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Employee’s Wedding Plans Destroyed By Boss, So She Leaves Him With A Digital Nightmare

by Katy Nguyen
November 11, 2025
in Social Issues

There are few things worse than a boss who can’t see how his decisions are wrecking everything, especially when it’s personal. One company’s attempt to digitize its records turned into a textbook example of mismanagement.

With a “Genius” in charge, promises were broken, and deadlines were ignored. The final straw came when one employee’s long-planned wedding and honeymoon were canceled, all in the name of a failing project.

Her response? A resignation on her last day, followed by a phone call that left the company with a mess they still can’t fix.

Employee’s Wedding Plans Destroyed By Boss, So She Leaves Him With A Digital Nightmare
Not the actual photo

'I don’t work there anymore?'

My employer decided to convert all of a certain class of our records from paper-based files to digital. There were three immediate problems.

Our company was not going to buy a generic system, but develop our own unique, tailored system.

It was to be done on the cheap, with net savings for record keeping from Year 1.

The guy in charge (let’s call him Genius) always (and I mean ALWAYS) thought he was the smartest guy in the room. Believe me, he wasn’t.

Anyway, one of the girls I worked with took on the project on the condition that she could have the next July off for her wedding and honeymoon.

She worked hard, and the project was actually making progress. One of her duties was passwords, none of which could be written anywhere because Genius knew this was ‘bad’.

She periodically reminded Genius about the July wedding, and he told her it’d be fine, but never signed off on the paperwork.

Come mid-May, the project is WAY behind, mainly because Genius told management it could all be done in-house at negligible cost, and Genius kept changing the design every time he...

My friend was then told 6 weeks out from the Wedding that her leave was cancelled.

The project took priority, and she’d just have to reschedule her wedding, honeymoon, and the works. Genius could not see that this might be a problem.

So she did her job, updated the passwords as required, never recording them anywhere, as required, and resigned without notice on the last day of June.

On her honeymoon, she gets a frantic call from Genius demanding all the passwords.

"Sorry, I don’t work there anymore." Click. That’s why, a decade later, our company still has a few hundred electronic case files we can’t access.

From the expert’s perspective, the OP’s story describes a classic case of unmanaged project risk meeting human resource breakdown.

The organisation decided to convert a class of paper‑based records into a custom-built digital system. They chose to keep costs down and rely on internal capability rather than choosing a generic solution.

The individual known as “Genius” was placed in charge despite a pattern of behaviour suggesting he considered himself the smartest person in the room, and the system slipped dramatically behind schedule, design changed constantly, and ultimately a key team member (the bride‑to‑be) was told, very late in the day, that her approved leave for July would be cancelled.

When she resigned without notice, she refused to hand over the passwords, leaving the company locked out of critical files.

This scenario triggers multiple failure modes in project governance and IT security. One major issue: passwords and access control.

According to a report by LastPass, “password mis‑management is the leading cause of breaches” and organisations with weak password oversight see serious exposures.

In this case, the team’s reliance on informal password rules (“no writing them down”) without a secure, documented hand‑over procedure increased the vulnerability of the project and exposed the organisation to operational risk.

From a project governance viewpoint, the expert sees that the company failed to provide adequate change control, schedule management, or contingency planning, especially in choosing a bespoke system under tight schedule with a key person’s departure looming.

The company’s leadership hoped to save money and likely believed internal control would suffice. The project manager (Genius) may have over‑promised what could be delivered and fought scope creep (changing design repeatedly).

The employee took on the project with the condition of leave (wedding/honeymoon) and likely did her best under difficult constraints, but when the leadership reneged, she exercised her agency by resigning and refusing to hand over the keys, essentially enforcing her exit.

The expert notes that while the method was dramatic, the underlying logic is strong, if the company cancelled her agreed leave, it broke the implicit contract and she withdrew her voluntary cooperation.

To avoid similar issues in the future, organizations should establish clear, documented procedures for password management and access control, ensuring all credentials are securely stored and handed over before key personnel leave.

Contingency plans must be in place for the absence or resignation of critical staff, especially when working on high-priority projects.

Additionally, companies should carefully evaluate custom systems for complexity, risk, and long-term support needs, as the upfront cost savings of a bespoke system may be overshadowed by future operational issues.

Finally, treating approved leave and other contractual commitments as binding is essential for maintaining trust and preventing drastic employee responses.

Here’s what people had to say to OP:

These Redditors were appalled by the boss’s unrealistic demands.

efrazable − Changes project expectations every week." What do you mean it's not done yet?!"

SpiderRealm − I can't believe that i__ot actually thought she'll just drop her wedding and honeymoon like that!

This_is_my_phone_tho − The amount of times I've seen people quit because their manager expected them to put their minimum wage job over a meaningful life event baffles me.

This group empathized with the OP, noting that it’s ridiculous for employers to leverage additional tasks as a condition for taking time off.

MultiLevelMonsters − I hope she had an amazing honeymoon.

mechengr17 − The worst part of this story was that she had to leverage doing such a horrible ADDITIONAL task in order to get her vacation in the first place.

I mean, it sounds like she asked a full year in advance...it doesn't make sense to me how she could be denied?

Kylynara − Well that's an unusual way to f__k two guys at once.

These commenters shared similar frustrations from their own experiences.

ilinamorato − I was taking a stupid online elective class the summer I got married.

When I signed up for the class, there was apparently a miscommunication between the instructor and the registrar about the date the class was to end, and the syllabus showed...

Drop/add for summer courses was something like three days, so by the time I knew this, it was too late to drop. Still, it was just a Music Appreciation elective.

Surely the prof would understand and let me take the exam early. That's a big nope.

I emailed him and asked, as courteously as possible, if I could take the exam four days early.

After the last class, but before my wedding. To which he replied, "No, sorry. Figure it out on your end."

What "my end?" My end is Jamaica. Plane tickets are purchased, and the wedding venue is booked.

There are about a dozen nonrefundable deposits and fees we're talking about here, not to mention, you know, my fiancée.

I'm not going through all of that for your stupid music appreciation summer elective.

Some people are just ridiculous in their inflexibility. You don't just "reschedule" a wedding.

EDIT: For those asking what happened: I contacted the Dean's office, but he was on vacation or something that month.

There was somebody there who I think was able to give authorization for the registrar to withdraw me from the course, and as I recall, I still got the end-of-course...

This was all eight years ago, and a somewhat busy time of life, so some of the details are a little hazy.

Except for the sentence "Figure it out on your end." That one is still burned into my brain by a white-hot rage.

Borngrumpy − As a manager, if you are the smartest guy in the room...you hired the wrong staff.

Genids − Why didn't she just go over Genid's head for her time off? Why didn't the company try to pay her off for the passwords?

Why couldn't they access the paper records anymore? They couldn't have been destroyed since the digital system wasn't finished yet.

This group focused on how managers’ behavior often makes situations worse for everyone involved.

gettodaze − Sometimes, I hope idiotic managers are reading posts like these and learning not to treat their employees like s__t.

AngelaMotorman − But what happened to Genius when it all fell apart on his watch?

nDQ9UeOr − Careful with the password thing if anyone is thinking about this. Read up on Terry Childs and the city of San Francisco (spoiler: it did not end well...

These users shared their own pearls of wisdom and advice.

marakush − A very good friend of mine told me these words of wisdom "Never mess with a women on her wedding day or any time leading up to that...

UseDaSchwartz − This is when you say you'll come back as a contracted consultant for at least triple your hourly rate or a ridiculously high flat rate for a certain...

Sometimes, the workplace drama writes itself. The Redditor’s friend had been flexible, responsible, and even sacrificed her wedding plans, yet her employer still couldn’t see the value in respecting boundaries.

Do you think the OP’s friend was justified in walking out, or could she have found a way to protect her time without burning bridges? Share your thoughts below!

Katy Nguyen

Katy Nguyen

Hey there! I’m Katy Nguyễn, a writer at Dailyhighlight.com. I’m a woman in my 30s with a passion for storytelling and a degree in Journalism. My goal is to craft engaging, heartfelt articles that resonate with our readers, whether I’m diving into the latest lifestyle trends, exploring travel adventures, or sharing tips on personal growth. I’ve written about everything from cozy coffee shop vibes to navigating career changes with confidence. When I’m not typing away, you’ll likely find me sipping a matcha latte, strolling through local markets, or curled up with a good book under fairy lights. I love sunrises, yoga, and chasing moments of inspiration.

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