should i stay or should i go?

Worth saying and leading with: I'm ok and I'll be fine. But some big changes, and big decisions are on the horizon. Hopefully, for my sake.

For the past few years, there's been a slow tension of indecision on many fronts - continuing to affect me more and more as the months go on. Either I'm just getting older or I'm finally wising up.

Whether geographically or professionally, I'm not sure if I'm where I should be.

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Geographically. I hate to jump on the bandwagon of "maybe we should just move to Canada" but that's actually an option. It's getting terrible out there, and I think it's going to get worse before it gets better. And when I look north, I see a society that exhibits values I hold dear, sometimes more than the ones we declare so proudly here. We have family just a few hours north, there's a cultural community for my kid. Though, worth noting, I have thoughts on too much VS the mix of forced assimilation/diversity I experienced growing up in the South. Also, Toronto/Montreal is not as far away as California (and less risk of falling into the Ocean). 

But then I think about my (partial) regret for leaving the South. Our country is not going to get better any faster with people like me leaving. It's those who stay (and return) who are going to accelerate a long overdue change. Just by being there and raising their families, and bringing their values to the local communities. I also think about what a home we are slowly making in the Northeast, and the access to jobs we have being on top of one of the greatest cities in the world, where I go daily, and the pizza and bagels are far superior. Also, buying a house, though for us, that does not yet indicate the permanence that others chose it to be.

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Career. A (more successful) friend recently told me that he hopes he wasn't put on this earth for advertising technology - which happens to be the industry I've slipped into over the years. When I try to explain what I do to friends and family, they kind of get it. And franky, what they distill about it at the macro level, is more accurate. "So you help sell ads?" It cuts through the makreting BS we tell ourselves (few companies/industries are innocent here). Don't get me wrong, being at a small company I often enjoy what is afforded me - the perks, flexibility, and sometimes-autonomy (when politics/culture don't get in the way, which they rarely don't). And while shifting gears every couple of years keeps it interesting, despite a theme/thread/story I can weave about my career journey (to a founder, investor, or recruiter), I question if I can maintain this level of enthusiasm as the years pile on.

Job/s. 8, 2.5, 3, 2, 1.5...so far. That's how many years I've been in each gig out of school (not counting the handful of other worthwhile jobs I had across the academic years). 

• My first job was a good run, having me do big things all over the world - but following the girl to NY, I chose life (per Irvine Welsh), as I often do. 
• I thought my next job, my second run at a big company, would be as long as the first, but I simply hit my "satisfaction point of diminishing returns" faster. If anything, quitting the first big company gave me the courage to quit my second one, something I fear many of my friends who are still at the first (20+ years later) lack. 
• The third company - my first startup - gave me even greater confidence on who I am beyond my company, especially since know one had heard of the logo on my business card. Probably one of my best (and challenging) career experiences, which made me even more  of who i am today. And for that I'm grateful.
• In the most recent 2 gigs, while interesting enough, seem to have me hitting that pleateau faster - based on what I'm sense and observe. Is it me or them? Probably a mix of both. Maybe I just need to pick better?
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But I am becoming more certain of one thing: this pattern is not sustainable, especially in the long term. I'm sure i can find another gig, but will that really change anything for me - professionally, mentally, spiritually? Doing my own thing doesn't feel like an option, as it has its own risks (and I don't care about anything more than my personal state), but is it the better path?

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I'm not worried. I'll figure this out. I always do. And I usually have a way of convincing myself that it's all ok. 

I just hope I'm more skeptical whenever this next go round comes around.