What is the elegant way to quit your current job for your startup?

I'm sure many of you have been in this situation before, where you want to quit your day job to focus more on the startup you have built.

Currently I'm having a hard way to tell my employer that I want to quit my job for the startup. Not that I don't know what to say, I don't know how to say it elegantly. I am afraid that my employer will look me down, if in the future the startup turn out to be unsuccessful and I'm back looking for a job again.

So what would you say and do if you are in this kind of situation?

I'm actually facing somewhat the same situation myself.

In my experience coming back to the same workplace once left is probably not going to happen. Basically because:

1. You have the urge to do something different (you are not quite satisfied with the current position) - otherwise you probably wouldn't consider leaving in the first place. The reason being either to try doing a startup or another employer.
2. The reason for not leaving is almost always the feeling of "security" which is I think you ask this question in the first place. But once you've left your current job you've already made the jump and I don't think getting back is something you would want to do.
3. I've been in the same company for over ten years and I've seen a few people coming back after trying doing a startup but they always keep leaving after just a few month to a year. I think mostly because of the above reasons.

Sometimes it helps to keep "bridges" in order to be confident enough to make the initial break but beyond that I think it is more of an academic question really.

Just a few thoughts...

Hmm why don't you try to think about what you would like to hear if you switched places with your employer? You know your work situation better than anyone here, so take your own advice.

Do you work flipping burgers (or equivalent) and can be replaced instantly? Then give 15 days notice, and tell them that you may enter the workforce again if your startup does not pan out. Be a professional about it. Be polite. Make it clear that you like working there, but that you have to pursue your dream. Any employer worth their salt will appreciate that forthrightness.

Do you work where you would cause a huge problem if you leave suddenly (ie, you maintain the main business application and have in-depth knowledge about it that will take someone else months to gain)? Then be a professional about it. Your employer does not need you to be "elegant" as you put it. They need to keep their business running. They need you to be "professional." So, give them ample notice (I once gave 180 days' notice, and it still seemed like it was too short). Be supportive of your replacement. Be proactive in your transition off the place (don't wait for your boss to scramble to replace you while you wait for him to take care of the transition). Write documentation. Arrange to work as a consultant should they need you to help in a crisis after you leave. There's no elegance in this that matters, only professionalism.

Depending on what type of place you work (that's why the decision on how to do things is yours alone), it will be handled differently. I know of places where you try to make a good transition and give them ample lead time to take care of things, and the boss fires you on the spot rather than do things in an orderly way. Some places and bosses are like that, so you decide how to do it.

Bottom line: Replace "elegant" in your question with "professional" and you are on your way to a clear conscience and a door that will remain open for a long time.

I've done this about 2 times (that means 1 failed startup :) ). There is nothing bad about it. And I'm still good friends with these 2 companies.

• First of all don't leave them in a bad place. If they need you for a project don't quit until someone can replace you, and they can move on without a problem. This is very very important.
• Be honest
• If they are decent human beings and not totally selfish people as business owners they'll understand why you are doing such a thing.

I am afraid that my employer will look me down, if in the future the
startup turn out to be unsuccessful
and I'm back looking for a job again.

BTW generally coming back to the same company after a failed start-up is not a good idea, I'd look for another job. I don't know what's you exact profession but I'm sure you can get a new at least as good as your current one.

It depends on the relationship you have with your boss. As an employer, if somebody wanted to do this I'd appreciate them being honest with me. If it's true, then you could tell him that this is a fantastic chance for you, and that you'd be forever kicking yourself if you didn't take it, but you're going into it with your eyes open and understand that startups are fragile things, and that you don't want to burn any bridges.

For difficult conversations like this it's always good to practice. Find a friend or colleague you can trust and ask him to pretend to be your boss and run through the conversation several times, with your friend taking different roles (enthusiastic boss, angry boss, unreasonable boss and so on).

It is very important to be honest with your employer. Tell him that while you like your job, and have no reason to complain, you have decided that it is time for you to try to start a startup of your own. Tell him that you are giving the two weeks notice, and that you are willing to go for a bit longer if he cannot find someone to take your place, since you don't want to leave him hanging, but that your are on your way out. If it is a particularly busy time of the year for the business, or there is a deadline to meet, you are also willing to work extra hard, but for a limited time, since you want to get started with your own business as soon as possible.

Given all that, you too should be able to part ways in a way that will not hurt you in the future if you ever do business together again.

You are under no obligation to tell your current boss that you are quitting to work on your own startup. You can just tell them you leaving to pursue another opportunity and if pressed say you are unable to discuss the specifics.

To open a startup a person has to have guts and self confidence. From your post it seems that in case of failure of your future startup you see the only place for employment - working for your current boss. Where is your entrepreneurial spirit?

The first thing you do, before you talk to anyone about quitting, is to make sure you take home any personal belongings you can't live without. Make sure that any coworkers you want to stay in touch with have your personal email address.
You should also bring to work anything the company is going to demand back from you. The worst case scenario is that you are not allowed to return to your desk, have to hand over your blackberry, and are immediately escorted out of the building by a couple of burly guys. (If that happens, don't take it personally).

As for informing the company you're quitting... Personally, I would only do it by talking to my manager face to face. Try to cover the following points

1. An exciting new opportunity has come up. Even though I really like working for you, I've decided to leave the company to pursue it
2. Therefore, please take this as my 2 week notice
3. Here's my list of current projects, their current status and due dates
4. I want to make my leaving as easy as possible for you and the department.
5. So here's a tentative 2-week plan I've put together to transition my projects.
6. Also a tentative list of coworkers who might be good matches to take on these projects

You should then hand over a copy of your resignation letter. Signed and dated, and containing the bare minimum needed to walk away.

Dear [Name of HR rep]
I resign my position as of [date 2 weeks in the future]
Regards

jpartogi

Stay focused on helping your boss deal with this unexpected and unwelcome new problem.
Your goal here should be to transition your projects and knowledge as efficiently as possible with the minimum fuss. Leave as amicably as possible (you might want to work with this person again someday)

When your coworkers ask, explain that you have the chance to work at an exciting new startup. Give them the elevator spiel about the project. Talk a little bit about how passionately you feel about it. Try not to go too overboard with it. You don't want your boss thinking you're poaching.

Decline to speak ill of the company you're leaving or any (soon to be ex) coworker/manager/etc.

You might very well face hostility from your soon-to-be excoworkers if they feel you're dumping work on them or if you appear to be belittling them for staying in their jobs. Do your best to remain totally professional and positive at all times. Keep your eye on the goal... quick, efficient, friendly transition of your workload.

Suppose your startup is successful and you've hired a few people, how would you want them to tell you they're quitting?

Honest, open, available.

I wouldn't go into a lot of the details of why you are leaving. I understand the nervousness though, it's a tough thing to do right?

Something that happened in a situation I was in that might be helpful. When I was quitting my first job, my boss was upset and let me know "You are putting us in quite a predicament. You are leaving me in a lurch".

He was trying to guilt me into staying I guess. All I told him was:

"There is never a good time to quit. I'm always in the middle of a project here, if it wasn't going to be inconveniencing you, it would be inconveniencing someone else at the company."

My answer I thought was obvious, but apparently it helped him realize this wasn't something personal, but just something that happens in business every single day.