Is joining AWS a bad idea? (MSFT, Oracle options)

Will the additional money truly impact your life in any measurable way? If it's just going to cause your investment account to grow a bit faster, unless you're planning on FIRE, you might as well strike that consideration from your decision making and compare the life/work balance you have versus the prospect of interesting work. The former could change if you stay but it sounds like you're pretty comfortable that it won't. The latter is by no means guaranteed. Really seems to come down to just how much is the boredom at Microsoft eating you up. If it's crushing your soul, taking some risk might be justified.

> Everyone on "BLIND" says AWS is absolute hell, unless you luck out on team/manager.

Blind self-selects for people unhappy with their jobs. So, I'm not sure Blind is a good source for any job information.

I don’t work at AWS, but believe they at least have a public image issue with the culture and work life balance. Review sites like Team Blind are markedly more negative regarding AWS than other leading technology firms. I know several friends and colleagues who are afraid to work at AWS due to the negative reputation.

AWS really needs to address some of these reputation issues if they wish to attract talent. It’s hard for me to believe all the negative feedback is true, but it doesn’t seem like AWS is doing much to address it.

In all the jobs I've ever had, I was soon working on stuff completely different from whatever I was tasked with when I started, undoubtedly because they were much smaller companies than Amazon/Microsoft/Oracle and so plans and projects were much more dynamic, but it did make for much more interesting work. In any case, it taught me that no matter what I was promised at the beginning, things change, so be careful making the assumption your assignments will remain as originally described to you.

At $250k/year, you’ll be paying 24% Federal tax (up to about $325k, at which point it goes to 32%), so AWS would net you about $32k/year more (excluding state tax) for 250 to 500 hours more per year (5-10 hours/week * 50). That works out to between $128 and $64 per hour. If you take into account the 401k difference, these numbers might drop even lower.

The Oracle job seems like a nonstarter since you’ll have to pay the self-employed tax (really just the 7.5% that your current job pays for you) plus benefits (which can be very expensive). It doesn’t seem like a financial step up.

I’ve been a consultant for years because my spouse has a great job with benefits. I’ve been able to save up to $50k/year in a solo-401k and take of lots of time to spend with the kids (coaching, day trips, vacations). This freedom has been the MAJOR benefit of consulting, but again my spouse provided the safety net.

What I haven’t mentioned is the tech stack. If you are in a dead end job, then you should definitely consider a change - if your position is eliminated (and it’s probably more likely than you expect), what could you do next? A sideways move now into a better career path could pay off in terms of safety (as in you could easily get another job). Being comfortable now could make life more difficult later.

You’ll obviously need to weigh these options yourself, but the best opinion I’ve heard so far is to seek out a transfer within Microsoft that might give you the tech challenge/ experience without the uncomfortable changes the other jobs would require.

Good luck!

AWS really does suck unless you luck out on team/manager. No one I respect has lasted longer than a year there - often to the day.

Neither option sounds all that good (that particular AWS offer sounds scary: if he's "estimating" 45-50 hours, why doesn't he know? It is probably more). Stay at MS for now and keep looking for the right position (including at AWS).

Honestly, for me, you cant put a price on life/work balance.

More Money != More Happiness.

My 2 pence.

If you were single, I'd say chase the money. Not that you shouldn't chase money with a family, but you seem to have a nice chill job situation. Family and chill is a good combo.

The AWS offer just seems... ewww. At 50 hr/week the money is WORSE per hour than what you currently make. And gives up the chill.

Perhaps try to move to a more unixy area/group/team at MS? Perhaps a research type area? Just an idea.

I'd just ask for a change at MSFT; they have a really good reputation for finding the right position for solid performers. I'm surprised you didn't mention whether you explored that in your post, so maybe you have already, but it's what I'd put all energy into.

I've never regretted changing jobs. Go to new place, learn and experience new environment, expand your network.

I'd bet if you don't like it you can always go back to MSFT later, likely for higher salary

Stay at Microsoft show them that your are loyal and that you want to work on other projects.

if work life balance is important to you and you already have it at msft, why change? if money > work-life balance than go for it.