📚 The Pathless Path: Imagining a New Story For Work and Life

This book does not argue for or against any singular way of living, but it contests the idea that the default path is the only way.

The default path

The default path highlights a path of social and cultural norms and expectations of success that people (by default) live to instead of taking steps to create their unique paths. They are the life scripts that many follow. Most of these moments occur before the age of 35: graduating from university, getting a job, falling in love, getting married and have a house.

A part of being on the default path is hoop-jumper. The term was coined by writer and former professor William Deresiewicz to describe the behaviour of his students at Yale, who seemed more concerned about getting A’s and adding bullet points to their resumes than using their time at one of the world’s best universities to follow their curiosity.

Many hacks and go for shortcuts (dress well, communicate well, being nice, being visible, saying yes, saying and doing the “right” stuff etc.) to get ahead and achieve success in the default path.

For many people, the expectations of life are centred around a small number of positive events that occur while we are young. Much of the rest of our lives remains unscripted and when people face inevitable setbacks, they are left without instructions on how to think or feel. While very few young people expect to have one job or career, most still rely on the logic of the default path and assume they need to have everything figured out before the age of 25. This limits the ideas of what we see as possible and many internalize the “worldly wisdom” that John Maynard Keynes once pointed out, “that it is better for reputation to fail conventionally than to succeed unconventionally.”

The default path defines success and prestige and brings about a sense of security, certainty, and being accepted and admired as we do well along the default path. While we may not be happy and feel disgruntled with the default path, it is an “easier” and socially accepted path to live along. Having money (and assets and wealth signallers) “proves” our worth. Many people will override their desires to meet the perceived expectations of others,

Questioning the default path

Crisis moments lead to “existential openings” that force us to grapple with the deepest questions about life. There are two typical ways this happens. One is the “way of loss,” when things that matter are taken from us, such as loved ones, our health, or a job. This is where we will ask:

1. What was I living for?
2. What did I want?
3. How did I want to look back on my life when it was time to go?

The other path is the “way of wonderment,” when we are faced with moments of undeniable awe and inspiration.

Professors Richard Tedeschi and Lawrence Calhoun have suggested that many people who face crises often experience “post-traumatic growth” and this manifests as an “appreciation for life in general, more meaningful interpersonal relationships, an increased sense of personal strength, changed priorities, and a richer existential and spiritual life”.

We didn’t want to see work merely as an obligation, we also wanted it to be meaningful, fulfilling and useful. While many think of their ideal life as living out on a beach, travelling the world, when given the option of following that path, few people take it. We wanted the modern version of the “calling” that Oprah talked about.

Many people dislike some parts of their jobs but they stay in their jobs because their suffering is familiar. To change would be to trade the known for the unknown and change brings discomfort in hard-to-predict forms. So people avoid change and develop coping strategies.

Uncertain Discomfort < Certain Discomfort + Coping Mechanism

Uncertain Discomfort + Wonder > Certain Discomfort

Living to an “ought to” self
One challenge to embracing possibility is knowing when to override what psychology Gilovich and Davidai call our “ought to” self.” It makes us stick to the default path. We “ought to” keep working; leaving a job is an abdication of responsibility. This impulse is helpful most of the time, but compounded over one’s life it stops us from moving towards what Gilovich and Davidai call our “ideal self.” When people reflect on their lives, these are the things that people regret most – not moving towards their ideal selves. The professors argue that people rarely regret the things they do in their lives. This is exactly because of the power of our “ought to” selves – even if we fail, we tend to take immediate action to fix those mistakes.

The author Gretchen Rubin decided to override her “ought to” self when she said, “I’ve come to a point where I’d rather fail as a writer than succeed as a lawyer, and I need to try and fail or try and succeed, but I need to do it.”

Making life changes requires overcoming the discomfort of not knowing what will happen. Facing uncertainty, we make long mental lists of things that might go wrong and use these as the reasons why we must stay on our current path. Learning to have a healthy distrust of this impulse and knowing that even if things go wrong, we might discover things worth finding can help us open ourselves up to the potential for wonderful things to happen. Only when you reach this state are you at the same point as Rubin was, with no questions left about taking the next step. And don’t worry, even if you do screw up a little, your “ought to” self is standing by, ready to help make things right.

Human existence is an infinitely unfolding process of remembering, forgetting, and remembering again. Ignore the shiny objects and distractions and strip away the stories that are not our own to remember who we are. A large part of choosing your path is figuring out which values will determine your worth.

Aspiration versus ambition
Callard defines aspiration as the slow process of “trying on the values that we hope one day to possess.” This is in contrast to an ambitious journey where we already know what we value. When we reflect, we find many examples of aspirational journeys in our lives. While ambition does not preclude aspiration, Callard argues that ambition “consumes much of an agent’s efforts and does not expand his value horizons.” Aspirational pursuits go hand in hand with the pathless path because they can appear incomprehensible to others and even yourself, sometimes for years. According to Callard, people on aspirational journeys, or what the author calls the pathless path, are “characteristically needy people.” Because their worldviews are incomplete and evolving, they are dependent on the support of other people.

Boonie Ware has taken care of many elderly people in the final stages of their lives. In a blog titled, “Five Regrets of The Dying,” one of the most viewed online posts, she shared her reflections.

1. I wish I’d had the courage to live a life true to myself, not the life others expected of me.
   This was the most common regret of all. When people realise that their life is almost over and look back clearly on it, it is easy to see how many dreams have gone unfulfilled. Most people had not honoured even half of their dreams and had to die knowing that it was due to choices they had made, or not made.
2. I wish I hadn’t worked so hard.
3. I wish I’d had the courage to express my feelings.
4. I wish I had stayed in touch with my friends.
5. I wish that I had let myself be happier.

The Pathless Path

We must let go of the life we have planned, so as to accept the one that is waiting for us.

Joseph Campbell

Nothing good gets away, as long as you create the space to let it emerge.

John Steinbeck

Doing nothing ≠ Laziness
Explore and experiment
Living in a world with infinite distractions and interesting goals can make it impossible to stop moving forward. However, doing nothing does not mean laziness. It allows us to explore, be reflective and open to experiment where possibilities start to emerge. Many people credited these breaks from work as one of the most important things in helping them see the possibilities in their life. The author observed that the shifts people experienced were predictable and four stand out:

1. People become aware of their suffering as we untangle from all the things they get from work.
2. Curiosity re‐emerges — try new activities, revisit old hobbies, explore childhood curiosities, explore our interests deeper, start volunteering, connecting with people.
3. People often desire to continue their “non‐work” journey.
4. People write.

We become aware that our previous paths (busy work lives) had kept the possibilities for our lives hidden, and in a short time, we started to recapture a youthful energy, one that enabled us all to take bold steps towards different kinds of lives.

Waiting for retirement versus mini-retirements
For many, the default is to wait for retirement to take a break. This version of retirement is a core part of the default path and while it still works for some, others are less satisfied with retirement. When people stop working, they struggle to replace the meaning and joy they got from their work.

Instead, have several long breaks spread across our lives (Tim Ferris’ idea of mini-retirements) instead of a long retirement at the end of our working lives. He described these are not an escape from our lives but a re-examination (the creation of a blank slate). He asked himself three questions while designing these breaks:

1. How do your decisions change if retirement is not an option?
2. What if you could use a mini-retirement to sample your future plans now?
3. Is it really necessary to commit fully to work to live like a millionaire?

The power of these questions is that they force you to be creative and experimental.

The spirit of the mini-retirement is not about escaping work. Rather, it allows us to experiment and experience different circumstances to see if we want to double down on them or change directions while we are younger and healthier. Technology and increased prosperity make this a good time to experiment and explore. Slowly, we question the default path and start to deviate and pivot.

Smell the roses and have fun along the journey
Even though the pathless path does not lead to a specific destination, there may be what Venkatesh Roa, a writer and consultant, calls “fixed points”. They are non‐negotiable goals that we plan to achieve, no matter what. These fixed points are often a product of our unique cultural scripts — get a degree, get a good job, buy a house.

The problem with these default fixed points is that they are culturally derived rather than a product of our unique motivations and desires. Over time, they can become detached from what is possible or reasonable.

The answer is not to abandon goals altogether but to take them more seriously and to put more thought into identifying unique fixed points; ones that align with the things that bring us alive. This is to allow people to embrace individuality and perform “experiments in living”.

John Stuart Mill argued that conventional ways of loving tend to “degenerate into the mechanical” and that if societal norms are too strong or rigid, original thinkers who would otherwise experiment will be stifled.

The fixed points along the default path are not inherently bad, but they do tend to push people towards doing what others do. This can be a good starting point, but if you lean into your unique psychology, interests, and sense of humour, your journey will be a little more fun and much more meaningful.

Redefine money
When everyone you know builds their lives around a steady paycheck, it is easy to lose track of what we give up for that paycheck.

“Misery tax” (coined by Thomas J. Bevan) is a spending that unhappy workers allocate to things that “keep them going and functioning in the job.” These can be alcohol, cigarettes, expensive food, branded clothes, gadgets, cars and vacations. The longer we spend on a path that is not ours, the more misery tax we will pay and the longer (and harder) it will take to move towards a path that is.

Ramit Sethi asks a great question: “What is your rich life?”. The purpose of this question is to stop us from looking at money as the most important and only measure but looking at it as something that might help us live an ideal life that is less money-centric and more enriching and meaningful.

Opting out of work and opting into other aspects of your life can create questions about who you used to be. No amount of money can buy the peace of mind that comes with finding a path that you want to stay on. Once we know, as Vicky Robin argues in her book Your Money or Your Life, that “money is something we choose to trade our life energy for,” it is nearly impossible to give up your time for money without thinking deeply about the trade-offs.

Have a little faith

Belief clings, but faith lets go.

Alan Watts

Having faith is admitting that you don’t have all the answers for what comes next. Faith is an essential part of the pathless path and many people mention it when talking about embarking on an uncertain path. Having faith does not mean being worry-free. There will be worries. This is being the CEO of our lives. The right response is not to restructure our lives to make these worries disappear. It is to develop a capacity to sit with those anxieties, focus on what we can control, and open ourselves up to the world.

Redefine Success

Paradox of life
In a 2019 Gallop survey, responding to the question: “How do you personally define success?”, 97% of the Americans surveyed agreed with the following statement: A person is successful if they have followed their own interests and talents to become the best they can be at what they care about most. However, in response to the question, “How do you think others define success?”, only 8% gave the same answer. Instead, 92% felt that other people defined success as follows: A person is successful if they are rich, have a high-profile career, or are well‐known.

This disconnect can be attributed to aligning with externally accepted cultural and social norms versus keeping and disguising our intentions that we believe are not socially acceptable. This results in the arrival fallacy (created by Dr Ben-Shahar), the illusion of reaching a destination or goal and realizing that the achievement doesn’t make you as happy as you thought it would.

When you adopt the standards and the values of someone else or a community, you surrender your own integrity. You become, to the extent of your surrender, less of a human being.

Eleanor Roosevelt

The second chapter of success
A better way is what the author calls the “second chapter of success” in which we shift our mindset from what we lack to what we have to offer, from ambition to aspiration, and from hoping that joy will result from a specific outcome to experiencing it as a byproduct of your journey. People are reluctant to flip the page to the second chapter of success because it requires rejecting paths that are not only more accepted but also promise money, respect, and admiration.

As we redefine success, the concept of prestige and admiration shifts. We admire people who seek to live their lives on their own meaningful terms. The pathless path is a define-your-own-success adventure.

Default path = Good
Any deviations = Bad
On the default path, you are automatically a “good egg.” On the pathless path, people default to seeing you as a “bad egg.”

The comfort we feel when we do what is expected (default path) keeps us from developing the skills we need to face uncertainty. The pathless path is about releasing yourself from this way of seeing the world and realizing that the number of career paths worth following is infinite.

Every man has to learn the points of compass again as often as he awakes, whether from sleep or any abstraction. Not till we are lost, in other words, not till we have lost the world, do we begin to find ourselves, and realize where we are and the infinite extent of our relations.

Henry David Thoreau

Find your “enough”

Enough is the antithesis of unchecked growth because growth encourages mindless consumption and enough requires constant questioning and awareness. Enough is when we reach the upper bound of what’s required. Enough revenue means our business is profitable and can support however many employees/freelancers we have, even if it is just one person. Enough income means we can live our lives with a bit of financial ease and put something away for later. Enough means our families are fed, have roofs over their heads and their futures are considered. Enough stuff means we have what we need to live our lives without excess.

Paul Jarvis

On the pathless path, knowing you have enough is what gives you the freedom to say “no” to clear financial opportunities and say “yes” to something that might bring you alive and might even pay off much more over the long term. If we don’t define “enough,” we default to more, which makes it impossible to understand when to say no.

Related post with a section of “enough”: Redefining our meaning of money and life towards financial independence

Beyond the scarcity mindset towards an abundance mindset
Overcoming fears
Most people attached great importance to money. They avoid any discomfort related to their financial situation. This makes quitting full-time employment seem terrifying and a steady paycheck so addictive.

The money fears brought about by the pathless path are existential fears like the fear of death or the fear of not being loved, respected and admired. These fears are likely not solvable but we can learn to coexist with them. Tim Ferriss’ “fear setting” reflection exercise can help to reframe the fears and see them in a completely new way:

1. Write down the change you are making.
2. List the worst possible outcomes.
3. Identify actions you could take to mitigate those actions.
4. List some steps or actions you might take to get back to where you are today.
5. What could be some benefits of an attempt or partial success?
6. What is the cost of inaction in three months, 12 months, and in a few years?

Writing about fears can help to transform abstract worries into concrete issues. The last two questions are the most powerful. They shift the focus from the future which is inherently uncertain to the present which helps us to see our tendency to overestimate future costs and underestimate costs related to the status quo.

Financial worries can be infinite and people can chase more and more their entire lives. The flip side is that if we can learn to coexist with our financial insecurities, it can open up that opportunities of the pathless path are infinite too. It can be so infinite that we have to be disciplined and prioritise.

The Real Work of Your Life

On the pathless path, the goal is not to find a job, make money, build a business, or achieve any other metric. It is to actively and consciously search for the work that you want to keep doing.

With this approach, it doesn’t make sense to chase any financial opportunity if you cannot be sure you will like the work. Else, you will end up on a different default path again. What does make sense is experimenting with different kinds of work and once you find something worth doing, working backwards to build a life around being able to keep doing it. It is a shift from the mindset that work sucks towards the idea that you design a life around work.

Finding work you want to keep doing is the great work of your life.

Stephen Cope

Work on what mattered and is worth doing. Bring forth what is within you. Be resolutely and faithfully what you are.

Unleash our creativity
We have lost track of our basic human creativity, convincing ourselves that only people who use certain tools or work in arts, advertising, movie and drama production, and other artistic areas are creative. Corporate policies may also prevent us from getting creative with our ideas and plans.

We are all creative in our own ways. With technology, there are many ways and tools available to be creative with many stages available to showcase our creativity. There is no need for permission. We can explore and experiment. Do it and decide whether we continue.

The biggest challenge to creating your virtuous cycle and one of the most dangerous failure modes of the pathless path is cynicism. Many people who leave the default path do so because they have become cynical and are driven by a desire to escape. But escaping is only the first step of leaving a certain path behind. Creating a sustainable journey and path, requires finding ways of orienting to the world that leave space for hope.

When I quit the New York Times to be a full-time mother, the voices of the world said that I was nuts. When I quit it again to be a full-time novelist, they said I was nuts again. But I am not nuts. I am happy. I am successful on my own terms. Because if your success is not on your own terms, if it looks good to the world but does not feel good in your heart, it is not success at all.

Anna Quindlen

Beyond money, the second most common concern people have about working less or building a life less centred around work is what they do with their time. On the default path, we may not realise how much energy it requires to simply go through the motions and stay on the path (bureaucracy, office politics, seeking consensus), so it is easy to mistake the lack of energy outside of work for a lack of interest in anything else.

Only by taking action do we learn and only by learning do we discover what we want. Find out who you are and do it on purpose.

Define your own culture and mission
The author’s culture: Being able to get to a state of being where I can spend almost all my time helping, supporting, and inspiring others to do great things with their lives.

To create your own culture on the pathless path you must identify the assumptions you make in your approach to life:

• Many people are capable of more than they believe.
• Creativity is a real path to optimism, meaning, and connection.
• We don’t need permission to engage with the world and the people around us.
• We are all creative, and it takes some people longer to figure that out.
• Leisure, or active contemplation, is one of the most important things in life,
• There are many ways to make money, and when an obvious path emerges, there is often a more interesting path not showing itself.
• Finding the work that matters to us is the real work of our lives.