Ask HN: Start-up while having a day job?

I worked on a side business for about a year, right after I got married. At the end of that time, when the founder of the company I worked at and I had some irreconcilable differences, we parted ways and I worked on my side business full time.

That was 3 1/2 years ago and now I own two companies; the first one I started which is a quite successful marketing business and the second which is a mobile/social app startup that just graduated from an incubator here in SD and is raising a round of capital.

What I ended up doing to stay sane was relatively simple:

1. I set effective boundaries with my day job. I wasn't paid to work extra hours or do stuff above and beyond my job. I did what I could but made sure that I also stuck to my guns when I wasn't willing - or was unable - to do something. With this I could focus when I got home and not feel completely drained (most days).

2. I planned out my side work-time and stuck to it. Instead of just working every available second, I did my best to plan out when I worked on it and when I didn't. By sticking to these rules, I avoided largely burn-out and was able to move forward at a steady pace. However, when you are on something hot, be ready to give that extra push if it will pay off; you'll know when it happens :)

3. I didn't forget my home life. My wife and I had just married and were both working our asses off. We did our best to get time out and be together, whether that meant playing video games or going to the park. One of the perks of my job was that I could take a bit of time off if needed (Friday off meant working a bit longer during the week) which made things easier.

4. I didn't quit my day job prematurely. When I ended up leaving the job, it was too early, but I didn't give in to the temptation to leave far too early when it would probably have sunk us. Be patient and methodical with your side business until you are pretty damn sure you're ready. If you just hop off willy-nilly, you can be sure things can go south quickly.

This was my experience with it, and I'm thankful every day I did it this way. Everyone has a different experience and different priorities, but hopefully this can help you too.

If your unsure about the projects potential success, then defiantly dont quit your job just yet, as you might end up with no project, money and job. To me it sounds like you need some out side help, either in the form of another 'founder' or may be hire some coders etc to get a prototype up and working. Once you have an initial version of the website/server it's a lot easier to get some user feedback and see if the project actually has some potential, it doesn't need to be 100% or even 50%, just something you can show.

It's not easy and glamorous as the highly publicized ones you and I read about. I started a project last year and every night after putting my son to sleep, then I start my project work. Most nights it's from 11pm until 2-3am. Then up at 8am to start my day job. After while, I was used to the 4-5 hrs of nightly sleeps. I tried to separate the day job from the side project. Like others said, set goals for each time you sit down to work. What do you want to accomplish. Slowly but surely you'll get your demo done then beta. There were times when I was too tire to work or think, I still sat down for an hour or two to fix a few bugs. I made sure each day I do something to get me closer to my goal, which was the beta. Bottom line is that it won't be easy at first. It's probably the most difficult thing you've ever done. Challenge yourself and push yourself beyond the limit. It gets easier as you get use to your new life/routine. And when you demo product and people start to get it, all the efforts will be well worth it. Good luck!

One thing that I have found to help me is to break things down into very small tasks, something that I can get done in about 1/2 an hour. It can be as small as creating the signup page or doing a password reset page. I found that sometimes when I got started I would roll through a few of them, but even if I only did one thing making progress every day would feel really good.

If you do not feel strongly about your idea and, more importantly, you do not believe the product is needed by the market, then do not quit your job. Only when you have satisfied these needs, then take the step of deciding whether it is worth the risk to pursue your startup dream...

I had the same problem. This is why I feel that it's better to save 6 months-year of salary and quit.