Draft Four: Freelance lessons revisited

Technically, this is about repeating mistakes. But I’ll be generous and call it a reminder that time is finite and freelance work can swallow it whole.

Last weekend was the first one with theoretically no commitments to others in almost three months: no travel, no workshops, no coffee-work-dates. It even followed a mid-week break in Italy, where my partner and I fawned over food and Mumford & Sons. In a balanced person’s universe this should have carried over the weekend. In my upside down one, Saturday became Monday. I was tempted to skip this week’s letter entirely but writing this down felt like the clearest way to remind myself how I can choose better in the future.

The reason for these grueling few months is because in 2025 I pledged to generate more of my own projects. The upside is that they deliver the most meaning and fulfilment. But they are not quite paying the bills. So, over the summer, I committed to a few freelance projects. It looked feasible from the distance – they would be Future Me’s problem.

Last year, I made a similar mistake, and jotted down some lessons. This letter is a rewrite and an update.

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Money. This year has been more stable, but the combination of Romanian inflation and uncertainty still makes it hard to feel secure. Which means I said “yes, I’ll do it” more than I should have. One reason to say “yes” as a freelancer is because incomes aren’t predictable. Back when I ran DoR, we were never able to pay ourselves great wages, but steady precarity felt safer than earning more, but erratically. When resources are dwindling, you can overcommit simply out of fear.

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Workload. When you freelance in journalism and other creative fields, especially when you are not the one making the work itself, but an editor, supporter or coach, things are unpredictable. Many journalists I know string together two-three long-term gigs of this kind, but when you’re not able to control the process, there’s scope-creep, things fall apart, you pick up tasks others have dropped and soon realize there’s no time for the personal projects you dreamt of, which was why you began freelancing in the first place.

I was involved in several projects as an editor/coach/coordinator. Doing them as a freelancer is more about quality than hierarchy, so usually the most I can offer is support (I do carrots, not sticks). Here is a familiar pattern: we build a sensible process, something derails early, and by the final week everyone is scrambling. It gets done, but at the cost of the other commitments we thought we had protected.

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Bandwidth. Precarity of all kinds – especially money, but time as well – messes up your brain. Your long-term thinking is crap, you run from fire to fire, you don’t make progress on larger projects, you’re never satisfied, you blame others. It doesn’t feel like freedom; it feels like a trap.

Capitalism plays its part, of course, but it’s not the whole story. A lot of us need time to learn the gap between how a project looks in our heads, and how it unfolds in reality. (And it can take years).

Where the structure of capitalism feels most oppressive is in what work we value. Artists – most, I’d argue – are walking around dazed and burned-out because they don’t have a choice. It’s burnout or career-change. Same for journalists I’d argue, and many activists, too. The organizations we labor in rarely generate or attract enough funds to pay a wage that allows one to be more mindful. Not enough money, not enough bandwidth, and all the consequences that follow.

There is genuinely well-meaning advice out there: want more peace, ask for more money. Let’s say you want to do comms in a three-person NGO fighting for the rights of an underrepresented group. You do the math, you look at Bucharest’s insane cost of living, and you ask for three or four times the minimum wage. They panic – maybe they can give you twice that, and even that might require some contract wrangling.

Two entities that both deserve more end up in tension, even though the real culprit is the larger system that allows for the scarcity. So don’t fall into the trap of saying: fix your business model, bring in more money, and pay more. But what’s the business model for helping migrant workers? Campaigning against domestic violence? Documentary theater? Climate journalism?

In these fields (and not only), and in this part of the world (and not only) we’re overworked, and underpaid. I do think we’d work less and work better if we felt safer. But guaranteeing that safety is not solely an individual responsibility – especially if we say, as a society, that such work is valuable to democracy or the human spirit. 

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Working conditions. I suspected it for a while, but now, in my mid-forties, I have no doubt: I don’t work well on the road, I could never do the “digital nomad” thing, and I’m more productive if I have “desk time”. Zooms are great when working with colleagues abroad, but in other cases they are painful. This is my experience and my preference, and I work hard to make Zooms inclusive and relevant. But do I enjoy them over sitting together with people? No.

Also this: remember that accommodating one’s flexibility comes at a cost for somebody else. In working relationships, the boundaries we so proudly draw can become somebody else’s burden.

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Deliverables. Here is a conundrum: what are people buying from you? Time or a quality product? Seems easy, right? Both, as it takes time to deliver quality. In practice, it’s fuzzier.

Let me give you an example. Someone asked our NGO to do a project; I said we’re no longer an established organization that can vouch for one, but what I can do is get together a bunch of freelancers, who’ll set time aside over a few months – say five – to be able to deliver on the expectations. The information to advance the work kept coming late, so little work was done in the first three months. The time set aside was wasted. We knew we couldn’t deliver what was requested within the remaining time, and none of us had more time to give to catch up, so we backed out.

No one was happy – from our point of view, we were paid for a time we couldn’t use right. From theirs, they paid and didn’t get the goods.

Often, I am on the other end, the one contracting freelancers. No matter how specific the conversations are or what gets put in writing, something will go off track, and this situation will come up. Someone will eventually say: my time is up even though the project is not done. Or they’ll settle for “this is good enough for me”.

I’m not saying it doesn’t happen in more traditional working relationships or in teams – of course it does. But it’s often harder to fix in freelance relationships, because most of us treat them as “not the real thing”. It’s a situationship, and if it’s not good, what’s the incentive of putting in extra work to make it good?

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Utility, quality, experience. The final piece of this puzzle. I’ll start with something I’ve said numerous times in the past year: How can we make more things that are useful to people, that are built with care and intention, that last, in ways in which we don’t cut corners, and that also bring in enough resources to cover costs and pay people decent wages?

Funny, right? In this economy? In this political climate? Still, in the privileged spot I’m in, what I mostly wonder is: isn’t it a shame if it doesn’t deliver for people on utility, quality or experience?

I enjoyed most of the things I’ve done over the past couple of years but also learned to accept this obvious fact: when I join others’ projects, I don’t have as much input or control over the utility or quality of the outcome.

I’m not talking about the illusion you can control what happens to a story or a project or an event or a team (or life, in general).

I’m talking about the decision making, and the execution, and the process that isn’t calibrated to deliver the best a particular group can deliver. Things happen in a way where you don’t know if your work was good or bad, because the messiness of the process obscures a full assessment.

It’s hard to do good work when the process keeps slipping from what we agreed on. The result is rarely as strong as it could be, and no one is quite sure why. I’m not saying this is how you should look at it, or that it’s advisable to treat everything as such, or that every project warrants an obsessive level of care and attention (especially with so many structural obstacles), but I am saying that I am at my best – and feel at my best – when these are the terms. This is why it’s sometimes easier to build and set your own terms, hence my attempt to pivot to those projects.

I know I can veer into overthinking, and some of you have found lighter ways to deal. But for my temperament, in this context, these are the lessons I’ve drawn and the things I’m trying to think through. Do share your own thoughts, revelations or tips for handling the freelance life, the dynamics of projects you run for yourself vs. those you run for others, or any other ideas about making things that you deem meaningful.

In the meantime, I’ll start sketching a wiser 2026.

A NOTE: Thank you for your response and your messages following my letter from two weeks ago, Build With Humans. I've already had some great conversations thanks to it, which I'm grateful for no matter where they'll lead.