How to make a living without a job
This is what happened when I actually started valuing myself
A year ago I left my career.
I was working for Elon Musk, at the pinnacle of a 25-year design career that I never imagined would go as far as it did.
I’d ended up in the position because I wanted to use my skills to help further humanity’s evolution, and I finally had the confidence to believe that no job was too big for me.
I was completely naive to his character at the time, and—by extension—what I was saying yes to when I accepted the offer.
When I’d gotten recruited, relocating my family for the role was one of the most exciting things that had ever happened to me.
I posted about it on LinkedIn and told everyone I knew.
It was my moment of having finally arrived.
One of the smartest guys in the world (how I saw him at the time) wanted to pay me a bunch of money to bring my skills to his business. And in service of something I’d spent my life caring about: our planet.
But after 2 years, I finally accepted the reality I’d been denying when friends asked me how it was going, and I responded:
“It’s really an incredible company…and he isn’t anything like how he’s made out in the media.”
Among other things, I was taken aback when—in my early days—I proposed to another of his inferiors using something more innovative and creative than PowerPoint for company presentations, and was emphatically told:
“That’s not how we do things around here.”
It wasn’t a phrase I’d expected to hear.
But it was the kind of thing I heard a lot of.
I’d previously spent over a decade art directing some of the world’s most innovative ad campaigns, then a decade helping develop the connected device industry.
I earned over 100 patents on technologies used today on devices in your home that connect to the internet—sorry.
This included playing a major role developing a brand that got acquired by a tech giant in a 10-figure deal that was headline news.
I’d been aggressively recruited because it wasn’t just 13-year-old me anymore who thought I had good ideas.
And now I got to combine my boundless idea-generating capability with my design skills in the most high-profile position I’d ever held, working for the real life Tony Stark, to do good in the world.
It took a couple of years to admit that the job was more about surviving office politics than saving the planet.
I’ll explain the details of my departure another time, but for now will share that there was such a breakdown of professionalism that I had trouble believing I was at a global, generally well-reputed, company.
The most important thing I’ve learned about success is that it requires choosing which narrative you want to believe.
What narratives are you choosing to believe in your own life right now?
While I was devastated by how badly things turned out at what—at one point—had been my dream job, I committed to stepping into an empowering narrative where I found an even better opportunity.
I figured that with my resume at that point—and charming personality—it would be easy, and I got interviews for exciting leadership roles at some of the biggest companies in my industry.
So I was surprised when I didn’t get called back for a couple I thought I was perfect for.
I found myself tempted to doubt my abilities.
But—in both cases—I was being assessed by people who were younger than me, and so eventually concluded that they were just too inexperienced to see the value I brought.
But it hurt.
I’d worked hard to reach a point in my life where depression, and my past, no longer defined me, and I’d accomplished things I was proud of.
In my late 40s, I finally knew I was valuable, and wanted to find a company where I could give my gifts and feel seen.
How I helped develop an industry
I ended up getting into the connected device industry because having our first kid changed my wife.
When we met (at a yoga retreat), she was a successful VP at a public company that she had helped become a global leader in the industry she was in at the time.
But she fell in love with motherhood, deciding to leave her career and, instead, prioritize raising our son and, then, 3 years later, our daughter.
So…
💰 I needed to make more money 💰
What I was doing at the time—designing websites for blockbuster films and hit TV shows in Hollywood, California—was a lot of fun, paid well, and had perks.
I even walked the red carpet once.
But being a new parent motivated me, not just to find a way to make even more money, but to use my skills to build something that endured longer than the average lifespan of my work at the time, which was a few weekends at best.
We were living in Santa Monica, which—in the early 10’s—was receiving an influx of venture capital leading to a boom in new startups.
I started going to “Silicon Beach” meetups, and learned as much as I could about UX design and how to build apps, made friends with developers, and found people with capital looking to build things.
Over a couple years, I helped a number of founders raise seed funding, and launch products that promised to revolutionize industries—but in every case, they ultimately lacked the conviction necessary to truly innovate.
🤝 The introduction that changed everything 🤝
Then I got introduced—through a friend—to a founder who had just built a connected hardware device that held the potential to change the way people lived.
I immediately knew that what he was building—and the team he was building it with—was the reason I’d left advertising.
He had just raised a Series A, and moved his small team—who sat around the same table every Wednesday to eat chili cooked by his nanny—out of his garage, and into their first office space.
Their product was technically complex, and brilliant—and he, as a founder, oozed conviction—but his product was clearly designed by an engineering-minded team who didn’t understand customers as deeply as I did.
I knew that I could help him bring his product to a mass market, and that doing so could be transformative to society. So I created a pitch deck that convinced him to hire me and give me equity.
I was completely naive to his character.
How a Deadhead ended up in Big Tech
In the 7 years that I worked for him, I kept pushing myself, stepping as fully as I could into whatever challenge appeared in front of me.
The early years were a blast—the entire team was always on our toes as we navigated the complexities of connected hardware, Chinese manufacturing, and rapid growth.
Every day contained new lessons in product development, electrical engineering, customer research, user experience design, and more. Then as the company grew, I became a leader, managing distributed teams around the world engaged in many of the functions that I’d personally handled when we were smaller.
I learned that to rapidly grow an innovative company requires constantly growing yourself.
At every step along the way, I had to evolve my view of what I was capable of.
Through challenging myself to maintain a growth-mindset over many years, I helped turn one of the first connected hardware startups into a household name in the US and Europe, and a $1 billion acquisition.
The acqusition was headline news, and afterwards, a team at one of Elon’s companies—that was bringing a new category of connected hardware to market—found me. They convinced me to leave the team I’d grown and led with love, at a company that had come to feel like home to me, to help them.
It was the most promising opportunity of my life, and so I said yes.
But reluctantly at first—because it also scared the shit out of me. 🙀
This was a serious role working for a guy I thought was a certified genius at a company notorious for its ruthless work ethic.
When I showed up at the yoga retreat where I met my wife a decade earlier, I was taking a sabbatical to go on tour in my Volkswagon Vanagon as a singer/songwriter.
I’d spent most of my life following my muse, but now that I was a parent—and the sole breadwinner in my family—I figured I had to get serious about a career.
However I still struggled with confidence and focus.
Developing an industry—and getting named on over 100 patents—helped me feel moderately competent, but I still felt almost as insecure as I’d been when I was a kid.
But a voice inside of me said:
“If you take the role and succeed,
you’ll get the confidence you’ve always wanted.”
The prospect of failing terrified me, and so I oscillated between staying in the comfortable position I was in—known and respected throughout the company I’d helped build—and leaving the familiar behind, until it struck me that I’d rather live life facing my fears than feeling imprisoned by them.
In the few months between saying “yes,” and getting started on my first few projects, I discovered the most self-assured version of myself I’d ever known.
When was the last time you felt like you could accomplish anything?
That’s how I felt with a lot of pressure, and eyes, on me.
And—apart from losing my dad when I was a kid—I’ve never experienced anything more painful than how I was treated after the honeymoon phase was over.
Meeting Molly
As it would turn out—these things (how I let myself be treated in the job, and my childhood) had a lot to do with each other.
Two experiences I had working with MDMA in a therapeutic setting over the following two years—one shortly after leaving the role and trying to put the pieces of my psyche back together, and the second, more recently—made this abundantly clear.
Becoming an internet entreprenuer
My first MDMA experience helped me get on the path back home to myself, and I started considering the idea of doing my own thing professionally.
Surely, it couldn’t be that hard to figure out how to make money through an internet-based business—right?
I had a habit of pleasantly surprising myself in my career—including in that last role.
So—for the first time in 25 years of being a designer—I started channeling my skills into my own inspired ideas.
I created a t-shirt line, a product incubator with a friend, a communication workshop for corporate teams, a meditation program, a manifestation course, and a business coaching program.
I was having fun and learned something new with every venture, but none of it fully replaced my most recent salary, so I was continuing to polish my resume.
But losing hope.
When my wife came across a listing.
“VP of Design” at one of the leading meditation apps.
A New Hope
Reading the job description gave me the boost of confidence I needed.
I knew, without question, that based on the unique combination of things I’d accomplished over 25 years as a designer—and almost as many as a meditator—that I could turn their app into the most popular in the world.
💪 I’d never felt more sure of anything in my life.
And, sure enough, I got an email back from a recruiter the day after I sent in my resume to set up a call.
As soon as we got on the phone, I asked enthusiastically about her meditation practice—I assumed everyone in the company must be a devout meditator.
But she awkwardly changed the subject.
Regardless, she was enthused by my professional background, and scheduled a call with the hiring manager.
I’d never been more excited about a job interview, and spent the days leading up to it brainstorming new ways for them to reach a broader audience, and (with the help of AI) drafted an impressive strategy document—I’d never cared this much about a fucking job.
And the conversation with the hiring manager was completely awkward.
I wanted to talk about the role design could play in getting more people around the world to meditate.
And he distractedly peppered me with questions about how I “navigated ambiguity,” or “resolved stakeholder conflict.”
I shouldn’t have been surprised when I got an email back from the recruiter a couple days later saying they’d:
“Decided to pursue other candidates
whose experience better mapped to the needs of the role.”
But, at the time, it was heartbreaking.
I’d been so convinced that that role was made for me: a fricking meditation platform—the one place in the entire tech industry where I figured I was practically guaranteed to be welcomed with a company-wide loving embrace.
While at the time, I felt crushed by the rejection, looking back it feels almost as if the universe was saying,
“There’s no company for you.
So please create one of your own already.”
The people I’d worked for in the tech industry, and other founders I knew at the time, shaped my perception of the type of person who ran a company:
White, alpha, male, doesn’t give a shit what anyone else thinks.
They were also always dealing with investors, and advisory boards, and getting on planes early in the morning, and returning home after their kids were in bed.
That didn’t sound like what Joseph Campbell meant when he said:
“Follow your bliss.”
Return of the Dreamer
But as I spent time on YouTube, trying to figure out alternatives to going back to work, I started to form a different perception of an entrepreneur, and found myself thinking:
“Maybe there’s a way to make a living without getting a job,
but also without becoming a CEO.”
I wondered why if I was able to be compensated by a company for my skills, I couldn’t just sit at my computer and use similar skills to make money on my own.
I was almost 50 and I didn’t want to work for any more shitty people.
My last role had gone the way it did partly because I was completely unable to fit myself into the boxes they wanted me to operate in, and stay in the lanes that the company had drawn for someone in my position before I’d even shown up.
I oscillated between working the way I naturally work, and trying my best to fit into the culture.
Despite arriving with decades of—at that point—specialized experience, and joining at the top of the company, if I drifted outside of the lines, I was reprimanded.
Which was embarrasing.
But trying to fit in was painful.
It was inauthentic.
The reason work is so exhausting for so many of us is not because of how hard the work is.
It’s because of how hard we work at adapting ourselves to do things we don’t really want to be doing because of what others expect of us.
How I became a midlife influencer
I started fantasizing about becoming an influencer.
And it seemed like everything most 47-year-old men would think about it:
Vain
Delusional
Ridiculous
But the more research I did, the more I realized it wasn’t such an outrageous idea.
There were a lot of people my age online, but not a lot of influencers speaking directly to them.
And most who were didn’t understand branding, marketing, and design the way I did.
I created a few different (anonymous) accounts, and started posting on social media with all the confidence in the world, and my boundless wisdom, expertise, and creativity was met with:
🦗🦗🦗🦗🦗🦗
I kept trying different characters: the designer, the chef, the character from a Picasso painting, but nothing I shared found an audience.
The birth of The Mystic
Over time, I started thinking more about the psychology of engagement and desire (if you’re interested in this topic, please let me know in the comments and I’ll write about it separately) that I had used to make an endless number of ad campaigns take off over the years, and help startups gain traction, and that’s when I finally started to have some success on social media.
But it was still harder than I thought to capture attention among a sea of others trying to do similar things.
Then one morning, I was lying in bed after 10am.
I had no prospects for what I was going to do with my life, and prayed for direction.
When I heard a voice.
It said:
“You are The Midlife Mystic.”
Something about it felt so obvious.
I hopped out of bed, ran down the hall to my home office and changed my account name, then I started manipulating a selfie in Midjourney, until—after a few prompts—found the multi-dimensional version of myself staring back at me:
I was reading the book “Breaking the Habit of Being Yourself,” by Dr Joe Dispenza at the time (if you haven’t read it, please order it now), and I started thinking of The Mystic as a vehicle for reinventing myself (in midlife).
He also became a vehicle for sharing what I’d first learned about mysticism in my 20’s, when I spent a year and a half backpacking through Southeast Asia, then India and Nepal.
I started writing about midlife reinvention along with what I was personally navigating, and some of my posts went viral and reached millions.
I led to me finding my first significant post-career success.
I channeled the attention into my first online community, where I continue to help people find easier ways to build soul-aligned businesses and lives.
After decades of pushing, and reaching highs that ultimately let me down, I now find myself engaged in what feels more like my life’s work than anything I’ve ever done.
On my community calls, participants started calling me Mystic, and it felt right, so I stuck with it.
Meditations of a Midlife Mystic
I started this newsletter because I love writing.
I always have.
I’ve often felt happiest when I can organize my often chaotic mind into a coherent series of words on paper (or a screen).
But I realize what’s going to make you most want to read them is if they can help you benefit from some of the wisdom I fought hard for.
So this newsletter is my attempt to do that.
How to Make a Living Without a Job
In the time since leaving my last role (2 years as of the latest update to this article), I’ve learned a lot about how to develop an effective and successful online presence through both developing my own, and helping countless others with theirs.
An online presence is an incredibly valuable asset for anyone looking to make a living without a job—whether you’re a founder, an artist, or don’t fit into any boxes.
But instead of a personal brand, I refer to it as a “creative persona,” inspired by the work of Carl Jung.
Our “persona” is the face we show to the world. Carl Jung discovered that for most of us, this face is shaped by our unconscious motivations to hide aspects of who we really are—both to ourselves, and to others.
The Midlife Mystic is my own creative persona, and a vehicle for letting myself be seen in ways I was afraid to show up in the past.
A Creative Persona is an opportunity to express aspects of yourself you’ve kept hidden, and in novel ways, because…
It turns out these are the parts of you that others find most compelling.
These are the parts of you that make you most likely to attract new opportunities.
These are the parts of you that will lead you to new avenues of success.
Whether you want to be successful online with a Creative Persona, and promote your work, your business, or just your thoughts, I’m going to teach you the 5 core skills that will help you succeed.
These are also foundational skills for success in general that you can apply to anything you’re working on, and especially if you want your work to reach a larger audience.
These are drawn from my experience spending 25 years art directing global ad campaigns for the world’s biggest brands, then building multiple products that became household names.
But before I get into logistics, what I most want you to know is that it’s entirely possible.
Even if:
You’re in midlife
You’re completely incompetent on social media (I was too)
You feel like you have nothing interesting to share
You’ve tried and it hasn’t worked for you
You’re not entrepreneurial
You don’t have a lot of time
The most important prerequisite to getting anything you want in life is the belief that it’s possible for you.
If you're hungry for something new, whether that's income, influence, or simply a truer way of showing up in the world, sharing authentic aspects of your story with others can be both rewarding and more healing than you expected.
I promise you that making a living without a job—whether with an online business, a soul-aligned venture, or through some other unique combination of your abilities—is absolutely, 100%, possible.
So let’s get into it
If you want to make a living without a job, there are 5 basic skills you need.
Master them, and I’m confident you’ll never need another job.
