[pjmorris]

> I kept my current job because of the money and flexibility they gave me to stay, > but now that working here isn't worth it anymore,

So, what does 'worth it' mean to you? I see money and flexibility as the plusses of your current job... maybe that's all you need from the job. Could you keep this one and do something additional to get at whatever 'worth it' means to you?

[RefactorCareer]

I thought money and flexibility would be enough, but working on simple client requests is boring me to death, and I miss the ownership of working on a product. I'm sure I could milk this out until I retired, but there are other issues with the company, and I don't want to be miserable at something that takes so much of my day.

[pjmorris]

I've found the principle 'Run toward things, not away from things' to be helpful. If you don't know what'll really make you happy, you've got a shot at winding up just like you are now, somewhere else.

Finding, or starting, a relevant project, using technology you want to emphasize, seems to me like a step you could take independent of what you do about the job. As for the job, I think what they say about 'Change your organization, or change your organization' is true.

Of course, in similar shoes, I did something radical. I wasn't fulfilled in my monied, flexible job, so I'm taking a leap at what I really want to do: teach in college. It started when I came home from work one day, with a plan for how I could help local high schools with their AP classes and computer clubs, and my wife asked whether that would really do the trick of making me happy. I said 'No' and, 4 years later,I'm now ABD on a PhD, and could tell long stories of the highs and lows. It looks like it'll work out, but there's still a really strong case for having kept the boring job and looking for fulfillment elsewhere. Look up Eric Hoffer, who was a longshoreman by day, and philosopher and author by night.

[a3n]

No job lasts forever. That money and flexibility could disappear at the drop of an email. It sounds like his current job is comfortable, but it doesn't demonstrate to his next employer that he's relevant. I'd worry about that.