2946 8:59 Q&A

Q&A: “When should I hire a virtual assistant?”

In today’s episode, we help a side hustler decide if it’s time to hire a virtual assistant. Learn how to assess your readiness, find the right help, and delegate tasks effectively without breaking the bank.

8:59

Subscribe Now For A Free Five Step Tutorial

Get a free five-part email course that shows you how to find, validate, and launch your side hustle idea — no experience required.

Episode 2946

Running a side hustle can sometimes feel like a full-time job, especially as you try to balance daily tasks with growth opportunities. Today’s question comes from Caleb in Huntington Beach, California, who’s feeling overwhelmed by the demands of his business.

He’s considering hiring a virtual assistant to lighten the load but isn’t sure if he’s ready or how to go about it without overspending. Let’s explore how Caleb can assess his readiness, find the right help, and manage a virtual assistant effectively while keeping costs under control.

"Hey Chris, this is Caleb from Huntington Beach, California. I’ve been working on my side hustle for a while now, and I’m starting to feel buried in daily tasks like answering emails, managing social media, and shipping orders. I’ve heard about hiring a virtual assistant to help, but I’m not sure if it’s worth the cost, or how to even start looking for one. How do I know if I’m ready to bring on help, and what’s the best way to hire and manage a virtual assistant without breaking the bank?"

Listen to today's episode to learn more...

Yours in the revolution,

cg-sig-newsletter

Read more
How to Start a Virtual Assistant Side Hustle (and Actually Get Paid Well)

How to start a virtual assistant side hustle and charge premium rates. Real income data, specialization strategies, and how to find clients who pay well.

Read the full transcript

This transcript was generated from the episode audio and may contain minor errors.

When is the right time to hire a virtual assistant? There is so much advice out there about this topic that I think is counterproductive or not always helpful to the average side hustler. I feel like everybody these days they get this advice of once you start any type of project, you know, any type of moneymaking project, you immediately need to start thinking about hiring VAs or otherwise going on to expand your team and such. Sometimes that's good advice, other times not so much. So let's talk it out today. Welcome to Side Hustle School, it's Chris Guillebeau here. You know, running a side hustle or any kind of micro business can sometimes feel like this full-time job, especially when you're the one who does everything. So it's only natural that you think well maybe I can get somebody to help. So we've got Caleb here in California, he's considering hiring a VA to lighten the load but isn't sure if he's ready or how to go about it. Let's explore what a couple of good next steps could be for him and anybody else out there in this situation. Hey listen, I want to lighten the load for you. I want

to help this year make it possible for you to start or grow your side hustle and do it in a way that is not stressful, that's not just taking your energy but in fact hopefully bringing you energy. Wouldn't that be great if you could have a project that is financially helpful to you but also creatively energizing, you know, that's the whole goal. So that's what I try to focus everything around here on the podcast. Let's take a look at this question after the short break. Hey Chris, it's Caleb from Huntington Beach, California. I've been working on my

side hustle for a while now and I'm starting to feel buried in daily tasks like answering emails, managing social media, and shipping orders. I've heard about hiring a virtual assistant to help but I'm not sure if it's worth the cost or how do you even start looking for one? How do I know if I'm ready to bring on help and what's the best way to hire and manage a virtual assistant without breaking the bank? Caleb, I will share the conventional advice with you but I'm also going to give you my contrarian opinion. Of course, that's why people listen. I always want to give it to them straight and of course you can do what's

best for you. A lot of times people say things like, you know, it's never too early to hire help, right? It's never too early to think about outsourcing tasks and you can't do everything in your business and so on. Well, it depends on what kind of business you're going to run and I think that's the reality. A lot of our listeners are not trying to scale their business. They do this because it's

fun, like they want to make money but it's also fun and so they like actually having control over all the different elements and aspects of the business. So the time to start thinking about it is when you start to feel stressed. Okay, so Caleb is starting to feel stressed here. You know, he mentioned like the daily tasks, managing the social media, shipping orders. So that is the time to start thinking about it but a lot of our listeners are just kind of trying to figure things out and starting different ideas. And you actually, when you're

starting business, you do want to be able to touch every aspect of it so that you understand how it all works and then eventually you can train someone if you decide to go that route. But lots of people own their business and operate it entirely on their own for years. They build six-figure businesses doing that, so nothing wrong with that. It really comes down to what are your goals, which is, you know, probably the answer for lots of things in life. I just feel that that is often skipped in a lot of business advice so I want to make sure we hit that. But

if you're gonna do it, decide what to delegate. Make a list of tasks that are taking up too much of your time or that you don't enjoy doing and it really helps that these tasks are as identifiable and concrete as possible. So they can't be things like brainstorming ideas, you know, for my next product or something. They need to be something that can be taught, you know, answering customer emails, especially emails that are about repeatable topics so you can write scripts and explain, "Oh, when customer asks about this, here's what you answer." The more you can systemize, the easier it's going to be for you to work with VAs because VAs tend to come and go sometimes. If you work with an agency, they will send you different people. You know, VAs are, you know, they're doing it

because it works well for them. So I don't mean to suggest that it's not good for them but, you know, it's usually hard to find like a long-term commitment with a VA, especially if you're working with a site like Upwork or Fiber. So you want to systemize as much as possible. Start with clear expectations, use tools, you know, like Trello, Slack, Asana, Notion, anything that kind of helps you assign tasks and keep things on track. That's really the best thing to do as opposed to like creatively giving people like an open brief to do stuff. That has not worked

well in my experience. So I think you're ready for a VA when your workload is predictable, when your time is more valuable than the cost of delegation, and you have a clear plan for what to outsource. Caleb, everybody else out there, I'm wishing you well, cheering you on. It's gonna be a great year for so many of us and lots of fun things to come. You can always subscribe, follow wherever you get your podcasts, and guess what? The cost is zero dollars. That's right, it's

completely free. New episode comes out tomorrow. My name is Chris Guillebeau. This is Side Hustle School. From the Onward Project.

Find your side hustle

Search 450 real case studies by income, difficulty, and business model. The Side Hustle Finder helps you skip the browsing and find ideas that actually match your situation.

Explore the Finder →
Side Hustle book
From the Host

Side Hustle: From Idea to Income in 27 Days

The step-by-step guide behind many of the stories on this show. Find your idea, validate it, and start earning — no experience required.

See all books →

Keep in Touch

Chris Guillebeau speaking to a packed crowd

There's a new story every single day on Side Hustle School. Episodes are produced to be short and to the point — I know you're busy. Be sure you subscribe to get a weekly recap of each episode!

Email hello@chrisguillebeau.com
Say Hi From your favorite airport

To infinity and beyond,
Chris Guillebeau