Sometimes I Miss Having a Boss to Blame
By Ken Hollow, freelance by choice, regret by default When I quit my last real job, I walked out of the office with a box…

By Ken Hollow, unwilling time traveler through calendar chaos
Project deadlines are fictional. They’re not based on reality, resources, or reason. They’re dates picked out of thin air by a manager who thinks slapping “Q3 Deliverable” on a calendar is the same as project planning. They’re made-up milestones we all pretend to chase until panic mode hits.
Deadlines are conceived during a meeting where no actual work is happening:
Congratulations. A deadline is born. Reality was not consulted.
Repeat quarterly until morale collapses.
One time, I saw a Gantt chart with overlapping timelines that would require three versions of me working in parallel. If cloning existed, management would mandate it.
Nana doesn’t do deadlines. She does prophecies. Her system:
Shockingly, her track record isn’t worse than actual project management.
It’s not about progress. It’s about maintaining the appearance of progress.
Deadlines are less “commitments” and more “corporate horoscopes.” They give structure to chaos, but they’re fictional dates set by people who won’t actually do the work. And when they pass unmet, leadership spins it as a “learning opportunity.”
So next time someone says, “We need this by end of quarter,” just remember: you’re not managing time. You’re participating in collective calendar fanfiction.
Ken Hollow, unwilling time traveler, victim of fictional dates, survivor of Gantt chart lies
Hi. I’m Ken. I run Two Second Solutions, a one-man agency that somehow landed a fox spirit influencer as a client. I drink too much coffee, blog when I need to vent, and regularly update my résumé just in case she sets the office on fire again. I’m not crying — it’s just spell residue.
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