What’s the Job Your Job Is Doing for You? with Simone Stolzoff
“Just becoming a solopreneur or someone who works for themselves does not rid you of all the internalized narratives about grind culture or your self-worth being yoked to productivity.”
If you’ve ever tried to “do what you love” for a living and wondered why it still felt hard, Simone Stolzoff has some wisdom for you. The author, speaker, and career designer has spent years exploring the role work plays in our lives—and what happens when we make it the centerpiece of our identity.
Simone’s first book, “The Good Enough Job”, is a powerful invitation to rethink not just what we do, but how we relate to doing. Through research, personal anecdotes, and cultural critique, Simone helps us see what intense pressure we put on our career and gives an alternative vision of where our meaning center could be.
It’s fitting that I first met Simone (or “Simo” as his friends call him) at our coliving house. As I’ve come to know him, he is incredibly dedicated to friendships - old and new - and invests in communities through sports, art, and volunteering. At the time he joined the house he was still working at the acclaimed design consultancy IDEO. By the time he moved out of the house he had left IDEO to finish writing his book and to build his own consulting and speaking business.
Declaring Before You're Ready
In true millennial fashion, Simo didn’t wait until everything was polished and ready—he just posted on Twitter, “I’m writing a book.”
Simo describes the moment of publicly announcing his book before writing a proposal or landing an agent as the inflection point in his career. At the time, he was worried his writing muscle might atrophy if he didn’t stay connected to it. The book gave him a structure to keep creating, and a reason to take himself seriously as an author.
“The naivete worked in my favor,” he said. “I think the logic back then was simple: I want to write a book, so I’m going to write a book, and then I’ll figure out how to do it.”
This willingness to act before everything feels certain has been a throughline in Simo’s journey. And it’s something that comes up often in his cohort-based course, “Design Your Next Career Step”. He’s seen how many people get stuck in analysis paralysis, waiting to have the perfect plan before making a move. Simone’s story suggests the opposite: sometimes the clarity comes after the commitment.
Choosing Between Two Versions of Yourself
Simo’s career path had an ambivalent streak. He studied both poetry and economics in college (“an existential crisis waiting to happen”) and spent his twenties bouncing between writing, marketing, journalism, and design. Eventually, he faced a professional crossroads: continue working in journalism or pivot to a full-time role at IDEO.
It wasn’t just a job decision. It felt like a choice between two versions of himself. That tension—of trying to be everything all at once, of hoping for one perfect job to hold all your complexity—was what ultimately inspired his first book.
“The book is about the value of diversifying your identity beyond your professional life… not just to be a well-rounded worker, but to be resilient when life changes.”
It’s a powerful reminder: your job does not reflect you as a whole person. And if we tie our entire sense of worth to our job title or output, we’re at risk of having too many emotional eggs in the same basket.
The Fantasy and Reality of Working for Yourself
After leaving IDEO to write full-time, Simone expected a wave of relief. No more endless meetings. No more client politics. But the freedom came with an unexpected realization.
“I always thought my tendency to overwork was a result of the culture I was in. Then I started working for myself and realized—I’m the worst boss I’ve ever had.”
This is something so many self-employed people eventually discover. Leaving traditional employment doesn’t automatically remove internalized hustle culture. The to-do list still looms. The guilt still creeps in. Simone had to learn how to set his own boundaries, manage his own expectations, and actively build a life that reflected his values—not just his ambitions.
From Juggling to Focusing
In his first year of self-employment, Simo tried everything: freelance journalism, consulting, course creation, public speaking, and writing his book. He called it an “experimentation mindset.” But after a year of juggling multiple income streams, he paused to take stock.
He conducted his own business audit—mapping each income source against time investment, earnings, and fulfillment. The result? He decided to double down on just three things: writing books, teaching, and public speaking. The rest, including consulting and freelance journalism, didn’t make the cut.
“You might feel like you’re leaving money on the table by narrowing focus. But what I found is that my business actually did better when I got more focused.”
This level of honest evaluation—what he calls getting “a little ruthless”—can be hard for multi-passionate creatives. But it’s part of treating your business like a living thing that evolves. And remembering that not everything has to be permanent.
Designing a Life with Many Containers
One of the most striking metaphors Simo offers is the idea of “containers.” Work is just one container—and it holds certain values: output, performance, income. But we all need other containers too. For Simone, those include his ultimate Frisbee team (which doesn’t care how many books he’s sold), his communal living experience, and his Jewish identity, especially around rituals like Passover.
“A value expressed on its own is only so deep. It’s the behaviors and the community around it that make it real.”
This is where Simone’s philosophy shines: he’s not telling people to care less about their work. He’s encouraging us to care more about other things. Instead of shrinking your passion for work, expand your capacity for fulfillment elsewhere.
Halfpreneurship and Designing Your Own Hybrid Path
As he looks to the future—especially with a baby on the way (update: his baby is here!)—Simone is experimenting with what he calls “halfpreneurship.” It’s the space between full-time entrepreneurship and traditional employment: a hybrid path that offers the best of both.
This could look like part-time teaching, ongoing contracts, or retainer work. The key is that it creates a little more stability and community, without giving up all autonomy.
“I used to idolize the idea of a traditional paternity leave. But my therapist said something that shook me: ‘You’ve already designed a life you don’t need to take paternity leave from.’”
Rather than chasing one ideal structure, Simone’s mindset is about using the dials—turning up or down income, flexibility, community, structure—as life evolves.
Experimentation over Perfection
In his course, Simone sees common themes: people waiting for clarity before they act, people trying to mentally plan their way into a perfect career. Instead, he recommends prototyping—getting close to the actual experience before making big decisions.
Some of his students realize they don’t need a total career overhaul. Others decide to shift their priorities or change how they think about “enough.” And for many, the most liberating insight is this:
“Your next job isn’t your last job. You can course-correct. You can always reevaluate.”
That perspective doesn’t just apply to job titles. It applies to how we design our lives, our businesses, and the way we think about success.
You Are More Than What You Do
Simone’s story is a roadmap for anyone questioning the role of work in their life. It’s a reminder that fulfillment doesn’t always come from optimizing every aspect of your business. Sometimes it comes from subtracting, simplifying, and making space for more of who you are.
Whether you’re fully self-employed, navigating halfpreneurship, or still figuring out what kind of life your job is supporting—this conversation is for you.
“We are not fragmented pieces. We are whole human beings. And the more we build lives that reflect that wholeness, the more sustainable our work—and our joy—can become.”
