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An Instagram DM became a freelance project, and the freelance project became a full-time role three months later. I wouldn't have predicted any of those steps.
I'd been working as a freelance brand designer in Buenos Aires for two years. The work was inconsistent. Some months were fine. Some weren't. I'd been thinking about going back to a studio environment for the routine and the team, but most of the studios I wanted to work at were either based in São Paulo or paying in pesos at rates I couldn't make work.
One Buenos Aires design studio was different. They were small, six people, and they paid in USD via Deel because most of their clients were US-based. They had a public Instagram where they posted their work for a specific recurring client, a US-based health tech company. I'd been following them for about a year.
I had a thought. What if the studio would be open to a small spec project? I picked their main public client and rebuilt three concept variations of how I'd reposition the brand. I was honest with myself about it: this was speculative, the studio almost certainly hadn't asked for my opinion, and I was just going to send it as a portfolio piece, not a job application.
I DMed the founder. The message was three sentences. I'd been following the work, I'd built three variations of how I'd approach a brand refresh for the public client, did she have ten minutes to look at it? I attached a single Figma link.
She replied two hours later. The variations weren't what they were going to ship, she was direct about that, but they were the kind of work she wanted to be commissioning, and was I available for a one-off project they'd been needing to outsource? I was.
The project was a brand refresh for a different client. Three weeks of work. Five-figure fee, paid in USD. I shipped it on time. The client signed off without revisions, which is rare.
A month later the founder asked if I was open to a longer engagement. We agreed on a three-month rolling contract. After two months she asked if I'd consider going full-time. The role was permanent, paid in USD via Deel, and would mean working with the studio's existing six-person team rather than continuing as a contractor.
The offer was US$30,000 base. A number that doesn't look like much in dollar terms but works at the current exchange rate and is meaningfully better than what I'd have made independently. I asked for US$36,000, citing the depth of the work I'd already shipped and the cost of switching from contractor to employee structure. They came back at US$36,000.
I accepted. I'd sent two real applications during the entire search. Both went to job boards and both went unanswered. The Instagram DM was the application. I keep telling other designers that the studios you actually want to work at hire from their DMs, not from their job listings. They mostly don't believe me until they try it.
I'd been applying selectively, only four applications over those two months, because I didn't want to waste time on roles that weren't actually interesting. Most of my search was quiet and slow, and honestly a little discouraging. Then I came across a Substack post by the CTO of a New York data company about their decision to refactor their entire data pipeline around dbt and Snowflake. The post was technical, specific, and honest about the tradeoffs they'd made. It wasn't marketing. It read like someone who actually lived inside the problem, and I recognized a lot of the same pain points from my previous role.
I spent a couple of evenings on a cold email. I didn't pitch myself generically. I referenced specific paragraphs from the post and linked a public GitHub repo I'd built for stream-to-batch reconciliation. The repo wasn't perfect, but it was real work: documented, tested, and directly relevant to what he'd described. I figured if he was the kind of engineer who wrote that post, he'd at least look at the code. Three days later he replied. No recruiter, no application portal, no automated acknowledgment. Just a direct response asking if I wanted to jump on a call that week.
The process ended up being four rounds over about nine weeks. The first call was conversational, more mutual vetting than a formal screen. The third and fourth rounds brought in the broader data team and covered system design and past-project deep-dives. But the second round was the one that stuck with me. It was framed as a live SQL pairing session, and it started that way, but somewhere around the thirty-minute mark we were both heads-down on an actual production query they were struggling with. We went ninety minutes. I didn't solve it completely, but how I reasoned through it mattered more than any clean answer would have.
The offer came in at $145,000, hybrid in New York. I accepted without hesitation.
The freelance piece I pitched in March became a full-time role in June. The thing that made it work was that I never asked them for a job.
I'd wanted to write for a Madrid magazine since I moved to the city four years earlier. They were a serious publication, long-form, edited, careful about facts, and they paid their writers, which is increasingly rare. I'd read every issue I could find for a year before I tried to do anything about it.
When I started job-hunting, it didn't go well. I sent thirty applications across three months, mostly to content roles at SaaS companies that wanted "blog posts" rather than journalism. I got two interviews, one of which was the most depressing forty-five minutes of the search. A content marketing manager told me, plainly, that the role was generating SEO content with the help of an LLM and that the human writer was there to "make it sound better".
I went home that night and decided to stop applying for content jobs and just write the kind of piece I wanted to be paid to write.
I picked two ideas I thought the magazine would actually publish. One was about a small Madrid neighbourhood that had been gradually transformed by remote workers. The other was an interview with a local food cooperative. I wrote three-paragraph pitches for each and emailed them to the editor.
She replied to one. The neighbourhood piece. She liked the angle, she'd been considering pitches on the same beat, and she was willing to commission a 1,500-word draft on spec. The fee was €200, paid within thirty days of publication.
I wrote it. Took ten days. The edit was thorough, she pushed back on three sections and I rewrote them. The piece ran in the May issue.
In late May, two months after the freelance piece had been agreed, the editor emailed me. They'd opened a permanent staff writer role and she wanted to talk before posting it. The shortlist was already her, the editor-in-chief and the publisher. The "interview" was a forty-minute conversation about the work I wanted to do, what I was reading, and one piece in the magazine I'd have edited differently.
The "test" was a 600-word writeup on a topic she gave me the next day. I had two days. I wrote eight hundred words, cut a hundred and fifty, sent it. They sent the offer two days later.
The offer was €26,000 base, which is staff-writer money in Spain and is fine. I asked for €30,000, citing the freelance work I'd already done for them and the fact that I'd be running their newsletter as part of the role. They came back at €28,000 plus a small monthly stipend for assignment travel. I accepted.
What worked: writing the kind of piece I wanted them to pay me for, before they were paying me. The freelance work was the interview. The actual interview was a formality.
30Applications
2Interviews
4 monthsSearch length
Cold outreachSource
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