New Year, New Job
Advice from my exhaustive journey to design Phase II of my career, what you can learn from it, and where I've headed next
A few months ago, I realized I might want a new job. The job hadn’t changed. It was a good job, and I liked it. The people I worked with were great. The work was interesting, and I was learning a lot. But I felt like I had achieved what I had hoped for when starting, and I began to desire to try something new. What that new thing should be, I wasn’t sure.
At Dartmouth, so many alums go into finance and consulting (~40%) that it feels like the only decision to make when graduating is whether to pick finance or consulting. I saw my path as existing in that same binary. I explored the options, chose consulting, and was happy I did. But as I thought about what could be next and how to approach it, I came to realize how limiting it was to think only in two career paths, especially at such a young age. I wanted to set out on a new exploration — a deeper one this time. Where I blew open everything it meant to work. To reduce jobs into fragments from which I hoped to build a career suited exactly for me.
I started with a control group to seek advice from: people who started their careers the same way I had. Who had gone to competitive colleges and then worked in a formal, high-intensity training program (e.g., banking, consulting, rotation programs at large companies). After meeting those characteristics, I wanted variability of experiences.
Over the past few months, I have had dozens of coffee chats. I have listened to podcasts about successful people’s career journeys. I have read self-help books. I gathered a thousand opinions. I learned the downsides of gathering a thousand opinions. I retreated into myself to process the advice, and I did a lot of self-reflection. And ultimately, I found a new job. While I could probably talk for hours about my own decision, it likely wouldn’t be too relevant to others. So instead, I thought I’d share the best advice from all of those conversations in case it can help anyone considering their next move.
10 best pieces of job advice (paraphrased and in no particular order):
1. Find a job that plays to your few strengths instead of one that tries to fill in your many weaknesses.
2. Find a job that is an adventure in itself.
3. Do something in a space you find genuinely fascinating – this is more important for work satisfaction than society gives it credit for.
4. Feeling ownership over your work is key to job happiness.
5. Success is driven by expertise. Work to develop expertise in something.
6. Trying to keep doors open can be unhelpful; Decide on a path, run with it, and if you’re wrong, change it.
7. Take risks early in your career. If it works out, great. If it doesn’t, failure opens doors too.
8. Pay should be measured first in learning and then in salary. Learning can be cashed in for money over time.
9. To make an impression on someone, learn what makes them tick. Highlight authentic commonalities between you and them.
10. Work for someone who sees more potential in you than you see in yourself.
At the end of this research, I ended up less with an idea for a career path and more with guidelines for what I wanted to feel while working. I also developed an entirely new set of people I admired in business. People who are professionally trained, entrepreneurial, and values-driven, such as Josh Kushner, Ben Leventhal, Jordan Cooper (
), Alex Friedman, Jeff Jordan, and Erica Jain. I also came away incredibly impressed with humanity – how many people responded to cold emails; how many people took an investment in my career.Introducing Phase II.
I am excited to launch Phase II of my career — the second in probably many. Starting in December, I took a job as Chief of Staff at the a16z-backed, seed-stage startup HelloCreator. HelloCreator was founded by Tim Westergren (founder of Pandora Music) and Gordon Su (founder of video game company PennyPop) and leverages AI technology to redefine the way creators are understood and supported. As Chief of Staff, I am excited to combine my enthusiasm for business strategy and entrepreneurship with my love for the arts. Our team is mainly engineers at this point so it will be a great test of my consulting skills — to understand how to approach any business problem and then execute. I am excited to learn from Tim, Gordon, and the team. I am also excited to build something epic.
One month in, it’s too early to tell if I have “chosen correctly.” It’s also hard to begin trying to measure that. But what I do feel in this new role is that the pieces of my life (interests, career, personal life) seem to snap together and make sense. That is certainly reason for hope.
Searching for jobs, finding new careers – those are tough and widespread questions. If this inspired reaction, follow-ups, or stories about your personal journey I’d love to hear.
Appendix:
Some pieces of writing I thought about when drafting this:
Sylvia Plath’s quote from The Bell Jar about decision making. “I saw myself sitting in the crotch of this fig tree, starving to death, just because I couldn't make up my mind which of the figs I would choose. I wanted each and every one of them, but choosing one meant losing all the rest, and, as I sat there, unable to decide, the figs began to wrinkle and go black, and, one by one, they plopped to the ground at my feet.” Shoutout to Annecy for reminding me of this one.
Arthur Brooks’ writing about job happiness which I read after I took this job, but it confirmed the way I thought about it. Arthur says, seek a role that gives you “earned success” and “service to others.” Earned success gives you a feeling of accomplishment while service to others gives you satisfaction in knowing what you’re doing is helping the greater good. Shoutout to Max for introducing me to Arthur’s research.
This chart from
showing the amount of your life spent working.
Joan Didion’s line from Goodbye to All That: “It is easy to see the beginning of things, and harder to see the ends.” Shoutout to Joan for being a legend.