Accidentally Sending a Risky Text to Your Boss Artwork

Pessimistic at Best

Welcome to Pessimistic at Best, a podcast for those with a penchant for frequent frustrations, personal gripes, unpopular opinions, honest observations, and the like. Hosted by Sam, your resident Pessimistic Patty, this weekly show operates on the belief that no complaint is too small.

Each week, Sam sits down with a guest to explore the good, the bad, and the ugly. A surprisingly good country album by your favorite pop artist, a bad bang trim you gave yourself during a manic episode, a military homecoming video on the internet that made you ugly cry. The list is endless, and therein lies the beauty. Come on in, we saved you a seat!

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Pessimistic at Best

Accidentally Sending a Risky Text to Your Boss

September 29, 2026 • Sam Georgson

0:00 | 1:23:21

Have you ever fired off a text to the wrong person? Was it an (accidentally) explicit text that you sent straight to your boss? Were you surprised to be offered a promotion afterwards? We might not all be this lucky, but Kate sure was — we have a good laugh about this one!

Then we get into the good, the bad, and the ugly: maintaining a sense of childlike wonder, the meta glasses takeover, and having the audacity to litter.

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