Member-only story

4 Lessons on When to Sell $400,000 Worth of Stock in an Unpredictable Market

Jeffrey Goodman
10 min readSep 19, 2022

--

Tools and pearls of wisdom for framing and managing risk; knowing when to sell stock and when to hold; and keeping emotions at bay.

Photo by Alexandru Zdrobău on Unsplash

Related

Is the Stock Market Really in a Bear Market? Maybe. Maybe Not.
When Is a Stock Market Crash Not Really a Stock Market Crash?
MBA Guide to Dealing with Higher Mortgage Interest Rates, Part 2 — How Much Money Will You Save?

Recent

The Deafening Silence on Stock Buybacks from Centrist Democrats
2 Reasons Populations Are Collapsing in Developed Countries
3 Key Facts Everyone Is Missing About Biden’s Student Loan Debt Relief

Potential to Change the Way You Think

Why Are Fundamental Human Values Critically Important for Successful, Enduring Brands?
Life Expectancy vs. Healthcare Costs in the U.S. (and Japan, Germany, France, Spain, Portugal, etc.)
• (1a/9) “Top-Down” Makes More Sense Than “Left-Right” in the U.S.

Photo by Fred Moon on Unsplash

My friend, Matt emailed me on a Friday afternoon. He had just “come into” 4,500 shares of stock in a hot software company, Siebel Systems — a $450,000 windfall!

A startup company he used to work for had been acquired by Siebel. It was entirely unexpected, but Matt’s stock from the startup would be converted into Siebel stock and was going to be worth something.

Matt wanted to ask for my advice about buying stock options as insurance in case Siebel’s stock price went down. The Siebel stock would be deposited into his brokerage account three days later on Monday morning.

We made plans to meet for lunch on that Monday.

But it was clear to me that he had asked the wrong question.

Quick background

Matt (not his real name) had just finished graduate school a few years earlier. He…

--

--

Jeffrey Goodman
Jeffrey Goodman

Written by Jeffrey Goodman

Navigating facts and numbers to help people. Strong opinions on climate change and healthcare. Objective, not neutral. MIT engineer, Wharton MBA.

Responses (3)

Write a response