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Lester's Letters

Latest Letters


The MINDSET Is Dead. Long Live The MINDSET
I killed The MINDSET twice. Admittedly, the first time was neglect. I let it rot in suspended animation like every other abandoned project. The second time was intentional, I unleashed a controlled burn. What follows is why it had to die, what emerged from the documentation of my own reconstruction, and what The MINDSET becomes now. This is the origin story of a counterinsurgency.
Dec 2, 20257 min read


The Index: Everything In One Place
My pool of ideas is massive and somewhat unwieldy. So Bobert & I are going to commit to throwing down on a "series of series", and that will be the vibe for the foreseeable future. The Way Forward will allow for the ongoing writing of evergreen topics as well as sharing complete stories with clear endpoints. In this way, each article to become a chapter in a much larger narrative which work together to build the momentum of my story.
Nov 18, 20254 min read


The Reconstruction: A Map for the Journey Ahead
This orientation piece breaks down the 12-week arc structure: Escape (weeks 1-4), Rebuild (weeks 5-8), System (weeks 9-12). But stated goals vs unstated goals means the exact path bends to what's alive when I write.
Nov 11, 20256 min read


Going On Campaign - What Q1 Actually Looks Like
I spent years unable to build publicly. Those years were not wasted because they became the foundation that let me deploy in days instead of months.
You might be in your own basement right now, literal or metaphorical, unable to move. That's fine. Use the time to learn the terrain. Map the systems. Plan the campaign.
Nov 11, 20255 min read


Using Obsidian to Run My Entire Business
I run an entire digital empire from my 31-foot sailboat with zero required monthly software costs. My blog, newsletter, YouTube channel, community, products and social posts are all orchestrated through one free tool that finally taught my Neurospicy brain how to think in public without losing my mind in private.
Nov 11, 202512 min read


Freedom Means Saying No to Your Own Plans
I've burned bridges, walked away from family, quit jobs, donated a sailboat I just bought. You know what I never regretted? Making the hard pivot when I knew something wasn't working.
Nov 11, 20256 min read


Course Correction: When SpicySadness Comes Knocking
The Promise I promised audio drops yesterday. They didn't happen. The articles I drafted last week were supposed to go live in audio form, accompanied by updates from the boat. Instead, I got knocked sideways by what I affectionately refer to as: " The SpicySadness ". You're familiar with that occasional grey visitor, I'm sure. It used to be a permanent companion of mine, but now just shows up occasionally to fuck with my head and remind me where I've been. The bit that matte
Nov 11, 20254 min read


What to Actually Do When Starting From Zero
When you burn your old life to the ground, the silence that follows is a challenge. The first thirty days after starting over are brutal, raw, and honest. This is a field manual for survival, reconstruction, and rebirth. From wreckage to routine, this is how you build when there’s nothing left but you.
Nov 2, 202512 min read
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