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It was a good job, not a cool place, but paying well. After watching many Peter Thiel videos, in which he was telling his life story mot à mot over and over, I became fond of how he just walked out the front door to quit the job, voilà. I made up my mind.

I cleaned up my desk, packed up my things, thinking I will be the next Zuckerberg. My supervisor told me that I was making a big mistake, a career suicide, he said that I will never be like Zuckerberg, all I said was 'adiós'. He kept contacting me from Facebook for the following days. To burn the bridges and focus on my new entrepreneur life, I blocked him as I read burning bridges is a good thing for entrepreneurs.

Fast forward to today. I lost 40K on my startup adventure, I am broke. I just want to find a job. Should I mail my former boss and say that I made a big mistake, and I want to return now or should I just cold call him, and act like I'm doing good, and wait him if he has any offers for me.

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    What do you have to lose by reaching out? Worst case scenario they say no and you're right where you are now. – pip install frisbee Aug 30 at 15:31
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    Where did you read that burning bridges was a good thing??? Also, you have nothing to lose at all by reaching out to him in humility, except maybe a dose of pride. I say good luck & go for it! – Crosbonaught Aug 30 at 15:34
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    @JCrosby The concept descends from the "point of no return", "crossing the rubicon", "burning the boats", etc. The idea is to remove alternatives, thus ensuring you have no choice but to press forward and thus serving as a kind of forced motivation. Most people who apply it seem to misunderstand the difference in a commander burning the boats to prevent retreat of their enslaved underlings, and doing it as an individual - a misunderstanding of the power of optionality. Good Wikipedia page on the many variants of the idea: en.wikipedia.org/wiki/Point_of_no_return – BrianH Aug 30 at 16:02
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    ...particularly as your approach to social encounters doesn't seem to have substantially improved in the intervening time. Or perhaps your recent spate of posts indicate more of a trolling situation.... – Lightness Races in Orbit Aug 30 at 16:37
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    This is a good time to remind everyone that not everyone who writes self-help is actually trying to help you. More often than not they are just trying to sell a book. Please try to be more critical of things. You bought into this without so much as a thought and threw away your career, connections, and 40k because a book by someone you don't even know told you to. You don't know what his motivations are just because he told them to you. That is playing fast and dangerous with your life. Entrepreneurs need connections more than anyone, not less. – DetectivePikachu Aug 30 at 18:39
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Be honest, be serious, be remorseful.

You were dumb, and got seduced by a power fantasy. You were unnecessarily rude on your way out the door. You deliberately did things to burn that bridge, and now you're hoping to unburn it. At this point, your old boss (if he's still in the old position, if he has a position open) is going to have to ask himself if you're really worth it. He probably has some personal feelings about how it all went down, and how you treated him, at a time when he was both completely correct and trying to help you. There's also a very real risk that, having gone off to do the dumb thing once, you'll do it again later, and leave him in the lurch again.

Your best bet for handling that (it's not at all guaranteed, but it might work) is to accept that you screwed up. Admit that you screwed up. Apologize for how you treated him, and try to make it clear that you have learned a very painful lesson. Make sure that you have, in fact, learned that lesson.

Basically, people work on narratives. "The repentant prodigal son returns" is one such narrative, and one where he can (if he has the opening) decide to hire you back and feel good about it. If you come to him pretending to be successful, though, he'll have no direct reason to think that you need or want his help (you certainly didn't want it before) and if he figures it out (not hard, given the circumstances) he'll be much, much less inclined to give it to you, for a number of reasons. The narratives for "prodigal son comes back a failure, trying to pretend that he was actually a success" go a lot worse for you.

Essentially, it's time to eat crow, and learn (and express) some humility. Even if he doesn't hire you, it'll be good practice. From the sounds of things, you could use the practice. Useful phrases include things like "You were totally right.", "I'm really sorry.", "I should have listened to you." and "I screwed up."

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    +1 - great answer! This was put much more eloquently than I was trying to say, but the exact same message I wanted to convey! – Crosbonaught Aug 30 at 15:36
  • @Ben Barden I have no problem admitting that I am dumb, but I do not want to seem needy at the same time. Just saying that I was dumb will transfer the notion I am desperate, is not that so? – Denis Smith Aug 30 at 15:38
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    @DenisSmith Don't go begging, but do go apologetic. You were both dumb and rude, and you didn't appreciate the efforts he clearly put in on your behalf. You have now learned a very painful lesson, and have strong incentive to not do it again. These are the things you need to get across. It's true that too much begging and whining is likely to hurt your position, but "act like I'm doing good" is entirely the wrong direction. Repentant. You need to be repentant. – Ben Barden Aug 30 at 15:41
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    Even if the former boss does not have an opening, he may be able to give the OP a reference and possibly some contacts. To do that, he has to be sure the next time the OP wants to quit a job it will be done right, with proper notice. – Patricia Shanahan Aug 30 at 16:03
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    Also - take a moment to reflect. Why do you want to go back to your old employer? Is it because you genuinely think that's the right place for you? Or is it just because you're desperate and broke? Follow the advice in this answer if you're sure it's the right place. Don't try to go back if you're not sure, get a job somewhere else that's more appropriate for you. In other words, don't put yourself in a place where you may decide, again, that you're not happy. – dwizum Aug 30 at 17:41

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