Ask HN: Should I quit my job?

If it’s what you desire, then yes, you should quit.

I’ve done it before and it’s a great experience. 100% worth it. Follow your dreams.

Just don’t delude yourself into thinking you will grow your side project into a full time income. You may. But don’t count on it.

I think the first thing is to establish why your current job is making you so miserable and exhausted, and what you can do to organise your day so that you are not left wrung out at the end of the day. Optimising your time and energy is a better option than quitting a job and dipping into your savings. Once you’ve worked that our THEN you can think about whether to quit your job. Because the problems you are suffering now are unlikely to go away if you make such a major and fundamental change in your life. They might - but they might get much worse.

Working with a therapist or a coach might help you unblock whatever is holding you back and identify how to increase your energy and reduce frustration. That would be a better use of your savings - right now - than quitting your job.

You also don’t say whether you have any experience on the business side of things. A side project supported by a stable job is very different to something being your primary source of income.

I’m not saying don’t take the jump - but get everything lined up and address the disorder first.

You'll probably hear advice that makes silent assumptions about personality types. I'm the type that can't have a cushy FT job while also building my own business. Hasn't worked. It sounds great in theory, but I make far less real progress on the business than I think I do. I also think having a cushy full-time job inherently steers you towards "taking it easy" and distracting yourself with "lifestyle" things, relatively random hobbies, etc.

Quitting my job to pursue my own project, with a few years of runway, massively accelerated the development of my project, accelerated my rate of learning - ideal for staying employable, while basically subconsciously removing "lifestyle" distractions that come with making > 200k/year.

So yeah, chalk it up to personality type, but if you're serious about building your own business, the best advice, since you have the runway, might be to quit your job as soon as you can.

If you have five year's worth of savings it's a no-brainer. Give it six months and then get back to employment if you don't succeed by then. Then work for anther 12 months and repeat the process if you have a new project.

As long as you are strict with yourself in only giving it 6 months, it should be fine. Tell everyone you know that this is your plan. If you don't get any traction within six months it's very unlikely that it makes sense to drag it out longer. Just cut your losses and move on.

You're mixing issues a bit.

If your current work is, as they say, "soul crushing"... you should invest some of your personal time to leaving that job. This is an independent decision of what you want to do/should do afterward: yes, you can quit/work on your own stuff.... but there are other possibly good outcomes that include the "quit" part, but something other than bootstrapping a business.

As for starting your own business, I found it hard to bootstrap something meaningful without being full time on it... so that part of what you're talking about does make sense. But you need to be ready to burn cash for an extended period, consider: 1) how long it will take to get your product/service into something making reliable income (meaning enough to cover business expenses, your expenses, as well as enough to bank some cash so that you can ride out the hard times); 2) if things don't work out, you still will need cash to burn while you look for new employment... or more seriously risk having to take the first thing that comes along and being, perhaps, in a worse position than you are now. Not having dependents is helpful, but you have your own needs that, no matter how meager, must be accounted for.

I did the bootstrapping thing myself, but I was lucky in a sense. I had run out of runway cash and had to take a job quick: the job I took saw my bootstrapping effort as a plus, and after I was there for a few years, I was allowed to moonlight on my original business to get it stable... and later when I left that firm, they were a client for while. (my business has been self-sustaining for about 7 years now) Don't count on that kind of luck, though, and to that point. If you don't have the cash (or access to it)... get out of your current job, but almost certainly get another.

As for people's / family's opinion: meh... you need to have sufficient confidence and independence to pull off a bootstrapping project. If you second-hand your self-worth to the opinions of others: then you need to question how successful you are likely to be. Much of being an entrepreneur of any type is being able to see opportunities that others don't. If you rely on the opinion of others... well, you may see a contradiction in goals. None of this isn't to say that well qualified or well reasoned opinions shouldn't be listened to or taken seriously: they can give valuable perspective... but fearing those opinions in determining if your vision is legitimately right or wrong is probably going to put you on the wrong path. The only valid fear that comes to mind is if you intend to use those people/family as a safety net if you fail.... I would suggest planning and preparing so that you don't need to call in help should you fall.

Also, be aware that your business will take a life of its own. I was able to bootstrap and get stable because I did smaller consulting gigs across a lot of long term clients, but ultimately I wanted to build products. Well, great... now I have a good cash flow as my client base come to me with new projects and I have "hard times" buffer, but I have so many client obligations that I have trouble getting to product building part... which really needs to be full time. There are solutions to this, but they are not easy to pull off at my scale... I do well, but not so well as to staff up, for example.