Midlife Career Exploration


Over the years Ada and I have both enjoyed being informal career mentors to countless of our friends and colleagues. We were recently reflecting on how dramatically those career conversations have changed as our friends and colleagues have aged from early in their career to mid-career.

In many ways, early career conversations were actually far simpler in nature. Like a video game, most individuals were focused on leveling up as quickly as possible and wanted to know how to acquire the hard and soft skills they needed to climb the career ladder laid out in front of them by their current employer. Or they were exploring a new role or company that might meaningfully accelerate their timeline for leveling up. When asked about their dream job, they often aspired to one of just three roles: a VP in their discipline, a CEO, or ultimately a startup founder.

In stark contrast, the midlife career conversations we've been having look entirely different. While to some it may initially feel a bit like a midlife crisis, the reality is that through the course of their careers many friends and colleagues have developed unique insights and a deeper self-awareness that enable them to now re-orient their career towards truer fulfillment.

I wanted to share some of the most common insights friends and colleagues have at this stage in their career that lead them to be more thoughtful about their next career move.

My Home Office


So many of my colleagues have recently been introduced to working from home for the first time and will likely have to for the foreseeable future. But many are finding their home environment to be far less productive than their traditional office. I, on the other hand, have now been working from home for over four years. Each year I've found a variety of ways to optimize my home office setup to maximize productivity. And I can now safely say that I'm far more productive in my home office than I've ever been in a traditional office setting. So I thought I'd share all the gear that has contributed to my productivity.

Remote Work Tips From Basecamp


Given all the recent interest in remote work, I spent the weekend reading Remote: Office Not Required by Jason Fried and David Heinemeier Hansson. As the founders of Basecamp, they have been practicing remote work for over a decade now, well before the present-day excitement around it. In the book, they cover everything they have learned from their experience, including why remote work is good for a company, how to hire for remote work, collaborating effectively, managing remote workers, and more. However, what I found most interesting were the tips for how individuals could cope and ultimately thrive in a remote work setting. I wanted to share five such tips I took away from the book.

How I Write


When I started writing 11 years ago, I did so the same way most people do: by opening a blank document and typing my thoughts on the page. But each year since then I've subtly refined and evolved my process in an attempt to improve the quality of my writing and its impact. Now with 150+ essays published with over 1.5 million views, I wanted to share every detail of my writing process for fellow or aspiring writers who might benefit from it.

5 Skills Every Product Manager Can Learn From Elon Musk


This weekend I had the opportunity to read Ashlee Vance's Elon Musk: Tesla, SpaceX, and the Quest for a Fantastic Future. I've been a huge fan of Elon Musk since the early days of SpaceX and knew I wanted to dive deeper into the story of both SpaceX and Tesla. The book did not disappoint: it was a fascinating history starting from his childhood, to his early startup adventures with Zip2 and PayPal, to a deep dive into how he willed SpaceX, Tesla, and SolarCity into existence and ultimately to success despite the odds being continually stacked against him.

We often paint the picture of Elon Musk as a superhuman who has a boundless work ethic, willingness to take massive personal risk, and an incredible mind to make it all happen. All of this is certainly true and contributed meaningfully to his success. But as I read his story I came across so many examples of skills that Elon had mastered that any of us could also master to enable us to achieve our goals. I wanted to highlight five of those skills that are particularly relevant for product managers that can help them reach new heights in their own craft.