This is the second issue of my monthly newsletter, originally sent to subscribers on June 19, 2026.
What’s it like being retired?
It’s officially been a month since I left my W2! Time flies … even when you’re “semi-retired”. This was definitely a month of transitions and (re)building relationships that had been out-of-touch too long.
Since I always wanted to know what people actually do when they retire early, I’m going to share. Turns out that the “family and travel” cliché has a lot of truth to it.
- My first “retired” week was as a “solo dad” while Ania hosted a women’s writing retreat with our business Quill & Cup (insta) in Virginia. We spent this week in Arkansas, where I grew up and where my family still lives. I’m blessed to still have three living grandparents, so we’re trying to get Nora as much time with her great-grandparents as we can.
- Then we flew to Philadelphia for a long-overdue visit with my college mentor (top left, an amazingly spry 85 years old!) and stayed with friends in their camper, which gave us a lot more time with them! Bonus: the friends we visited were part of the “train”, where we all had kids one month after another.
- The third week, we flew to Chicago for my niece’s high school graduation celebration (and a 1:1 catch-up breakfast). We also caught up with Ania’s high school mentor too. Otherwise, this felt like my first “typical” post-W2 week, where I tried to balance family and productivity in an intentional way. More on this below.
- The fourth week, we flew back to Arkansas. We needed to pickup our storage on wheel minivan for wherever life takes us next.
But the real fun thing is that you get to focus on stuff you liked doing anyway:
- Officially finished stabilization for La Estación Apts, my first syndication! We’re sending the first 7% distribution on Tuesday!
- Helped my partner talk through strategy on Stella Apts, resulting in a successful disposition of this syndication at 1.55x MOIC in 5 years, before including the 7% distributions sent from day one.
- Signed my second SMB minority investment, this one is a niche industrial manufacturing company. This time I’m not the lead investor, but a distant second to the Acquisition Lab Fund. I still expect to be able to learn, advise, and help the operators.
- Pushed 100+ changes to a new WIP app for Quill & Cup. Yes, I’m still using Claude and JetBrains (WebStorm in this case).
- Talked with someone selling a portfolio of nail salons(!!) in Arizona at an incredibly attractive price. Chatted with someone else raising money to buy a specialty contractor focused on programmatic 28-day remodels for fuel/convenience store fleets. So many interesting opportunities out there!
Of course, all of this is the culmination of stuff I was already working on as side hustles. It’s fun to think of it as my “real job” now though. 😊
In the next update, I’m considering one of these options:
- retrospective on the La Estación syndication to date
- peek into the industrial manufacturing company investment
- look at some of the deals in my SMB pipeline
Which of these do you want to hear about next? Or is there something else on your mind?
🧠 What have I learned?
My first “lesson” was that it’s really easy to fill my days with administrative work. Emails, organizing files, random calls or meetings. “Fake productivity.”
For now, I’m using my calendar to make sure I’m living intentionally. This is partially scheduling tasks (planned in Notion) and partially me tracking actual time usage.
I’ve been (passively) using RescueTime for like a decade on the free plan. I just subscribed for active tracking and may upgrade to assign calendar events to projects, sort of like I did with Hubstaff time tracking when I was running the fitness software company.
The second “lesson” was that it feels a lot easier to be a good friend now. I have a couple friends going through hard times, and I doubt I’d be making as much time for them if I were still working full-time. Blaming work is an easy excuse, but was also my reality.
I’ve started using Beeper - it lets you see messages across all chat platforms in one place. I’ve got my Texts, WhatsApp, Instagram, Linkedin, Facebook, and Twitter DMs all hooked up.
Slack is supported, but each community is a separate channel. Beeper is only free for the first few channels, so I still have Slack installed too.
Relationships are critical to happiness, but especially post-W2.
COBRA is really easy to sign up for, but really expensive insurance. I’m sure this is because my company had a great plan. But I definitely need to find a cheaper long-term option.
My COBRA with Anthem HDHP/HSA for a family of 3 is $2600/mo
You have 60 days to signup which means you can also switch to another plan within that 60 days; otherwise you’re stuck until the next open enrollment window (typically at the end of the year).
Freddie Mac retired their Small Balance Loan (SBL) program, so now they only support $2M minimum loan balance. Fannie Mae still supports their $1M minimum Multifamily Small Loan program. This means that the buy-rehab-rent-refi-repeat (BRRR) game is harder for small buildings, forcing us to larger opportunities.
✈️ Where are we traveling next?
We’re going on a road trip!
- We’re driving up to Nashville, where we’ll spend a few days doing all the responsible adult things, like annual checkups at the doctor, dentist, and optometrist.
- Heading to Knoxville to visit friends and to spend our 11th wedding anniversary in the Smokies (we ♥ mountains!)
- Then through Asheville, into Charlotte to visit our niece who just moved there post-college, and to Savannah, which Ania fell in love with when she was younger and wants to show us.
- Stopping in Serenbe (outside Atlanta), an intentionally planned, walkable community focused on wellness and sustainability that I want to visit on my intentional community exploration.
- Going to the Wisconsin Dells for a “friendcation” with our Chicago crew and their families.
- Landing back in Chicago, where we’ll have more swim lessons and family cuddles. We’re still figuring out what’s after this.
We are very “open itinerary”, so if you want to meet up with us or know someone we should meet along the way, reach out and let us know!
📚 What I’ve read recently
The Inheritance Games — A mystery, a puzzle, and a billion dollar inheritance. Fun fast read. Just got the second one via Libby.
A Parade of Horribles — The latest in the Dungeon Crawler Carl series (#8). This is a fun series, but you have to give it time and suspend disbelief, because it’s goofy. The latest book isn’t the best, but it keeps the story moving forward.