I've been following this thread with interest. Here a bit of my long and rambling work story:
I have been working for a startup company for the last 5 years that has paid me a significant % of the company in shares (I'm 1 of 5 founders), but no actually $$. Only 2 of us are left doing anything significant with the company. So I "own" a good part of the company. (Who knows what is real "value" is... more than 0, less than billions.)
I don't know if we will every "make it" or not, but I continue to put in anywhere from 10-50 hours a week. (depending on whats needed). Most of the time because the "product" is complete its closer to the 10 than the 50. Every now and then we put in a new feature, a serious bug is found... whatever.. and 50 hours happens.
I also started a "real" job about 9 months ago. A friend that use to work for me, told me that the company he is working for was looking for a sysadmin. Wanted to know if I was interested. I told him sure, but I only want to work 25 hours a week. (partially because of my other "job" partially because I enjoy my free time). The deal was that I was going to stay on for a couple months (they said 3, I figured 6) and help train a current employee in Unix (he was a windows help-desk person). I would then leave (This was one of the big things that managed to draw me in was an exit plan, and their willingness to train an internal employee and create a nice career for him). Things changed, the guy I trained got a Unix admin gig somewhere else
and I am still there... and I am actually enjoying myself. So I was his boss, now he's my boss.. Life is so much fun.
One job is Unix admin, the other is software/web development, both things I enjoy. So since I don't need the $ (or the shares) and both companies know it, I don't get pulled into the work "crap" near as much as I used to. (probably helps that I'm not managing anybody to)
The "$" job gives me a little extra spending money, some extra savings money, and some human interaction which my "shares only" job doesn't give much of.
I've known my business partner for 20+ years, (long before we started the business) and he gave me some advice a few years after I met him that has turned out to be true each time I've used it. If you are good at what you do, companies will give you just about whatever you ask for to keep you happy. (except for more $)
I worked for a university as my first job (10 years). I got an job offer to go to a private company, but was hesitant. I talked to my boss before I accepted and asked if he would be willing to put me on unpaid leave for 6 months while I checked out this other job. He said... Yes... because he wanted me back if the other job didn't work out. (The job did work out, but I did do a couple projects for the university as well, so I think we both benefited from that deal)
In that job after 5 years I had the opportunity to do the startup company. So I told my boss that I really needed to go hourly and only work 20-25 hours, and I wanted something less "on-call" like more in the software development group. They moved me from managing the sysadmin group to web development and I stayed with them for about a year until the startup consumed all my available time.
When I got hired in my current "$" job, I told them I could only give them 25 hours, and based on the recommendations of my ex-employee about my abilities they decided to hire me even if it wasn't for the 40 hours they wanted.
So my point is, if the people in your current job want to keep you, and the people in the new job want to get you, there might be something you can arrange to give everybody mostly what they want, and find the best of both worlds. I think you have the right idea thinking outside the box. How to fit the puzzle together I don't know, to many factors of who you know, and what they think of you.
I'd be really hesitant to try to keep it all a secret. It was easier for me in that I was entering the "negotiations" knowing that I didn't need $ out of the deal.That makes it easier to say, "The job sounds really interesting, but I can only be there for 25 hours a week. I have other interests that I'm unwilling to give up. I have kids, so my hours can be X-Y"... "and I'm happy to work for only 3-6 months training my replacement".
So, not knowing your relationship with your boss, or your CEO, I can't say if you should tell them or not that you are looking. Only you can make a reasonable guess as to how your boss, or the CEO would react to this. Would the current company support you, try to keep you, but see that the current $ issue they can't keep 100% of you. Do they like to look for outside the box solutions, or if they would fire you on the spot because of your "lack of loyalty". You will be the best judge of this, not us here
. If you trust your boss he might be a good judge of the CEO.
We also don't know your relationship to the new company, and what they "think" of you, which plays a role as well.
I thought I'd just share my story so you know there are other outside the box ways of doing this. Keep thinking about whats best for you, and whats best for both companies, and can you come up with a middle ground to get everybody something.
Laters,
-d.