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Chronicle

Day 1000 and The Milestone

When I first started writing every single day I had modest goals. I wanted to instill a habit of writing more often. My initial goal was to write daily for one month as that seemed both significant but also manageable. But I deliberately didn’t put any pressure on what I would write or for how long I’d keep at it.

Once I had reached my first milestone of writing daily for an entire month, I began considering extending the habit. Maybe I could do it for two months? Maybe I could do it for 100 days? Every new milestone made me excited to reach for a new one.

Once I got to 500 days, I began to feel confident discussing the possibility of reaching 1000 days of writing. I even called that blog post my halfway point. Still I wasn’t sure even then that I’d actually make it to a thousand days. A lot can go wrong in a year or two. But as I learned, with a little bit of perseverance, a lot can go right. Or if you will indulge the pun, a lot can go “write” too.

Still, even as I became accustomed to the habit, I didn’t want to do anything to jinx it. Locking myself into an outcome seemed like a recipe for disappointment. But locking myself into a daily habit? That seemed like a recipe for success. I knew I could keep showing up.

My philosophy for writing has been to take it one day at a time. Habits compound just like money. Small change over time can have a dramatic outcome. I committed to showing up and putting the proverbial pen to paper every day.

And here I am a thousand days later with enough writing for any number of other goals. I’ve got answers to most of the regular questions I encounter in my personal and professional life. I’ve got enough content to turn into a book if I’m so inclined. The volume of my writing is so extensive I could easily train my own artificial intelligence agent.

I don’t know what I’ll do with this body of work other than continue to hyperlink it together and see where it takes me.

And to answer the most obvious question, I do plan to keep writing. I don’t have any desire to stop. I enjoy this practice. It’s conceivable there are other milestones ahead of me. Maybe I double it. Or maybe at the end of the year I decide three years of writing daily is enough.

Who can say? I reached the stretch goal I set for myself. It’s an unbounded journey from here.

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Chronicle

Day 995 and Finally Fall

Maybe it’s the sheer busyness of day to day life but I didn’t notice it becoming fall. I felt as if I was in the clutches of summer forever. But then the first day past after the autumnal equinox we turned on the heat.

I woke up to the comforting sounds husband building a fire in our wood stove. What a relief to have a chill in the air. You’d think in Montana we’d have scant need for air conditioning but we easily had two straight months of running it daily this summer.

We installed mini-splits this year because we got caught in a heatwave last summer without so much as a window unit. It was brutal. Air conditioning just isn’t a standard feature in Montana because it didn’t have to be. But it sure seems like going forward it will be. Invest in HVAC companies if you are looking for a growth sector.

I’m happy for the reprieve. I don’t intend to be anywhere hot anytime in the near future. My travel for the remainder of the fall will involve colder climates. The seasons will favor me till April. That old aphorism “make hay while the sun shines” doesn’t apply well to me. I’m more of a “do business when it’s dark and cold” type.

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Chronicle Media

Day 994 and Good Conversation

There are few pleasures in life as gratifying as having a good conversation with someone. I recorded a podcast with one of my absolute favorite Twitter mutuals and LP in chaotic.capital this morning. I don’t want to ruin the surprise (click here if you do) but it was a very good time and a very good conversation. I can’t wait to share it with everyone.

I’ve had the good fortune to be in a few deep dive podcasts recently if you want a preview of the kind that of thinking and conversations that bring me joy.

I was recently a guest of Frazer Rice’s podcast Wealth Actually to discuss how the venture asset class has changed over the course of the last fifteen years. I was also a guest of Stewart Alsop III on his podcast Crazy Wisdom where we discussed the complexity spectrum of bringing our present into our future.

One of the most challenging aspects of doing the earliest stage investing in technology, and startups in general, is that we simply have no idea what the future will bring us. We have our best guesses.

That doesn’t mean we are flying blind. Like Captain Kirk, I trust some people’s best guesses a lot more than other people’s facts. But the harsh truth is that we are all doing our best with heuristics and humility.

And it’s through conversations with others do we get to improve our best guesses. Sharing insights and history helps us refine our process and worldview such that our knowledge broadens and deepens.

In conversation we share what’s worked for us and what we’ve seen across our own experiences. A good conversation is a pleasure unto itself but it’s also a window into the world of someone else. And I cannot imagine a more joyful way of improving yourself.

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Chronicle

Day 990 and Rounding The Turn

You see the marker up in the title that says “Day 990?” Yeah, it means I’m getting close to a thousand straight days of writing.

It’s not a thousand posts interspersed over years or weeks or decades. Though that would still be impressive. It’s a thousand days in a row of writing. No days off. No vacations. No missed days. Every single day I write something and post it on here publicly.

I got started with this experiment in the middle of the pandemic on January 1st 2021. A lot has happened in the intervening years. And I’ve chronicled so much that happened in my own life. I still have quite a bit of 2023 to go but if you want to see my favorite posts from 2022 and 2021.

Because I approach this as a habit, I am intending to make to my thousandth post but I can’t say for sure even with ten days left that I’ll make it. A lot can happen in ten days so it’s entirely possible I won’t. Though the odds have never been better.

I do intend to continue the habit of writing every single day past day 1000th. It would be weird to stop in the middle of the year and I like the symmetry of an entire year of writing as much as I aspire to write Day 1000 in a title.

At this point changing how I write would be an adjustment. I often wonder if I could manage being more polished or more researched or more focused. But I suspect that those types of documents come on their own timelines and I’d simply write more to accommodate them. I wouldn’t necessarily want to lose this daily journaling habit. Something about keeping it simple and consistent appeals to me. So I’ll round the turn and see if I make it to the finish line. And then I’ll see if I keep going.

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Chronicle

Day 955 and Logging

I keep a private journal of my daily life and it’s undulating metrics addition to this daily public log that has now stretched into its nine hundredth and fifty fifth day.

I use an application called Day One that is actually now integrated with my blogging software Jetpack so I probably could easily put the archives online. In an era of closed social media walled gardens, it’s nice to trust your open source software provider. Thanks WordPress for having my back for nearly twenty years.

Having a log of your life over a long enough period of time is a blessing and a curse. I noticed an upsetting anniversary when I opened up Day One today. I lost someone last summer and had forgotten that today was the day. Sometimes memory can be kind to you. I wasn’t thrilled with the reminder of the pain. But I’m glad that it was marked.

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Chronicle Emotional Work

Day 941 and Unreasonable

Today marks our one year anniversary of moving to Montana. I noted yesterday just how much we achieved in just 365 days.

I’ve tended to think in terms of time in terms of days over the past three years because no other metric seemed sensible. Too much changes every day even as too little seems to be different.

I do believe that what gets measured gets managed. So it makes sense that someone like me who writes every single day thinks that days are the manageable metric. Not that being manageable means anything is under control. Merely that I have some metric to measure back into to make life seem more reasonable.

I am however all too human. We are feeling animals with the capacity to reason. It’s important that it’s not the other way around. Much as I like to reason my way through life I’ve learned to remember feelings matter. This has made me both much more open and also much more careful about how I treat myself.

I suppose this makes me unreasonable simply by definition. Humans are unreasonable because we do not operate through reason entirely I’d encourage even my most autistic friends to remember that this means you are unreasonable too.

Narratives are the comfort we seek as our apophenia runs rampant. Spotting the one thing that is not like the others is how we survive. We seek sense in the chaos. It’s an unreasonable thing to do when we know we’ve not yet managed to measure even a fraction of our reality. One day I hope I come to terms with that.

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Chronicle Preparedness

Day 934 and Planning Ahead

I have been doing a short “season of no” over the last few weeks. I’m pruning my calendar and letting go of some projects, people and attention hogs. I’ve reoriented myself to obligations that give me as much as I give them.

The upside of saying no is that many obligations I’d assumed were set in stone are now blissfully gone. You can say no to more shit than you think as it turns out. I had a death in my extended family that provided me with clarity.

I do however feel as if it’s going to be hard to make plans too far out into the future for a while. A lot is happening and schisms in every community make it hard to see how some things could turn out. I’m keeping flexibility in my life so I can be mentally and physically prepared for rapidly changing conditions.

Especially as we come to grips with a world that is more chaotic, and a future that is less predictable, planning becomes the kind of exercise you hold gently. I’ve got goals and ambitions for the near term but I’ll play it as it lays.

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Chronicle

Day 933 and Hot Hot Heat

It would seem that we’ve officially entered the high season of summer that even northern latitudes like Montana cannot escaped entirely.

I wish I had the capacity to work out a circadian rhythm that entirely accounted for how miserable long hot days can be even if you are inside in the shade. Siestas and late evenings could work but I’ve got the hang of it. I need my eight hours.

I never get cabin fever in the winter. Even the worst storm usually abates within a couple days. I can happily layer up and enjoy being in the cold and dark. I can be outside if it’s cooler, darker and clearer. If it’s not I’m basically a caged animal.

But there is nothing to be down about the sun being out till 10pm and with temperatures crossing over the 90F/32C degree mark, all that is left is escape indoors to a cold dark place and wait out the season.

Last year on July 21 I wrote about summer season affective disorder so it’s clearly a pattern I notice around this time. I’m simply grateful it’s starter later than it did when I lived in Colorado where hot streaks are beginning even earlier.

With Montana summers, I go to sleep when the sun is still out and I wake up and it’s already sunrise. If the heat weren’t so intense I think it would be bearable but the heat domes are becoming pretty common. I remain grateful it’s only six to eight weeks unlike most of continent where summer is longer and crueler.

Another factor in all of this is how challenging fire season can be for spending time outside comfortably even if it’s not combined with a heatwave. I went out this morning before temperatures climbed to get some sun and exercise. The air quality was still decent but multiple fires are popping off in Montana and I expect this to change shortly. I suspect I’ll need to find a way to manage more time indoors as the summer rages on.

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Background Chronicle

Day 729 and My 22 Round Up

I scrambled a bit to do round up of this year’s posts. I went through through each day individually and attempted to sort posts that grabbed me into succinct categories. I don’t want to call it a “best of” list so much as a set of themes and experiences that made up my 2022. It was quite a year.

The most popular post I wrote this year was my viral hit about dickriders by a huge margin. The tweet got several million views and the blog post got upwards of 50,000 readers. Nothing else even compares. I think my some of my most honest writing came through two days in May when Alex and I decided to buy our house in Montana. Day 499 and 500 respectively. But I cover a huge breadth of topics over the year so without further ado here is the list. In no particular order.

Twitter Shit

Dick Riders or Don’t Outsource Your Credibility

Excession, Nerd Wounds & Needing to Be Liked

Gender Politics.

Mommy Issues, Girlbossing, & Chivalry for Women After Feminism

The Cuckservatives

The Fuck Boys

The Thot Leaders

Startup Content

My #5Before40 Project to Build Chaotic Capital in Public

Managing Founders or The Rule of 3 Asks

How To Do Cold Outreach

Managing Winter As A Metaphor For Downturns

The Importance of Corporate Governance for Startups

Glass Cannons, Gaming & Going Critical In Startup Life

Accidentally Ahead Of The Fraud Trend

Shoot The Puck or Letterkenny as a Metaphor for Startups

Vibe Shifts, Web3 and End Times at EthDenver

High Agency People

How I Sensemake My Investments

Emotional Work

FTX, Crashes, And History Repeating

A Love Letter To My Husband About Chores

Being A Daddy’s Girl

Halfway There or 500 Days

Vinegar or Why Boundaries Are Good

The Emotions of Buying Your First House

The Emotional Security of Owning A Home

A Painting Without Shadows is Flat

A Deep Sense of Okayness

Watching Others Drown

Montana

Bozeman, Boulder and the Uncanny Valley of Progress in The American Mountain West

Hospitality, Guest Rooms & Welcoming

Leaping into Action or How A Wilderness EMT Course Helped Me Work in Chaos.

We’re Not In Colorado Anymore & Our Digital Barn Raising Move

Health & Biohacking

The Personal Politics of America’s Drug War

Aesthetics, Religion and Botox

The Poetry of Migraines & Stretched Time

A Meditation On Heat, Social Mores, Pain, and Texas

Tracker Jacker or When Your Health is Outside The Mean

Politics

Preparedness, Consumer Culture & Distrust

Margin Call & Collapse

Women & Bodily Autonomy, Young Male Reactionaries and Groypers

The Humiliation of America’s Broken Immigration System

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Chronicle

Day 574 and Brain Fog

My mind is in such a haze today. We are in the middle of the final packing job for our move to Montana and I’ve been removed from the house as I’m just getting in the way at this point.

I am surprised at how mentally tired I am from the move. I assumed it would be physically and emotionally draining. But why would my mind not be sharp? I’m just bumbling though basic communication. I cannot even finish a Duolingo lesson. I am struggling to form sentences in any language.

It is days like this that I am grateful my rhythms hold together my life as even though I’m teetering on the edge of complete incompetence I am still here writing. It’s a forgettable three paragraph kind of day and that is alright.