Entrepreneur Tips and Discussions

Extreme Guilt About Resigning

The title says it all. I’m at a small start-up and found another opportunity (at another start-up) better suited for me; and not as risky as my current start-up, which honestly is struggling due to the pandemic. But I feel incredibly guilty for leaving as I’ve had a short tenure there and there’s still an immense amount of work to be done; and I truly want to help the co-founders and my co-workers out. Also worried that the co-founders and investors, who I have close relationships with, won’t take it well. And to make matters worse, because of the pandemic, I won’t even be able to have a face to face discussion.

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35 replies on “Extreme Guilt About Resigning”

It’s just business, most professionals understand that.

If there’s nothing that your managers / investors / leadership can do at your current position to address your concerns, then they should be supportive of you doing what’s right for you and not right for their business – that’s just empathy and common decency. Yeah it sucks, but it’s life.

If you haven’t raised your concerns nor given them a chance to address them, then perhaps a bit of angst is to be expected – you will be blindsiding them, but again, hallmarks of good leadership generally is understanding what’s best for the people and the company, and ensuring those are aligned.

Be respectful, provide a reasonable timeframe for departure that gives them enough time for handover / training of colleagues, and be willing / open to hear them out too if they are willing to change circumstances to better match what you want. Make yourself available post-departure for any missed things too, as that’s something that always earns respect.

Just be mindful on both parts about companies wanting to drag things out or take advantage without renumeration for your time post-departure.

Good luck.

From my experience I can tell, never keep an emotional relationship with your company or your company founders. You just exchanged your time and professionality for their money, thats it.

I just had this exact situation. No one will
blame you – and if they do it won’t last. Bottom line work is work is and it’s up to you how you spend your time. No one will fault you for that.

I will echo the other commenters and say don’t feel guilty.

You did work and they paid you for it. You don’t owe them anything.

Besides, if they wanted to lock people in, they would have made you a cofounder or given more equity on a vesting schedule to make it a harder decision to leave.

Don’t worry about them, they will be fine.

In fact, if they were overly reliant on you, they might actually be better off by having to “learn to swim on their own” so to speak.

If you had committed to stick around for a certain amount of time, then I would suggest completing that tenure and then leaving.

If you made no such commitments and aren’t bailing on a deal or understanding, there should be no guilt whatsoever. This is a business contract, after all. Just don’t negotiate in bad faith.

Do what’s best for yourself. However emotional / close you guys seem, at the end of the day it’s business. Unless you have equity in the startup, you don’t have a reason to stay.

I’m assuming you’re in college/recent grad?

This is a tough one. Start-ups aren’t like regular jobs and esprit du corps is crucial. A key resignation at a crucial phase could doom the company you’re leaving . However, if you’ve only been there a short time I doubt your departure would break the company.

Work your notice period. Any less than that then feel guilty. If the employer wants you to work more than your notice period then don’t feel guilty for sticking to your notice period.

It’s natural to feel guilty, especially since they have probably treated you well and you have built up friendships with them. But they will need to get used to people leaving, it’s going to happen a lot. It’s ok to grow. You don’t need to feel guilty about bettering yourself.

If you’re a company person, your job is not to *stay forever*, it is to ensure that if something were to happen to you : leaving, getting hit by a bus, or anything else, your job could be taken over with minimum hurdles.

However, you don’t have to be a company person, but your company does have to be a people company.

It’s your company’s job to make sure you want to stay, and to make sure that if you were to leave, your job could be taken over with minimum hurdles.

They should have kept in touch with you to know how you’re feeling and should be expecting that you’re about to leave. If they have not, that is on them.

Do what you gotta do. BUT, you have a responsibility to make the transition easier assuming the company didn’t fuck you. If you’re a CTO, spend a couple days writing up as much documentation on key pieces of code as possible. If you’re in sales, organize your prospect list for the next person. If you know other people that might be a good fit and can handle the risk, give them a shout.

I relate to this soooo much… Going thru the same thing. The org00 comment is good advice, I think… Cheers dud hope we make it thru this and end up w a wise desition that will make our lives better. The hardest part is the unknown… Like u already love and know this startup and u dunno much about the new one… Except what they want us to know

I’ve been there before.

The tricky part is that in small startups and under pressure your co-founders/co-workers often become friends and that will make acting professionally harder. You have to balance what is good for you vs what is good for the startup you are currently working for.

Do you have anything to give your current start-up more leverage and/or buy them more time to deal with the situation? You can try to fix up loose ends, document your processes, and prepare everything for a future hire/others who will take over your job. How long will the other opportunity be waiting for you? Maybe they will understand that you can’t rush out of your current job and wait for you if you explain the situation to them.

I think you still need to make up your mind. Are you sure that that other opportunity is worth it for you? It’s also a start-up, doesn’t sound risk-free to me during a pandemic…

Dont. Be open to help out as much as you can with the transition.
Most founders are extremely selfish or they need to be. plus at this time hiring is not difficult. There is more talent getting in the market due to lay offs and all.

Its likely they wont maintain any personal or professional relation with you hear after but thats ok. Been through such situations multiple times. What i thought was a good relation never continued the day i resigned.

Every man for himself

I think at any given point in a business relationship, extreme honesty is a good solution. If you’re honest about why you’re resigning, explaining that it’s better for you personally, and they *still* don’t understand- that’s on them.

You can worry about what other people will think- that’s only human nature. But you shouldn’t allow that worry to affect your long run decision making. If this is best for you, do it. Everyone else should learn to live with that, and those people that support you as a person rather than as just a coworker will accept it.

It’s ok. Just be professional in the manner you inform them. Understand it is a sucky situation but you did like them; you’ve just found something better for you personally.

Do what you can to set them up for success in the transition period if they let you.

Keep the transition period less than 1 month; 2 weeks is fine. It will settle in quickly. Your teammates will adapt to the news in 2 days as life keeps moving. They’ll focus on offboarding you. Just work through those items diligently and leave.

Don’t gossip. It’s irrelevant.

Society benefits the most when the individuals within it are optimally productive and their talents leveraged optimally.

It sounds like your talents will be better utilized and leveraged at the new place. Therefore, society will benefit more.

You can always agree to ween off as a consultant and help with the hiring of your replacement. As founders, we understand it’s business but it will be hard. Showing that flexibility and willingness to not leave a crater will go a really long way in salvaging the relationship.

Tell them when you’re leaving, give up remaining equity, train your replacement, and work as a consultant for them/ bill them hourly in your free time.

That’s the best faith way to go about leaving. If they can’t swim at that point, it was never meant to be.

I’m on the same boat as you, literally. I joined a startup 3 years ago. It was struggling when I joined them and it’s struggling even more now due to the pandemic. About a year and a half ago I wanted to leave because the drive and personal motivation that’s required to succeed at a startup went away. The pressure of delivering a high quality product with few people didn’t weigh up against the financial compensation.

You know what I did? I stayed, because I didn’t want to leave the founders and my coworkers in a “tight” spot. Hiring for startups is extremely difficult after all, right? I’ve been justifying it for over a year. “ah, this quarter has been difficult for us, I can’t leave now”, “that client didn’t renew, they won’t be able to afford another engineer, I have to stay”. I kept putting the weight of the founders decision on myself, in a way. Until I finally realised – it’s not my company. It’s not my product. I do have somewhat of a say in how the product evolves but it’s besides the fact. Every decision the founders have made has led them to this point. I don’t have to sacrifice my own time for their dream if I don’t want to.

I’m in the process of interviewing now. Don’t make the same mistake I did. It’s really easy to keep putting off the inevitable. The company will die if the founders can’t manage it properly. It’ll survive if they know what they’re doing. Do what’s best for you. At the end of the day, you’re living your life for yourself.

I have been leading teams for a decade. Many people have resigned from under me. I’m never mad. People should strive to get to the next level.

I’d rather people move to something else that excites them, than stay for ‘loyalty’ and become bitter and frustrated.

These days, it’s incredibly easy to hire. Your boss will have hundreds of resumes to choose from. Probably paid less.that you were.

Don’t you think the founders of the startup quit their past jobs also to create this venture? Everyone should be looking out for themselves, and your no different.

Struggling startup founder here with a different opinion from most of the comments.

My opinion is this: I don’t have enough information from your post to know if what you’re doing is okay.

If the startup is very small and struggling and there’s a good chance your leaving will kill them, then there’s something there to carefully consider. Extended notice, ongoing support for the transition, all things to consider if you care about them.

If they’ll be fine, you’re fine. But to the people who are saying “it’s just business, and you don’t owe them anything”, let me add that this is EXACTLY what I was told by other business owners when I mentioned my developer who is supporting his sick mother on the salary I pay him. I was told to “just be honest” and “the needs of the company come first”. Fuck. That. These are people. As an employee you don’t owe them your life, but you CAN carefully consider how your actions might impact them and do your best to move forward in a way that’s good for everybody.

So how will your leaving impact them, and what, if anything, does that mean to you?

Don’t be. We are mercenaries who exchange our time and talent for money. Never feel guilty for wanting something better.

Another thing: most of the time, this feeling of guilt is not two-way. Your co-workers and co-founders might not think twice about letting you go for any reason.

Never fall in love with an organisation. Period!

You work and you get paid for it, that’s the only transaction there is.

An employer will not wipe your child’s ass or feed your dying parent. Leave the right way but try not to feel guilty about it. Do what’s best for you. People definitely understand with the current circumstances. We’re all in this shit together! Best of luck!

If you didn’t make any promises that you would stick around, there is no reason to feel guilty. You don’t owe them your time and effort and you can do with your life what you want. If they don’t take it well, they are the ones being rude.

I would not take it to heart as u/org000h said at the end of the day its just business, and most professionals understand that and will not take it personally. If they do all take it personally, then you made the right choice anyway.

When they need to let you go, they won’t be feeling bad. Take care of your own career first. Don’t feel bad.

This is called resignation without cause. If you do this you are walking away from the opportunity and you should not expect to take equity with you. Imagine you are the only person in the startup, if you left you would lose everything. The same thing is happening here, you’re leaving and you were forfeiting your position in the company. If you have any cash investments in the business, it should be paid back to you at a later date when the money is available. But ask for your time, you’re walking away from that. That is the only fair way to do this. One of the tragedies about startups is when people leave early and take money with them, they are often the only people who ever get anything…

Mike (

If your co-founders are angry that you are leaving then probably you made the right decision. If they are co-operative and nice I would suggest offer them some help in your downtime (if they and you are open to that).

You are not doing anything wrong, so do not have any guilt about resigning. Good luck.

Do what’s best for you. Give them enough time to look for a replacement or reassign the workload. Think of other ways you could help them, for example finding a replacement for your role, working for a few weekends for them in the meantime, etc.

They wouldn’t think 2x about making the best business decision for the company if it involved firing you, you shouldn’t think 2x about making the best financial decision for yourself if that means job hopping. Just try not to job hop too often – or if you do, leave it out of the resume because obviously it’s not desirable from a hiring perspective.

Consider your resume as well. Don’t be the person who jumps from company to company every year for the fatter paycheck. It will catch up with you and will be obvious on your resume that your not going to be loyal at your next job either. I absolutely avoid hiring the mercenaries who don’t care about anything but their resume and paycheck. Those resumes go in the trash, regardless of the claims they make on their resume.

If you’re under 6 months, it’s not a big deal. It was not a good fit. If it’s one year, then you look like you are flipping jobs for money. Don’t do it repeatedly or you won’t get great job opportunities. Startups have to build scalable organizations and look for people that are loyal and can scale up.

On the other hand, if the company continues to struggle, they could toss you on the street without warning. They fail frequently; and the board can toss the founders suddenly and you might find yourself working for new bosses you do not like. Execs and boards can be ruthless or kind.

In difficult times the claws come out and unfortunately seemingly kind people can suddenly do nasty things to others to protect their own pocket book.

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