The book is aimed to career-oriented people that reached what it can be seen as professional success but do not feel meaning in their job.
It offers a great read for those considering a non-traditional career path and challenges your beliefs about a work-centered life and the default path as the one-and-only way of living.
Table of Content
Personal opinion: Best and worst of the book
Best
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It is not a practical guide of how to leave your tedious job. What people might consider “fluff” is the best part of the book (e.g. his feels at different stages of leaving the default path, the references to Taggart or Callard philosophy, the different views of working as a part of life across history…) .
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It gives a perspective of living a life outside of the 9-5 path, challenging your prior beliefs. My beliefs about how a good life should be are deeply rooted in finding a good job that you like and find meaning. This view is inherited from my family/society, and I never really look at other ways of living outside this rather narrow focus on finding the right job that leads a good life.
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For anyone that it’s in the early stages of the “pathless path” or thinking about living a non-traditional life, this book is very useful. The story is inspirational and real (no Lamborghini with 24 years old working 4 hours per week). The author is honest displaying his fears, emotions, and struggles (e.g. lack of stable income), and offer tools to learn how to be comfortable with it and adapt. He walks the path.
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It forces you to think about what do you value in life, if you are prioritizing what you believe is important.
Worst
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His experience relate better to you have business/corporate experience. He tells his own professional career story, It’s not a catch ‘em all book for all audiences.
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The path of “meaningless corporate job to traveler content creator” is becoming a bit boring to read. I wish someone wrote about corporate clerk becoming carpenter and moving to Utah. I guess it’s also “survival bias” + only writers write about their life.
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It is easier to go rogue when you have an impressive CV like the author, as the risk is minimum - you have plenty of savings and can always find a job if self-employment doesn’t work. It’s a privilege position. However, leaving behind a comfortable life in paper to face the uncertainty is precisely the story of the book.
1. The default path
The default path is the path that most people take: go to university, find a good job with good salary and working conditions, do what you like on the weekends and free time.
Let me be clear. For me, this is a reasonable good life path.
A bad life path is working 12-hours shifts in a factory.
The default path however comes with drawbacks. Most jobs that provide good salaries they demand a lot of energy and responsibility. What was a nine-to-five job on paper is more 7:30 to 19:00 taking commuting and some time to stop thinking about your last meeting. By 19:00 you barely have energy for that much besides having dinner and prep for the next day. Your hobbies…better do them on the weekends.
Most people embrace this lifestyle without that much hesitation, simply because everyone is doing it.
Why would you do something else? Your family and friends often comment on how lucky you are for your conventional job. The most common alternative to full-time is… being unemployed and sad faces when people ask you “So, what do you do?”.
If unhappy, try looking for another job.
The lack of different lifestyles that do not include a full-time job limit your beliefs of whats possible. It seems that everyone is embracing full-time working and so do you.
I never realized how much I was constraining my imagination when I was only considering paths or jobs that already existed.
What if it could be another way?
By my late 20s, I had oriented my entire life around work. I was always thinking about how I could get a better job or a higher salary. At the time I could not imagine any other existence. Where I lived, what I did, how I thought about money, and the people I hung out with were all connected with my work identity. […] I just wanted a different relationship with work.
One signal that you might be heading towards other paths is this slight uncomfortable sensation about full-time work. Nothing big enough to make drastic decisions, only a sensation that something is off.
Choosing to leave full‑time work was not a single bold decision but a slow and steady awakening that the path I was on was not my path. Going pathless is not a single act of bravery, It’s more like having a pebble in your shoe. Where you’re walking and something is off, and it’s mildly uncomfortable. It wasn’t enough of a feeling to make me do anything dramatic, but it threw me off just enough that I was forced to pay attention to my life in a different way. I became frustrated with the snail’s pace (of corporate) and that’s when the pebble in my shoe feeling became too powerful to ignore.
Reflecting on yourself can start revealing this “pebble in your shoe”. These simple questions can help to start a process of reflection:
- Are you building a life around the things you value?
- Are you trading pay-checks for work you don’t value?
- Are you sacrificing excitement for control and stability?
Maybe you actually only need a job change to get rid of the uncomfortable sensation, but if the answer to the previous questions are 3 “Yes” it would be foolish not to contemplate other life options.
1.1 Burnout in the default path
Living slightly uncomfortable for 8+ hours per day while pretending all is alright comes with a cost: burnout.
The most usual cause of burnout is the emotional exhaustion for job-related stress.
But its not the only one.
Burnout can happen when a person does a job that they doesn’t align with their identity for prolonged time. This kind of burnout is caused by “loss of self-identity”.
Too Smart for Burnout I told myself I was smarter than other people. I knew what I was good at. I always took all of my vacation days. Didn’t work crazy hours. Made time for friends and family. Changed jobs when I stopped learning. I had done all these things with the idea that this was how I would not only avoid burning out but that I would thrive. I wanted to hack the system and make it work for me. On my final day of work the feelings that flowed through my body told me I wasn’t so clever.
When you spend most of your energy time doing something that do not value, think is meaningless, or a waste of time, it is only natural to link yourself with that emptiness and feel loss.
The distance between what you do and yourself can be underwhelming a source of burnout.
Being successful means keeping clients, customers, and managers happy while fitting into a company’s cultural norms. Unfortunately, success for the company does not always align with what is best for the person, and over time, a disconnect can emerge. This is what happened to me.
At that last job, I wasn’t a team player and I could have tried harder to say the right things, dress the right way, or spend more time pleasing my manager. But I couldn’t do it. The norms of the organisation were pulling me too far away from the person I wanted to be and the energy I used to manage this disconnect undermined anything good I had to offer.
1.2 Prestige in the default path
Why would you do a job that you don’t enjoy?
To impress others.
A classic soul sucking corporate job provides both:
- Intrinsic prestige: the attention or respect you receive when you mention where you work or what you do.
- Extrinsic prestige: the paycheck from the job that can buy shinny objects that other people want.
Prestige is “a powerful magnet that warps even your beliefs about what you enjoy.” (Peter Thiel)
My friends all had impressive plans after graduation, and I didn’t want to be left behind. People were impressed by the job I was taking at GE, and I liked how the attention made me feel. I felt smart. It didn’t matter that I had never worked in finance and had never spent any time in Ohio or the Midwest, where I would be located. Out of all the jobs I could get from my school, this was one of the best and the magnet of prestige convinced me that was what I wanted.
There is nothing wrong for wanting to be loved and get attention. It’s only human. What its wrong is trading 8 hours per day for it.
Don’t get caught the prestige trap. Job titles and “great” companies cannot make you liking your job tasks. It only provides recognition and praise to cope with them.
2. The pathless path
So, what its the pathless path?
The pathless path is an alternative to the default path that encourages you to find ways to center your life around work that you value instead of a nine-to-five job.
The pathless path is “pathless” in the sense that nobody will tell you what to do. It is uncertain by nature. It’s a path that you decide to take without knowing what you will find on it.
On the pathless path, the goal is not to find a job, make money, build a business, or achieve any other metric. It’s to actively and consciously search for the work that you want to keep doing.
Instead of copy‑and‑paste what our parents or friends had done, you have to figure out what to offer to the world and start experimenting off-road.
A typical one or two-week vacation it is not enough to provide distance from your “work-self”, so you can expect a process that takes months.
There is a catch with this plan. Even if you decide to embrace uncertainty, going pathless cost money. Its only cool to have sabbatical in another continent to figure things out if you can pay for it.
3. Controlled risks
Jumping into the pathless path requires financial preparation. At least a bit of cushion to pay the bills (or travel, test, experiment) while you explore without a stable income.
The trick is preparing financially (and else) as much as possible while you have a stable income. Don’t be reckless, simply eliminate financial risks as much as possible.
Focusing not on being brave, but instead on eliminating risk, is common for people who take unconventional paths.
For most people, life is not based on all‑or‑nothing leaps of faith. That’s a lie we tell ourselves so that we can remain comfortable in our current state. We simplify life transitions down to single moments because the real stories are more complex, harder to tell and attract less attention
Preparing will not avoid facing uncertainty. It is unquestionable that you will, and not only financially. However, it gives you the most chances to succeed and not to muddy your vision of what you like to do for what you have to do.
The author spent years to make the switch from full-time to freelance/writer, so he had plenty of time to progressively explore while saving.
As I started to test my boundaries, I split into two different versions of myself. One, “Default Path Paul,” focused on continuing my career, looking for the next job. The other, “Pathless Path Paul” was finding his footing and starting to pay attention to the clues that were showing up.
You will still need faith on yourself. It is easy to think that you need an obscene amount of financial security to make “the pathless jump”. Once you remove the superfluous expenses, the purchases we use as coping mechanisms and all other “misery tax” we need to carry on with our jobs - the amount can be surprisingly low.
If you don’t value money, you can pair making less with working less.
Beyond financial insecurity, making this kind of life changes requires overcoming the discomfort of not knowing what will happen when you do.
4. Uncertainty in the pathless path
I had embraced a question that would shape my decisions: “How do you design a life that doesn’t put work first?” The answer, my dear reader, is simple. You start underachieving at work.
While leaving your job is very daunting, you might discover that there is not that much to lose once you write down exactly what you’d lose. To check if this is true, consider writing down Tim Ferriss’ “fear setting” exercise. It has the following six steps:
- Write down the change you are making.
- List the worst possible outcomes.
- Identify actions you could take to mitigate those actions.
- List some steps or actions you might take to get back to where you are today.
- What could be some benefits of an attempt or partial success?
- What is the cost of inaction in three months, 12 months, and in a few years?
Once you consider the risks, or simply decided that you had enough of your boss at your job, a world of free time can open to you. It is up to you how to spend this time and what problems you would like to solve.
The bad news is that you will have no idea what are you going to do next, neither you should. Otherwise it wouldn’t be pathless.
The good news is that removing yourself from your job release a bunch of energy to explore.
Creative work runs on uncertainty. With the extra time and energy, think in blocks of one to three months and within each block pick one or two things you want to prioritize and test.
Beyond money, the second most common concern people have about working less or building a life less centered around work is what they will do with their time. On the default path, we may not realize how much energy it requires to simply go through the motions and stay on the path.
The main mission is getting a better understanding of what really makes your life better.
Instead of being consumed with thoughts about work and my next step, I had time to continue to experiment, and in the space that emerged, a creative energy entered which started to become a central force in my life
5. Finding meaningful work
My biggest barrier was my inability to imagine an alternative life. My creative experiments were exciting, but they didn’t suggest an obvious next step.
There are some tips in the book to guide you in the right direction on finding work that you like:
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Experiment with different types of jobs and work.
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Try to write down on some characteristics that define the person you want to be. You can turn the characteristics into a self-assessment and review each of the characteristics with your life. In other words, are you heading to the kind of person you want to be or your best self?
In business school, I created a vision of the kind of leader and person I wanted to be, and five years later I realized I was headed in the wrong direction
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Ask an old friend when they have seen you in your best self.
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Start thinking about what you don’t like from the work you’ve done, and the kind of jobs that involve that. What a miserable life entail?
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Once you know what you don’t like, work backwards to find the things you like or used to like doing.
Exploring activities that you like is an essential step of finding meaningful work. Out of those activities, some of them can become job opportunities if there is people out there willing to pay for them.
Remember, first comes the exploring phase, then the business phase - Otherwise you will come at risk of starting another job you dislike.
5.1 Practical example
I have in mind a good example of “Finding meaningful work” that it is incredibly simple. His name is Kris, and the guy makes keyboards and usb cables. I have no affiliation (or even know him), I just like his products.
In an interview he tells his story about how he started his business:
The generic black cable wasn’t really a great fit for a custom mechanical keyboard that I was building. I tried searching for one but didn’t find anything appealing to my taste and wallet.
I decided to buy materials and learn/build a few. My friends really liked the work and bought from me some too. After sharing my work on the local forum, I was asked to build more. This is how Kris Cables was born.
You can tell that he likes what he does by the way he talks about his craft in his Discord channel, or how he interacts with his costumers. Kris is good at it because he likes it.
It is also quite successful I assume, since he has literally cues of people waiting for what he does. If you want a product made by him you will have to wait a couple of months in the line:
I like his business story because it cannot get more simple. He liked usb cables and keyboards and tried to build some, that’s it. Then the business came with the opportunity that he saw in the market, but that was an extension of exploring topics he liked.
Kris is only an example of the hundred of thousands of people that found a way to make his craft his job.
The “real work of your life” is searching for the things you want to commit to and that make your life meaningful. Once you find them, you can dedicate your time to creating the environment to make those things happen.
Reflect, prepare, face uncertainty, and go have some fun.