Failure Is Always an Option: Three Stories
Last year on Side Hustle School, we introduced a new segment called Failure Friday.
After 1,800+ episodes, including more than 1,000 detailed case studies (which are basically success stories), I thought it would be interesting to look at “all the times it doesn’t work out.”
Failure Friday turned into one of my favorite segments. Listeners have really enjoyed it as well, especially the stories that get really personal and go into lots of detail.
There’s now a whole collection of stories—and like everything else with Side Hustle School, you can listen to all of them for free. Here are three of my personal favorites.
1. “They promised the boat would be ready, but it wasn’t.”
- Link: Episode page
- Link: Direct audio (story begins at 2:49)
In this story, an Australian who leads small-ship Mediterranean tours commissions a new ship from a local builder—but doesn’t turn up to collect it until a week before his next tour was starting. This story is epic! It’s a true disaster tale, complete with a happy ending … eventually.
Chris Tabone operates Koda Sail, a set of sailing tours that operates in Croatia and Turkey. A few years ago, he commissioned an all-new ship, but failed to arrive much buffer time in between the promised delivery date and the first sailing with paying customers.
In a comedy of errors, the shipbuilder kept telling him “Don’t worry, man!”
But Chris was worried, and rightly so. In the end, the ship arrived at the very last minute, but far from complete. How did he handle it??
Listen to the episode for the full story.
2. Weighted Blankets Get Weighed Down in Customs
- Link: Episode page
- Link: Direct audio (story begins at 1:55)
After scaling up to serve thousands of customers with weighted blankets, this Canadian experiences a truly disastrous holiday season when his overseas shipments are delayed.
Can you imagine ordering 17,000 weighted blankets in time for the holidays … and then having them arrive much too late?
Yeah. That’s what happened to Aaron Spivak, who operates Hush Blankets from his Toronto headquarters.
Weighted blankets aren’t cheap, by the way. It looks like Aaron is selling them for $199 on the website now, but in the story he mentions that the retail price then was over $200. Just think of it … $200 * 17,000 is $3.4 million!
Not a small loss for the average small business. Somehow, Aaron and team survived after issuing all the refunds—and now, they place their wholesale orders much earlier.
3. “Hundreds of people were shut out of my webinar…”
- Link: Episode page
- Link: Direct audio (story begins at 2:00)
This boudoir photographer diligently planned for her first webinar with 400 excited attendees—but it turned out the platform could only handle 50 of them.
I could have written this disaster story myself, except for the part about being a boudoir photographer. (I’m still working on that.) When Tanya Smith held her first big webinar in her photography education business, she didn’t realize she had to pay extra to accommodate a large group. This has happened to me too, and it’s super frustrating!
Imagine having hundreds of eager people waiting to hear from you, only to be shut out of the webinar or call. Unfortunately, this is an all-too-common experience when you’re first learning how these things work.
Failure Is Always an Option
Most Failure Friday stories have a happy ending eventually. But it’s not usually instantaneous. Success is never guaranteed and doesn’t operate according to your preferred timetable.
You might have heard the saying, “Failure is not an option.” Well, guess what? Sometimes you don’t get to choose! Not everything in life is within your control.
Failure is very much a possibility in most business ventures, relationships, or risks of any kind. Besides, if there’s no chance of failure, are you really aiming high enough?
Sometimes things just don’t work out the way you’d like. And that’s okay—no need to hide from it. Perhaps your next failure will lead to your greatest success.
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