Newsletter from July 29, 2026

Art of a Great Summer

Benjamin Diedering

sent: July 29, 2026

Subject: Art of a Great Summer

Hello everyone,

I’m writing this on my way to Wyoming! This is the first real trip I’ve taken just for myself in a while, no panel, or meetings. Just enjoying the summer out in nature and some much needed down time,

I love the energy during the summer… the pace is different, and the days are more fun. With the world cup going on there seemed to be a buzz around cities. But___

So this week, I want to share a real game plan for making summer great. Not abstract life advice, but a step-by-step framework that’s actually actionable.

YOUR MINDSET

Before anything else, this is the one that matters most: your mindset going into this season determines your summer.

It’s easy to talk yourself out of a good time. It’s a lot harder to talk yourself into one.

Most of us default to work mode because that’s the groove we’ve been sitting in all year. Choosing to actually be present in the season, takes effort.

I keep coming back to something I wrote about a few weeks ago (Jeff Bezos’s idea of work-life harmony). He talks about how when he’s happy at home, he shows up better at work, and vice versa.

Summer is the perfect season to put that into practice. But only if you decide to. Think about how exciting summer was when you were a kid. The feeling of possibility, no alarm clocks, nothing but time. We can’t fully recreate that as adults… but we can borrow the energy.

THE GAME PLAN (5 STEPS)

Start a hobby with the intention of quitting
Earlier this year I signed up for a half ironman, 1.9K swim, 90K bike, 21K run. I started training and planned out routines,
But unfortunately, couldn’t go through with it because of work obligations. And that’s okay… no regrets.
I tried something outside my comfort zone, learned what I enjoy, and walked away with something I wouldn’t have had otherwise. The reframe: instead of committing to a hobby forever, commit to it for the summer. The time limit removes the pressure, gives you permission to be bad at it, and removes the embarrassment of stopping. Just pick something and go.
Eat outside and lean into the season
Summer has the best food and most people barely notice. Everything is in season strawberries, corn, peaches, cherries. Go to the farmer’s market. Fire up the grill on a Wednesday evening and eat in the park. Get ice cream after dinner and eat it outside. The point is to slow down enough to actually be in the season.
Dress for summer, not just the weather
The way you show up affects how you feel. Summer is a state of mind, and dressing for it is one of the fastest ways to shift into it.
Light shoes, the right shirt, something you actually feel good in… you carry different energy. You’re more relaxed, more present.
Do it on purpose, I started keeping a dedicated summer bag when I travel, lighter fits, the right shoes. It’s a small thing that immediately shifts my energy the moment I land somewhere new.
Change how you get around
Leave the car at home sometimes. Ride your bike, go for a walk or run. Take the scenic route and leave early enough so you don’t have to rush. The way you move through the world changes your experience of it.
Making these tiny decisions is what makes ordinary days feel like something worth remembering. On my last trip to NYC I walked everywhere instead of taking cabs. Stumbled into three conversations I never would have had otherwise.
Make specific plans and be the person who initiates
Stop with the vague ‘we should hang out soon.’
Send the specific invite: ‘That new spot just opened, you free Wednesday after work?’
Be the person who makes things happen. Plan the fun first, then build work around it, not the other way around. And make sure at least one plan gets you out of your city. A long weekend somewhere different does something to your head that no productive week can replicate. Wyoming this week is the first trip I’ve planned purely for myself in months. I haven’t looked forward to something this much in a long time

NAME YOUR SUMMER

Give your summer a name.
It creates a small amount of pressure, in the best way, to actually live up to it. Think about what you want from the next few months: more adventure, a specific project, a relationship to invest in, a version of yourself you want to build toward.

Pick the thing that feels most true and name your summer after it. Then go build it.

WHAT’S HOT

Hope you liked today’s letter, lots of info I hope you learn from. See you next week.
-Benni

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