How do I resign from a tiny company without burning bridges?

[Wynter123]

I am one of 3 employees in a very small, very chaotic company run by the founder. He and I have a good relationship (in his eyes), but in reality I have spent 8 years basically building his business and ensuring it doesn't implode each day. (Not blowing my own trumpet - the other 2 employees are part time/freelance, I am the only person who deals with our actual product/purchasing/operations/export/logistics/suppliers etc). Because it is such a niche, and because I've essentially created my role from day 1, it's not going to be a straightforward one to replace.
I've been pretty miserable for a long time, but have held out until now, mostly due to this weird complex I have of "I can't quit because I've poured so much into this". It's of course not my business, but it feels as if it is because I have put in so much. I have worked 6 days a week, 12 hours a day, pretty solidly for 8 years now. My boss genuinely has no idea because he is really just focussed on sales, so as far as he is concerned, a product magically 'arrives' and he just has to sell it. (I am aware how mad it is that I've dealt with this for so long and am aware that I need to work on my boundary setting. But I was actually so enthusiastic about what we were doing/building that for a long time, I was happy to do the crazy hours... I also have share options, although they are basically meaningless until he takes the company public which is very unlikely to ever happen).

So... I have finally decided that I do need out, and have been offered a new job somewhere much more structured/low-stress. I know this is ridiculous but I genuinely am terrified to hand in my notice. Every forum I read about "how to have the conversation" gives advice for situations where there is an HR department / it is a very corporate company / your role is easily replaceable and people saying "just tell him you quit and don't give a reason". This is not that. My boss thinks we are good friends, and we are very close just by virtue of having spent the last 8 years on this thing. I obviously don't want to say "I'm quitting because this is a terrible workplace, you have no clue, you're taking advantage of me, I'm burnt out" etc, because he will not take that well at all (defensive ego!). But I'm worried if I try and make it more "it's not you, it's me" he will just try to offer ways to keep me (which I am not interested in). It is true that a large part of my decision is due to wanting more work/life balance, being able to move away from this area (job/area are tied together), and even if he/the job were amazing I would probably have reached a similar position of wanting to just change my life up a bit.... however if I take this approach I am worried he'll just say "we can make xyz changes and then you'll have a better work/life balance", and I'll then need to tell him why I really want to leave (basically "you're awful").

No idea if this makes any sense outside of the very specific context of this job/working relationship, but I really just need some advice/insights on dealing with this sort of resignation. There is a very high chance that once I go, the company will start to fall apart (again, not bigging myself up - he has just allowed it to get to this point where everything we do is in my head and not easily transferrable). I know people will say "that's not your problem", which is true, but I can't help but feel responsible and somewhat sad about the idea that this place which I have put SO much of my life into could crumble if I walk away (not to mention that he will blame me for that happening).

TLDR: Need to quit, but am in a v small business and deal direct with owner. If I leave, he is likely done. Don't want to tell him I'm going because of his poor management, but if I say it is due to 'worklife balance' he will just try to throw fixes at me which I will then still need to reject. Help!

I would be really bouncy and enthustiastic about the job and tell him that you know he is going to be really thrilled for you

I was recently in this position. I told boss face to face stating I needed a change for me. He refused to accept it at first but came round as I stood firm.
Some advice i got was sometimes you have to be selfish and do what is best for you. Keep reason brief and factual but state its not him/firm but you and your priorities have changed.

This. Everyone needs to move on, it’s only fair.

If you are happy to give 2 months notice, you could spend this month preparing notes for the future you, then give a month's notice but hand over the notes you have ready. That said, you don't need to.

I think you'll find that you aren't as indispensable as you fear.

If you’re working 6 days a week, it’s ok to mention work/life balance and wanting an easier life. I only lasted a few weeks in my very first job where unpaid overtime seemed to be expected every single day but I refused to stay late. It’s the only time I was ever sacked and I’m quite proud of it!

You are allowed to leave for another job and you just need to be honest with the boss. You’ve accepted a new role and that’s why you’re going.

As I have found out to my cost, you can't continue to do all your normal work and also find time to write a load of procedures and copious notes covering every single thing you do for the next person.

Goodness, you are over-thinking this! Your boss is no kind of friend if they are oblivious to how hard you've been working and how burnt out you are.

So - not your friend, no need to tie yourself up in knots! Just hand in your notice in an entirely neutral, non judgmental way. Rip the plaster off. Just get on with it. Don't dilly dally. Etc.

Just tell him you’ve been offered a really good opportunity that you’d like to take and that you’re more than happy to work longer notice to help him find a replacement and to do a thorough handover.

This! No need to agonize or make up reasons. People who’ve been in a job for va long time often think they are irreplaceable. No-one is.

If you’ve been ln there 8 years some of those options should have vested by now? Depends on the scheme rules obviously, but definitely worth running the agreement past a lawyer (or just claude to begin with!) to see what you need to do to extract max value before you leave.

They are share options, not shares, so no dividends.

OP I agree with some others, you should have vested at least some of the options by now, so they won’t be all voided. I understand about the lack of value, I’m in a similar situation, with options in a company which is unlikely to go public any time soon so it seems a bit hollow when I’m given more share options instead of a pay rise.

Regarding leaving, don’t overthink it. Give the month’s notice, don’t rush to anticipate his hurt feelings, that is for him to manage.

If you are set on leaving, I wouldn’t give him anything he can negotiate with. Not burnout or pay, because he will counter offer and you’ll feel stuck again.
Just tell him you feel like you want a change and an opportunity came up. Be clear, measured and dont discuss your burnout or your hours. You’ll end up getting dragged into a conversation you don’t want to have

This ⬆️

There’s quite a good episode about having difficult conversations on the What’s Up Docs podcast with Kimberley Wilson - she has a 10 point plan on how to do it. Might be helpful in planning how to do it?

www.bbc.co.uk/sounds/play/m002c3gb?partner=uk.co.bbc&origin=share-mobile

Just write a standard resignation letter, if you wish you could attach a less formal letter saying you have been offered another job and thanking him for the opportunities you've had. It will be difficult but don't get drawn into any further discussions about the situation

No-one's THAT indispensable. Do whatever you have to do. They'll manage.

What are the terms of the share options -how much to buy the shares or when can they be exercised?
true you can then only sell when there is a buyer but that’s a risk to weigh up. He also may not pay dividends and extract value in his salary.

Op no one is indispensable I learnt this from a young age you just tell him you have found it hard going and your ready for a new job it’s not your issue if he goes bust is it. If he stopped trading tomorrow or sold the business he would not be arsed about you. Take the new job you’re miserable why put yourself through that when you have a chance to move on. Go girl.

You’d be bonkers to offer to work more notice. This ‘of course I’ll do more than I have to’ default is precisely why you’ve got into this situation of being over-worked and under appreciated for years. Stop it right now and work the notice that your contract requires. It’s not your business, it’s his and it’s entirely his problem how he replaces you. And he will. As someone once said, the graveyards are full of people who thought they were indispensable. Stop putting his work first, prioritise yourself and hand in your notice like a professional. You’re giving notice and your last day will be in 4 weeks as per contract. Get proper advice on the shares and don’t be pushed around or bargained with or shortchanged. And start the new job with a new approach so this doesn’t happen all over again.

what is the status of the business? Is it profitable and does it have cash?

I would definitely start with the share options - how much would they be worth at the moment? Check that they are not near expiry if you have been there a long time (some will expire at 10 years).

tactically I would be trying to get some value out of the shares. Then move on. You’ve put so much into the business, it’s reasonable to try and get value out.

the business does not have to ‘go public’ for you to get value

at the most basic level, you could say to boss that you’ve put a lot in and need to start seeing some recompense. Can you negotiate a payment to surrender options? (Not most tax efficient but still potentially simple enough).

more complicated to exercise the options.

Adding do not resign then try and negotiate on shares. You’ve put will lose your major leverage.

If he makes a counter offer to keep you, just keep saying that it is ‘time for a change’. Also, I agree with PPs that you should not work more than your contracted notice period. If you can afford it, take a few weeks off and put your feet up. Starting a new job is always tiring, so take time to recharge your batteries.

You have to accept that he may be angry and it may fall apart without you, and then decide whether those things are enough for you to stay - if they're not, then you have to do it regardless of whether those things happen.

I think you're trying to magic a way where you can leave and those things don't happen (I get it!) but that doesn't sound likely, so you just have to get to a point in your head where you accept that.

Prep an exceptional handover and give as much notice as you can and if you want to ease things then have a fairly solid 'excuse' why the new role is one you can't turn down (location seems like a good one). I also think you can get in something about the burnout and workload without it being too accusing - maybe if you're helping him plan for a possible replacement you can point out that probably a new hire is not going to be willing to put in the same hours/days you did and that he needs to consider capacity etc etc.

You have given this person a lot of power. You have worked hard and well and over your hours for 8 years. He can't have not noticed that you have been working 6 days a week - he just doesn't care as it benefits him. And now you're tying yourself in knots not to offend this person who has thoroughly taken advantage of you for nearly a decade.

Watch his reaction when you tell him, and it will make it easier for you. You are the lynchpin in the company, not him.
And I bet he knows this only too well. He won't react nicely.