When I left my job I thought I was having an n=1 experience. I became fascinated by how people make life shifts and talked to hundreds of people.
I started to notice many common experiences and patterns and love helping people realize they are “normal.”
When I point these patterns out to people and tell them “this is normal” it can have a powerful effect.
A “pathless path” means you don’t know where you are going but people have a hard time accepting this. This creates tension and usually keeps people stuck at a certain point.
One interesting thing that people have a hard time with is there’s usually no magical “moment” where people decide to quit and take a leap. Deciding to leave is usually a minor moment that seems inevitable and obvious looking back but can feel inconsequential in the moment.
Similarly, many of these phases aren’t in order and can occur at different times. Think of them as puzzle pieces of a larger journey - each of which you will go through to some degree but can’t quite predict when and in what form.
1. Unsettled
People know something is wrong in their current work situation. They may jump from job to job for years. Complain about managers. Feel like they are meant to be miserable. Convince themselves they should be struggling.
People feel shame. They are scared to talk about what they are feeling with anyone, including spouses! This can be more painful for people that see themselves as “successful” or make good money. They sense, rightly, they may lose that part of themselves.
2. Experiments
At some point people start taking action. Looking back it looks like a first step but at that point people usually rationalize it: “oh, I’ve always wanted to do this.” People do things like take classes, host events, take online courses, write, create art…
People have this excess energy that keeps finding its way into things outside of their job. Some people get overly excited and feel the need to turn everything into a side gig as a sort of escape plan. But it’s usually better to take it slow.
It is hard to differentiate work you might end up liking doing over the long term and just random experiments you are doing in a desperate need to feel “active” in the world. But the key is giving yourself some confidence a non-work mode is possible.
3. The last stand
Right before a pivot they tend to double down even harder on their existing path. “I can make this work.” They make commitments they’ve never followed in the past: “I’ve never been in a job more than two years, but this time is different.”
When people double down it is often a sign that the decision to walk away is near. As people double down on their previous path they often experience more tension and pain, which heightens the awareness that this may not be the right path.
4. Walking away
I think of this more as a subtle turn of the wheel in a new direction rather than a dramatic leap. There is an acknowledgment deep inside that we are steering away from the previous life even if others don’t see it yet.
People might lean into the script of a bold leap and orchestrate that. But often the decision is still months or years after the first ounce of doubt appeared about the path.
As the default path has loosened its grip on us, people are getting smarter too. They are prototyping or testing their new path, trying to mitigate mistakes. I sense people’s skill in navigating paths will get better because of more sharing.
5. Money fear
A companion at every stage of the journey that never leaves. The pressure to make money is strong in most countries but strongest in the US. Most people except the ultra-wealthy feel as if they need to make money to prove their contribution to society.
This is often strongest immediately after leaving a job or income source. Harder if you don’t have anything lined up. A defense against this feeling can be committing to a story of non-doing, non-earning (a sabbatical) for a set amount of time.
People underestimate the positive power of this too. Like a starved person that thinks about food all the time, someone cut off from flows of money will imagine tons of ways to make money. For some this calms them down; others need to make money.
A surprising number of people are able to lessen their money insecurity by making less money or cutting their income. I sense this is because it forces you to deal with your emotions instead of making more and buying away your insecurity.
6. Wandering storyless
You might have a “cover story” but you’ve never felt more powerfully that you don’t know where you are headed. You might get defensive. Attack people that ask too many questions. Feel like you are failing. Feel like you should do “more.”
The key is to figure out how to communicate your vulnerability. This is a way to own the situation. But don’t be surprised if others are still uncomfortable.
People internalize scripts for themselves and other people at the same time.
7. Anti previous path
You left your previous path for a reason. You didn’t like it. You don’t want to go back. You are afraid of embodying some of those feelings and modes of being. So you naturally are skeptical of things on your new path that “rhyme” with the old path.
Examples can include work very similar to previous work, working with types of people from previous jobs, or even having clear, strong goals (this reminds you of the tired leaders you didn’t want to become).
8. Creative explosion
At some point almost everyone has a period where they have the sense of more space and time in their life, and past hobbies, interests, or things they like doing start flowing back into their lives. People start creative projects and learn new ones.
These often link to the “Experiments” phase but in a deeper way. This is when people start podcasts, write online, create art, get involved in movement practices. All of this is a path to reconnect with the body and soul.
9. Finding the others
This “against” phase is why finding others on a similar path is so important. You will have fewer active supporters from your previous life and family than you expect. Two or three people on a similar path who also don’t know what they are doing are absolutely vital.
This can mean travel, living in different places, and experiencing new cultures. A powerful way to detach from your past identity can be to see that people in different countries live in many different ways.
Your past path wasn’t destiny.
10. Practicing freedom
Freedom is often overwhelming for people at first. They want someone to tell them what to do. They want to have easy choices. But over time people learn to lean into the expanded freedom, usually in a stepwise way.
This can include basic things like extended travel, or deciding not to work during standard “workdays,” also saying no, designing non-doing breaks into the work year, cutting costs, changing lifestyle.
11. Finding your footing
This is often a time thing - 1-3 years is what I’ve seen - of people making some money, finding work they love, meeting a few new people, distancing from the past identity such that they are starting to find a new way of moving forward.
Ambitious plans seem possible. You have fun with your path. Take it less seriously. Detach from stories and labels. Forget about the previous path. Imagine possibilities.
12. Commitment
You may not be “all-in” for life but you are ready to commit to your new path for at least two years. You stop hedging in your heart and start making bolder bets on yourself. Some people start companies.
I first wrote this as a thread on Twitter in October 2022. A lot of these ideas are in my book too.