Missionaries, Mercenaries, and Free Agents
the pitfalls of solely pursuing only money or only meaning
In startups, the terms missionary and mercenary describe two different types of employees. Missionaries are mission-driven and find meaning in empathizing with the customer and solving their problems. On the other hand, mercenaries are financially motivated and don’t have a strong sense of loyalty to the organization.
One is not better than the other. In my career, at times I’ve felt more like a missionary, drinking the kool-aid and excited to show up to work everyday because I genuinely thought what I was doing was saving the world. At other times, I’ve felt more like the mercenary, viewing the job as just a job, while appreciating the money for the lifestyle that it enabled. The interplay between these two modes shifted whenever I changed jobs, but it also morphed even when I was in the same role at the same company, showing how complex and dynamic this can be.
These two archetypes have shown up in different contexts beyond corporate work for hundreds of years. Missionaries were (and still are) devout religious people that travel the world spreading the word of God. Mercenaries have traditionally been the “hired guns” that fight in wars for money rather than political allegiance or patriotism.
The longtime advice from Silicon Valley legends1 has been to hire teams of missionaries, not teams of mercenaries. By employing people who deeply care about the mission and feel passionate about the problem, entrepreneurs will recruit people who are more engaged, motivated, and perhaps even work harder.
Today, I see the cracks beginning to form in this career strategy, for both employers and employees. It’s no longer tenable to promise meaning, empowerment, and glory to every one of your employees. Today's corporate 'missionaries' can dedicate years to a company's mission only to be laid off via email.
A century ago, Ernest Shackleton’s Antarctic expedition posted an ad that was brutally honest: “Men wanted for hazardous journey. Low wages, bitter cold, long hours of complete darkness. Safe return doubtful. Honour and recognition in event of success.” It’s hard to imagine, but back then there were people who signed up for this big adventure. Actually, I’d be willing to bet that many of us today are actually seeking something similar: a meaningful challenge that stretches and transforms us and requires total commitment and focus.
But it’s hard to find if we are only looking at full-time jobs to fulfill those expectations. Companies can only be successful to the extent that they solve customer problems and generate a profit consistently over the long run. Things don’t always go smoothly and as a result, downsizing, layoffs, and hiring freezes are all quite normal.
The trade is no longer fair. In the past, you could work at the same company for 40 years and along the way, start a family, buy a house, and then retire with a healthy pension waiting for you. Founders and CEOs, despite some being benevolent dictators, are not always going to have your back. They certainly can’t match the same level of power as kings and religious leaders. Devoting your life to a company is a fundamentally different thing than devoting your life to a kingdom or religion. Walk into any church, mosque, temple, or ashram, and you’ll likely be met with open arms and a bowl of warm food. That level of reciprocity is simply not the case when it comes to modern work, nor should it be.
After getting burned as a missionary, it’s tempting to swing the other way and treat work as nothing more than a paycheck. But it’s hard to sustain. Forty hours a week is too much of your life to fake indifference.
The missionaries I met through writing my climate tech newsletter moved with incredible conviction. To them, saving the planet was the most important thing, and that meant pouring everything into their work. But the mismatch between that passion and market realities (customer adoption, unit economics, fundraising cycles) often created an impossible tension. They'd keep giving and keep grinding until burnout became inevitable.
That's the cruel irony of being a missionary in corporate life. You're encouraged to treat the company like family, to bring your 'whole self to work,' to find your tribe. Then when layoffs come or the startup fails or you simply burn out, it feels like that family abandoned you. Whether you leave voluntarily or get pushed out, when you've given all of yourself to the job, the loss carries the heaviness of grief.
The mercenaries, mostly in finance or law, face a different void. At 18 and broke, money feels like the gateway to everything. At 27 and making $400K, they discover there's nothing more to buy2. It's one of the strangest phenomena I've witnessed: young, wealthy, unencumbered, yet spiritually bankrupt. They never spent time figuring out who they are or what they want, so the money just accumulates without purpose.
To be clear, I'm not against high-income careers. The VP at Google making $1M a year with three kids might feel deeply purposeful, even if primarily motivated by money. There's meaning in providing security, funding college, and creating opportunities for others. But without connection to something real, money stagnates. Money that doesn't flow, like water, turns rancid.
I've oscillated between missionary and mercenary myself, each swing bringing fresh disappointment. It’s not fair to expect all your sense of purpose and fulfillment to come from your one full-time job. It’s also a fool’s errand to think that there’s a specific number of dollars that will allow you to feel happy and at peace in perpetuity.
So where does this leave us? If the missionary path leads to burnout and betrayal, and the mercenary path leads to spiritual emptiness despite material abundance, what's left?
Rather than swing between two bad choices, I propose a third option: becoming a Free Agent.
The Free Agent recognizes what both missionaries and mercenaries miss. You can be sovereign without being solitary. They channel the passion of missionaries but refuse to martyrize themselves for companies that would post their job opening before their obituary. They practice the discipline of mercenaries: earning well, saving aggressively, negotiating fearlessly, but refuse to let money be the only scoreboard.
Like athletes between contracts, Free Agents understand they're always looking to join a team, to contribute to something meaningful. But they also know that trades happen, seasons end, and sometimes things just don't work out. This awareness is sobering clarity.
It's a double entendre that captures the whole philosophy. As a free agent, you're liberated from the scripts others have written for you. And you're agentic, capable of making choices and then actualizing them.
This isn't about wandering aimlessly between gigs. Free Agents do the upfront legwork of constructing what many call a portfolio career. What makes it a coherent patchwork isn't some neat story about how everything connects. It's coherent because each piece serves a specific purpose. They look inward to identify what they actually need from work: money, community, stability, learning, impact, creativity. Then they deliberately seek different elements that satisfy each requirement.
Free Agents take many forms. Some run agencies while exploring new ventures. Others keep full-time roles but pursue side projects, like producing films, hosting pop-up bakeries, and operating online pottery stores. Remote workers chase powder days or surf swells without asking for permission. Parents (presumably with more years of experience) leverage their seniority to expand mornings and evenings with their kids. The setup varies, but the principle remains: consciously designing work to serve your actual needs, rather than blindly oscillating between missionary and mercenary.
The Free Agents I know are ex-bankers, engineers, and consultants reimagining their relationship with work. They’re not throwing it all away. They’re experimenting with ways of working that feel creative, meaningful, and financially solid while remembering to lean on the skills they’ve worked hard to hone.
I've embraced this concept for myself, and it's given me both the freedom and the responsibility to figure out what work means to me, and how I want to relate to it. It's harder than just following a playbook, but it's also more honest and fulfilling.
After years of roleplaying missionary or mercenary, I feel more refreshed and energized with this Free Agent mindset. It’s given me permission to explore things that I wouldn’t have if I was solely optimizing for meaning or for money. I’m able to pursue my own work like my coaching or my writing, but I’m also able to explore working with others and teaming up to build something that is bigger than what any one individual could create on their own.
The shift from missionary or mercenary to Free Agent isn't a one-time decision. It's an ongoing practice of choosing sovereignty over scripts, integration over optimization. It starts with asking yourself: what do I actually need from work, and how might I construct that rather than hoping someone else will provide it?
This seems to be catching on. More people are rejecting the false binary and creating their own third way. At a time when people are starved for meaning yet balancing the practical demands of an ever-more unstable world, the Free Agent approach offers a path to honor both your need for purpose and your need for security, without sacrificing one for the other.
If this resonates with you, I'd love to hear about your own journey between these modes. I've been connecting with folks making the shift, and it's always exciting to hear how different people combine these elements of work.
P.S. I’m a coach.
I help people find work that actually matters and design their version of the good life (i.e. become Free Agents). If that sounds interesting to you, learn more here.
It was John Doerr who said “we need teams of missionaries, not teams of mercenaries.”
Other than a house, but the people that I’m referring to don’t actually want to a house yet