Jonathan Endicott

Jonathan Endicott, full name Jonathan Weston Endicott, has founded and run direct-to-consumer e-commerce businesses. He writes short essays about what that kind of work teaches: how to start before the plan is finished, how to survive the stretch where nothing is exciting, and how to make a call when the data you want doesn't exist yet.

This page is the map. Every essay, audio piece and video is linked from here, and so is every account that is actually his. If you have five minutes, read The Second Person to Do the Job, the newest essay. If you have one minute and a pair of headphones, play Deciding Without All the Answers.

What the writing keeps coming back to

Three ideas show up again and again. The first is momentum: a rough start beats a perfect plan, and routines beat bursts of motivation. The second is evidence. Test the assumption that would hurt most if it were wrong, and undo cheap mistakes quickly instead of agonising over them. The third is the way teams actually talk, which is often not the way the meeting invite says they talk. That last thread has taken over recently, with pieces on hallway conversations, basic questions nobody wants to ask, and why an apology costs less than the fix that should follow it.

Essays

The full archive lives at Jonathan Endicott — Essays. Newest first:

• The Second Person to Do the Job · Nov 9, 2026
  Handing off work you could do better yourself, why the first handoff is supposed to go badly, and writing down the reasons instead of just the steps.
• The Meeting After the Meeting · Nov 5, 2026
  Why the honest conversation keeps happening in the hallway after the official one, and how to make it cheaper to say the thing in the room.
• Ask the Dumb Question First · Oct 30, 2026
  The basic question asked in minute three is worth more than the homework you promise to do afterwards.
• Rest Is Part of the Work · Oct 29, 2026
  Years of hard work need planned recovery, not just planned effort.
• Building and Running DTC E-commerce Businesses · Oct 29, 2026
  Unit economics, cash, a focused catalogue and earned trust, seen from the operator's chair.
• Deciding Without All the Answers (audio) · Oct 29, 2026
  A minute on reversible versus irreversible calls, and why ordering half is often the right answer.
• Good Hours vs. Long Hours (audio) · Oct 29, 2026
  Twelve tired hours against seven focused ones, and why the second person wins by month three.
• Discipline Is a System · Oct 27, 2026
  Decide once, arrange your surroundings so the decision sticks, and keep the promises small.
• Evidence Over Opinion · Oct 27, 2026
  Find the assumption that would hurt most if it were wrong, and test that one first, cheaply.
• The Boring Middle · Oct 27, 2026
  Once the novelty wears off most projects stall. Routines carry you further than motivation.
• Start Before You're Ready · Oct 26, 2026
  The feeling of readiness shows up after you begin, so make the first step smaller.

On Medium

Some pieces run on Medium rather than the essay site:

• The Apology Is the Cheap Part · Oct 31, 2026
• The Compliment Sandwich Is Stale Bread · Oct 29, 2026
• Simple Beats Clever · Oct 28, 2026
• Play the Long Game · Oct 27, 2026
• Make It Useful, Then Make It Again · Oct 27, 2026
• Build Systems, Not Willpower · Oct 27, 2026

Listen

Two of the essays are short audio pieces, each just over a minute, with the transcript underneath. They are collected on the Jonathan Endicott audio page, and there is a podcast feed if you would rather subscribe in an app.

Watch

The YouTube channel has one longer video, Start Before You're Ready: 7 Rules for Momentum, and a run of Shorts that each squeeze one idea into under a minute:

• Sorry Is the Cheap Part
• Decide Without All the Answers
• Simple Beats Clever
• You Don't Have a Talent Problem
• Most People Don't Fail. They Quit.
• Your Goal Isn't Too Big. Your First Step Is.
• You'll Never Feel Ready (That's the Point)

Profiles

A few other people share the name, including an audio engineer and a college lacrosse player. The accounts below belong to this Jonathan Endicott. If an account isn't linked from this page or from the profiles list, assume it belongs to someone else.

Writing

Medium · Substack newsletter · Substack profile · WordPress: Jonathan Endicott Writes · WordPress: Jonathan Weston Endicott · Blogger · Hashnode · DEV · Tumblr · Wattpad · Issuu · Quora

Video and audio

YouTube · Vimeo · SoundCloud

Social and link pages

Instagram · Threads · Bluesky · Pinterest · Linktree · Taplink · Lnk.bio · about.me · Gravatar · Wakelet

Code and projects

GitHub · GitHub Pages · GitLab · CodePen · Replit · Kaggle · Stack Overflow · Hackster · Instructables · itch.io · Product Hunt · Behance

Support

Buy Me a Coffee · Gumroad

The three sites

jonathanendicott.com is the home page and the short pages, like the bio and the FAQ. essays.jonathanendicott.com holds the full text of every essay. jonathanwestonendicott.com is the profile site under the full name, with the operating principles and career overview. For where the work gets republished, see Jonathan Endicott, elsewhere. For what he is working on this month, see Jonathan Endicott — Now.