Late 30s here. I was just broken up with, and as cliche as it sounds, I really didn’t see it coming. Blindsided is an understatement. It hasn’t yet sunken in that this is real. Not my first rodeo, but this stings more than I thought it would.

My situation is this: I have a job I don’t love in a city that I’m not enjoying.

My lease ends soon. I could find a new place and continue at my job. This would be the smart thing to do. The job market isn’t great and I at least have an okay job in terms of pay and flexibility.

On the other hand, I have Montgomery GI Bill benefits that will expire eventually. I started a masters degree a few years back that I abandoned when life got busy. Having a masters won’t do a whole lot for me in terms of career progression in my current field, however it would provide an opportunity to get paid while not working.

My idea is to grab an Airbnb in southern Europe or SE Asia or somewhere exotic and cheaper than the US, work towards completing the masters, get a change of scenery, and take my mind off of everything back here. Unquestionably running from my problems, but doing it in style at least.

The issue with that plan is that it almost feels like I’m trying to live out a dream that is more appropriate for a guy in his 20s rather than someone my age. During this time I wouldn’t have income to continue contributing to retirement accounts. All for a piece of paper that does nothing for me and means nothing to me.

What do you think? Continue down the path that is miserable but makes sense financially, do something stereotypically midlife crisis, or try to find a Plan C?

Look forward to reading the different perspectives.


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