Three steps to reinventing your career—even if you’re not sure what you want to do next

Life as Laboratory
Life as Laboratory

In 2012, I was working in the Park Avenue offices of BlackRock, investing in hedge funds. I managed a great, diverse team of people, and every day I got to chat with the most successful investors in the world.

But I felt an itch. I wanted to learn about a new industry. I wanted to be more creative. I wanted to tweet using my real name, and break out of my rotation of the same five Brooks Brothers slim-fit shirts.

Here’s where you might expect to hear about my big epiphany—how I decided to reinvent my career and strategically worked my way to a new job in an entirely different field. These kinds of narratives make the process of disrupting your life sound enticingly simple. But my own journey to my current job writing and collaborating with Quartz as their entrepreneur in residence was a windy, indecisive one—spanning four years and a lot of uncertainty.

That said, during this time, I kept a detailed spreadsheet about my activities. That data has helped me to identify three things I did that wound up helping me reinvent my career. The spreadsheet has also allowed me to appreciate how much my new path owes to serendipity as opposed to planning. But as Thomas Jefferson once said, “I am a great believer in luck, and I find the harder I work, the more I have of it.”


One behavior that led me to my current job was to help others with no expectation of anything in return. That meant introducing people who seemed like they might be interested in one another’s work, doing some work for free, and offering professional advice to those who needed it.

This approach was inspired by Adam Grant, a management professor at the Wharton School of the University of Pennsylvania and the author of Give and Take: Why Helping Others Drives Our Success. In the book, Grant argues that being a “giver” pays off in the long-term across many industries. The New York Times summarizes his view: “The greatest untapped source of motivation, he argues, is a sense of service to others; focusing on the contribution of our work to other people’s lives has the potential to make us more productive than thinking about helping ourselves.” When younger mentees ask me for career advice, I recommend they develop this practice as early as possible.

 Whenever you meet a new person, think about your friends and colleagues and ask yourself, “How could I make an introduction where two people could benefit from knowing one another?” My free work consisted of “micro-internships,” mostly for startups in financial technology. This was a natural segue for me, since I knew the industry well but wanted to develop skills in the tech space. My work consisted of reviewing pitch decks, financial models, and ghostwriting blog posts. This kind of work helped me put my existing skills to use while also dipping my toe into the startup world and developing friendships with a new group of people. It also helped me realize that I liked the collaborative, open, adaptive environment of startup culture.

But even more impactful was the habit of making mutually beneficial introductions. This behavior is pretty self-explanatory, but it requires a touch of creativity and a heavy dose of consistency.

Here’s how you do it: Whenever you meet a new person, think about your friends and colleagues and ask yourself, “How could I make an introduction where two people could benefit from knowing one another?” The pairings can work on a straightforward business level (an investor and an entrepreneur) or have more to do with shared interests (say, putting two impassioned sneakerheads in touch).

My records show that I’ve been deliberate about this practice, having made 977 pairs of introductions since October 2013. In this way, despite starting my career with a small group of peers (mostly in the finance industry and from my alma matter), I’ve been able to create a groundswell of friendships across industries and age groups.

Some of those introductions wound up leading me to Quartz, albeit very indirectly. Over the course of three years, a high-frequency trader introduced me to a Navy Seal, who put me in touch with a vintage eyewear designer. The designer and I co-hosted an event where I met an entrepreneur. Then, in October of 2014, I hosted a talk featuring Adam Grant, and the entrepreneur brought along Lauren Brown, editor of special projects at Quartz. It’s a path I couldn’t have predicted—but these seemingly unrelated relationships kept quietly pushing me towards a new vision of my future. That’s the power of community: often, other people recognize qualities in you that you may not recognize in yourself, and can usher you in the right direction.


The second behavior that helped me get to a new place in my career was organizing events to bring together like-minded individuals. I organized these events under the name Building 20, a reference to a space created at MIT during World War II. Its raw, unstructured nature served as an incubator for interdisciplinary scientific research. My events started small, but sought to provide a space where entrepreneurs, investors, creative types and philanthropists could mingle.

Beginning in 2013, I organized an event each quarter, including everything from happy hours and book clubs to talks and dinners. Then I let serendipity take over. Companies got funded; an eclectic group of philanthropists, entrepreneurs, and fundraisers coalesced to help during the Ebola crisis; and a few folks even began dating.

In retrospect, I can see that these events were all about strengthening “weak ties”—a concept explored by sociologist Mark Granovetter in the early 1970s. He found that people were more likely to find jobs and access new information and ideas not via close friends, but through contacts they saw infrequently.

But weak ties are hard to form if you stick with alumni networks and more homogenous industries. The key to organizing these events was to include a diverse range of people. I might invite the artist I met at a party, but skip the additional finance bro. And I used the following criteria for Building 20 events: Is the person gritty, curious, and generous?


The last thing that helped get me here was to find a way to use my skills to add value to the lives of people I cared about. When I share this with friends, their initial pushback is typically “there’s nothing I’m passionate about.” But with a little probing, a music aficionado might decide to curate Spotify playlists, or a foodie could start a blog that highlights the undiscovered gems of the city. For me, it was starting an nerdy email newsletter.

Eighty-eight weeks ago, I began sending my friends RadReads—a weekly email that would share five interesting articles on leadership, introspection, and wellness. In this noisy world of content, curating the articles that stood out from the pack was something people appreciated.

The newsletter’s consistency, both in terms of its voice and its timing, helped make it a part of people’s weekly rituals. It also contributed to my landing the gig at Quartz. In early 2016, Mia Mabanta, Quartz’s head of marketing, subscribed at Lauren’s recommendation (and unbeknownst to me). This gave her five months of context on my thinking and ideas, well before I actually met her for an interview. How’s that for pre-selling a vision?

A lot of people are intimidated by the prospect of reinventing their careers because they feel like they need to first hatch a master plan. But I didn’t have one, and you don’t need to either. If you’re not sure what you want to do next, yet you know you want a change, you should go ahead and get started—with a focus on helping others, organizing (or attending) events where you’re likely to strengthen those weak ties, and finding a way to contribute something to the world that other people will value.

With this deliberate practice, you’ll be amazed to find that serendipity seems to strike more often than expected. Once you get rolling, you’ll inevitably gather momentum. You may well be pleasantly surprised to see where you wind up.

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