Writing Prompt: Technology Challenged

My old supervisor was  man with a bushy mustache and a penchant for plastic trucker hats before they were co-opted by the fashion forward. His name was Justin and he drove a white Ford F150 with rust creeping up from the underside and a bumper sticker that said "Food Not Bombs!"
He taught me some aphorisms I still use to this day when I want to sound wise.
"It is easier to get forgiveness then permission."
 I use that when I tell my co-worker if she should just promise a client the extra foaming soap for a discount. I tell that to my Warhammer figurines as we rise over the felt and plastic rest of the terrain. Let's go, Space Marines. To glory, damn be our orders!
"Past is prologue."
Once, in a parent teacher conference, I said that to my son's principal and she paused and leaned back in her chair. I had sounded wise. My ex had taken him to the psychiatrist and confirmed he has ADHD and then manic spinning when he did math problems made sense "What is 3 + 7?" He would tap on his head summoning the answers from some first grade chakra. And wobble and gimble on his hips until he blurts out "10!" before making a "blrb blrb blrd" noise with his lips. It all made sense then.
"All it takes to be an expert is to know more than the person you are talking to."
Im horrible at bullshitting but excitedly honest about the sundry of my knowledge.
Let me tell you why Dragon Shield sleeves are not necessarily the only "good" option anymore for card sleeves
Let me tell you how I do just OK with hang over the back filters in my aquarium
I update my Windows machines regularly.
So when I offer to update the computer of my current boss before she goes into a meeting my momentary glee becomes panic.
Did I overstep?
Does she think I am going to mansplain to her?
Fuck! Fuck! Fuck! I just love updating Window OS. I should have gone into network engineering but I hate fiddling with wires. Let me just run software wizards all day and clear caches and delete junk. Memory miser
"Oh, how do you know it needs to be updated?" She asks sincerely. So sincerely that she grabs the machine by the left corner and tilts the whole perpendicular thing to the floor. Her wireless mouse slides to the floor and the batteries tumble out onto the carpert. "Ah fuck!"
"Oh, its because the little button in the corner is red. See?"
She is crouching down to pick up the cover to the mouse fiddling around the water catch of a potted plant in the corner "Uh-huh"
"I just noticed it at our last meeting."
"Oh are you checking me out!?"
Fuck. No! I mean, yes. I mean...haha good one. Yeah, that will work.
"Oh, always! You know me!" Dying inside I want to take all this back.
She laughs and then hands me the machine. "Ok, well I trust you. Will it fix my mouse problem? Or did I just make it worse by dropping it?"
I don't know but I recall the advice. "The update will take care of a lot. That I am sure about."