Hi Jason,

Maybe our therapists are comparing notes!

This right here: “I miss out on entire emotions, because I’ve already rationalized.” Yep. That’s a whole way of being. And the truth is that it has a purpose and, in some cases, it’s a strategy that serves us well. A tough part of growth is realizing when it’s time to let go of strategies that worked in the past but don’t help us move into the future we want.

I’ll take full responsibility for diving into the conversational deep end without pausing for preliminaries. It’s kind of fun to do things backwards though, and I like that our last week of this letter writing month is coming to a close with introductions and light stuff.

So here’s my own paragraph of introduction:

I’m 41 and pretty excited to turn 42 next month and know (or be?) the answer to life, the universe, and everything. I’m a single mom of four kids: three teenagers (13, 15, and 16) and one 12-year-old going on 27. So that’s where a lot of my time and attention goes, and it’s wonderful and difficult and all the things, all at once. We have two enormously spoiled fat cats and live in a cozy apartment in a St. Louis suburb. We moved back to St. Louis in the middle of 2020, after being in Puerto Rico for 5 years. It was an unplanned relocation in the midst of an unexpected divorce, and since then I’ve been rebuilding my life from zero. I really miss beach life (and speaking Spanish… I’m getting rusty) and my PR community, but it’s wonderful to be near family and lifelong friends and have their support and help. I’m a freelance writer and most of what I do is take tech-speak from the dev team and translate it into readable, hopefully interesting material for the people who want to use whatever the dev team is making. I’m innately curious about pretty much everything and being a writer is a free pass on asking questions and doing research. I love reading and usually have 3-4 books going, a mix of nonfiction and sci-fi/fantasy. I also love a good memoir. I spend a lot of time thinking about the why underneath things. I grew up in a religious home and was very involved with the church until my early 30s, when I left the faith. I didn’t want to, but that whole curiosity/asking questions/looking for the why underneath things… Well, sometimes it takes you places you don’t necessarily want to go. I’m happy to be where I am now, though. Life has 100% not turned out as I expected, but I feel so grateful for what I’ve gotten to experience and who I’m getting to become as a result of those experiences. I love food and adventures and dancing and a good whiskey and trees and solitude, not necessarily in that order.

It’s been an absolute pleasure exchanging letters with you over the last few weeks. I’m going to sign off with two book recommendations (and would love to have a couple from you as well). First: Finite and Infinite Games by James P. Carse. This book is one I reread about every year. It colors the way I look at everything. Second: Systemantics (or The Systems Bible) by John Gall. As a structures/systems person, you might particularly like that one. Easy read, entertaining, pithy.

Here’s to good things ahead,


Hi Annie,

Yes, we’re moving backwards, but I reject that book recommendations are “light stuff”. I had to think about that one a bit, since I know that you’ve already tackled Tomorrow, and Tomorrow, and Tomorrow, which will be my default recommendation for quite some time.

I decided to go with books that are not huge commitments and that I don’t feel had any recognition in my own circles. I think all four of these recommendations (well, it’s really three) are best read knowing very little:

Now that the serious business is attended to…

I fell into “product management” largely from a similar skillset– I was able to talk to the dev team about what everyone else wanted built and they were able to build the right thing, whereas in the past that was a struggle. In many ways, my job goes in reverse of what your role does.

I think something I didn’t quite understand when I was younger was just how much work we all have to keep putting into ourselves and how many new things we find when we keep looking for whys and let go of old strategies and pick up some new ones. It feels like the kind of thing you never really understand as a kid. Maybe it’s the time I grew up in, but so much of what society coded as a midlife crisis or a failure to launch or whatever reads so different as an adult. I don’t know where the norma came from that we are meant to be consistent rather than constantly adjusting and discovering and changing along the way. Rebuilding from zero with kids that rely on you sounds… daunting, even without the major relocation. But letting go of strategies and identities that no longer serve us to head out on our next adventure with food, dancing, good whiskey, trees, and a bit of solitude– that sounds like exactly where I’d like to go.

Well, except for the dancing.