How Guys’ Trips Change As We Age
Five observations after a great time in Sedona with long-time friends
Ed Elson: “What's been the most effective friendship maintenance strategy you've used to maintain close friendships since childhood?”
Scott Galloway: “Well, now it's texting, just little pings. But my go-to is I do a lot of guys' trips. I do a lot of trips with friends.”
— The ProfG Pod with Scott Galloway, December 23, 2024
Back in January, I wrote about things I should say “yes” to, and guys’ trips was one of them! Today is Thursday, and I am still beaming from a great trip over a long weekend with friends of 30 years (Wayne, Kent, and Larry) that live in California. Like with other subjects in this Substack, I also had some reflections on this experience in the context of aging, so I thought I’d write about them here! I’m also interested in sparking discussion with those of you willing to share your experiences staying connected with friends at a distance over the years!
Top-level reflections
I met Wayne back at Oracle in 1990 and joined him at Latitude Communications in 1994. It was his first startup after Oracle (and my second after I got laid off from Visioneer) in 1994. Kent already worked there, and Larry joined in 1996. We have a lot of history together. These friendships evolved at a very interesting time for me, as Marsha and I got married in 1995, a year after I joined Latitude. We had our first child in 1997, a year after Larry joined the company.
Both Wayne and Kent got married and had kids just after we did, and Larry was already married with kids before we all met. When we were expecting our first child, Larry and his wife (Edye) invited me and Marsha to their home to preview what parenting was like!
Since then, we’ve been friends since leaving Latitude over 20 years ago. After I moved away from Silicon Valley, I was interviewed about this friendship in Fatherly magazine. Since then, we’ve still been getting together from time-to-time. Now, we maintain a daily text thread where at a minimum we exchange Wordle solutions, and often we exchange other thoughts. Getting together face-to-face this past weekend was nice for a deeper set of conversations covering a range of topics, including life planning, health, aging, family life, retirement, financial stuff, and overall reflections. It was also fun to share “dad humor.”
Speaking (writing) of dad humor, I am still laughing at being exposed to an excerpt from “Family Guy” episode about the trauma of pooping in public places. (I am pasting it here, laughing, as I write this.)
Still, there are differences between trips when we were younger and trips now that we’re all older, retired guys!
Efficiency of planning
Comfortable accommodations
Daytime hours
Relaxed pacing
Easy finances
I’ll summarize each of them below!
Efficiency of Planning
As we are all now dads with adult children, we were all able to get the trip planned pretty efficiently together. We utilized a set of technology tools, including:
A shared Google Doc to keep a central plan
Microsoft Teams and Google Meet for conference calls
ChatGPT to suggest agendas based on our preferences
Travel websites, including Google Flights and AirBnB to reserve flights and accommodations
OpenTable and SevenRooms to schedule restaurant reservations
Google Maps and AllTrails to suggest distances and time on trails
Splitwise to log expenses before, during, and after the trip
Here was the basic timeline of meetings to prepare for the trip:
1/19/2025 - Kick off to socialize the trip, potential dates, and potential locations.
1/26/2025 - Finalize dates and location. We picked Sedona with the dates of 5/30 through 6/2.
2/2/2025 - Discuss details for AirBnB, rental car, and agenda possibilities
4/13/2025 - Finalize agenda. Book e-Bike rentals, restaurants.
And, of course, each of these calls served as a fun excuse to catch up, too! It was nice that planning didn’t feel like a heavy lift at all, and we were well-organized going into our trip! I remember past trips in our younger years being much more about deciding what to do (or how to do it) once getting to the destination. This trip just felt more “efficient.” Some of this efficiency was just about having better technology (like ChatGPT), but a big factor contributing to efficiency was the combination of all our experiences doing stuff like this in other parts of our lives.
Comfortable Accommodations
For the four of us, we chose a 4 bedroom / 2 bathroom house on AirBnB. So, we each had a bedroom and shared a bathroom with one other person. Unlike our younger years where we might have optimized more for cost, it was nice to strike a good balance between getting good rest with our own bedrooms, plus great common areas for us to all hang out, chill, and talk! Still, we also agreed on a good price point! (The place was only $1,276 total or $319 each for 3 nights!)
I was happy with the bedroom situation, with the right “creature comforts” to feel at home. My bed was comfortable. From my nightstand, I had USB ports for my iPhone and Apple Watch, plus an easy outlet for my CPAP. I was able to hang my clothes in the closet, and unpack into a nice dresser. The Internet was fast!
To hang out, the place had a great living room where we could spend time together chatting, a nice dining room where we had breakfast and lunch, a good TV where we hooked up a computer to watch a guy’s movie (Deadpool & Wolverine), and a firepit in the backyard where we could hang out and chat at night.
In addition, we were able to literally walk out the door and get to the Sugarloaf Trailhead. It was funny to me that our street name was Maxwell House Dr., named after the Coffee Pot Rock close by!
While in our younger years, accommodations were just a place to crash after just being “out” all the time, it was nice to be able to just “chill” with the guys together!
Daytime hours
One mark of an older guy’s trip is that we weren’t partying until dawn. For the most part, we went to sleep before 11pm. We also typically took a little bit of “alone time” after showering before dinners for a little bit to recharge with naps or personal electronics. (I brought both my laptop and my iPad).
Instead of partying until dawn, we were typically up at dawn, with our early morning coffee. The mornings were generally spent chatting, scanning the news, and playing Wordle!
For example, here’s a Wordle thread on our first morning in Sedona when Larry got up to play at 5:37am. The rest of us all finished shortly afterwards, but we didn’t end up all sharing our solutions until after breakfast before we left the house at 8am!
Relaxed Pace
We didn’t have to “pack it all in.” When planning the trip, we discussed having lots of flexibility and relaxation to give ourselves time to hang out, perhaps watch a movie together, and have flexibility for naps. We also discussed going to a grocery store to pick up snacks, drinks, and food for breakfasts and lunches at the place for some casual downtime together.
The good news is that we’re all still active, so we weren’t afraid to do hikes and bike rides. Other than the two travel days, I did achieve the “200% Move Goal” on my Apple Watch on both active days. So, the level of physical activity was above baseline, but not out of control!
The hikes were beautiful. While Cathedral Rock was rated as “hard” by AllTrails and did involve some scrambling, we all made it to the “End of Trail.” Our other hikes were rated as “moderate.”
The e-bike tour was a lot of fun, and it provided a totally different way to see Sedona!
Overall, the “anchors” for the trip looked like this:
Friday, 5/30:
2:30pm - Get rental van @ PHX
4:30pm - Arrive in Sedona
7:00pm - Dinner at The Hudson
8:30pm - Drinks at Mooney’s Irish Pub
10:00pm - Grocery shopping for snacks
Saturday: 5/31:
6:00am - Breakfast in AirBnB
8:00am - Cathedral Rock Hike
11:00am - Devil’s Bridge Hike
3:00pm - Snack at Oak Creek Brewery & Grill
4:30pm - Showers, naps & downtime
7:00pm - Dinner at Elote Cafe
9:00pm - Movie in AirBnB (it ended up being Deadpool & Wolverine)
Sunday, 6/1:
6:00am - Breakfast in AirBnB
8:00am - E-bike tour
12:30pm - Lunch in AirBnB
2:00pm - Sugarloaf Loop Summit Hike
4:00pm - Showers, naps & downtime
6:30pm - Dinner at Mariposa Latin Inspired Grill
8:30pm - Time outside around firepit at AirBnB
Monday, 6/2:
6:00am - Breakfast in AirBnB
9:30am - Drive back to PHX
11:30am - Return rental van
12:00pm - Lunch at airport
So, there was a good balance between activity and downtime!
Easy Finances
It’s nice being at a place in life where we don’t have to sweat the finances too much, as long as we stay within reason!
We had our share of budget-friendly activities. Hiking, of course, is free! We also bought groceries for breakfasts, lunches, and snacks in the AirBnB. We even checked out a lower priced bar in the area! Pictured here is Wayne with his Smirnoff Ice (he didn’t know what it was going to be!) You can also see my PBR and Kent’s Rolling Rock in the photo, too!
Still, we were able to splurge on our e-Bike tour, and we were able to splurge on some very nice meals out (including highly rated Elote Cafe and Mariposa Latin-Inspired Grill). There are some beautiful views to be had in Sedona, even from the restaurant scene!
Overall, the trip felt like a relative bargain to me. All-in, I spent less than $1,500, including airfare, parking, and our shared expenses in Splitwise. My share of all the shared expenses, including the AirBnB, rental car, e-bike rental, food, and drink was less than $1,000! This was totally worth it!
Final Thoughts
I am grateful to be navigating the friendship recession, and these guys have been a critical part of this journey over the years. I’ve also appreciated how we keep evolving our time together as we get older. We’re already talking about how we might best carry forward a tradition in future years!
Do you have any suggestions?
Note: While I normally do my best to keep names anonymous in these posts (with Marsha being the notable exception) Wayne Fenton, Kent Kawahara, and Larry Stein gave me permission to use their names and photos to make this easier for me to write and hopefully to make it clearer to read! Thanks again, guys, for the great trip!
Wow, how nice to see all of the old faces from LATD days! Inspiring. Although an E-coaster, I still partake heavily in road and mountain biking as often as I can. Nature, the great motivator! Looks like you all had a blast. Let me know when you go next year. I may even travel out to meet you .. so long as you can tolerate a Sales Guy :)
I love that you guys are still connected and planning trips together. As friend groups disperse, and life moves at different paces, these trips and the regular check-ins help maintain valuable connections.
Thanks for continuing to document your retirement journey.