Max didn't start over. He showed me I don't have to either.
What my AI teacher taught me about leaving a job without starting over, staying safe in a faker world, and building a life that's actually yours.
When I lost my corporate marketing job last year, my first instinct was that I would have to become someone new.
A new field, maybe. A new set of skills. A clean slate. That is the story we are told about change: that it means starting over.
I had met Max in summer of 2025, in an online classroom. I was studying AI, and he was my teacher, the one who told the whole class to start working with Claude, the recommendation that quietly changed how I work and, in a way, how I see myself.
What I didn’t notice at the time was that Max was living proof of the opposite story.
He hadn’t started over either.
That is the place I was sitting in when I invited him onto the podcast.
Max X. Grossgebauer spent years inside Microsoft many years ago, in their European headquarters in Dublin, as a corporate account executive. The obvious next step in his world was another big name maybe Google, Facebook. Most people take it.
He didn’t.
He did a 30-day hot yoga challenge instead, listened to something quieter, and moved to São Miguel, a volcanic island in the Azores Portugal he had only ever hoped to live on. He had never even been there. He packed two cats and a life and went.
He calls himself a “digital immigrant,” not a nomad. He didn’t go there to keep moving. He went there to stay.
But here is what struck me most, listening to him.
Max didn’t reinvent himself. He didn’t burn his old life down. He took everything he had learned in corporate IT the project management, the digital fluency, the years of teaching people how to use technology, and he carried it with him to the island. Same skills. Completely different life.
He didn’t become someone new. He just took who he already was somewhere that fit him better.
What stayed with me
Three things from our conversation that I keep returning to:
You don’t have to start over. This is the one that undid my whole assumption. Max left Microsoft and didn’t abandon a single thing he had learned there. He repurposed it. The corporate years weren’t a cage he had to escape they were the toolkit he left with. Leaving is not losing. Your skills travel with you.
The world is getting faker so you had better know what’s real. Max teaches digital safety, and his practical advice is gold: check the email address behind the name, use two-factor authentication, never react to urgency, don’t trust a logo just because it looks right. But the part that stayed with me was subtler. He told me AI tends to agree with you “they don’t say I don’t know.” I had experienced exactly that the same week, when Claude confidently handed me a wrong phone number for a co-working space. The tools are getting more convincing, not less. Staying safe is no longer only technical. It is about staying awake.
You only have about four thousand weeks. Max mentioned the Oliver Burkeman book. If you live to eighty, that is all you get. Four thousand. Not infinite. And the thing that follows from that, he said so simply: if there is something you want to do, do it now, because the chance might not come again. Do a little bit toward it every day.
My reflections
Here is what I cannot stop thinking about.
Max could leave because he knew what was real for him.
He knew he wanted quiet, and nature, and to teach what he loved instead of selling what he didn’t. And this is the part I missed for years, he trusted that what he already knew would come with him. He didn’t need to become someone else to live somewhere else. He just needed to trust his own shape.
The people who are most afraid to leave a job, a city, a version of themselves that stopped fitting are usually the ones who believe that leaving means losing everything. That they would have to start from zero. That the years behind them would evaporate the moment they walked out the door.
But they don’t. That is the lie fear tells.
I know this now because I am living it. I left the corporate world, not entirely by choice, and for a while I believed I had to reinvent myself. I didn’t. Everything I do now this podcast, my consulting, my writing is built from skills I already had. I didn’t start over. I took what I knew somewhere new.
That is what Max did, only with more years of it behind him and a volcano in front of him.
And underneath it all is the same thread I keep finding in every guest: you can only make a brave move from a place of self-knowledge. When you know what is real for you and what travels with you, change stops being a threat. It becomes a door.
When I asked Max why he left, his answer was almost embarrassingly simple:
“It just didn’t make sense anymore. You finish a good quarter and the next day you start again from zero. You need to do more than the year before.”
The chase. The treadmill that gets faster every year.
Most of us are still on it.
We don’t pause long enough to ask whether the life we’re climbing toward is actually the one we want. We don’t trust that the skills we’ve built can travel with us. We tell ourselves that leaving means losing everything.
So we keep climbing.
And then we wonder why none of it feels real.
A question for you
If you walked away from what you are doing tomorrow, what would you take with you?
Not the title. Not the desk. The actual knowledge, the instincts, the way of working that lives in you and would follow you anywhere.
Most of us have never made that list. We are so afraid of the leaving that we never stop to notice how much we would carry with us.
There is no wrong answer. But the answer tells you something.
If your honest reaction is “nothing, I’d have to start over”, that is worth sitting with, gently. Because it is almost never true. It is usually just fear, wearing the serious face of practicality.
And if you can name even three things you would take with you three skills, three strengths, three things you know how to do, then you are already more free than you feel. You are not trapped. You are standing at a door you simply haven’t decided to walk through yet.
Max walked through his. He did a little bit toward it every day, and one day he woke up on the island he had only hoped to live on.
You have about four thousand weeks. That is the whole point.
Listen to my full conversation with Max on YouTube or Spotify (linked above). We talk about leaving Microsoft without starting over, how to stay safe in a digital world that’s getting faker by the year, the festival he is organising in the Azores for street cats and dogs — Decibels & Animals, on 6 September and how he recognises a green light when it comes.
It does not cost you anything to share. And sharing is caring!
Until next week,
Cris