At 17, I had no vision for my future – I remember leaving my hometown – and on my last week, outside my favorite coffee shop, there I burned a tin full of all the letters from my first relationship. My friends were there with me. We smoked Parliament’s. I drank a flavored Italian soda. At that time, this felt symbolic for ‘moving forward no matter what.’

Today, I don’t keep a tin full of letters, nor a device full of texts (they auto purge), but rather I have memories from twenty five hundred days fading in my head. I spent these last months reliving, processing, and journaling about the years between St Louis and now; how I remember them in the present.

As a way to close this season, here’s a few selects.

Road Dawg

This past week I’ve been on tour. The activity itself is beautiful – a road trip with friends (everyone in the van), a sense of purpose every day (the show), and adding a few new and old friends each day (locals, often sharing with you what they love about their city at that time).

I experience every moment of my friends life for the length of our time together – the moments we open our eyes, when we take off our shoes before bed, sharing meals, inside jokes that span days, and problem solving everything from itinerary to van troubles. Over days on the road, rhythm as a team grows. There’s someone that’s great at loading the gear into the van, others are better at driving, and still some are simply built for drinking beers in the back seat and procuring places to stay. There’ll be a time when a pal needs help procuring a cup of coffee. They definitely need help loading the bass cabs up a flight of stairs. Sometimes they simply need a breather. All of this I think can be similar to a point to point marathon, in that it is necessary to find a comfortable pace you can maintain AND we may as well finish once we’ve started. With attention to the duration as an input, I believe the activity helps to develop patience, and maybe even empathy. The best tours are those where those involved embody agile values. For me, tour is better than any work trip, any resort, any extended-airbnb nomad trip; honestly any vacation I’ve taken.

Inside these creaking van doors, barreling down the highway, I’m with a chosen family; we’ve all radically welcomed these experiences into our life and with each other. I love the time I get to spend with these fools. I hope to continue this.

Rewind The Video

This quarter I reached a new checkpoint in life. I’m delighted for my future self, but my present self doesn’t feel like I hoped – I’m the only one home to celebrate. When I set this checkpoint, I kept my key result vague. This OKR had room for multiple narratives. While in this situation it was only a disservice to my own life; in business I suspect vague key results are methodical.  

Falling back a decade ~ I recall sitting in a college class focused on making a viable business from within the Photography industry. The final project for this class was to build a 5 year plan for this career path. Its purpose, at least that I took away, was to really think forward – committing these ideas to paper (or a google doc). To define the steps needed to reach the desired outcome. Later in tech learning about OKR’s and Jira Epics – these I consider near-synonyms.

I love these types of plans today; the plans that really can take me into a new meta. With these plans, I find myself also noting specific timeframes. By x I should complete y – and so forth. 

Life is gamified for me in this way – a shot clock. I don’t make time for videogames because what I consider main quests haven’t slowed down. One of these years I plan to beat the N64 Zelda’s – just not in 2023. Each time I make these plans, I’ve gotten a bit better at predicting what I can accomplish. I’ve been out of school less than a decade and I’ve lived at least 15 years of plans. The quarterly plans – what I think I can complete in 3 months – these I tend to overestimate how much I can do. This is sometimes froth, but sometimes it’s just miscalculation – it’s often an additional week or two. If I continue to be interested; I roll this activity into the next quarter. The alternative is tossing this froth over to a side quest – sitting along with those Zelda titles. 

At the beginning of May, I finished one of these longer 5 year epics. It just doesn’t feel like I thought it would; I was hoping it would be better than great. I’d say it’s certainly ~ around ~ great, yet definitely not better. I’ve felt just as great from riding my bike or talking with friends. Though, I think I narrowed why this feels different. In my _every day_, I’ve lost my best friends. They were in my life when I set these goals. They were in my life for most of the plan – so much so that I just took it for granted they may not be waiting at the checkpoint. Today, all I have is photos from past moments where I felt they were proud of me. I wish there was a video of these times – to replay – a camera on me as well.

As I write this it’s Memorial Day weekend. To share another look back, this weekend in 2021 I was on a backpacking trip. I remember not having a campground reservation; rather driving down a Forest Road until we reached snow so high the hatchback couldn’t pass. In the morning, we hiked on foot to the trailhead – this took nearly all day. We didn’t get far up the trail as it was still snowy, yet soft enough to break with each step. We saw 2 other hikers near the end of the day. They said about 10 minutes back, they saw a bear. We ate boxed Mac and Cheese and played the card game War until dark. In the morning we walked back to the hatchback. I tried to be into the moment, but I just thought about my shoulders, then my feet. 

In my own life, backpacking is not appealing. I live on acreage. I hear birds when I go outside. I could go on a long bike ride with no weight on my back, take a shower, cook a meal with my preferred tools, enjoy the benefits of refrigeration at any time, and still sleep under the stars in a tent. I also don’t have to drive to the mountains. That’s a con rather than a pro from my current position. For some, particularly folks who always hear traffic outside, I’m sure it’s great.

And now that I’m reflecting, I think I’ve made out better than had I included more details in my narrative when the checkpoint was set. Today I’m 95% sure I don’t like backpacking, albeit I expect I’d try it again in the distant future just to be sure.