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The line went quiet for a second. I'd just told her, almost as an aside, that I'm done with remote work, and she'd been chasing a remote job for over a year.
I've been sitting with why that moment stuck with me, and I think I finally know.
Chasing a remote job and chasing actual freedom are not the same pursuit. They look identical from the outside. I spent years confusing the two, so I feel qualified to say that with some confidence.
I used to be exactly where she is. Back in 2017, when I quit journalism, I went chasing remote jobs specifically, quietly assuming "remote" was just another word for "free." It isn't, as it turns out. My most recent one wanted me starting 8am Jamaica time, which is exactly, to the minute, when I'm dropping my kids at school. 1 hour lunch, which I needed for pickup. Done at 5, right as dinner needs to start.
Two questions I wish someone had asked me back then, so I'll ask them of you instead: what are you actually trying to get back by going remote, time, location, income, something else? And does this specific job give you that, or does it just give you the word "remote" stapled to your old schedule?
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Here's what I've slowly pieced together since, in no particular order, except maybe the last one:
1. Remote doesn't mean flexible. It just means somewhere else.
My most recent role wanted the same 8-to-5 structure as any office job. Same cage, honestly. Just a nicer view.
2. You don't need to keep interviewing for the right version of it. You can build the container yourself.
I stopped chasing remote roles and went back to freelancing instead. Not because remote work personally wronged me once. Because I'd sat through enough interviews since to know the schedule problem wasn't a fluke, it was just the default setting.
3. Nobody else gets to define what flexible means for you.
I'm building toward 4 hours a day, 4 days a week, on my own terms. One freelance client and one coaching student at a time. Nobody's handing that out as a job listing. You kind of have to build it yourself, slowly, on purpose.
4. You don't owe anyone an explanation for wanting something different than they do.
The person on that coffee call was genuinely shocked I'd walk away from something she wanted so badly. I didn't need her to get it. She doesn't need to want what I want either. We're just after two different things that happen to share a job description.
All four of those, if I'm honest, come down to one decision, made slowly and then all at once: stop optimizing the job title, and start asking what you were actually trying to get to in the first place.
Stephen
P.S. The person on that coffee call asked me how to stop being afraid to tell their own story, the way I'd just told mine. Reply and let me know if that question finds you too.
