· Medicine
The Day I Realized I Didn’t Want My Old Life Back
For 25 years, I was an emergency physician. Then came divorce, federal prison, and an abrupt separation from the medical world I had built my identity around.
Permanent archive
Difficult Problems
One difficult problem at a time. Medicine, AI, business, systems, and beyond.
· AI
If AI Can Do 80% of Your Job, Why Would I Hire You?
If AI can do 80% of the work you currently do, what makes the remaining 20% valuable?
· Medicine
I Became Four People for Labor Day. That’s the Point.
This Labor Day, I found myself thinking about what work is becoming.
· Medicine
Who the Hell Is Tommy Hilfiger? The Brand Is the Brand
When I was a teenager, Tommy Hilfiger was everywhere, and I kept wondering: who the hell is Tommy Hilfiger, and why does his name mean anything?
· AI
Before You Trust AI, Give It a Referee
AI can give you a polished, confident answer and still be wrong.
· AI
I’m Not a Web Designer. So Why Am I Building Websites in an Hour?
I never set out to become a web designer.
· AI
AI Won’t Replace You. Someone Who Knows How to Use It Might.
You do not need to become an AI expert.
· Medicine
Your Experts Disagree. Don’t Hire a Third One Yet.
A difficult case can have tens of thousands of pages, conflicting experts, competing medical explanations, and a client waiting for a decision.
· Business
Rich on Paper, Broke on Tuesday
A commercial property can look healthy on paper and still run out of cash.
· AI
Your Project Is 6 Months Late. Do You Fix It, Replace It, or Kill It?
A project is months late, over budget, and everyone keeps saying it is “almost there.”
· AI
Don’t Let AI Make You Fast at Being Wrong
AI can make a new hire much faster before they have the judgment to know whether the output is any good.
· AI
AI Can Make You Fast Before It Makes You Good
AI can make a new employee dramatically faster before they have developed the judgment to know whether the output is actually good.
· AI
Are Documents the Real AI Bottleneck
We are wasting a ton of money and energy on stuff that is unnecessary. If we change the documents we use to more intelligent documents, we won't need as many data centers!
· AI
Maybe AI Isn’t the Bottleneck. Maybe the Document Is.
We are spending enormous amounts of money making AI more powerful, then handing it documents that were never designed for machines to understand.
· Medicine
A Second Career for Physicians: Expert Witness Work Without Quitting Medicine
You do not have to leave medicine to create a second professional lane.
· Medicine
When Smart Executives Disagree, Find the Assumption
CFO says cut. Sales says spend. Who do you believe? Find the decision variable. Full talk on The New Physician.
· Business
When Smart Leaders Disagree, Find the Variable
This Loom addresses how a CEO should handle a disagreement between the CFO and the head of sales about cutting spending during a bad quarter. Instead of picking a side, the CEO should identify the decision variable by asking what fact would make each person correct, such as cash runway, conversion rate, gross margin, customer acquisition cost, or the sales cycle and payment lag. The discussion contrasts scenarios where there are 16 weeks of cash left versus only six weeks, showing how timing can settle the argument even if both executives are smart. The key is to agree on the scoreboard before funding decisions and make disagreement useful without humiliating either side.
· Business
A Fast No Can Save You 3 Months
In serious business negotiations, a clear no today can be far more valuable than a vague maybe that drags on for three months.
· Business
Say the Hard Thing Early: How to Stop Wasting Months on a Bad Deal
In serious business negotiations, avoiding the uncomfortable issue rarely makes it disappear. It usually just wastes time.
· Business
Revenue Is Down 20%. What Should the CEO Do First?
Revenue is down 20%. The CFO wants cuts. Sales wants more investment. Operations warns that cutting too deeply could break service.
· Systems
Stop Wasting Job Applications: Verify, Match, Reach
Most people track how many jobs they apply for. A better question is: how far does each application actually get?
· AI
Will AI Take Your Job? Ask These 3 Questions
Will AI take your job? Maybe that is the wrong question.
· AI
AI Gives You 20 Answers. Paper Makes You Pick One.
AI can give you twenty answers in ten seconds.
· Business
Stop Trying to Save Everything: The Turnaround Rule for Business and Real Estate
When a business or property is in trouble, the instinct is often to save everything. That can be exactly the wrong move.
· AI
AI Gives You More. Paper Helps You Decide.
AI is brilliant at expanding your options. It can research, summarize, compare, brainstorm, and give you twenty possible ways forward in seconds.
· Business
Bread, Butter & Jam: Why Real Estate Can Make You Rich on Paper and Cash-Poor
Commercial real estate can make you wealthy on paper while leaving you surprisingly short of cash.
· AI
AI Isn’t Killing the Career Ladder. It’s Moving the First Rung.
AI may not eliminate the career ladder. It may simply move the first rung.
· Beyond
What To Do When Your Tribe Tells You Who You're Supposed to Be
This episode began with a question brought to me by an investment manager of Indian origin: what do you actually owe the racial, cultural, religious, or social group you happened to be born into?
· Business
Commercial Loan Maturing? Your 5-Step Owner Playbook
Commercial loan coming due? Don’t wait for the bank to tell you that you have a problem.
· Beyond
HOA Can They Really Do That Short
Can your HOA really do that?
· Beyond
When Your HOA Goes Rogue: Can They Really Do That?
What do you do when the organization enforcing the rules appears to stop following the rules itself?
· Systems
Where Good People Create Bad Systems
Some of the most dangerous failures in organizations happen not within departments, but between them.
· Business
Sometimes the Business Isn’t Broken The Financing Is
Sometimes the Business Isn’t Broken. The Financing Is.
· Medicine
Help Vaccine Hesitant Parents: Trust, Listen, Recommend, Make It Easy
How do we help parents who are unsure about vaccinating their children?
· AI
The Biggest AI Mistake Smart People Make
What is the biggest mistake smart people make when using AI?
What difficult problem should I examine next?
Send me the question, problem, or system you think deserves a closer look.
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