I was the news editor of smaller of the two sister papers from 2003-2006, when I was pushed out by the IT manager (offsite at the other paper). Life conspired to keep me in town, as my fiancee was wrapping her undergrad. I got laid off the next year because the next place I worked shut down. I was able to quickly find a temporary position out of state via networking, but after signing a six-month lease, that job evaporated in only 10 weeks. Next job ran five months before layoffs were threatened, prompting me to find a position at a small weekly in the town I wanted to retire in but turned out to be nominally editorial but functionally advertising, leading to my first panic attack and resignation.
Owing to a lot of other shit happening, I wasn't in a position worth even putting on a resume for 14 months. On the other end of that was 19 months at the local paper where I'd landed, cut short because I decided a 50% raise to go into marketing was worth the ethical costs (and would return me to where I'd started in 2003). I only had to endure that for 10 months, when our three-year contract was terminated. I quickly found work at an audiobook publisher, but nine months into that, I walked out from a dressing down from my boss, on the production floor, for doing what I'd been told to do (and not in a malicious-compliance sort of way).
A couple months later, a SWAT team rousted my family from our hotel room Christmas Eve, and to my wife's surprise, before we got to the ground floor, I'd dialed the batphone at the paper. After being a source on A1 for the Christmas edition, I figured I had nothing to lose by emailing the editor. The old IT guy was gone, and they were looking for a part-time, temporary copyeditor ahead of the desk being shipped off to Texas, so I started the new year working across from the city ed from back in the day.
I did not follow my job at first, as it was a pay cut in a far more expensive city, but after nine months of fruitless searching, I got back in touch and took the job here, which I had three roles at over nearly five years.
So I'm seriously considering removing several of the intervening positions and stretching both stints to paper over both the gaps and the instability itself, as there's no one to call to verify when I worked there. Being midcareer, it's hard enough to get past software gatekeepers in the first place, but seven mostly nonconsecutive positions in as many years can't be helping my score.
The two main wrinkles I can foresee are a wholesale refactor of my LinkedIn could be a red flag, and the most basic of background reports would place me in two other states before remote journalism work was a thing.
I don't like the idea of lying on my resume, but what I'm doing now isn't working.
Are there other risks I'm not considering? I'd love some stability going forward, but I'm not going to expect any job to last long enough that this could stymie a promotion.
Want to make a point clear here -- never put anything on your resume that you aren't prepared to answer questions about. That means if you're lying about freelance (whether the above commenter means to imply you should), then you should be ready to answer questions about your freelance lie.
Same goes for any projects. For CS, if you have a pet project you wrote 12 years ago, but it's interesting enough to note on a resume, glance over it enough to know what it's about. You might be surprised by your interviewer installing your app on their phone or something.
I don't think you should lie about freelancing and 100% agree about "not putting anything you aren't prepared to answer questions about"
If you're thinking about it as "lying" you're doing it wrong. You should think about it as “explaining what I was doing professionally, to learn, grow and strengthen my skill set during these periods of less active employment.” Is glossing over the vast majority of your time that you spent living your life instead of hustling lying by omission? Maybe… but “I wasn’t doing shit professionally because reasons” is not a message you want a potential employer to hear.