September 11, 2025 at 11:35 am

Her Boss’s Boss Denied Her Request To Pursue Her Side Hustle, So When They Were On Vacation, She Applied For A Demotion

by Jayne Elliott

businesswoman looking at a piece of paper

Shutterstock/Reddit

A lot of people have one job and that’s it, but some people have a day job and a side hustle that fulfills their passions.

If you had a day job and wanted to purse a side hustle as well, what would you do if your boss refused to let you pursue this side hustle?

Would you quit your day job, give up on the side hustle, or find a workaround?

In todays’ story, one employee is in this position, and she finds a way to have it all. She just has to time it right.

Let’s see what she did.

Applied for demotion

Back in 2008 I earned a promotion at the bank, and was licensed to sell mutual funds. The increase in pay was marginal.. maybe 2-300 more a month take home.

By being licensed in Canada through the MFDA it was tough to do any work outside of the bank without a ton of approvals.

Any outside jobs would need to be approved by the manager, her manager and also the MFDA.

Her boss didn’t see a problem with her second job.

I used to partially perform at gigs for a living, and had a few ins to get gigs for some extra cash (and also to do what i was far more passionate about than banking), and my manager said it should be fine as it was unrelated to banking and not a basic job that could cause issues if clients saw me doing it.

Not that there’s anything wrong with min wage jobs, it’s just that her explanation was “how would you feel if you just invested X amount of money with your adviser and then saw them flipping burgers that evening?”.

Personally i wouldn’t mind as i’d think the person was just working hard to get ahead, but also i understood how she meant it.

She also told me that her boss would approve it and it would come down to the MFDA, who would also very likely approve it.

She waited, and waited.

Flash forward 2 months.

I asked somewhat regularly on the progress of my request and was told i should open up a business account for my side hustle as it would likely get approved soon.

It didn’t.

My manager approved it, but it never made its way to the MFDA because bosses boss changed her tune and said no.

She was so disappointed!

No justifiable reason given AT ALL.

I was incredibly unhappy because my pay wasn’t great (Calgary circa 2007-2009 when i lived there had great wages almost everywhere because of the oil boom) and i felt like i couldn’t get ahead , especially with the licence to sell investments keeping me from extra income.

Some other personal bankers and tellers worked at Stampede doing bar work and made a KILLING.. so i was missing out.

There was a temporary change in management.

My manager, who was amazing, got sick. She took time off and there was a shuffle at the bank.

This particular branch of this company had a satellite branch not far, maybe 10km, that shared the same transit code.

My assistant manager (also awesome) went across to manage the satellite branch while their manager came to our big branch to manage it while main boss was away sick.

At the same time the bosses boss was also on holiday for 3 weeks.

She decided to apply for a job that paid less.

Turns out the satellite branch was recruiting for a personal banker level 1 (no MFDA license).

I asked my friend who was now managing it if i could apply and if she would put me at the top of the salary band.

She happily did and supported my reasons why.

I got the position and was now WITHOUT the MFDA licence and only making about 50-100 less a month as i wasn’t high up on the level 2 personal banker pay band.

Her boss’s boss was not happy.

Bosses boss comes back and is livid.

She told me and the manager at the satellite branch she never would’ve approved it, but in her absence the person who approved it at the same level didn’t know the back story and said yes.

I ended up enjoying life a lot more until the end of 2008 when i moved back to NS after leaving the bank to pursue other things.

Final note: i was one of only two people who could train new personal bankers to to mutual funds as you had to be shadowed and shadow them so many times before they could be signed to deal. Without me they were screwed for a while. I loved that their shady decision making went against them.

Sometimes when the boss is away it’s the best time to apply for a different job! Even though it was a demotion, I’m sure she ended up making a lot more through her side hustle.

Let’s see how Reddit reacted to this story.

Seriously, what a horrible boss.

Screenshot 2025 08 20 at 2.19.36 PM Her Bosss Boss Denied Her Request To Pursue Her Side Hustle, So When They Were On Vacation, She Applied For A Demotion

This person misread the title.

Screenshot 2025 08 20 at 2.19.45 PM Her Bosss Boss Denied Her Request To Pursue Her Side Hustle, So When They Were On Vacation, She Applied For A Demotion

This person answer’s the boss’s question.

Screenshot 2025 08 20 at 2.19.56 PM Her Bosss Boss Denied Her Request To Pursue Her Side Hustle, So When They Were On Vacation, She Applied For A Demotion

This is sadly often true.

Screenshot 2025 08 20 at 2.20.11 PM Her Bosss Boss Denied Her Request To Pursue Her Side Hustle, So When They Were On Vacation, She Applied For A Demotion

That was perfect timing!

She really pulled it off.

If you liked that post, check out this one about an employee that got revenge on HR when they refused to reimburse his travel.