A stock tip from the soul

Investing in a stock involves taking disparate bits of information and unifying them into a thesis. There’s an approach called Mosaic Theory, in which an investment analyst acts like a detective or investigative journalist; pulling on threads to see if something juicy will materialize. The process requires rigor, creativity, and inter-disciplinary breadth. And the humility to accept that you may be wrong. Mosaic Theory after all, “is as much art as it is science.”

Help! I’m stuck (in my career)

“I have no idea what else I could do.” This is the common refrain from RadReaders who feel stuck and are contemplating a career change. Some have spent decades honing a specialized skill, yet can’t see how it translates outside of their industry; others are aware that the tech stack can power new types of entrepreneurship but unfamiliar with what approach to take; and many have sacrificed their hobbies in service of their careers and growing families. I felt this viscerally during my 14 years on Wall Street. I was a specialist in the tiniest sliver of the hedge fund industry and so much of my learning was centered around deepening that specialization. I wanted to be an entrepreneur, but didn’t even know where to begin.

What makes you come alive?

“What were you doing when you last felt time melt away?” (And no, drinking with your homies doesn’t qualify.) You’d be amazed by the answers that this questions elicits from people looking to change careers. Producing electronic music. Canvassing. Playing golf. Reading to my niece. I hear people come alive for a split second when they describe these activities. But then they buzzkill themselves by claiming with resignation that “there’s no way I could make money doing this.” And so back to work. But you’ve just missed a stock tip from your soul.

Let’s bring back Mosaic Theory. Our lives are indeed important puzzles (dare I say, investments) that we’re continuously trying to piece together. It’s careless to categorically dismiss something purely on the basis that it can’t make you money. On the contrary, it’s these moments when we come alive that we require us to activate our listening and curiosity. Who knows where it will take us?

The clues can come from anywhere

I recently sat on a panel for a company’s offsite. My friend – a first time moderator – was understandably nervous. This was well outside her job description and the audience was large (and filled with colleagues). So she followed the classic Type A playbook, over preparing by incessantly rehearsing in front of the mirror, recording herself, and with her husband. And despite some early jitters, the panel was a success. Afterwards, she was both relieved, and radiant about having done something well outside of her comfort zone.

“I haven’t felt this alive in a long time,” she gushed. But then reality set in, “What do I do with this?” she wondered aloud. I told her that she had just received a gift, a stock tip from her soul. People spend their entire lives looking for them, yet often miss them because they’re too busy or wrapped up in traditional career narratives.

But then I immediately talked her off the ledge: “No, you should not become a professional speaker.” Trying to turn an interest into a career is a natural instinct, especially if you feel stuck. But making such a large mental leap can prematurely close too many doors.

The “passion playbook”

So we brainstormed how this clue could be used to build the mosaic: joining Toastmasters (a speaking club), taking standup classes, experimenting with different topics in front of the mirror, self-producing a podcast with friends, or volunteering at work for more client-facing opportunities. All possible with a few hours around the workday or on the weekends – the time spent was less important than a commitment to consistency. It could lead to a dead end. Or a dope new hobby. And who knows, maybe a new career? Regardless, the exploration could be just as fun as the end goal.

And you never know

When I left Wall Street, I thought that my next career would involve two of my interests: finance and tech. I thought I’d be a Fintech entrepreneur. And look at me now.

For me the stock tip was writing (which was ironic given the fact that I had ignored English classes like the plague while at Yale). Four years ago, when I started the blog and newsletter I often found myself overanalyzing how I would make money. But given that I had structured some financial guardrails, my biggest entrepreneurial leaps were from pulling at this desire to write and doubling down on things that made me come alive.

And for the pragmatists in the audience, both skills and sources of income emerged – most of them completely unrelated to the act of writing itself. Some examples include storytelling, public speaking, podcasting, copy writing, digital marketing, search engine optimization, graphic design, typography, executive coaching, organizational design, product design, moderating, pricing, A/B testing, video production, and PR and communications.

I’m blown away by the new set of skills powering my second career. But beyond the skills and revenue, the best gift has truly been this journey of self-discovery. I guess the mosaic is working!