How to upskill as a freelancer

Feel like you’re running around in circles doing the same thing over and over again?

It’s easy to get caught up in your day-to-day as a freelancer, but building your skill set is important if you want to charge more over time.

+ [This] is important because that’s how you get better and that’s how you’re able to charge more over time. Because you want to build on that foundation of knowledge that you already have.—KM

Discover how to incorporate learning and development into your busy schedule and which learning paths to take.

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What is upskilling?

Kaleigh: Hi. Hello, we’re back. Today. I am dressed as Ethan Hawk, so that’s something for your viewing pleasure. Today we’re gonna talk a little bit about upskilling. 

One of the things that we hear pretty often is that when you are a freelancer, it’s so easy to spend all of your working hours just working on client work. So there’s no time to grow your skillset or increase your education around what you’re doing. [This] is important because that’s how you get better and that’s how you’re able to charge more over time. Because you want to build on that foundation of knowledge that you already have. 

So how do you do it? How do you make time for it? What are the options? What’s worked for us? I wanna start with a question for you. Tell us about how long you’ve been freelancing so far, and what are some of the things that you do on a regular basis to kind of upskill. 

Michael: Oh, okay. So I just wanna start, I’m dressed as Michael Keenan. I didn’t have a great theme on hand today, but I love your Ethan Hawk look.

So I’ve been at it for about eight years now, and I’ve always been a fan of learning. I think learning is important—I have a curiosity mostly for life, for business, for people. I love to learn, whether it’s someone’s stories or a new skill.

What does upskilling look like?

+ “What I do periodically (like maybe once a year), I sign up for a big course… I do things related to my craft, but I also like to expand out a little bit.” —MK

Michael: What I do is periodically (like maybe once a year) I sign up for a big course. For example, last year I had a CXL membership and I took nice some CXL courses [with that]. I do things related to my craft, but I also like to expand out a little bit. 

For example, I took a course on conversion rate optimization. I probably will never use that [directly], but having the knowledge—I think it subliminally works its way into the copy that I write and the way I can upsell things on my own website or Peak Freelance’s. 

So usually every year I try to take at least one or two courses that are either related to or directly impact my craft. When I first started, I was picking up a lot of blogging and SEO courses through HubSpot and Ahrefs.

The thing that I never did though (which I was always very curious about) was Masterminds. Kaleigh, have you had experience with doing Mastermind classes and stuff? Because I’ve only ever taken a traditional—

Kaleigh: I haven’t.

Michael: But you’ve given mastermind classes. 

Kaleigh: Yes. So I’ve worked with a group of people. I’ve been the teacher, but I’ve never been on the attendee side of things.

I know other people have done them. Not only did they really like the learning experience of hearing what other people are working on and having multiple points of view to pull from, but [they] really liked the community aspect of it. And having those tangible connections that are good for referral building too. 

So while I haven’t done it, I’ve heard good things about it. I talk to people who’ve taken the Mastermind in the past and get some authentic unfiltered feedback on what they thought of it.

That’s kind of the best way to evaluate your options. Get some real—not the testimonials on the website, which are great—but find somebody who took the thing and ask them, “okay, what’d you really think? Was it worth the money? What’d you get out of it?” Make notes. Do your homework. I think that Masterminds are a great option. 

One thing I wanted to ask you was, what’s your stance on business books? Do you read them? Do you listen to them? Do you like them? Have you read any that you think are worth reading for other people? 

Why is upskilling important?

+ “Once you’re not in the formal school system, you still have to do things to work on your brain.”—KM

Michael: Oh, okay. Yes. So part of my reading list regularly is a mix of fiction and business books.

For example, in my list of books, my favorite is How to do Great Work Without Being an Asshole by Paul Woods. It’s a little sun tanned—the book cover that I have—but it was just an excellent book about how to be nice to people in the workplace.

He speaks from an agency perspective. So it was really useful for client communications and managing a workload of people. If you’re working with researchers and juniors and whatever. So similar to my course style, I read a bunch of different stuff.

I’ve read obviously Company of One by Paul Jarvis—we love you if you listen to this episode. I also like to read stuff about information technology or how to organize information. So another great one is How to Make Sense of Any Mess by Abby Covert. [I read] things that [are] not directly related to the craft, but they may teach you how to build a better process or just do business development better. 

That’s usually how I like to approach upskilling—through books. And I think they’re super important. Super, super important.

Kaleigh: I’m glad you feel that way because I am very anti-business books. When I read, I want to escape. And the thing that happens to me is, when I read business books, it makes me anxious because I feel like, “Oh my gosh, there are so many things I should be doing. This is stressful.” And that’s probably like a really unreasonable viewpoint.

But yeah, I have a really hard time listening to stuff I do better with. So I read a lot of fiction and non-fiction just because I feel like as a writer, that’s really important practice for me to [have] out of the context of my working environment. And I enjoy it. I think it’s just something I do every day, just because I like to do that.

I also listen to some podcasts though. I think podcasts are a good passive way for me to consume some business or skill-related information. I can do it while I’m walking the dog or fixing dinner or whatever. I think other [the] thing too is, I’m not a big course person, but I know that there are some excellent courses out there, so like you said, investing in one or two courses a year is something you can do.

When I took the creative class, when I was earlier in my freelance business, I would set aside an hour each night after dinner, after I’d been done with working for a day. I had some time to unplug so I’d give myself an hour every night, and it was almost like going to night school. You have this set block of time that you dedicate to consuming the information and doing the projects if that’s part of the course. And I think good courses usually have some sort of assignment where you’re putting the theory into practice. 

And it’s a business write-off, so why not? Why not try to find a couple of courses every year, either on up-leveling your skillset related directly to the work that you do, or on the business side of things? Learn how to run a better business or be a better communicator, or learn things that’ll help you charge more down the road.

That’s the thing. It’s so easy to be down in the daily details that you don’t ever give yourself time and space to focus on, “I need to continue growing my skillset here.” Continuing education. 

Once you’re not in the formal school system, you still have to do things to work on your brain. 

Michael: I haven’t taken any general freelance [courses], but I have taken stuff that’s related to the craft. 

One of them being, Erin Boss’s. She has [one on] how to build out a research report. So doing the customer research all the way to writing it.

I’ve also taken a journalism course this year and that’s because I think the art of storytelling is important in most applications. Whether you’re a photographer, a designer, a writer, [or] a marketer. 

If you’re a writer, read…anything

Michael: That’s why I read fiction books alongside business books. Because it stimulates that creativity in your brain and it helps you think outside of the box, which in some client problems, it’s not just a direct application of knowledge. You need to critically think, “How are we gonna solve this problem together?” And that takes creativity and thinking outside of the box. 

So that’s why I love to read both fiction and non-fiction books. And reading business books that are neutral, not like the ones that are yelling in your face, saying, “You’re not good enough. You need to do this, or you’re not gonna make it in business.” And you’re like, “No, I just wanna read [about] information that works.” 

I think it’s very easy to get caught in that rabbit hole, especially with those types of business books where they just yell at you for 200 pages. Basically telling you that you’re not good enough. The truth is, there are a lot better books out there that will tell you that you’re good enough, here’s just some new knowledge that you can apply to your skill. 

Kaleigh: I really enjoy reading about psychology, which is kind of business adjacent. Because the more you understand people and the way we think and why we do things, the more you can use that in your day-to-day—on the business side of things or in your storytelling efforts, whatever it is. 

Those [are the] kind of business-type books that I like to read. I like to read Malcolm Gladwell or Chaldini, of course, is the kind of classic example of this book influence. So not necessarily tactical, ‘how do I do stuff in my business’, but more on broader, ‘how can I better understand people’, which is who I’m writing for and who I’m working with. 

That’s something to think about too. You can also just follow your interests, and I think that also makes a nice segue into creative projects as part of this process.

We’ve talked about burnout before. I think it’s really important to have those creative outlets, whether you have a creative story that you’re working on just as a fun project or if you like to paint in your garage at night, or if you like photography. Give yourself an hour at the end of the day to go out and take some photos.

I think a lot of it has to do with making time and space and not just being chained to your computer all day and giving yourself permission to do those things. Do you have any things that you do that stimulate your brain in that way? 

Use upskilling to stimulate your brain, prevent burnout, and try something new

+ “I do give myself a little bit of time at the end of the day to do fun, creative projects too…I wouldn’t say I make time every day for a creative project, but I do work creative stuff into my week.” —MK

Michael: Another way that I’ve upskilled myself throughout the years is by actually making test projects. Right now I’m working on one—we just bought the domain the other day. It’s gonna be called Cases for Collectibles, it’s an expired domain that we picked up, and we’re gonna work on it as an SEO affiliate site.

I’ve had a few experiences in the past with similar works like that. Making test projects so you can test stuff on yourself if your project is a client. [You] test stuff out there that then you can apply it to your clients because, yes, you want to apply new skills, but maybe you’re not sure how they work yet or if they’re actually gonna work. So you can apply strategies to your own test projects.

If you’re a designer, you can design some really crazy shit in Webflow (if that’s your thing) and try it for yourself. Make it for your own website first and do all the tweaks and everything.

Because a lot of learning models show that the best way to learn is to actually do. So that’s one of the best ways to get hands-on upskills. Get hands-on. 

I do give myself a little bit of time at the end of the day to do fun, creative projects too. I do photography for fun. I read every day, even if it’s just like a half hour after work or whatever. So I wouldn’t say I make time every day for a creative project, but I do work creative stuff into my week. 

Kaleigh: And that could be structured so many different ways. Some people do a four-day work week, some people do three weeks on, one week off. Paul Jarvis, for example, would take off the last two or three months of the year to just unplug and do whatever he wanted and then reset for the new year ahead. Make plans, work on the business instead of in it. I think there are so many different ways you can do it. It doesn’t have to be an everyday thing. 

That’s another thing we hear all the time, people are busy. Especially people who have families or just a lot of responsibilities. There’s just not enough hours in the day. So maybe if you have a slow period or if you know that December’s a super slow month for you, blocking off a week to work on the business instead of in it is a really smart move.

The other thing I would say is if you’re somebody who’s like, “I don’t have the time or the attention span to sit down and read or do a full course, or I don’t wanna paint a picture. I’m not interested in that.” Sometimes a more passive way (aside from podcasts) to level up your skills is to just subscribe to paid newsletters which condense all the good curated information around a topic and make it more bite-sized.

And that’s another expense that you can write off. So sign up for those niche newsletters. You’ll get some good information. They’ve done all the heavy lifting as far as synthesizing information and pulling out the good bits and pieces. That’s a great option as well. 

Michael: Oh, I love that. That’s how I learned how to trade stocks and cryptos and whatever, because I signed up for a paid newsletter and they would just send all of their thoughts and ideas and the charts. So I learned how to do technical analysis through this paid newsletter that I signed up for, for a year. And I think it was like two or three times a week, I would just be able to open my phone and kind of read through their thoughts behind it.

Don’t just trust everyone and anyone—vet the information you’re consuming

+ “I think the important thing is there are a limited number of hours every day. You have to really invest those wisely.”—KM

Michael: This is actually something to tie in quickly, make sure you know who you’re getting this information from. Because nothing on the internet is reliable. This dude seemed reliable and I did learn a lot from his paid newsletter for the year. But then I felt like it was just the same stuff on repeat, so I didn’t sign up for it again. But that year I learned a lot about how to read a stock chart. 

Make sure you know who you’re buying this stuff from—vet those people. I don’t expect anyone to buy anything from me unless they vet me also. Ask who is this guy who’s telling me all this information and who wants me to sign up for this or do that? 

How do you vet someone or something when you’re going to upskill yourself? 

Kaleigh: I look for social proof on Twitter especially. Because that’s where I spend most of my time. What are the resources that a lot of people are talking about and tweeting about and saying that they’re getting a lot from? That to me, is a good indicator. 

Then if I’m super curious, I’ll reach out to an individual person and say, “Is this worth it? Can you tell me do you feel like you’re getting a lot out of it? What are the top three things you really like about it and what’s the one thing that could be better or you wish there was more of?” That’s kind of a good way to evaluate without getting too in the weeds on things.

I think YouTube is another great one. There are so many great short-form YouTube videos that are educational. I always open up the YouTube app at the end of the day on my TV and I have subscriptions to the channels that I like, but a couple of them are related to freelancing or writing.

There are great videos [out] there—this is a great example here. I mean, you could be watching one of these episodes at the end of the day and you’re educating yourself, you’re getting information, you’re getting to see our lovely faces, which is a pro. 

I think the important thing is there are a limited number of hours every day. You have to really invest those wisely and you have to make time for this because it’s so easy to be like, “Ugh, I’m tired. I don’t want to, or I wanna watch TV and unplug.” And there’s nothing wrong with that, but give yourself like 10 minutes. Take just a little bit of time.

Michael: Ten, fifteen minutes, you’ll be thankful. Treat yourself. You know, like they say, treat yourself. I love that. And also, I forget, YouTube is not for just watching SNL reruns, so that’s amazing.

Kaleigh: I mean, it’s great for that too. So the bottom line here is:

PSA: Creative Class is opening for enrolment on May 29, 2023. Join the waitlist for a special launch discount.

Creative Class reopens for new students in Spring 2023:

PSST... You'll get a special launch discount.