These days, as I sit here with no debt but little savings, low expenses but few choices, I think about the “what if” situations regarding the last few decades of work.

I’ve never been a good fit for the conventional 8-to-5 office work life. I need more downtime than that, more flexibility in my day and my schedule. I never did well in the office, always having to be “on” and losing my oomph halfway through the day. I don’t do well when someone is observing me work, or especially watching me learn. I require a great deal of autonomy to do and be my best. And, while I’m not a night owl, I don’t get enough sleep if I have to get up early five days a week.

Also, the internet was in its infancy when I was graduating from college. So the options that are out there today (many kinds of computer-oriented work, working from home, text-based interactions, etc.) were pretty much unavailable, or not on anyone’s radar yet.

But most of all, I didn’t know what careers to consider. Having to choose a line of education and a line of work while you’re in high school, and sometimes when you’re in college, is just too early for people like me, who don’t come into their own until 10-20 years later. But, by then, I had kids and was out of the working world (for a while) anyway.

(Sorry, this is a bit rambly. And I may be repeating things I said in earlier posts.)

And, now, I’m 50 and am on the cusp (in a couple of years) of my kids both being done with college, and I don’t know what line of work to try to get into. I need something that requires few hours but pays well per hour. I’d love to have benefits, but those seem to be reserved for people who can sustain full-time work. I have work now, but all of it either doesn’t pay well, or it does pay well but is so demanding of my mental energy that I can only do a half dozen or so hours a week. I’ve cobbled together the things I have now, but I’m still looking for answers.

I wish I’d been able to find a more solid way to make a living that was compatible with my emotional needs. I wish I’d had help finding areas of work that were more non-traditional. I wish I’d had a mentor who could have helped me think about what I wanted and needed in a job and a career, asking me directed questions to make me think about more things than just subject matter. I wish I hadn’t had student loans that required me to get whatever job I was qualified for when I graduated so I could afford to pay them back. I wish I’d been able to grow as a person/in a career that was a good fit for me.

I keep having to tell myself that I haven’t lost the past 30 years. Many of those were spent raising my kids and homeschooling them, which was my absolute favorite thing in the world. But, as I said a couple of days ago, I feel a bit lost, and I don’t want to have to start at the bottom of something.

I’m decent at a lot of things but I don’t excel in many focused areas. I don’t have deep knowledge about many things. Being a generalist has significant downsides.

So I wonder, what if… What if I’d had a mentor, a guide, and a clear line of effort toward a cohesive career, even if it got split up with my parenting years…

What would I be doing? Where would I be? Would I be happier? Feel more secure? Understand myself better?

There are no clear answers.

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