[rubicon33]

Similar boat to you. Had the exact same question in my life.

I decided for a totally different option, lets call it option #4:

#4 Take an "easy" programming job and use your spare time on nights/weekends to build a software business.

I chose this option because I wasn't willing to risk my savings. Plain and simple. I want to retire some day, and blowing 60k for a ~5% chance at making a profitable business wasn't worth it to me.

[GoToRO]

For sure #4. Because if you never launched anything then it will almost for sure not work the first time around. It's a skill like any other skill and you need a few tries to figure things out.

A caveat: I took an "easy" job but it turned out it was the job from Hell. Because "easy" job was surrounded by people that didn't know what they were doing. So a truly easy job might be one where everyone is overqualified and you only need to do your own thing (as opposed to expending a lot of energy explaining to people how to do the right thing, all the time, because they just don't get it).

[randycupertino]

Vote for this one as well. Also an easy way to get health insurance and 401k squared away while you're at it. OP, I suggest doing this- get a cushy 9-5 programming job and scrutinize the onboarding paperwork to ensure you're in the clear to own anything you work on in your free time if not using company resources.

Best of luck!

[longnguyen]

While I am on the same boat, there is definitely a caveat that you should aware.

Those "easy" job you think might actually be hard, because of politics/bad managements/weird policies etc. And even if you're lucky enough to get a relaxing job, the differences between those 2 jobs might damage your mindset/thinking/focus.

[driven20]

This is what I'm afraid of...My previous job wasn't hard. What was tiring was forcing myself to work on stuff I don't care about.

[rubicon33]

This is one of those "have my cake and eat it too" scenarios.

You want a job that inspires you and which you care about AND you want to start a business or at least pursue some side projects which you think have a shot at making you money.

I've never seen that happen, personally. Something has to give whether it's your savings (you don't work a job) or your enjoyment of your job (you keep your savings).

I think for you given you've tried the "easy" job route and found it draining... You should spend your time now finding a job which excites you and energizes you. Put your time, and effort into that. When you have spare energy, work on your side projects.

[gere]

This is a sensible advice, but how do you recognize an easy programming job?

[rubicon33]

There are (at least) two ways in which a job can be "hard":

1) Technically. Having to constantly learn new things, new technologies, etc. Unable to rest on your laurels. Learning new things can be very rewarding from a career growth standpoint, but it can also leave you drained at the end of the day.

- Avoid a technically challenging job by choosing one which is in your skillset, and unlikely to change. For instance, if Java is your thing, find a back-end Java job at a big company (startups will often ask you to change roles and learn new things).

2) People. Dealing with shitty bosses / managers / coworkers can suck the "easy" out of a job and make it very challenging to get anything done.

- Try to get a feel for the leadership in your interview process. The interview should come off as warm, and inclusive, even you aren't doing well. Overly complex questions, riddles, or hide-the-ball interview tactics generally come from insecure interviewers.

[jlelonm]

It's hard to from the outside, but I would guess the biggest factor that correlates with easy is amount of red tape. The more bureaucratic, the more non-work is done in place of actual work, the easier the job.

So I'd say large corporations or government jobs would skew easier. Maybe work for a large government organization?

[anotheryou]

less then 5 days/week helps