This will sound odd, but hear me out: assuming that whichever way you choose, it will be wrong, which would you choose? If you quit this job to pursue your side project, and that doesn't pan out, will you forever regret having given up this job? Or, if you don't quit this job, will you forever hate your career because part of you is wondering what would have happened if you just "went for it"?
Figure out which mistake would be less crushing, and do that one. If it happens to actually work out, great. If not, at least you won't be spending the rest of your life regretting.
By the way, for reasons I won't speculate on, this method (assume failure, which would you pick) turns out to be a pretty good way of picking the option more likely to succeed, actually. But assume you won't succeed no matter what, and use that scenario to decide which way to go.
A product manager I've recently worked with had a similar approach. Don't ask: Why is X important. Always ask: Can I skip Y for X? Can I not do X to invest the same time to do Y?
That kind of thinking has kind of put a very big truck into my thought train in a lot of situations. Not doing things suddenly seems a lot more appealing.
And don't get me wrong. I'm an operator with legal and other non-functional requirements at heart. But there's still many things to ignore as much as possible.
This sounds good, but it doesn't really work, at least not in the way you think it will.
There's no way you can imagine yourself in an unknown future. You can not estimate how much you will regret one thing or the other, because you don't know the situation you will be in. All the variables affecting you (economy, health, family situation) are constantly changing. You're not going to picture yourself as a homeless alcoholic who somehow is still really glad he built that app once and would do all it all over again.
The first bad thing that'll probably happen after he quits his job is that his girlfriend will leave him. Not necessarily immediately, but it'll be a strain on the relationship. Even though she will not admit it (perhaps because she isn't even aware of it), she is probably dating him because he is a guy that has a decent job, not some dreamer with a wacky business idea (unless maybe that's how she got to know him). Breakups can be really tough on men, why can negatively affect work and motivation. Not being the guy with the decent job, it will be tougher to find a new partner as well.
The second bad thing that will happen is the realization that "being your own boss" and "working on the stuff that is important to you" versus "showing up" and "collecting a paycheck" always sounds better when you're doing the latter. Doing the former is actually a lot of stressful work and you can not tell how it works on you until you have done it.
Lastly, living with regrets is not such a big deal. Who doesn't live with regrets? Whatever you do, you can rely on your brain coming up with rationalizations on why this-and-that just wasn't meant to be.
Having said all that, with "five years of savings" (more like two years, am I right?), doing a sabbatical just to try it out should be in the cards. There may not be a need to quit the job, many companies offer this. If after six months to a year you aren't on the right track, it probably isn't working out, but you will have learned a lot about yourself.
Well, I had a girlfriend who, when I decided to quit my job and go back to college, didn't want me to. I did it anyway, and sure enough, that relationship didn't last. I found another one in college, and married her. Later, when I wanted to quit my engineering job and start over as a programmer at a university, making 1/3 the money, she said "go for it".
Breakups suck, but sometimes it is a way to find out if you are with the right person (not that this is why you should do it of course).
Being a programmer at a university is still a "decent job", the difference in money isn't necessarily the crucial part. Instead, try telling her you want to quit so you can become an (eventually unsuccessful) painter and then observe how the relationship is working out some months down the line.
Also, what are the odds that a modern educated self-respecting independent woman would admit (even to herself) that she quit the relationship over that bit of money? If money really was the problem, she'd still have to come up with another reason to break up. Plus, it's not clear if you were already married, that's another threshold of course. Divorces are usually many years in the making.
Of course I'm not saying this is 100% exactly what will happen all of the time (though I've seen it happen shockingly often) and you will certainly find people whose dysfunctional relationships lasted a lifetime. That's called "survivorship bias".
While probably echoed in other comments, I want to second the sentiment in this comment. Personally, I don’t believe there is a “happiness optimization” algorithm. Instead, what I believe, and mentor, is a “regret minimization” algorithm.
Think through the choices in front of you, which of them do you think you would regret more when you are on your death bed.
I will note, there is a risk to this approach I didn’t fully appreciate while younger: you don’t always know what in the future you will regret.
However, at least in my life, I have very few genuine regrets by following this advice.
That's a very interesting approach. Do you have more data/anectodes etc. on your point:
> By the way, for reasons I won't speculate on, this method (assume failure, which would you pick) turns out to be a pretty good way of picking the option more likely to succeed, actually.
I'm going to try to keep this one in mind for big decisions.
Anecdata: quit my job at age 29 to go back to get a Master's in EE, studying neural networks, in 1996. Quit my job in the semiconductor industry in 2004 to become a programmer at a university. Quit my job at the university in 2010 to go into the private sector. All three turned out to be the right decision, as far as I can tell, but in all three cases I was mostly motivated by knowing that if I did not, I would regret that more than I would regret quitting a position I was no longer interested in.
But, I wonder if it would still work well if, in the back of your mind, you were thinking "but it won't really fail, it always succeeds". You really do need to take seriously the idea that it will not work out, and only do it when you would still rather try it.
I am obviously in the minority, but I find this terrible advice. If you suffer a lot from 'regret' perhaps this approach makes sense.
But it completely sidesteps your inbuilt missile guidance system. A human being with a goal is a powerful thing. Just seeking to avoid the worst of 2 scenarios is a little sad.
Unless your goal is just to seek comfort, which is fine, but then be up front about that choice.
The idea is that the correct choice is the one that you will feel good about choosing, not matter how it turns out. Plenty of people who feel good about having done a startup, even though it turned out badly. But, plenty of other people who only did it because they thought it would make them rich and successful, and for any startup there is always a good chance of that not being the case. Most startups "fail", in the sense of they don't make anyone rich and eventually get shut down. So, only choose the startup if it's what you want to do, regardless of whether or not it will succeed.
I've also used the aversion to regret to make several big decisions. When I explain this to people, the reaction I sometimes get is pity. Having ones life dictated by the fear of regret seems repulsive to some people. I don't really understand that perspective myself, but it may be one to consider.
Living defensively may be good for one's chance of survival but is not that glamorous to tell. That should, as you correctly pointed out, be taken into account. What happens now when one's fear is ending up without having a life to talk about or not living fast enough? Joke aside, I think that, besides a fringe minority whose choices are dictated by kicks and thus subject itself to the high risk of natural (de)selection effect, most of us have lifes dictated by the self preservation instinct.
That's the thing, I usually end up using this metric to take the more risky choice. "Making decisions to avoid future regret" and "playing it safe" are two different things.
That's a really interesting way to put it. I once remembered and applied a quote something like "if you could choose one thing to do if you were guaranteed to succeed, what would it be?" Luckily and paradoxically, both questions have the same answer for me.
Figure out which mistake would be less crushing, and do that one. If it happens to actually work out, great. If not, at least you won't be spending the rest of your life regretting.
By the way, for reasons I won't speculate on, this method (assume failure, which would you pick) turns out to be a pretty good way of picking the option more likely to succeed, actually. But assume you won't succeed no matter what, and use that scenario to decide which way to go.