Ask HN: Should I quit my job?

If you're 29, you could quality of a Holiday Work Visa for several countries. Look them up, they're very cool and cheap. I got one for Australia when I was 29, got one for NZ before I turned 30 and then aged out of them. I had two big breaks in my career, one where I lived off my savings for 11 months (3 of those were with my girlfriend in Germany) and I took a road trip across the US for 5:

https://khanism.org/perspective/minimalism/

https://khanism.org/perspective/a-tale-of-two-journeys/

It will set you back a bit. I used up a good amount of savings, but I never had to dip into or borrow against retirement. I probably wouldn't do it again (unless I get accepted into a PhD program; one of my big goals), but I'm really glad I did. I literally traveled around the world and lived in three different countries. How many people can say that?

> I have enough savings to survive for five years.

That's three to four years more than most people who make the jump.

If you're already making money from your side project, again, you're ahead of most people who make the jump.

Sounds like you should go for it!

The biggest thing to watch out for is getting lonely. When I went off on my own, I had a wife and kids. So I get to see them every day. If you work alone, you may not have any human interaction for a day or two, or longer. Human interaction is important to maintaining sanity. So make sure to make up for it somehow. Go to meetups, join a social club, be proactive about meeting up with friends, something to get you out of the house and interacting with other humans daily. Even if you're in an introvert, you still need human interaction. Find something that works for you.

> To not stick to a schedule/routine once I am solo

A lot of people have that fear, and it's pretty easy to solve. One trick involves starting every day with a walk around the block and ending each "work day" with another walk around the block in the opposite direction. This is your "commute" and puts you in the right mindset. You can do something else if you don't like walking, like make sure you start with a workout or a shower.

> People's and family opinion.

That's a hard one. Every family and culture is different. But in this case profitability solves a lot of problems. If you can respond to the naysayers with "I'm making money not losing" then that's a good way to appease most criticism.

> Failing and losing motivation.

Another hard one, especially if you have a lot of savings. You need someone to hold you accountable, either a cofounder or even an employee. Or depending on your relationship, maybe your girlfriend. As her to check in with you specifically about the business every week. Or if not her, another solo founder somewhere.

My advice, for what it's worth, based on my experience:

1. Every time when I delayed making a significant decision in my life related to big changes, I regretted only the delay. I was always happy with the outcome, but always wished I had made the decision sooner. I now take this into account and decide faster. Life isn't that long.

2. Starting something on your own takes years. Unless you are very lucky, building your own business will take at least two years until you can live off it. In SaaS that's because how it works, in consulting it's because you usually need to find clients and work your way up via referrals. The only exception is if you can get consulting work from companies you already know (such as your former employer). So don't quit your job without a very good idea of what you will do next and plan to live on savings for two years.

3. There might be other jobs that will leave more time for side projects, so changing your job first and then starting something as a side project first might be a safer path.

Wow! Sometimes it really is about asking the right questions!

This question seems to be the right question to ask, but whether it is or isn't, thanks for reminding me.

Just do it. You will learn a lot and no matter what make a bunch of mistakes. Just don’t burn out. Work hard but make sure you spend time with friends, your partner, and most of all yourself just relaxing. Evaluate how you are working regularly and make changes. Forgive yourself for mistakes, errors, flawed thinking and keep hacking. It will not be smooth but entrepreneurship is awesome and you should go for it if you have the itch.