Nija
you had two full-time IT jobs right? I'll most definitely be getting a really juicy offer from them in the relative future but I really like my current job and they're investing a lot of resources in my professional advancement.
How did you manage the two schedules? I have no doubts I could with WFH and it will certainly not be hard for me to do.. I don't think.
WFH is key.
Here's how it went down for me. I left Company A on good standing to rejoin a past boss at Company B, which was just getting started. I had a good relationship with the CEO of Company A, chatted on gchat, etc. I made a lot of performance related suggestions, and really wanted to try a new role as a performance engineer, but they weren't ready for that kind of position.
About 20 months pass, he messages me and says they are ready for that position I wanted. Really cool situation. At that point I was deep in Company B, building everything still, so what I could agree to was 20 hours a week, part time, no benefits. Work from home. This was a 60k "salary" position which was effectively a static 20 hour a week hourly job. Go figure. The set hours here were 10-2. At this point I kept my full 40 hours at Company B, sold my gaming PC, and pretty much stopped gaming. I did a real 60 hours a week for about 2 years.
After 2 years, Company A was growing like crazy and they wanted me at a different role and wanted more of my attention. They wanted to bump me to full time, give me benefits, and get me involved in more projects. I approached Company B and told them what was up, and offered that we could cut my salary and hours in half. Here's where I am extremely fortunate - the owner of Company B said that he's fine with cutting my hours in half, but doesn't see a need to change my pay. I flipped from 20 / 40, A/B, to 32/20, A/B, while keeping the same salary at Company B. Moving to "full time" (minimum hours full time which granted me benefits) with Company A, I negotiated a payment parity between the two companies. I think A paid me 5k more than B at this point.
This change meant that I simply started work at 8, still finishing at 2. I then added a nap after 2pm, picked up the kids, and then I did 4 to 6 30 minute work sessions for Company B after that. I started coaching kids sports at this point, so I'd do something like 3 chunks before 5pm, 3 after 8pm. Honestly, sometimes I missed a few but my output was still good. Using one of those stupid "Getting Things Done" systems really helps when you want to do do this kind of thing.
Currently, my lauded move to Arkansas brought another change. Changing time zones. I kept the same "sign off" time of 2pm Pacific, but that's now 4pm Central. I added two additional hours beforehand, again for a new role, and they adjusted my pay accordingly. (no cost of living bullshit or anything like that) To be completely honest, these additional hours plus my coaching has made keeping on top of my work at Company B extremely difficult. I've moved twice over the summer, kids are at two (soon to be three) different schools, and my focus is lacking. I need to get back on top of things, breaking tasks into 30 minute chunks and knocking them out. I've gotten kind of lazy and putting more emphasis on working on my new house, my shop, my kids sports, instead of this company.
In short, after a giant post of course, I would say that you should negotiate some kind of split between the companies, where you're not working 40 hours for either of them. You probably want benefits, or at least I would suggest getting benefits at one company, which you can use as a bargaining chip for the other. I think 32 hours is technically the minimum for benefits, I negotiated a flat 6 hours a day because I said I'd spent the other 2 outside of set work hours, focusing on training. Companies will sometime make exceptions for the right person. I was the first (and still the only) part time employee this company of (now) 450 people has ever had. Focus on the value that you bring to both companies, while explaining the value both companies bring to you. I know that sounds cheesy, but it's the summary that works for me. The only way I can work at a mid size company and put up with the dumb politics and (sometimes) dumb decisions is that I get to do anything I want, technology wise, at the other company. It lets me relax and not stress to much over every single technical decision made at the larger company. If and when I start doing a tedious task or project at one company, I make sure to do rotate over to doing novel / pilot project at the other. I also have two training budgets, one at each company. That sort of thing really does bring value to your life. There are tedious things that have to be done with any job, and it does help (at least it helps me) when I can recognize those, and schedule them at a time when I'm doing the complete opposite kind of work at the other company.
Let me know if you have any specific questions. Obviously I can go on and on about this stuff.