Work, Ambition, and Identity

A decade wrestling with overlapping arenas of renewal

People love to ask what you do for work and understand your professional trajectory. Often, it’s a surface question. Or, used to quickly categorize people in familiar boxes. But beneath this lies a far more interesting story. 

I don’t think you can truly answer questions about work without exploring ambition and identity. Looking back over the last decade, I see how interconnected they are for me. Tracing my trajectory with work only makes sense within the context of my evolving ambition and changing identity. 

So I’ll share my journey with work but it’s less about what I did and more about why I did it. It’s the story of how my ambition evolved from being externally driven and narrowly career-centric to internally inspired and broadly dispersed. It’s how my identity expanded from individual labels into a web of multifaceted and interconnected areas. 

Beginning

I started my career in Management Consulting working with Fortune 500 companies on strategy and growth. I wish I could tell a powerful story about why I did this. In truth, it was because competition was at the core of my identity at the time.

I was a college baseball player. Each class was a battle in the war of “winning” school. I studied economics in case I wanted to compete in business and philosophy to train my reasoning skills in case I wanted to enter the legal arena. When it was time to pick a professional launching pad, I just asked: “what is the most competitive job to get”. Seriously. I was told Investment Banking or Management Consulting and pursued both with great enthusiasm and effort. 

Luckily, Consulting turned out to be a good launching pad. Fast-paced. Constant learning. Tons of variety. In the first year, I soaked up the chance to explore industries and participate in projects far above what my experience justified. Then I hit a wall. It wasn’t physical exhaustion but existential angst that I was climbing the wrong mountain. I looked around and realized I didn’t want my boss’s job. Worse, the idea of working for our clients at a big company repulsed me. It looked like bureaucratic hell.

Questioning

For the first time, I started to question my ambition. Since I didn’t want to move up in the consulting world, maybe I wasn’t that ambitious after all. If others were more driven to succeed here, they must be more ambitious than me. Next came my identity. If I wasn’t a deeply competitive achiever, who was I? 

I found a safe solution: just externalize the problem. Instead of reflecting inward, I blamed the environment and circumstances. I wasn’t a corporate guy. Not enough risk and reward. I must be a start-up guy. That’s where I’d find my real ambition. Innovator. Builder. New exciting buzzwords to build an identity around.

I tried working for a start-up and it only made me want an even more aspirational identity. The problem must be that I was still an employee, not an entrepreneur. No true, “skin in the game”. The most ambitious people wouldn’t respect someone with “just a job”. I craved higher stakes. Responsibility. Calling the shots. I had to start my own thing.

This is when my ambition and identity really started to battle. My ambition said: “go big”. Create a venture-backed start-up. But my identity countered: “chase independence”. Create something you can fully own. For context, this was in 2015 during the peak of the anti “lifestyle business” sentiment. Before people like Nick Huber made owning a small business cool and things like the Calm Fund existed. I knew I wanted to start a local business but choosing that path felt like another mark against my ambition. It’s funny to write this now with the hindsight of knowing how hard it is to start and run a local business.

Complicating

I had a background in personal training so I thought about starting a fitness business. Yet, it didn’t feel right. So I leaned in on another of my personal passions: food. I came up with a crazy idea to try to make healthy food more fun and flavorful. 

We’d start a food truck to introduce people to dishes like braised local meats, harvest rice bowls, and cauliflower mac and cheese. The truck would do the marketing to unlock corporate catering clients and acquire home-delivery customers. The master plan was called Medley-At-Home where you’d get a bountiful collection of pre-cooked healthy food that you could mix and match throughout the week. 

I could and will eventually go deep into all my experiences and lessons from the days of Medley. For now, the takeaway is simple. My biggest mistake was making this business too much about my identity. Small businesses are hard enough. The food industry is brutal. My values around things like ingredient quality and nutrition made it 100x harder to be successful within the business model we picked. It wasn’t enough for me to create a thriving business. I needed to do something that would also project my point of view onto the world. My identity was shaping my ambition and my ambition was adding layers of unhelpful complexity.

The business didn’t fully fail but it didn’t live up to my vision. We ended up selling it to our chef and his family so they could run it within a sustainable business model. But it did bruise my ego, shatter my identity, and alter my ambition.

Wandering

I was completely lost. I felt empty. I didn’t know who I was or what I wanted. I stumbled around. I did some solo consulting to pay the bills. Got swept up in maximizing my income. Sucked into the allure of FIRE (financially independent, retire early). It appealed to many parts of my identity but left me feeling hollow. My ambition fought back. I “needed” to make a dent in the world

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. Wanted an arena that felt meaningful. Craved more social approval (though I wouldn’t have admitted this then). I was once again looking to the external world to rebuild my identity.

This led me to replace “entrepreneur” with “healthcare fixer”. I knew how broken the system was and I decided to channel all my energy to help transform it. The job title didn’t matter. The salary didn’t matter. It was all about playing on the frontier of healthcare transformation. I shifted from being obsessed with income and investment growth to largely ignoring them. 

I took a job that would have been unthinkable just a few years prior. I joined a 5,000+ person healthcare system and plunged deep into the world of value-based care. I won’t bore you with the details (for now) but I learned more than I ever wanted to about how we deliver and pay for healthcare. And, I learned even more about myself.

Releasing 

This journey into and out of the healthcare industry is when I finally started to shift my thinking around Work, Ambition, and Identity. I had naively thought I might be able to help fix the system from the top-down. After working with everyone from doctors to hospitals and insurers to employers, it's clear to me that the only solution lies with each of us. We must all take ownership of our own health. Renewal begins from the bottom-up, with each of us. 

Instead of looking outwards to others and society for answers, I began to look within. I started to reconnect with my body. I began to garden. I shifted from a mindset of competition to one of cultivation. I created space for things to unfold instead of ruthlessly planning my life and strategically designing every step.

This space created a "fertile void"

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that let me see these three words in a new light. I started experiencing an identity that was independent of my Work. I encountered a different form of ambition. At first, it was uncomfortable. Before, my identity felt contained and explicit. My ambition was easy to digest. Now, they both felt nebulous and murky. 

As my work-driven identity dissolved, I felt a burning ambition across all facets of life. Instead of a desire to achieve goals that society told me were valuable, I felt a hunger to discover what makes me feel fully alive. Instead of a commitment to “winning” other people’s games, I felt a commitment to design a life that I deeply enjoy inhabiting

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. I saw how my ambition can be unleashed not just in work but as a husband, father, friend, gardener, writer, citizen, and whatever other components now make up my fluid and evolving identity. It’s not that I didn’t previously value or participate in these areas; it’s that I now felt permission to engage them with greater intention and intensity.

This shift dramatically improved my relationship with Work. Before I was asking too much of it: to pay the bills, define my identity, and support my ambition. Now, it’s just one piece of the puzzle contributing to my broader aim to live fully across my life. Necessary but not sufficient. Surprisingly, this doesn’t mean I take Work less seriously or put in less effort. In fact, this shift has unlocked greater energy and opportunities for meaningful Work.

Reimagining

So, what does this actually look like?

It means writing and sharing this without any goal. It’s hosting the On Renewal podcast without knowing where it’s going. It’s running a fitness business without letting it define my identity. 

It’s helping other small businesses to explore ideas around “renewal” and “generative capital”. It’s building a suburban food forest to bring my love of nature into my backyard. It’s learning about self-sufficiency to scratch my inklings for independence. 

It’s letting go of a life in North Carolina to move our daughter to New England to be close to our relatives. It’s investing effort to rebuild and create a true connection to place. It’s contributing to build local community and connect virtually with people around the world.  

It’s channeling ambition across all these areas, letting identity emerge from within, and realizing that “work” is not just what you do to get paid but everything you do to live your life fully.

1. Dan Shipper wrote a powerful essay called “Changing the World to Change Yourself” that argues that many people’s desire to change the world comes from a desire to change something about themselves and experience love or respect. We just recorded an episode of On Renewal exploring this and other similar ideas that will be released soon.

2. Fertile Void is a phrase from the Gestalt Cycle of Experience developed by Fritz Perl. He described it as an experience where “meaning-making ceases and being begins.”

3. I shared a loose formation of these ideas on Twitter and Paul Millerd captured the essence perfectly by replying that it’s a “shift from legible ambition (grind) to illegible ambition (flow)”. He then expanded on his thoughts on ambition in this great thread. I had Paul join the On Renewal podcast and we explored these ideas in depth. You can listen to the episode here.