The Twenty Percenter
Weekly advice for top business professionals.
The Cost of Comfort (2 Min Read) | Vol. 201 May 1, 2026 “Tension is not conflict, and discomfort is not harm.” – Charlie Gilkey The Cost of Comfort The biggest tax on your business may be the conversations you’re avoiding. Addressing underperformance, chasing a late payment, delivering bad news, renegotiating a deal, or parting …
The Leadership Question Nobody Wants to Ask (6 Min Read) | Vol. 200 April 24, 2026 “Your silence gives consent.” — Plato The Leadership Question Nobody Wants to Ask This is not an opinion piece. This is a coaching conversation. And I believe coaches don’t tell their clients what to think. They teach them how …
Almost There (4 Min Read) | Vol. 199 April 17, 2026 “Nothing in the world can take the place of persistence. Talent will not; nothing is more common than unsuccessful men with talent. Genius will not; unrewarded genius is almost a proverb. Education will not; the world is full of educated derelicts. Persistence and determination …
How Billionaires Set Goals (4 Min Read) | Vol. 198 April 10, 2026 “If more information was the answer, then we’d all be billionaires with perfect abs.” – Derek Sivers Ask a room full of entrepreneurs how they track their goals, and you’ll get a dozen answers. Post-it notes. Notes apps. Project management tools with …
Let’s be Friends! (3 Min Read) | Vol. 197 April 3, 2026 “Find a group of people who challenge and inspire you; spend a lot of time with them, and it will change your life.” – Amy Poehler Let’s be Friends! Last year, my publisher asked me a curious question. “Jay, do you know how …
You’re Not as Stupid as You Think (2 Min Read) | Vol. 196 March 27, 2026 “The fundamental cause of the trouble is that in the modern world the stupid are cocksure while the intelligent are full of doubt.” — Bertrand Russell You’re Not as Stupid as You Think In 1995, McArthur Wheeler and Clifton …
Great is the Enemy of Good (2 Min Read) | Vol. 195 March 20, 2026 “You’re only as good as you’re willing to be bad…The fact that you’re not going to be good at something or that you’re going to fail at something—that’s OK. Because you’re never going to get good unless you’re willing to …
The Delegation Matrix (3 Min Read) | Vol. 194 March 13, 2026 “Some decisions are consequential and irreversible — one-way doors — and these decisions must be made methodically, carefully, slowly, with great deliberation and consultation.” – Jeff Bezos The Delegation Matrix In my coaching, I see the same pattern over and over. A business …
The Red Right Hand of Resolve (2 Min Read) | Vol. 193 March 6, 2026 “It is not enough that we do our best; sometimes we must do what is required.” ― Winston S. Churchill The Red Right Hand of Resolve Wendy and I have been binging Peaky Blinders before the movie comes out this …
Two Laws Every Leader Should Know About Time (4 Min Read) | Vol. 192 February 27, 2026 “It always takes longer than you expect, even when you take into account Hofstadter’s Law.” – Douglas Hofstadter Two Laws Every Leader Should Know About Time Read that quote again. It’s a riddle wrapped in a truth bomb. …
