About the creator
Former community newspaper reporter. Former vacation rental owner. Current writer, storyteller, and night owl. NightOwlOS is where those lives overlap.
For thirteen years, Jacki worked as a reporter for a community newspaper in rural Nebraska. She covered city council meetings where nothing happened and then wrote the story that made it matter. She covered farm auctions, county fairs, high school football, and the slow fade of main street businesses. She wrote about the people the regional papers didn't think were worth a paragraph.
That beat taught her something a journalism degree never could: how to listen without an agenda, how to find the story underneath the official story, and how to write something that respected the reader's intelligence without confusing them. She was never a "man on the street" reporter. She wanted to understand things before she wrote them.
She won a few awards. She got better. She also watched the industry gut itself — layoffs, buyouts, papers folding, the slow strangulation of local journalism. She stayed longer than she should have, partly because she believed in the work and partly because she didn't know what else to do.
"The best story in the room is always the one nobody wants to tell you."— Jacki Wood
In 2018, Jacki bought a small vacation rental property — a lakeside cabin that needed more work than the listing showed. She managed it herself: the bookings, the cleaning, the guest messages at midnight, the frozen pipes in January, the review management, the pricing algorithms. She became her own property manager, bookkeeper, customer service rep, and maintenance crew.
The business worked. It wasn't glamorous, but it worked. She learned how to run something without a boss, how to make decisions with incomplete information, and how to be disciplined about money when the money was hers. She also learned that she could be good at things that weren't writing — and that this was both a relief and a problem.
She sold the business in 2022. Not because it failed — it was profitable — but because she'd started writing again, seriously, and she couldn't do both at the quality she wanted. The rental had always been a way to make money while she figured out what came next. The writing was the next.
"Running a business teaches you that 'good enough' is a discipline, not a failure."— Jacki Wood
After selling the rental, Jacki started writing seriously again. She had ideas — more ideas than she'd ever had time to write. But she had the same problem she'd always had: she couldn't track what she was working on. Drafts lived in email. Notes lived in phone apps. Ideas lived in her head until they were gone. She kept starting things and losing them.
She tried every productivity tool. They were all designed for people who could work in daylight, who had reliable energy in the morning, who could sit down and execute a plan. She wasn't that person. She was a night person. She did her best thinking between 10 PM and 2 AM. She needed something that fit her schedule, not the other way around.
NightOwlOS started as a Kanban board she built for herself — a simple system with three columns (Ideas, In Progress, Shipped) and a dark interface she could stare at without hating herself. She used it for six months before she showed it to anyone. The first person she showed it to said: "Can I use this?" She said yes without thinking about it. Then someone else asked. Then another.
She made it a product because people kept asking, and because making it a product meant she'd have to maintain it — and maintaining it meant she'd have to keep using it. That was the accountability she needed.
"The best productivity system is the one that doesn't make you feel bad about how you work."— Jacki Wood
Good writing takes time. NightOwlOS doesn't rush you. The system is built for depth, not throughput — for writers who want to finish something instead of starting everything.
Most productivity tools assume you're a morning person with reliable energy and no kids at home. NightOwlOS assumes you're just a person — with a weird schedule, an inconsistent flow, and things you care about beyond the work itself.
Thirteen years covering rural communities taught her that the most interesting stories live outside the national conversation. NightOwlOS is built for that kind of work — the slow, patient, undervalued kind that matters to the people living it.
The best Kanban board is the one you'll actually open. Three columns. No setup wizards. No gamification. No push notifications begging you to come back. Just your work, organized.
A full beat — city hall, courts, schools, farm auctions, obituaries. Award-winning work on rural community journalism and the slow erasure of small-town news.
Hands-on operator for four years — pricing, ops, guest relations, finance. Sold in 2022 to focus on writing full-time. Profitable, not glamorous.
Built the tool she couldn't find — a Kanban board for night workers and writers who keep losing drafts. Shipped to public in 2024.
Operating out of Galesburg, Illinois. Available for editorial, freelance, and consulting work — and typically awake when you are.
Editorial writing, brand voice, blog posts, newsletters. Develops pieces that respect the reader's time and earn the click.
Learn more →Reported features, profiles, memoir work, oral history. Long-form writing from rural and working-class lives — told without nostalgia.
Learn more →For writers and creators who keep dropping threads. Setup, audit, and rebuild of writing workflows that actually fit how you work — not how a productivity blog thinks you should.
Learn more →"Jacki has a rare ability to take something complicated and make it feel obvious. She didn't just write our case study — she made us understand what we'd actually built. We've used it in every pitch since."
"She showed up with better questions than we had answers to, and that's when I knew we were in good hands. The final piece wasn't just on-brand — it was better than what we'd described wanting."
"I sent her half a dozen half-formed ideas and she came back with three sharp angles I hadn't considered. Then she wrote one of them into something I'll actually use. That kind of editorial instinct is hard to find."
Currently booking new projects
Jacki takes on freelance writing projects, editorial work, and occasional consulting. She responds to every inquiry — usually within 48 hours, always before midnight.
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