Walking the Pathless Path

Leaving the default, staying true to yourself and navigating the discomfort of doing things differently.

I had a chat with Paul Millerd this week. It felt like coming full circle.

I’ve been on my own version of the pathless path for about 18 months now. But it wasn’t until February this year that I came across Paul’s book The Pathless Path.

I was in Barcelona, visiting for the baptism of my friends’ daughter. Instead, I ended up locked in an Airbnb with food poisoning. Great. So instead of celebrating with cava and tapas, I spent the day horizontal, dehydrated and questioning my life choices. Too sick to do anything, I scrolled through my reading list, saw Paul’s book, downloaded the audiobook, hit play and had one of those “oh shit, someone else has lived this too moments.”

So honestly, bless the food poisoning. Or bless Paul. Hard to say. From the first chapter, it was like he had taken my internal monologue, made it coherent, and turned it into a book. He was putting words to thoughts I hadn’t even been able to articulate. His story mirrored so many parts of my own. I won’t write a full book review (tempting, but seriously - just read it), but let’s say I came out of that Airbnb with two things: and empty stomach but a head full of ideas. It left me fired up. The months after were a running streak of life. I started writing on Substack. Going to every climate event in town. Joined a book club. Met a ton of new people.

Which brings me back to this week’s chat with Paul. It came at the perfect time where things have slowed down a bit, a few old stressors and stories have started sneaking back in and I needed a reminder of what I’m actually trying to build. It was a good chance to reflect on the path so far and to confront what’s still hard.

Because I’ve realized that quitting wasn’t the big leap but staying out is the real work.

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Time to get serious

When I spoke to Paul, I shared two things I’ve been struggling with lately. The ones that tend to show up when the initial buzz of reinvention fades, and you’ve been out on the pathless path long enough to stop floating but haven’t quite landed.

The first is this creeping sense that maybe it’s time to “get serious” again. I’ve been out for a year and a half now, and lately there’s this voice whispering: Okay, that was nice, now go make (more) money.

Of course I know it’s bullshit. I haven’t had a full-time job, but I’ve been working hard lately, just not in the traditional sense. Since quitting, I’ve moved countries, learned a new language, rebuilt from scratch. I’ve gone deep down the web3 and investing rabbit hole to finance my transition, studied climate change, taken on a fractional marketing role, started writing on Substack - and that’s just the highlight reel. Without even getting into the inner work that’s been happening.

So no, I haven’t exactly been sitting still. That said, I’d set an intention to find more fractional work in climate and sustainability. But every time I sit down to apply or pitch to a company, something in my body shuts down. I freeze. I procrastinate. I write another Substack post instead.

What I’m really wrestling with is this: How do I stay true to what I want without filtering out the good-enough opportunities? Where’s the line between holding out for the right thing and just procrastinating? And how long can you say no to short-term money while trusting the long game will still work out?

Paul got this tension immediately. He told me that same fear of going back to “normal” work was very present for him in the early years. It’s part of the recovery process after leaving the default path. For him, freelance consulting covered basic expenses, but as soon as he had enough to breathe, he’d lose all motivation to keep doing it.

He encouraged me to see that “getting serious” is often a remnant of old thinking, the voice of the default path sneaking back in. The subtle pains of grief of starting to let go certain parts of yourself. He also made the point that most companies talk about hustle, but in reality, there’s more slack in many jobs than we assume. Especially once you have redefined what matters to you, you’re less likely to fall back into old patterns because you’ve already seen through them.

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Your insecurities, not mine

The second struggle is even more emotional. I’ve spent most of this year in Lisbon, in a kind of intentional bubble being surrounded by people who are freelancing, starting projects, living in that foggy-but-exciting middle zone between conventional success and something more self-authored.

In the past two months, I’ve been back on the road: weddings, hometown reunions, catching up with people I love but who live very differently. And suddenly, I’m back in awkward-conversation territory. Trying to explain what I do, or why I don’t just get a job. Smiling while someone tells me, “Not everyone can live like you,” as if I’ve won the lottery instead of spent the last 18 months undoing a perfectly decent life.

And even though I wouldn’t trade it and I know this path is right for me, I still wobble. There’s a split second where I wonder if they’re right. If I’m just avoiding the real world. If I’m being irresponsible.

So I brought it to Paul. He shared one of his articles with me where he reflected on some of his experiences of how people are actually projecting their fears onto you.

“When you step off the default path, you become a dumping ground for all people’s insecurities about work and life. Sometimes this is simple. Someone might say, “I could never do that.” Others mention their money insecurities, their fear of free time, uselessness, or fear of failure. I always agree with these people because I also have some dose of these fears. Yes you are correct, but for me it’s still worth it.”

Your Insecurities, Not Mine | #162

I’ve definitely felt the dumping ground effect and having language for it makes a big difference. Knowing what’s actually happening underneath those comments helps me take things less personally. I’m working on getting more comfortable with it. At the end of the day, the best (and hardest) thing you can do is live your own truth.

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Staying committed to the path

Talking to Paul reminded me that leaving the default path is a long, winding process of figuring out who you are, what matters to you, and how to build a life around that.

Finding your good work is a personal, non-linear and sometimes frustrating journey. One that everyone has to navigate in their own way and speed as it requires slowness, introspection and experimentation.

And yes, committing to this (pathless) path is hard sometimes. Especially when the old world keeps dangling safety and certainty like a shiny object. But honestly? For a lot of us, the trade is worth it.

I intentionally wanted to share some of my recent struggles here because I think it’s important to say out loud that it’s not all freedom-soaked mornings, journaling in the sun and lunches on the beach (though yes, that’s definitely part of it too for me). Some days are confusing. Some weeks are flat. Sometimes you question everything. But that’s true of the traditional path too. The difference is we’ve just normalised those struggles more. We think that the exhaustion, the Sunday dread, the inbox anxiety, the “is this really my life?” spiral is just part of being an adult.

Since I quit, I’ve had moments of doubt, yes. But I’ve also felt more excited about life than I have in years. I’ve become way more present. Way more optimistic. I see so many opportunities, so many different ways how life can be lived. I’ve rediscovered old interests. Learned things I never made space for before. I’ve been writing, connecting, experimenting. And for the first time in a long time, I feel like I actually own my life. And for me, that’s the better deal.

If there’s one thing Paul left me with, it’s this: Fully commit to the journey and have faith that it will work out.

Thank you, Paul - for the book, the conversation, and the reminder to keep going!