I recently decided to change jobs and move on to a startup after 6+ years at my job with a large (and prominent) web corporation. I’ve learned a ton in my time there but it seemed to be the right time for me to move on to something new for a little while. I don’t have much experience resigning from jobs (most of my moves have been from layoffs or acquisitions), but I did make an interesting observation. The process of resigning resembles, very closely, the process of breaking up with a long-term partner.

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1. You feel guilty

Yea.. no matter how “right” the time feels, it still makes me feel guilty. I know this relationship is stagnating and we’re both “comfortable” but I want more. I know that breaking up is for the better for the both us right now, but it doesn’t change the fact that the other person’s crying at the thought of going on without me and that crying makes me feel super guilty.

I’m pretty stretched across teams and I interface with many people in my day-to-day work. I keep having the thought that I’m letting people down and leaving them hanging. I just have to keep telling myself “its for the best” and “the time is right”. These are people and products that I feel very deeply about and I want to see them succeed in every way. I don’t want to cause any sort of setback for any person or project ever. …but again, I have to think about what’s best for me and my life right now.

2. The Other Party Is Confused

Unless you’ve been sandbagging for months in the relationship, the other party will be blind-sided and confused with your proposed breakup. The same holds true with your employer. The questions of why? and where did we go wrong? will arise. The old adage – “Its not you, its me” is something that helps here.

Let’s face facts though, in every breakup (or resignation), both parties have some responsibility for the event. The trick here is that you shouldn’t be negative about the other party. That negativity will eat what’s left of the relationship away and leave both sides bitter. Just suck it up and take the blame and move on. There is no need to harp on everything that could’ve or should’ve been done… its bad for your health and the process. Get over it. Just be happy you found another (hotter?) chick :wink: (or dude)

3. The Other Party Holds Out Hope You’ll Come Back

If you were as awesome as you think you are, the other party will think you’re making a mistake and holds out hope you’ll realize the err in your ways and come running back asking for forgiveness. This is normal and you may actually find that the grass was actually greener with your previous partner (or job).

Just realize that the moment you come back admitting you’re wrong, you’re handing over all the control to the other party. No matter how well you handled the situation, you’ll hurt the other person’s feelings… In the job world this can result in a pay-cut or loss of benefits when you return. Sometimes its better to just try to find another fish… after all, there are plenty in the sea. :fish: :tropical_fish: :whale: :octopus: …right?

Note: I don’t discourage you from going back if its the right thing to do… just make sure you don’t hand over all the negotiating power when it happens. This is how abusive relationships are cemented :no_good:

In conclusion,

its important to remember that you must always do what’s good for you! In any case, if the relationship (or job) takes away from who you are and doesn’t enhance your happiness, you should swallow hard and initiate the breakup. Life is entirely too short to waste even a day on something that doesn’t enrich your life.

Never stay just because you feel “comfortable”