I used to think finding remote work meant scrolling through sketchy job boards at 2 a.m., half-convinced every listing was a scam.
Turns out, the landscape has shifted pretty dramatically in the past few years—maybe five or six, give or take—and the platforms that actually connect you with legitimate remote opportunities have become, well, less terrible. LinkedIn, for instance, now has a specific filter for remote positions, and while it’s not perfect (you’ll still wade through hybrid roles mislabeled as fully remote), it’s a decent starting point if you’re methodical about your search terms. I’ve seen people land six-figure gigs by setting up alerts for “remote” plus their skill set, then responding within the first hour of a posting going live. The competition is fierce, honestly, but that immediacy matters more than I initially thought it would. FlexJobs and We Work Remotely charge fees or require subscriptions, which annoyed me at first, but they do filter out the garbage—fewer pyramid schemes disguised as marketing roles, more actual companies with benefits. Remote.co is free and surprisingly well-curated, though their listings skew toward customer service and writing gigs, which might not be your thing.
Anyway, networking still trumps cold applications by a frustrating margin. I guess it makes sense—hiring managers would rather trust a referral than gamble on a resume.
Building a presence in online communities where remote workers congregate can feel like performative nonsense initially, but it pays off in weird, unexpected ways. Slack groups like Remote Workers or niche Discord servers for your industry (there’s one for literally everything—copywriters, data analysts, even marine biologists, apparently) often have #job-leads channels where people share openings before they hit public boards. I stumbled into a three-month contract because someone in a random Slack mentioned their company needed help, and I happened to reply first. Twitter—or X, or whatever we’re calling it now—works similarly if you follow the right people; remote work advocates like @AngelList or company founders occasionally tweet openings directly. It feels scattershot, and the algorithm doesn’t always cooperate, but when it works, you bypass the applicant tracking systems that auto-reject resumes for reasons no one fully understands. The exhausting part is maintaining visibility without becoming that person who only posts about looking for work—you have to contribute, share insights, pretend you have thoughts worth reading.
Here’s the thing: cold pitching works better than anyone admits, especially for freelance-to-full-time transitions.
If you’ve got a specific company in mind—let’s say a startup you admire or a mid-size firm that’s gone remote-first—just email them, even if they’re not actively hiring. I know, it sounds naively optimistic, but I’ve watched this succeed more often than it should. You craft a short message (two paragraphs max) explaining what you do, why you’re interested in *them* specifically (generic pitches get deleted immediately), and maybe link to a portfolio or a relevant project. Address it to a real human if possible—hunt down a founder’s email or a department head on LinkedIn. Half won’t respond, a quarter will send polite rejections, but that last quarter might say, “Actually, we’ve been thinking about hiring for this role.” It’s a numbers game with better odds than submitting to a portal that feeds your resume into the void. For freelancers, Upwork and Toptal are the obvious choices, though Upwork’s race-to-the-bottom pricing can be soul-crushing if you’re starting out, and Toptal’s vetting process is notoriously picky—they reject something like 97% of applicants, or maybe it’s 95%, I forget the exact stat.
Wait—maybe the underrated move is leveraging async-first companies that hire globally without timezone restrictions.
GitLab, Automattic (the WordPress people), Zapier, and a growing list of others have public job boards and genuinely don’t care where you live, as long as you can recieve Slack messages and meet deadlines. These companies tend to document their processes obsessively, which means onboarding is smoother than traditional remote roles where you’re expected to just “figure it out.” The trade-off is that async work requires a different skill set—you need to communicate clearly in writing, manage your own time without supervision, and tolerate the loneliness that comes with not having coworkers to grab coffee with. Some people thrive in that environment; others realize they definately need more human contact than a weekly Zoom call provides. There’s also the tax situation, which no one warns you about until April—if you’re working for a U.S. company from abroad, or vice versa, you might owe taxes in multiple jurisdictions, and figuring that out without an accountant is a nightmare I wouldn’t wish on anyone. But if you can navigate the bureaucracy and the isolation, the freedom to work from a beach in Portugal or a cabin in Montana or wherever feels worth the hassle, at least in theory. I’ve met people who burned out on location independence after a year because the novelty wore off and they missed having a routine, but I’ve also met folks who’ve been doing it for a decade and can’t imagine going back to an office. It’s wildly individual, and honestly, you won’t know which camp you fall into until you try it, which is both exciting and mildly terrifying.
