New Year, New ??

Oh, hello there. You might not remember, but sometime since mid-2022, you signed up for my newsletter. It’s been collecting dust in a corner of Substack, but I set myself a “resolution” to try to find the older, smaller internet again. So here I am, and on beehiiv this time - Substack seems a bit controversial these days. If you don’t remember, or don’t care, you can unsubscribe. I won’t be offended.

I’ve been stumped at what to write for months now. According to my ChatGPT, I started putting this newsletter together in October. It started with me downloading the archive of my blogs from the dawn of my blogging days. I uploaded it to ChatGPT and asked it what I used to write about. As a surprise to no one who knows me, the theme was just “whatever I was focused on at the time” - a mix of travel, tech, work, life, projects. Pretty much the same as I am now, just with more time to write about it.

Like many of you, ChatGPT has become an outsourced brain and processor for me. It’s come to know a fair bit about my various interests. So, if I’m being honest, when it came to finally sitting down and writing this thing, I asked ChatGPT “based on what you know about me, what could I write a newsletter or blog about?” Turns out, it’s all of the above. With some financial independence, parenthood, and product management mixed in. When I asked it the common thread running through my interests it spit out: "Designing a Life of Intentionality: Balancing Leadership, Creativity, and Parenthood While Building Toward Freedom." I think - or at least I like to think - it’s pretty spot on. Yes, my interests are kind of all over the place, but they do all point in one direction. And that direction is one that I don’t think I’ve ever quite shared publicly: My driving goal in life, since my teens, has been to retire by 40. 

This year is one of those fork-in-the-road years. I have some (though vanishingly short) time before 40, and technically I have reached the financial number at which I could retire. But I don’t feel mentally, or logistically, ready yet. So my plan is to use this space to explore that to do list. And maybe do some unpacking of why I feel so scared to actually do it (spoiler: if I had to guess, it’s society, norms, pressure, expectations, and all that crap).

Here’s the list of things I’m noodling on as it stands now, in no particular order:

• What would soft retirement look like? I don’t want to be done working forever. I enjoy having some sort of “useful output.” Retirement looks somewhere between “I don’t have to continue to work a high-energy tech job anymore” and “I can open up that pop-up ice cream shop / bakery / co-working space / alpaca farm I’ve always wanted.” Time freedom is what’s important to me. Time to explore my interests, do fun things with my kid, travel, and not be attached to Zoom meetings 9 hours a day.

• Do I want to continue to live in this house? There are pros and cons. Considering school district, space, income potential, etc. it might make sense to move somewhere else and use this as an income property/summer house.

• Should I pick up some consulting/fractional work for a bit to ease out of working full-time in tech? I really enjoy what I do, and I think part of what’s keeping me from stopping is I don’t want to give it up entirely.

• Should I find a property to buy, renovate, and use as an income property (or flip?). I love renovating. That would be a fun combination of hobby-and-investment.

• Should I double down on my Etsy shop? It’s not nearly as successful as it was during that flash-in-the-pan spike of Holiday 2022, but I do still get orders with zero marketing effort. And again, I enjoy it.

• I’ve always loved to teach. I currently teach Product Management through Kellogg’s Executive Education program. Though, given the state of the market, It hasn’t been consistent as it used to be. What other opportunities are there

How can I give myself some structure to be able to do these things or test the waters before taking the plunge? This used to be a lot easier when I had nothing but time on my hands. But with a 2.5 year old, free time is almost a joke 😆. Though, I am excited about the idea of getting him involved in some of these projects.

I’m hoping that by putting these thoughts out there, somewhere, I’ll be able to find that small internet again. That old internet where multiple friendships and jobs came from comments on my blogs. Where I would learn about whole new things from trawling Twitter threads or scrolling my RSS feed. Where ideas were shared and feedback was given in a way that didn’t involve a war with comment trolls. So please, if this is of any interest to you, drop a note back! Or share what’s worked (or not worked) for you. As much as I loved yelling into the void on social media, I’m hoping that someone will start to yell back again and we can all learn from each other.

Until next time,

Jenn