I could use some advice about relocating.
For background, I live in a medium large, very nice midwestern city that’s highly rated for being a great place to live. I have a nice house, a spouse and young children (infant and 4 yr old). I make a good living here as a senior engineer (web ~90k). For the last 2 years I’ve turned down invitations to interview with several highly regarded, established names in the Valley. I’m 40 years old (but appear 5-10 yrs younger). The job options where I am now are limited to a handful of small start-ups and very large financial/insurance (where I’d stagnate). I’ve worked hard and had great luck. I really like where I am now (medium sized, well-known company) doing app development in a rich problem domain, under a great manager, team, stack - you name it. Our Business is finding it’s way through some rapid change though (layoffs, etc), and I’m not sure how much longer the current environment will last. I feel like in 3-5 years I will regret having passed these invitations up.
Reasons I haven’t made the move:
1. My son has a serious health condition. It will likely require a major surgery in the near future (3-6 months). We have great insurance and get great care from a well-respected hospital 20 minutes from our home.
2. My wife’s job is great, but it’s tied to the area. Financially, any increase in salary I might make out there, wouldn’t make up for the loss of my wife’s income and the increased cost of living. Longer term, her earning potential much greater than mine.
3. I love where I live. I grew up near NYC. I’m doubtful I would enjoy the same standard of living & quality of life I enjoy here, there.
I feel like I have some options here for the next few years, but I’m losing sleep over it now. What would you do in my situation?
You like your city, job, AND company. Yes, your company might change in a few years, but you'll still have options then. You'll be able to freelance at the very least. A bird in the hand is worth two in the bush.
You've said that your combined income would likely decrease if you left. That's a big deal, especially considering cost-of-living in NYC or SF is likely double what you pay now.
The startup world isn't a good fit for someone who needs to be as risk-averse as you, especially in SF. You need to have a plan for retirement and your children's colleges. You can't go bankrupt. In SF or NYC, you'd either have to rent (and burn a bunch of money) or buy a place that would also add a huge mortgage on top of your other expenses.
There are many small-to-medium software companies in other, cheaper cities. If you really want to jump ship, check out Houston, Nashville, Atlanta, Pittsburgh, and Charlotte. There are probably more that I'm missing. Obviously you need to filter for the kind of lifestyle/culture that you want.
Get your resume in the hands of some recruiters and see what turns up.