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Side Hustle School

Ep. 3030 - Q&A: “How do I prepare for tech failures without overloading my setup?”

Side Hustle School

Chris Guillebeau / Onward Project

Business, Entrepreneurship, Careers

4.83.3K Ratings

🗓️ 18 April 2025

⏱️ 6 minutes

🧾️ Download transcript

Summary

What happens when a tech glitch disrupts your side hustle? In this episode, we tackle how to prepare for unexpected challenges without overcomplicating your operations.

Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week.

Show notes: SideHustleSchool.com

Email: [email protected]

Be on the show: SideHustleSchool.com/questions

Connect on Instagram: @193countries

Visit Chris's main site: ChrisGuillebeau.com

Read A Year of Mental Health: yearofmentalhealth.com

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Transcript

Click on a timestamp to play from that location

0:00.0

Lemonada.

0:02.7

But we used to run this episode called Failure Friday, or a regular episode, a segment, in fact.

0:16.6

We did that for a couple years.

0:17.7

It was all about, you know, success stories gone wrong, basically,

0:21.3

like the opposite of a success story, mistakes, mishaps, disasters, and such. And how does one

0:26.6

recover from such a mistake or a disaster, whatever the case may be? And I thought about that in

0:32.1

working on today's episode, we've got a listener question, how do I prepare for tech failures

0:36.6

without overloading my setup?

0:39.0

Basically, well, you'll hear the story from the caller, but he had a mishap where his point of

0:43.8

sales system, basically how you take credit cards from customers, completely bonged out and did not work in a high pressure situation, such as one where he's trying to take money from customers.

0:54.9

Sometimes even the best laid plans can be thrown off by an unexpected glitch, especially when

1:00.2

this is not your full-time thing. You've got all kinds of other stuff you're trying to look after

1:04.8

and worry about. And a big part of what we hope to do at Sidesaw School is to simplify and reduce

1:09.8

the complexity so that you can

1:11.6

spend more time doing what really matters. So in this situation, we've got Neil here. He's going to tell

1:16.5

the story of the glitch, basically, and I'll offer some comments, suggestions on how to avoid

1:21.6

this in the future and how anybody else out there can also avoid it. All right, detailed question from

1:26.2

Neil and my answer coming right up.

1:35.1

Hey, Chris, this is Neil. I ran a booth at a local gathering recently, and everything was great,

1:41.3

until my payment system crashed, leaving me to scribble each sale

1:44.9

on random pieces of paper.

1:47.1

The vent didn't totally derail, but it was a big wake-up call about how vulnerable I can

...

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