Last week, I went live on Substack with
, the writer behind Still Wandering and founder of Midweek and True North.Alex has quickly become one of the most thoughtful new voices exploring how work and identity are evolving.
His viral essay “The Death of the Corporate Job” struck a deep chord across generations — surfacing something many people have quietly felt: that the traditional corporate path no longer guarantees fulfillment, stability, or even belonging.
Our conversation explored what comes after that realization — and how to design a career that actually fits the life you want.
Here are a few of the themes we unpacked together:
The power of a beginner’s mindset.
Alex shared how being early in his career has been an unexpected advantage. By leading with curiosity and empathy rather than expertise, he’s building a body of work around listening deeply and spotting patterns in others’ career struggles.
A beginner’s mindset has served me my entire career. It’s what enabled me to shift from industry to industry and function to function.
In this next era of work, careers are going to look even more fluid and dynamic. Having a beginner’s mindset is what will allow you to navigate the change.
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The loneliness of career transition — and why community matters.
We talked about how uncertain career moments can feel isolating, especially when so much of our identity is tied to our job title.
Alex’s Midweek community was born from that insight: the idea that clarity comes not from thinking harder, but from talking, testing, and being held accountable by others who understand.
When we are unsure, it might feel safer to stay quiet, but the opposite can be true. Conferring with and communing with others can help us find our way.
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You can’t think your way to clarity.
Both of us have seen how important it is to act your way into knowing — through experiments, conversations, and creative exploration.
It’s how I discovered writing and launched my coaching practice after two decades of corporate leadership, and it’s how Alex is helping people uncover meaningful next steps through True North.
Taking a step forward is the only way to discover what is right for you, over and over again throughout your career.
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Adopting an entrepreneurial lens — without needing to be an entrepreneur.
We explored the idea that every professional can think more like a builder: identifying problems worth solving, testing ideas, and aligning your skills and passions with what the world actually needs.
It’s not about quitting to start a company; it’s about reclaiming agency and designing your next chapter intentionally.
Entrepreneurs don’t wait for someone else to define the problem and propose a solution. They don’t need permission to dive into the work. They combine an owner’s mindset with a doer’s mindset.
Anyone can do this. And now more than ever, the professionals who will have the most fulfilling careers need to adopt this approach.
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Rethinking identity and worth.
We shared personal stories of what it feels like when a title disappears, and how to rediscover your worth beyond your role.
Culturally, Alex and I both have lived in societies where you can’t spend more than a few minutes with someone before they (or you) inevitably ask, “What do you do?”
It’s an innocuous question on the surface. But beneath the question is layer upon layer of assessment about status and power. And it generally results in two people exchanging superficial and limiting labels: job titles.
What’s even more sad than the label is how we become attached to them. I spoke about the panic I once felt when I knew my executive job was ending.
The C-level roles I hadn’t sought out had become part of my identity, a symbol of my worth. It was a significant shift to reclaim my full self. It was difficult, and it was an opportunity to rebuild my narrative.
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Why this conversation matters
Whether you’re at the start of your career, mid-journey, or somewhere between reinvention and rest, this conversation is a reminder that your career should fit your life — not the other way around.
If you’ve been feeling restless or uncertain about what’s next, I think you’ll find Alex’s perspective grounding and hopeful.
I’d love to hear what resonates most for you — drop your reflections or questions in the comments.
More Lead without Limits Substack Live’s
Recorded
Leading Through Fire: What I Learned from Former FDNY Commissioner Laura Kavanagh (Watch it here)
Our conversation delved deep into what it takes to lead through change and crisis, and her reflections on leading a 17,000 person, $2.3 billion budget major public service institution.
Upcoming
Tuesday, November 18th at 11am ET with
Call for Topics & Speakers
Is there a topic you’ve been hoping I would cover?
Is there a person I should be hosting on a Lead without Limits Substack Live?
DM me or reply to this post. I want to hear your recommendations.
Thanks for joining me this week!
May you lead without limits,
