This transcript was generated from the episode audio and may contain minor errors.
[Music]
What's up friends and welcome back to the podcast. My name's Chris Guillebeau, your host. And that podcast I should have mentioned by the way is called Side Hustle School. We are all about giving you case studies, ideas, actionable information you can use to start a new income generating project without quitting your job. And today we have a special segment.
We run this every other Friday. It's known as Failure Friday. Failure Friday, it's all about the things that do not go well. So yes, I'm trying to give you actionable information, but sometimes it is what do you need to look out for? And how can you prevent a mistake, a misstep, a disaster or an outright failure?
Often our Failure Friday stories go on to turn things around. They recover, they rally, they regroup. But of course there's also a moment of feeling discouraged when something goes wrong. So we like to delve into that. Today the story is about a virtual assistant who was a fan of quiet quitting.
You might've heard of quiet quitting. This guy has a virtual assistant and they basically quiet quit on him. The relationship starts well, but then the founder or the person making the hire stops paying attention, which is often a key point in this kind of situation and things go downhill. So let's hear the story. This is Jack from Milwaukee.
He runs this advisory service in his spare time. He works in finance during the day. He goes on to hire a virtual assistant and I'll let him tell you what happens next. [Music]
Yeah, my name's Jack and I first found you through the $100 startup. Since then I've been listening every day for at least a year.
Thanks for all you do. So in my side business, I have to handle lots of little logistic things like emails, scheduling check-ins and so on. I always done it all myself, but I started thinking it might be good to actually delegate it. That's why the experts tell you to do it, right? I wanted to hire like somewhere like an assistant.
So I wrote up a detailed description of tasks and got to work interviewing people from Upwork. After a few tries, I found someone who seemed awesome at least for the first three weeks. Problem is something changed without my knowledge. Maybe you read an article about quiet quitting and just decide to slack off. I didn't notice it for a while, especially since I'd been so happy about finding them.
It wasn't until three months into that I realized something was very wrong. I hadn't been checking his work much and when I did, I learned that much of it hadn't been done for weeks. I also had complaints from missed appointments, typos in important broadcast emails that went out and other mistakes that I only discovered with more investigation. Part of the issue was the many emails went only to the assistant. So I didn't know anything was wrong until I started digging in.
When I went to talk to him, he didn't have much to say and then he quit. The quiet quitting turned into a louder quitting, which I guess is just quitting. But anyway, now I was stuck. I already filled up the free time again. So now I needed to figure out what to do.
I went back to doing everything myself and it's been a bit of a struggle to manage it all. Looking back, I think I should have provided more support for longer. After the first week or two, I just kind of let my virtual assistant handle everything on its own. Even though he seemed competent, a bit more hand holding might have helped. Accountability and more regular check-ins would have been good as well, I think.
I'm currently getting ready for phase two of delegation. Hiring someone who I hope will stick around a lot longer. I guess I'll find out soon enough. [Music]
Never confuse a single defeat with a final defeat. That is the theme of Failure Friday.
Thanks so much to Jack for having the bravery to share this story. I too, in my hiring decisions, working with contractors and such, I often just kind of take my eyes off the prize or I just stop paying attention because I'm doing other stuff. And I imagine that when I first hire an assistant, I can just spend a little bit of time and show them stuff and they're gonna go off and figure everything else out. And sometimes that can work, but often you need to just have a lot more hands-on attention. And that's just part of working with people.
Delegation, outsourcing, these are not one and done kind of operations. They're more like ongoing operations. So Jack, thanks again, listeners. If you have a question, a comment, a story of your own, sidehustleschool.com/questions on that same website. We've got notes pages for every single episode.
You can download or stream whatever you'd like. It's all completely free. You can also subscribe or follow wherever you get your podcasts, Spotify, Apple Music, any other source directly on the website, et cetera. And we'll give you new episodes every single day, seven days a week, also free. That's all for now.
Thanks for listening. My name is Chris Guillebeau. This is "Side Hustle School." [Music]
from the Onward Project.
