This book will shape your work and life

10 insights from Paul Millerd's journey on the Pathless Path

Long-time readers might remember our framework for career design and the pursuit of meaning at work.

These concepts imply that the right choice lies in front of you. A path ready to be taken waiting for you to make the first step.

Reality is rarely this easy and increasingly more people opt for a different journey: the pathless path.

What is a pathless path?

If the default path is the notion that life is about getting good grades, getting a prestigious job, climbing the corporate ladder and gaining happiness, the pathless path is the opposite of that.

It’s about embracing the hard work of figuring out an alternative path to life and work, by questioning and re-writing scripts that define our lives.

It’s about letting go of the certainty of a laid-out career that promises prestige, money and accolades for something that aligns more with what we care about.

The beauty of the pathless path is that you can make it what you want. The secret is in the exploration of new ways of working that defy the standard notion of full-time employment.

For some people, it’s about becoming a digital nomad and working from all over the world. For others, it’s about becoming a fitness trainer. Some decide to launch a startup. Others to join one.

What they have in common is the desire for something more.

And if you’re reading this newsletter, you could be one of them too.

In his self-published book, Paul Millerd talks about his journey from the default to the pathless path and these are the 10 most powerful insights I got from his book.

The pathless path is an embrace of uncertainty and discomfort. It’s a call to adventure in a world that tells us to conform.

Paul Millerd

#1 - Change is never a sudden decision

Did you ever start a job full of excitement to soon realize that it’s not what you expected?

If you’ve been on the default path, you probably felt this way more than once.

But moving away from the default path is always a long transition filled with a series of events that grow our uneasiness over time.

First, we become aware of a subtle discomfort in going over the motions. What looked like an exciting task, now appears mundane.

But because humans are exceptional at creating coping mechanisms instead of facing the “pebbles in our shoes”, we decide we’d rather live with moderate and regular doses of discomfort than try a different path.

Your life is too short and too valuable to fritter away in work. If you don’t get out now, you may end up like the frog that is placed in a pot of fresh water on the stove. As the temperature is gradually increased, the frog feels restless and uncomfortable, but not uncomfortable enough to jump out. Without being aware that a chance is taking place, he is gradually lulled into unconsciousness.

#2 - The breaking point

Over time the pebble becomes bigger but it’s usually not enough and years go by in a heartbeat.

Until an unpredictable event wakes you up.

The first-born son. A sudden illness. The death of a loved one.

These events have a simple effect: they make the discomfort more noticeable until it becomes impossible to ignore.

#3 - The need for others

The default path comes with financial independence, which means relying less and less on others.

Money can solve most daily problems and it allows for a smooth existence where asking for help from others is a rare occurrence.

In the pathless path instead, finding other people and building meaningful relationships is key.

Things like supporting fellow freelancers or getting involved in the local community as a business owner become imperative.

Having a founder peer group who are on the same journey or meeting other people working towards your same mission is the compass to survive.

#4 - In history, leisure > work

For most of history, life revolved around pleasure and leisure activity. Work was considered like a means to an end and a “necessary evil” to survive and make time for pleasure.

After WWII instead, the Industrial Revolution created millions of factory jobs that guaranteed steady paychecks for a steady existence and life started to revolve around work.

In Western societies, this is not only a dogma but a noble aspiration.

Instead, in other parts of the world this is still far from true and we get a glimpse of another way of living.

Paul talks about an experience in Mexico (but I can guarantee this is not uncommon in the south of Italy too) where he overheard a business owner saying: “You can’t pay people too much because they’ll stop working!”.

In an era of hustle, ambition and mission-driven companies, the concept of wanting to work less is frowned upon.

#5 - The fears of the pathless path

Embracing a pathless path is not about retiring on an island and drinking mojitos on the beach. It’s about exploring work beyond the default employment path.

It’s hard to imagine a more uncertain path and only by facing our inner fears we can keep walking along the journey.

Paul highlights the 5 biggest fears of the pathless path:

  1. Success: “What if I’m not good enough?

  2. Money: “What happens if I go broke?

  3. Health: “What if I get sick?

  4. Belonging: “Will I still be loved?

  5. Happiness: “What if I am not happy?

Whether you are embracing the pathless path or not, these are questions everyone ends up asking themselves before (or during) a life crisis.

#6 - Misery tax

If you think your job is not that bad and the feeling of discomfort does not feel that strong, the misery tax is a signal you should pay attention to.

Unhappy employees pay the misery tax when they spend their income on things that “keep them going and keep them functioning in their jobs”.

This could be alcohol, Starbucks coffee, food, vacation, tech gadgets and so on.

Over time, it feels like spending is the main reason to keep working.

#7 - Arrival fallacy

Accomplishing goals won’t make you happy.

You know it. I know it.

But deep down we still hope that it will at least feel good and we’ll be a bit happier because of it. Plus we all crave prestige and we like making people in our lives feel proud of us.

You thought you’d feel happy after graduating college.

Or after getting that your first job.

But it did not happen. And it will not happen for your next goal either.

The ultimate way you and I get lucky is if you have some success early in life, you get to find out early it doesn’t mean anything

#8 - End of history illusion

Look back at yourself 10 years ago.

You’ll notice a completely different person and you will easily acknowledge how much you’ve changed.

But when we look into the future, you probably believe you won’t change as much as you did and you are convinced you will remain the same person forever.

This could not be further from the truth and it happens across all age groups.

Your rate of personal change will keep growing at the same pace (if not faster) in the future and there is no way to stop this.

The only thing to do is embrace the change and be ready for it.

#9 - Does work define our self-worth?

Why do people keep working even when they’ve lost all faith in a company/mission?

I’ve personally witnessed many people who keep working tirelessly for a cause they don’t believe in anymore, trying to deny evidence or lying to themselves, even when there is no money at stake.

Why do they do it?

A big reason is that work is the primary way they define self-worth. High achievers have been trained to always work, no matter what.

Paul shows us a different path where work is important but it does not define who we are. And it all starts with asking ourselves the right questions:

  1. Are you a worker?

  2. If you are not a worker, then who are you?

  3. Given who you are, what life is sufficient?

#10 - Should you jump on the pathless path today?

Paul’s book (and this post) is not about dropping everything right now to chase a life of exploration around work.

It’s about knowing there is another option and there are people out there who are laying down the path for many more to join them.

Once you learn that, you’ll start reflecting a lot on your relationship with work and it will spark many deep conversations.

Don’t shy away from fully engaging in these topics and maybe it will be the beginning of a wonderful journey.

If you want to know more about the pathless path and Paul’s journey from working at McKinsey to digital creator and writer, check out his book.

This week's top scientific reads

Read my comments on these articles here.

Latest funding rounds in health & bio

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