul Kalam

Good or bad results are transient – any accomplishment automatically creates another high bar for us to chase. It’s human nature. Instead of adopting a purely goal-oriented mindset, it is worth selecting pursuits based on how much we’ll enjoy the process of doing them. After all, the process makes up ninety-nine per cent of your life.

The actual pursuit in this strategy should be finding those rare things in life that you’re willing to sprint for when the distance is unknown. Put differently, we need to find the failures that feed fun, set them up in an infinite loop and speed it up. Most people don’t succeed because they’re either unwilling to fail or tired of failing before those failures pay off. 

Remember, we don’t fear failure. We are afraid of what other people will say about us when we fail. See Mental model 4 above. 

6. What do you want to want?

“To laugh often and much; to win the respect of the intelligent people and the affection of children; to earn the appreciation of honest critics and endure the betrayal of false friends; to appreciate beauty; to find the beauty in others; to leave the world a bit better whether by a healthy child, a garden patch, or a redeemed social condition; to know that one life has breathed easier because you lived here. This is to have succeeded.”

Ralph Waldo Emerson

Minding the gap between who we are and who we want to be is an ongoing balancing act, and we need to keep controlling the speed of our hedonic treadmill. If music is space between the notes, then setting that speed at too fast a pace likely means we’re chasing the extrinsic scorecard.

Pacing ambition means understanding that while we could always be “more” than we are, thinking about the time dimension of success is sometimes stretching the distance between achieving goals so that we can relish the journey. Managing our wants, i.e. really wanting to want what we want, becomes also about managing the speed of progress so that we don’t strangle happiness by chasing achievement too fast.

Letting Instagram interfere with this process will inevitably lead to us realising that if we play stupid games, we’ll win silly prizes.

How to stack your mental models

“When you’re nearing your end of life, your only measure of success should be the number of “people you want to have love you do love you,”
Warren Buffett

The power to define success should be ours and ours alone. We must reclaim this control on an ongoing basis. Real success is emotionally renewing, not anxiety-inducing.

Personally, I like the Norman Lear framework that success is ultimately a question of how you collect your minutes. And I want to collect my minutes by doing things I like with people I love.

I don’t remember where I heard it, so I can’t attribute it (perhaps Tim Ferriss?) The number of people in your life that you would gladly give a kidney to. This means that you are surrounded by people you feel such a strong connection with that you’ll go to extraordinary lengths to protect them.

Software updates

The wisest people don’t have the best answers—they ask the best questions. Realising that finding the truth is much more important than being right helps us enjoy being wrong. We then embrace new information as “software updates” to our brains. Change your questions, change your life. Here are a few to ponder if you want to take this further:

  • Is my definition of success my own, or am I allowing cultural definitions to bleed into it?
  • Am I asking myself “Will I succeed?” instead of, “What should I attempt?”
  • What do I have fun failing at? How has that paid off for me? What do I keep trying to excel but hate failing at? How has that held me back?
  • What do I believe is true only because assuming it puts me in good standing with my tribe?
  • What do I think is ambition (a good trait) but is actually envy (a terrible one)?
  • What actions got me there if I woke up in 10 years and was in flow?
  • What would Instagram look like if it were an honest reflection of people’s lives instead of a curated highlight reel?
  • What would I do if I knew I would definitely fail?
  • What would I do if I couldn’t fail?
  • Am I holding on to something I don’t need?
  • What would I do to make today horrible?

Wrapping up

The journey to success is deeply personal and multifaceted, transcending the simplistic benchmarks society often imposes. It is a delicate balance of internal satisfaction and external achievement, where the true measure of success is not in the accolades we collect but in the lives we touch and the personal growth we experience. By embracing mental models that prioritise personal values, resilience, and the joy of the journey over the destination, we can redefine success on our own terms. 

This approach encourages us to focus on what truly matters – our happiness, relationships, and the legacy we leave behind. As we navigate through life’s complexities, let us remember that success is not a race against others but a marathon with ourselves, where the quality of our minutes is the true currency of a life well-lived. Let us collect those minutes wisely, invest in our personal growth, and cherish the process, knowing that the fruits of our labour will ripen in due time, often when we least expect it.

Further reading

  • How Will You Measure Your Life?” by Clayton M. Christensen: This book applies business theories to personal life, prompting readers to consider their values and priorities in finding meaning and fulfilment.
  • The Power of Now: A Guide to Spiritual Enlightenment” by Eckhart Tolle Explores living in the present moment, freeing oneself from negative thoughts, and finding inner peace and fulfilment.
  • Man’s Search for Meaning” by Viktor E. Frankl: Explores the quest for meaning in life based on Frankl’s experiences in Nazi concentration camps.
  • The Subtle Art of Not Giving a F*ck: A Counterintuitive Approach to Living a Good Life” by Mark Manson: Challenges conventional notions of success and encourages defining values on personal terms.
  • Essentialism: The Disciplined Pursuit of Less” by Greg McKeown Discusses the importance of discerning what truly matters in our lives and eliminating non-essential distractions.
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