My Worst Day As A Business Owner (Part 2)

Guesswork Unveiled, Issue #21

Guesswork Unveiled: My Worst Day As A Business Owner (Part 2)

July 10, 2025 | Issue #21

This is the paywalled section of my blog, designed & written for SMB operators. To read Part 1 (free for all), please click here. Please consider supporting my writing as a paid subscriber — making money from my blog allows me to funnel more reinvestment into my tree care contractor.

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Last week, I walked you through the first 24 to 48 hours of a significant truck crash. Today covers the nitty gritty impacts beyond the first 48 hours.

My primary intention for writing this piece is to provide fellow owner-operators with a sense of camaraderie. After all, a TON of small business owner content focuses on wins. A good amount of SMB owner content focuses on the grind — the sustained effort required to build your business.

But very little SMB owner content features the moments you get punched in the face.

Honestly, there’s less to learn from in situations like this than there is from more “standard” failures. I didn’t even attempt to draw lessons learned in this post. I hope you’ll take this for what it is — more of a post-mortem and communal commiseration.

Here we go.