· Charlie Holland · Leadership · 5 min read
Stop Calling Freelancers Mercenaries
The 'missionaries vs mercenaries' framing is lazy and wrong. After 30 years of freelancing, I've seen full-timers who don't care and contractors who bleed for the outcome. It's not about employment status — it's about who gives a damn.
There’s a line that gets trotted out in every leadership book, every startup pitch deck, every all-hands meeting where someone’s trying to justify why they don’t use contractors: “You want missionaries, not mercenaries.” The phrase was popularised by John Doerr of Kleiner Perkins back in 2000, and it’s been parroted uncritically ever since.
The implication is clear. Employees are missionaries — devoted, passionate, aligned with the mission. Contractors are mercenaries — guns for hire who’ll take the money and disappear. Build your team with the former, avoid the latter.
It’s a nice soundbite. It’s also rubbish.
The framing is lazy
I’ve freelanced for 30 years. The freelance market has grown enormously in that time — over 70 million Americans alone now freelance — and I’ve worked inside startups, scale-ups, global banks, pharmaceutical companies, media conglomerates, and everything in between. My job has always been the same: fill the gaps, fix the problems, build the things that need building, and leave the team in better shape than I found it.
In every single one of those engagements, I’ve worked alongside permanent employees. Some of them were brilliant — passionate, skilled, deeply invested in the outcome. Some of them were marking time — doing the minimum, protecting their patch, resistant to change, and waiting for their next promotion.
And guess what? The same is true of every contractor I’ve worked alongside. Some are exceptional. Some are terrible. Employment status tells you precisely nothing about whether someone cares about the work.
The “missionaries vs mercenaries” framing persists because it flatters permanent employees and gives leaders a simple heuristic that avoids thinking. Even Marty Cagan at SVPG, who uses the framework, acknowledges that the distinction is about mindset, not employment status. But the way most leaders use it, it’s just a convenient excuse to avoid thinking.
You don’t call us for fun
Nobody brings in a freelancer because everything’s going well. You call us when the roof’s leaking.
The project’s behind schedule. The architecture needs rescuing. The team doesn’t have the expertise to deliver what they’ve committed to. The permanent hire you were counting on fell through and the deadline hasn’t moved. Something is broken and needs fixing, quickly, by someone who’s done it before.
That’s not a mercenary showing up to collect a bounty. That’s a specialist being brought in because the situation demands it. The same way you’d call a surgeon, a structural engineer, or a barrister. Nobody calls them mercenaries.
The incentive argument is backwards
The usual defence of the “mercenary” label is that contractors don’t have the right incentives. They’re not aligned with the long-term success of the company. They’ll optimise for their own interests, not the organisation’s.
This is exactly backwards.
A permanent employee has a salary regardless of outcome. Their incentive is to not get fired, which is a very different thing from delivering results. They can coast for years in a large organisation without anyone noticing. We all know people who’ve done exactly that.
A freelancer’s reputation is their entire business. Every engagement is an audition for the next one. If I do a bad job, I don’t get called back. If I do a good job, I get referrals. My incentive is to deliver — visibly, measurably, and in a way that people remember. I don’t have the luxury of coasting.
Who has the stronger incentive to care about the outcome? The person whose salary arrives regardless, or the person whose next engagement depends on this one going well?
”But they’ll leave”
Yes. That’s the point. I’m a fractional resource. I come in, deliver, transfer knowledge, and leave. The team should be stronger for my having been there, not dependent on me staying.
If your architecture collapses when one person leaves, you have an architecture problem, not a staffing problem. And that’s true whether the person who leaves is a contractor or a permanent employee who got a better offer.
The best engagements I’ve had are the ones where I’ve actively worked to make myself redundant. I pair with the team. I document decisions. I mentor junior engineers. I design systems that the existing team can maintain and extend without me.
That’s not mercenary behaviour. That’s professionalism.
It’s about who cares
Strip away the employment contracts and the labels and it comes down to something simple: some people care about the work and some people don’t. That split has nothing to do with whether they’re permanent, contract, freelance, or fractional.
I’ve seen permanent CTOs who couldn’t describe their own architecture. I’ve seen contractors who stayed up all night to fix a production issue for a client they’d been with for three weeks — because the system mattered and they took pride in it working.
It’s not missionaries vs mercenaries. It’s people who give a damn vs people who don’t. And in my experience, the ones who give a damn are distributed pretty evenly across both categories.
So the next time someone drops the “missionaries not mercenaries” line in a meeting, ask them this: when things broke at 3am, who actually fixed it? The missionary on salary, or the mercenary on deadline?
I know the answer. And if you’ve been in this industry long enough, so do you.
