Communication, DHVing studying and angling for success

EANx

My job isn't at risk and while promotions would be more likely with greater effectiveness, my job pays well (into 6 figures) and has both stability and a pension. While I have no plans to change employers, I am trying to position myself for a run either at the higher executive level of my current organization or if the politics don't work out, once the pension vests, to retire and work elsewhere where the benefits are cash/stock rather than stability and a pension.

I consider myself more of a thinker than a doer. While I have won awards for my "doing", it was 90% thinking everything through and 10% pulling the trigger. My current work tends to be more strategic direction than hands-on implementation, I manage managers, but my work also would benefit both from a Masters degree as well as technical training. While I may not be doing the work, staff are more likely to respect a director who doesn't give a Scooby-Doo puzzled look every time they talk. And I enjoy the tech-talk and the rare hands-on.

My GF is a doer. She can't sit still, her home is organized just-so, she has an extensive garden, etc. Having dated off and on for 2.5 years, I'm not afraid to contradict her on some yard things (showing my thinking side) but she's the driving force behind how that piece works. An example of where I jumped in was with her fig tree. It was becoming rather pathetic so last winter I asked if she minded if I worked on it. She said no so I trimmed it back, packed it in for the winter (which she wasn't doing) and now have been giving it extra water. Two months ago, she said she didn't think there'd be any figs but there are now 40 in various stages.

Ages: I'm 47, she's 40. Dating, not married but there's talk about long-term plans like "maybe we'll do X next summer". We met 2.5 years ago and have dated almost two years.

I'm looking at 5-6 years to get to where I want to be, giving myself enough time to both study and do activities with the GF and her family but I'm keenly aware that while the end result is a DHV, the sitting there "reading and playing on the computer" for several years, doesn't have the same impact that an immediate project does.

What's an appropriate level of communication here? I don't want to over communicate and seem like I'm trying for positive reinforcement for reading a chapter but I also don't want to plan for an exam a few months out, put in all the effort and her feel like I'm "always just sitting on that damned computer". This is complicated by the fact that different milestones will take a different amount of time to achieve. And let's face it, there will be times I want to decompress and surf or play a game and no doubt that will be when she comes to see if I need anything.

What are the most effective deliverables in this type of situation?  I was thinking exams were and that when possible, scheduling them well in advance would both give enough notice for planning as well as indicate progress. For the Master's, anything major that needed to be turned in and grades.

Where are the points of diminishing returns? When the bills are paid and there's an income stream from a pension, is there much of a benefit to me having that multi-100k C-level job? Bragging rights? The difference between a hotel room when skiing in CO vs renting a luxury cabin? Owning a cabin on a lake vs renting once in a while? Will this be angling for a level of success that actually harms the relationship? I don't want to be one of those guys that fights for success only to find out that the time I spent was resented but I want to have a comfortable retirement as opposed to struggling to pay medical bills.

frillyfun

I think you're not married, so if you want this then go for it.  I wouldn't let someone who's not a spouse hold me back.

EANx

It's less about her trying to hold me back and more about effective communication. How you communicate something is almost as important as what is being communicated.

Angeline

I think this is the key:

I want to have a comfortable retirement as opposed to struggling to pay medical bills.

If that's how you feel about it, then you should not let anything get in the way of it. And If you are strong and forceful and emphatic about it, you'll be fine. YOU get to decide how you get there, if you're on track, when you need some down time. I believe that if you're doing that, accomplishing what you want to accomplish, you will telegraph it.

And you bump back hard and strong to any suggestion otherwise, because who the fuck besides you gets to comment, when you have the track record you have.