Hi Friends,
Greetings from Brooklyn!
Fall is here.
McIntosh apples are back in stock and I can start cranking out apple pies with loads of cinnamon. Just like my mother taught me to make them, and just like my five-year-old loves to eat them.
On the way to school today, my son and I played a game: spot the trees who started shedding their summer mantle. I pointed him to the treetops where bright green starts changing into a fiery red.
Speaking of changing, my guest for this edition has mastered it down to a science, with several seasons to her career.
Let’s dig in!
Until next time,
Florian
🏹 Archers: Lindsey Grossman - Tech Executive/ Political Organizer
Lindsey and I first crossed paths over lunch in Washington, D.C. 15 years ago, both fresh-faced in our first jobs. Since then, our careers have zigzagged, but I know few people who’ve mastered the art of reinvention like she did—a true career chameleon. She's built products, struck deals, and shaped policies at places like Intuit, Stripe, Netflix, and Block. Now, she’s cooking up her latest pivot: knocking on doors as a newly appointed local Democratic Party representative while kick-starting her startup advisory business.
As someone who has successfully navigated multiple career transitions, what would you say is the secret to doing that effectively?
Staying curious and adaptable has helped me navigate career transitions. My journey's taken me from public policy to partnerships, then to product management and broader leadership roles.
I realized that skills from one field often translate surprisingly well to another. My background in government affairs and communications turned out to be incredibly useful in partnerships and product roles. I realized I could bring different teams together and find common ground, even when they were speaking totally different languages.
Of course, there were moments when I felt out of my depth. I remember joining Stripe in 2016 as the first non-engineer on my team and realizing I had to quickly fill some technical knowledge gaps. I found a few colleagues who created a safe space for me to ask those basic questions and eventually hold my own in deeper product and technical conversations.
I also enjoy putting in the extra hours to go very deep on topics. I do that because I’m genuinely interested in learning. I also found that it created some early credibility among my peers and managers and gave them more willingness to invest in coaching me.
You've often found yourself in new fields where you had little prior experience. Have you developed a specific approach or mental model for quickly getting up to speed in these situations? Is there some sort of common playbook to ramping up on any topic?
Jumping into new fields can be pretty daunting. That impostor syndrome hits hard, especially if you’re a woman or a minority.
One thing that helped was reminding myself that I brought unique knowledge from my different background. For example, when I joined some very technical teams, I was able to contribute with communications skills and deep empathy for the customer. Having started my career working on policy and regulatory issues, I feel I am a way better product person working in Fintech. The legal, compliance, and policy teams I work with often tell me, “You are one of the only product leaders we know who bring us to the table early.” And that’s because I know the products will be better, safer, and actually faster to market if I understand the critical legal and compliance issues we need to navigate. These are a few examples of the types of skills that come more naturally for people who have worked in different types of roles in their career.
Leaning into my curiosity also served me well. I've learned there's power in asking those "dumb questions” and not just privately. If I had a quarter for every time someone DM-ed me after a meeting where I asked a question saying, “I’m so glad you asked that! I was too scared to ask!”, I’d be very wealthy. I guess I just kind of gradually lost the fear of being seen as the inexperienced person in the room. Plus, people like to talk about what they know, and I’m always a grateful student who sponges up new information.
When people seek your advice on switching careers, what guidance do you typically offer?
When people ask me about switching careers, I tell them it's rarely a 180-degree flip. Think of it more like a tree's root system - there are twists and turns you can't always see from above. Look for connection points and ways to bridge the gap.
I also love this idea of "planned happenstance", a theory established by the late Stanford Professor John Krumboltz. It's about putting yourself out there in areas you're curious about, without any prior expectation of what could result, and taking advantage of opportunities that can magically present themselves. You'd be surprised how often this works if you let go of your desire to strictly control the future.
Here's a fun example: During my sabbatical, I ended up hosting our town's annual Pet Show. I'd never done anything like it, but I love our community and wanted to more deeply understand its history, plus I wanted to meet more people. Admittedly, I’d also been toying with the idea of trying stand-up comedy one day. So I channeled my inner Christopher Guest, learned about local traditions, and contributed some of my planning skills to help our town make it a success. In addition to savoring all the joy from the children and adults parading around their adorable common and uncommon pets that day, I also got connected to a local political leader. That eventually led me to start volunteering with local political efforts and later I was formally appointed to a vacant elected seat on the local Democratic Committee. Now, I'm knee-deep in political organizing and locally supporting the campaign efforts of the Presidential election, as well as critical Congressional and local state campaigns. While I would have eventually found myself in some version of this political engagement work, I do think it happened faster because I put myself out there to try something new.
Seek joy and follow your curiosity. You never know where it might lead!
I love this idea of "planned happenstance". It's about putting yourself out there in areas you're curious about, without any prior expectation of what could result, and taking advantage of opportunities that can magically present themselves.
Is there a book or author you’ve found yourself returning to for wisdom?
Specifically related to transitions, I’d recommend “Transitions” by William Bridges which is useful not only for career transitions, but also personal life transitions like the birth of a child, the loss of a loved one, marriage, divorce, or other big life changes. “A Liberated Mind: How to Pivot Toward What Matters” by Stephen C. Hayes is also pretty foundational in thinking through values, identity, and psychological flexibility - all things you need to be open and honest about when you’re thinking about a career or life transition. I also read “Women, Money and Power: the Rise of Economic Equality” by Josie Cox, a talented journalist who tells the untold stories of pioneers across women’s reproductive rights, Wall Street, big tech and more. I read it just at the right time as I was starting to get involved in some reproductive rights work and was also at the same time reflecting on my own journey as a female leader in these traditionally-male dominated businesses in finance and tech.
And just for fun, because this newsletter celebrates polymath vibes, here are some other books that I hold dear: “St. Pancras Station” by Simon Bradley which tells the history of my favorite building in the world, St. Pancras Station in London; “Made for Living” by Amber Lewis which I’ve been referring to a lot as I’m working on my house; and I’m currently hanging out by my mailbox waiting for my pre-ordered copy of Colin Greenwood’s “How to Disappear” - the photography book of his band, and my favorite of all time, Radiohead.
You're now launching your own business to help startups build and scale their products. Was there a specific "aha" moment that led you to pursue this path?
I figured my experience across policy, partnerships, product and marketing at companies like Intuit, Netflix, Stripe, and Block could be valuable to a lot of businesses at different growth stages.
But there was also this pull towards having more control over my life. Things like being able to choose who I work with and having a flexible schedule that allows me to dive into my political advocacy work.
It's early days for my advisory business. Down the road, I might still end up back in a full-time role if the right opportunity comes along. But for now, I'm pretty excited about building something that helps founders and operators create meaningful stuff for the world. The founders and execs who I have been partnering with all have diverse experiences and challenges - it’s been very fun so far!
We both love big city living, but in recent years you’ve embraced a more pastoral lifestyle. I’m curious, what effects have you noticed from living in a quieter environment?
Never in a million years would I have imagined that I’d be living outside of a big city! I was always a big city person – NYC, London, San Francisco, DC, even Delhi. But COVID changed things for my husband and me, just like it did for so many others. Our Brooklyn apartment felt suddenly much smaller, and we craved being around nature more.
After multiple visits to the Catskills and Hudson Valley for hiking, we ultimately bought a house about 90 minutes from Manhattan, and it's been amazing.
Living among mountains and forests gives you perspective, especially when you're dealing with Silicon Valley stress. We've built strong friendships here, many with small business owners. It's rekindled my passion for helping small businesses thrive.
Surprisingly, I've found myself more artistic and creative up here, surrounded by other creatives who've chosen this lifestyle.
Plus, the best part is that I didn't have to say goodbye to New York City. I'm there a few times a month, so I still get my fix of public transport, urban architecture, and a high density of museums and diverse food. It feels like we’ve found the perfect balance between pastoral peace and city energy. I feel grateful.
Your other big shift lately has been stepping in the world of politics. Can you share what motivated you to give local government a try?
Politics has been a passion of mine since high school. Then I studied political science in college and spent the early part of my career in government affairs before diving into tech.
Recently, I've been thinking about how to use my business skills to tackle issues like affordable housing, climate change, and reproductive rights in my local community. When the opportunity came up to serve on my local Democratic Committee, it was a no-brainer.
I'm loving the grassroots work. I've done everything from organizing postcard writing events and penning letters to local newspapers, to registering voters and canvassing door-to-door. The conversations I've had with neighbors, even those on the other side of the political spectrum, have been enlightening and heartwarming.
We need more connection and empathy, not more walls. That's what's really driving me in this new political adventure.
Lateral Thought
“The greatest events—they are not our noisiest but our stillest hours. The world revolves, not around the inventors of new noises but around the inventors of new values; it revolves inaudibly.”
Friedrich Nietzsche