Boss asks employee to spend $2.5k on work trip to be reimbursed later, employee resent the upfront cost and doesn't trust they'll get the money back: 'The business is hugely struggling'

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JR Atkinson • Writer and Editor
Jan 12, 2026 10:00 PM EST

Spending money at work is something you should probably avoid where you can. Sure, you have to buy lunch sometimes, or coffee on the way in, or even minor expenses while you're on a work trip. But no job should be asking you to shell out thousands of dollars at a time, even if they tell you you're going to be reimbursed later. The way things move through a company, it might be months before you get that money back. Meanwhile, you're upstream with no paddle, out thousands of dollars of your own money. Not many people have that kind of wiggle room in their budgets. That would set back the average worker, even if that money eventually made its way back to you. So it's understandable if you would bristle at this kind of request. After all, they're the company. They should be the ones with the money. 

It's also impossible to totally trust the company you work for. They might have a good history with you, and you might be loyal to them for good reason, but you can never let your guard fully drop, especially with money. Things can change in an instant, and it might come back to bite you when you least expect it. You never know when they're going to hit hard times, and you're going to end up paying for it, sometimes literally. It's better to avoid opening your purse at all, lest something happens while your head is turned the other way.

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  • A woman looks stressed writing on paper at a table, money stacked next to her.
    via Unsplash+ (Karolina Grabowska)

    The image does not depict the actual subjects of the story. Subjects are models.

  • But that's the situation this woman found herself in at a job she had been loyal to for years. She didn't want to have to mistrust them, but she felt put out by their request. She had been working to avoid that issue, and nobody would listen to her sound advice. And when they asked her to swallow an upfront cost, she bristled at the idea. Not only did she not have that kind of money to spare, but she also wasn't sure if she would ever see it back. Read on to see what happened in this story and decide what you would have done.

  • Employer asking me to pay thousands and reclaim for business trip.

    Urgh just ranting really and looking for advice. I have worked for this business for 8 years now- the business is hugely struggling but I won't jump ship yet as I have 3 month notice period, and would get a hefty redundancy pay. I'm a working mum and this job is super flexible and so I will be here until the bitter end!!
    via u/missmacleod2
  • Anyway- we have a business trip to the states in 6 weeks. For the last 2 months I have been telling my boss- here are the flights, shall we book? He is useless and refuses to commit. Anyway, at the end of last week he said oh just book and reclaim.
    via u/missmacleod2
  • I just went onto book and they are 2.5k because it is so last minute. I literally do not have that money. I feel annoyed that now they have doubled in price, and I've got to pull thousands of pounds out my ass, in JANUARY of all months. I've had to say I can't afford that and it makes me feel so uncomfortable.
    via u/missmacleod2

  • Commenters gave their take on the situation.

    Fantastic_Inside4361 No. Never. Not even for a company I trust. Not even if I'm the accountant and authorised and able to pay.
    via u/Fantastic_Inside4361
  • OP missmacleod2 Okay- I don't mind small expenses like trains and food. But to expect me to pay thousands really doesn't sit right with me, and I'm quite cross he has even put I'm me in this position.
    via u/missmacleod2
  • LauraBaura That's fair. Just say "I can't afford to do that, I need the company to pay up front". He should not have put you in that position to have to explain your finances. He's an AH. But it's your really only way through this situation.
    via u/LauraBaura
  • A female employee is stressed at her desk, looking at a laptop
    via Vitaly Gariev

    The image does not depict the actual subjects of the story. Subjects are models.

  • OP missmacleod2 Yes that's what I've done- I said I'm sorry I can't afford it. X
    via u/missmacleod2
  • haphazard72 Don't ever do that! Especially if they're struggling. And redundancy? Ain't no redundancy if they're struggling!
    via u/haphazard72
  • OP missmacleod2 In the UK you get statutory from the government even if the business can't pay
    via u/missmacleod2
  • fingersarnie If the company is struggling, do not do this. You will not get it back. If the company goes under, will you even get redundancy.
    via u/fingersarnie
  • OP missmacleod2 Yes I am in the UK and even if the company don't pay it, the government does
    via u/missmacleod2
  • haphazard72 Ah ok. Lucky!
    via u/haphazard72
  • OP missmacleod2 Definitely. So If tomorrow they went under and it all ended I'd have redundancy pay and 3 month of pay- if that was the case it would be like £13,000! I'd envision that I would have to work my 3 month notice period tho- but I'd use that time to get a new job! So I'd still get absolute minimum of over £5k tax free- I'd never let that be!
    via u/missmacleod2
  • fingersarnie Wouldn't that be statutory though? Admittedly I have no idea how much that would be though and just as a point of note, it's a lot easier finding a job when you're already in one.
    via u/fingersarnie
  • OP missmacleod2 Yeah but would still be over £5,000 (as the statutory minimum)
    via u/missmacleod2
  • haphazard72 That's great!
    via u/haphazard72
  • OP missmacleod2 Indeed- I actually worked for my boss years ago in another one of his business that also went bust (lol) and he was very generous with redundancy pay then, even tho I hadn't worked there long and wasn't actually entitled to anything. So this is truly worst case scenario- he loves me and we have worked together for years now so I know he will be as generous as the finances would allow x
    via u/missmacleod2
  • Wh01sthebear Unless you work for a subsidiary or contractor to the UK government they don't pay statutory redundancy pay, the employer does. And if a company goes bust, whilst you will be paid for outstanding work done, any further redundancy will be paid along with any other staff usually before creditors who are also owed money by the business. Usually business' are folding cause there's no cash or cash flow left so apart from going to court and trying to claim from outstanding assets or direc
    via u/Wh01sthebear
  • OP missmacleod2 Yes, the government pays redundancy if your employer is insolvent (can't pay), through the Redundancy Payments Service (RPS) on GOV.UK. You can claim statutory redundancy, holiday pay, and notice pay from the RPS, but you generally need to go to an employment tribunal first if your employer isn't officially insolvent, to get a ruling before the government steps in
    via u/missmacleod2
  • MrsBSK What exactly does this mean? To book and reclaim? I've never heard of it and want to understand why everyone is saying not to do it.
    via u/MrsBSK
  • OP missmacleod2 Basically often with large expenses the business pay for it. He is asking me to pay out of my own pocket, submit the receipt and they will pay me back.
    via u/missmacleod2
  • Future_Direction5174 If they can't pay for your ticket, then how can they reimburse you if you buy them and then try to claim the money back? It's not even a case of "I can't afford it" at the end of the day. It's the fact that THEY are asking you to buy your own ticket because THEY obviously don't have the money to buy it for you.
    via u/Future_Direction5174
  • OP missmacleod2 No, they do have the money. It's a complex situation, and essentially we are without a card- my boss can transfer money tho
    via u/missmacleod2

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reimbursement antiwork spending employee Professional At Work employees workplace work trip money
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