This transcript was generated from the episode audio and may contain minor errors.
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Have you heard the one about the virtual assistant who just kind of stopped working, stopped being an assistant, virtually or otherwise? Well, it's not really a joke. It sounds like a setup to a joke, but it's actually the introduction to our story today. Today is a failure Friday story. Welcome to Side Hustle School.
We're gonna hear today from a listener who's also a founder of an advisory service. He heard that delegation was like this cool thing you're supposed to do. You gotta outsource, you gotta find somebody to help, compensate for your weaknesses or just do the things that you don't wanna do so that you can focus on your strengths, et cetera, et cetera. I'm sure you've heard of that before and it sounds great, but does it always work that way? Well, in fact, it actually doesn't always work that way.
Unfortunately, it's all too common for it to go a different direction. There's lots of other directions that can go, not the one that you were hoping for. So as I said, this is part of failure Friday, a collection of short stories about mistakes, missteps, disasters, and of course, failure, all of the things that go wrong. We're gonna hear this story from Jack. Jack is from Milwaukee.
He runs that advisory service in his spare time when he's not working in finance during the day. Now, since Jack is a busy guy, as mentioned, he assumed that getting some help would be a good idea and maybe it still will be at some point, but this first go around didn't go so well. All right, let's hear the story from him. [Music]
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 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. Jack, I hope you take those words to heart. Thank you for sharing your story with us.
Unfortunately, I hear this kind of thing a lot in terms of I had a virtual assistant and it went well until it didn't. Sometimes the only variable that changes is how long the virtual assistant sticks around. It might be a few months. If you're lucky, it's a year or more. Sometimes it's a matter of weeks or even days.
I guess hours, although if it only happens for a matter of hours, then maybe you haven't lost too much time. The point is that it can be challenging, especially these days, good help is hard to find. So Jack had some good ideas there in terms of accountability, in terms of continuing to provide additional support. That definitely might have helped. I just know also that that then kind of, it doesn't really defeat the purpose of having a virtual assistant, but it does add something to you instead of taking something away, which is in fact the purpose.
So something to consider as we all move forward here. So thanks to Jack for sharing this story. Listeners, if you've got a question or an update for us about your hustle, let me know what's going on at sidehustleschool.com/questions. Speaking of being busy, this is a very busy time of the year. I know a lot of stuff is in the mix, so be sure to take care of yourself.
At some point, maybe let's all spend some time thinking about what we would like to see for the new year, the new year, and in fact the whole year that is coming up. All right, I will leave you with that today. Probably say more about it at some point. But for now, my name is Chris Guillebeau. This is Side Hustle School.
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From the Onward Project.
