Seek Out Quests
How to avoid wandering without purpose.
I’m writing this while on the flight back to New York City from Miami where I attended my first Summit at Sea, a 3-day excursion that gathers ~1,000 other business and creative leaders to connect, explore, and exchange ideas.
It was a transformative experience that I hope to share with you in the coming months.
During the voyage, I had the chance to reflect on my career journey, view it from a new lens, and to think about what’s next for me.
I’m sharing my thought process with you, with the hopes that it’ll inspire and help you, no matter where you are in your journey.
I spent a large chunk of my childhood playing a game called RuneScape.
It was like the Sims, but in a medieval world. You had a virtual character in a virtual universe that you could use to hang out with your friends, level up skills, and do quests.
I loved RuneScape. It was my obsession—and I've probably spent over 5,000 cumulative hours playing this game. That's equivalent to playing 2 hours a day, every day, for 7 years!
The purpose of the game was to level up skills, complete quests, and win rewards, which in turn, would allow you to level up other skills, complete more quests, and win better rewards.
Quests were delightful adventures you could do with friends that let you explore exciting new terrains, tackle challenging puzzles, and meet fascinating characters.
However, to complete quests you needed to meet certain prerequisite levels that were fairly difficult to attain (but it was always worth it).
To me, quests were the entire point of the game—and I would constantly seek them out.
Looking back, I’ve realized how much the game has influenced my worldview and the way I approach my life and career.
My journey has been a series of leveling up skills and completing quests, and as I think about what’s next—I’ll continue to use this heuristic to not only look back, but to explore ahead and plan for the future.
For those of you who are in a transitionary or exploratory period, I wrote this for you. Perhaps it’ll help inspire the journey ahead.
Levels & Quests
I think of my career as a sequence of quest-seeking, quest-preparing, quest-completing activities.
Quest-seeking (find the things you want to do)
Quest-preparing (prepare for the things you want to do)
Quest-completing (do the things)
With this in mind, here’s my career journey thus far:
Quest 1: My Foray into Business
My first quest was an opportunity to intern at an advertising company called J. Walter Thompson that did work for global brands like Burger King and Nike.
It was my foray into business, and I didn’t really know what I was doing—but I did know that I wanted to gain the skills and experience to land a job after graduation.
I went in with the goal of leveling up three basic skills:
Execution – I call this “doing the job well” and carefully listening to instructions to deliver quality outcomes on time.
“Business 101” – Building my excellence in business basics, like writing emails, giving presentations, running meetings, etc.
Building professional & business relationships – Working with leaders, peers, and cross-functional teams with proper business communication etiquette.
My theory was that by leveling up these skills, I would become someone who was diligent, personable, and business-savvy. To me, these were the most employable traits that would maximize optionality in my career search.
I succeeded! I graduated a year later and landed a job at Bell Canada, a telecommunications company, as an analyst.
On to the next quest.
Quest 2: Making the Leap to New York
After a while, I was getting comfortable. In two years, I had leveled up basic skills and even capped out on others. How good can you really get at booking meetings?
I had always known that Bell wasn’t the end game.
In fact, since a young age I had always known that I wanted to live in New York City. It a place that was vibrant, exciting, and seemed to be the central hub for creativity, ideas, and fun.
I had stumbled upon my next quest
But to get there I had to jump through a few hoops: I had to convince a company to hire me, sponsor my visa, and help with my relocation.
This was going to be a tough one and I needed to level up a different set of skills:
Analytical thinking and problem solving – Solving ambiguous problems through structured thinking.
Persuasive storytelling – Telling my story in a compelling enough manner to convince strangers to hire and invest in me.
Grit – The tenacity to do anything to get the job done.
My plan was to be a Swiss army knife of business—someone who can adapt and problem solve in a wide variety of circumstances. My theory at the time was that every organization needed one.
It worked—and two hundred interviews later, I made it to New York City.
I landed at Facebook (now known as Meta) as a Business Planning and Operations Lead for North America. Frankly I was grossly under-qualified, but that’s a story for another time.
Quest 3: The Art of Gathering
Facebook was incredibly rewarding and I adored my team, but after a while I was once again on the pursuit for a new quest.
It was 2020, and the idea of community building piqued my interest. The impact of COVID-19 drove a mass exodus of people from the city, and it was one of the most difficult and isolating periods in the history of the nation.
As someone who moved to New York City with no family, no network, and no community, I experienced the pain of isolation first hand. I knew how difficult it was for others, so I dedicated my time to gathering people together.
The gatherings started small but immediately took off—and what started as a community of dozens, became hundreds, and was quickly evolving into thousands. To properly scale, I needed to learn how to market, operate, and manage a community at scale.
So once again, I knew I needed to level up new skills:
Communicating at scale – Writing, speaking, and sharing information with tens of thousands of people. Example: Twitter.
Influence and negotiation – Convincing partners and vendors to work with me and provide the infrastructure to make the community gatherings possible. I talk about how I negotiated the cost of a venue from $65,000 to $0 here.
Building consumer tech experiences– Creating product experiences to facilitate human connection at scale.
Two years later, I was able to scale my community to 100+ events for 10,000+ attendees, building an audience of 60,000+ followers across 3 platforms.
I also started advising Cliff Lerner on building his social app, Saturday, and we saw a ton of momentum, onboarding tens of thousands of users and raising $2 million dollars. It was a clear signal that everyone was longing for human connection.
Cliff taught me a lot about product-building, which led to me serendipitously landing a job at Google as a Global Product Lead.
My Current Quest
Today, I’m a Global Product Lead at Google. I’ve been here for six months and I’m constantly grateful that I get to work with some of the brightest minds in the world.
Outside Google, the events, community work, and writing invigorates me, and I think I’ve found my calling:
To create unique experiences to bring together the most extraordinary and remarkable people in the world.
I’m rapidly scaling my events (I’m hosting 9 events in 4 cities in the next 4 weeks!), but also deepening the value by enhancing the curation, refining the ways in which people connect, and increasing the social and business value to attendees.
With that in mind, I plan to level up these skills:
Developing evangelists – Scaling my mission across the nation by building and delegating to future leaders and community builders.
Creating media – Creating content and leveraging publicity to invite the masses to participate in my mantra. Like TikTok!
Connecting humans – Designing experiences to encourage people to open up, connect, and support each other.
If I had to add a fourth: to continue to create consumer tech experiences to complement what I’m doing in the IRL space.
But I’ve just started on this quest, and I’m still learning, experimenting, and gathering information with an open mind.
Seek Out Quests
How can you can apply this to your own journey?
First, start by reflecting on the quests you want to take part in.
What things interest you?
What adventures excite you?
What causes do you care deeply about?
What life experiences do you want under your belt?
What do you want to have accomplished before you leave this world?
It helps to start with why. We all have a unique set of circumstances, characteristics, and traits that result in different motivations. What drives you?
Next, reverse engineer the skills required for that quest.
What soft skills do you need?
What technical skills do you need?
What do you need to be able to signal?
What experiences do you need to gather?
What stories do you need to be able to tell?
Focus on first principles: the broad, foundational tree trunks of skills, tools, and experiences required to get the job done.
Lastly, understand how you can acquire those skills.
Who can teach you?
Where can you learn these skills?
What projects can provide you with the experiences needed?
With this exercise, you should gain clarity on what your next quest is—and ideally have a plan to go after it.
I’ll leave you with this: at this very moment, there are an infinite amount of opportunities available to you, but without seeking out quests, you’ll just be wandering without purpose.