Episode 97

The Truth About Freelancing

Do you have what it takes to be a freelancer? This week on Overtime, Meg reveals what it’s really like to be a freelance professional and shares her biggest lessons learned after ten years of experience. Find out what qualities and skills make someone’s life as a freelancer way easier, and which might hold you back!

Where’s the next project going to come from? Am I completely irrelevant? Am I actually adding anything useful to the landscape? These are all things that go on in my head constantly.

But first, what the heck is a “micro-cafe”? Get the inside scoop on the latest pandemic-friendly coffee shops that have begun to emerge. Plus, get inspired to support, celebrate, and lift up all of the makers of the world. Let’s go!

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This episode was sponsored by:

  • CollectiveThe first online back-office platform designed for self-employed people. Collective handles company formation, taxes, accounting, bookkeeping, compliance, and more. Check out their exclusive offer for the Dribbble community and get 2 months @50% off with the code DRIBBBLE10.
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Meg: Yee-haw, hello and welcome back to Overtime! I’m your host, and I’m looking pretty good today, which I can say to you because you can’t see me. You can only hear me, so you have no idea how I actually look today, but I did actually wash my hair and dried it, so looking better than usual. Anyway, I’m your host Meg “She’s Just a Pile of Little Babies with a Trench Coat On” Lewis, and ah-ha, welcome back to Overtime. This is Dribbble’s weekly podcast where I give you design news and some tips to create your very best work. This week on Overtime, what the heck is a micro-café? Is it a tiny little cafe I can keep inside my body that will deliver coffee directly into my bloodstream? No, but I will tell you all about it. Plus, I celebrate people who celebrate people. Oh, and do you have what it takes to be a freelancer? Well, I’m going to go through my 10-plus years as a freelancer and outline my findings on what qualities and skills make someone’s life as a freelancer way easier and which might hold you back. Let’s go!

I am super excited to tell you about Collective. Collective is on a mission to redefine the way businesses of one work. They’re the first online back-office platform designed for freelancers like a me. Well, it’s not exactly just me because nearly 59 million people, which is like 36% of the workforce in the U.S., run their own solo business, so it’s time for a better platform to enable the largest group of entrepreneurs in this country to focus on their passion and not the paperwork. Collective handles company formation, taxes, accounting, and so much more, and as a freelancer myself, this platform really speaks to me as finances are not something I love handling. It’s my least favorite part of my job. I cannot stress that enough. I hate it. So, be sure to check out their exclusive offer for the Dribbble community: two months at 50% off with the code Dribbble10. So, go to

Now, I recently got tipped off to a new, contactless, very pandemic friendly coffee company that has started opening things called micro-cafés. Now, what is a micro-café you might ask? Well, I will tell you this, True Bird Coffee’s the name of the coffee company, and so, they’ve started opening what they’re calling micro-cafés. And I can’t really tell what the difference is between a micro-café and a kiosk, like imagine a little mall kiosk that serves coffee, and there’s no attendant, there [are] just machines and robots and an ordering station. That’s what it is. That’s what a micro-café is, although, I’m not doing a justice, it really is quite nice. It looks beautiful, and the coffee allegedly is great. They have different options for beans, single origin, all of that jazz. They have milk options, so you can get your oat milk. All of that. It’s great for, allegedly, it’s great for coffee snobs, meaning just people who know about coffee and what single origin means, I guess, and people who are having their very first, you know, cappuccino, I don’t know. Okay, so it’s for everybody.

But now, the whole gist of True Bird Coffee is that it’s all done by robotics and it’s contactless and it’s safe, especially now that we are supposed to be distancing and all that because you’re not putting a barista in danger, and that’s great. So, these little robotic arms twirl your cup around and you get to watch them make your coffee and they pass back and forth between the milking station – the milking station? I don’t think that’s what it’s called. They’re not milking a cow. They’re not milking a cow right in front of you or milking oats, although I would love to see them try to milk oats for a coffee, because where are the nipples? I’d love to know. Anyway, that was a terrible dad joke.

Okay, so the robots are taking your little cup, moving it around or twirling it around, your cup’s moving, it’s like you’re watching it thinking “Wow, ooh, wow, look at it go. Whoa. My coffee is being made by robots. Wow.” And also, by robots, I don’t mean sort of robot movie robots. They’re not robots that look like humans. It’s robotics. [It’s] just “robots” means robotics to me.

Anyway, so it’s all very good for this point in humanity where we don’t want to come in contact with other people, or we’re not supposed to at least, I know we all want to come in contact with other people, I sure do. But in thinking about it, because True Bird is fancy, it’s supposed to be a nice experience. But I can’t get over the fact that just because there’s no person there, and because it’s technically a kiosk, micro-café, whatever, it just feels like the quality is lower than a real coffee shop. And I really want to unpack why, and especially from a design perspective, why that’s happening to me.

So, if you have time to Google True Bird Coffee and maybe see a photo of one of their micro-cafés, you’ll see what I mean, and I’m interested to know if you agree, if you think that you would expect to pay less. And I wonder if it’s because there’s no handmade element, there’s not a barista, it’s a robotic situation, it kind of feels more like a vending machine, so I’m wondering if that’s the problem for me of why I just feel like I should be paying way less. And there’s no smiling barista, I don’t get to have a conversation with them, there’s not a person behind the counter that looks way cooler than me making my coffee for me, so I automatically feel like I shouldn’t pay as much. But does that make sense? Is that justified? Is that terrible of me to think that way? I don’t know.

And then I was kind of thinking about, okay, well, let’s think about the way that Carvana works. If you know what Carvana is, I guess it’s a tech-sort-of-ish company that modernizes car buying, so you don’t have to work with a car salesperson. You order your car on their website, and then you go to a car vending machine and you can get car away, or you can have your car delivered to you. So, the car vending machine through Carvana is a completely different experience where I don’t feel like it doesn’t cheapen it, it makes it way cooler, and the experience is why you want to shop, I would assume, that’s why I would want to shop from Carvana. So, the experiential aspect of going to see the robotics is very exciting with Carvana. But I wonder for me, this is my personal opinion, and the way that I feel about it is that with Carvana, I choose to go with Carvana instead of going to a car dealership because the car sales people are the worst part. I’d love to avoid that interaction. And so, if I could bypass that interaction and go straight to a car vending machine that’s completely contactless, that sounds great.

But I love going to coffee shops, I love interacting with the barista and maybe some of the other people there and watching them have meetings and just being around other people’s energy. And so maybe that’s why it cheapens it to remove all that stuff from the actual coffee shop experience with this robotic micro-café. I don’t know. And from a design and an experiential design perspective, it makes me think a lot about whenever you go into a store that sells really lower price clothing, say, you know, a thrift store, or Forever 21, or H&M, you go in there and the clothes are sort of disorganized and in disarray because humans are terrible and don’t respect the space, and so they just feel like they can throw the clothes around. And also, the clothes are really packed in there tightly, and so everything’s just kind of smushed together, so whenever you try to jam a hanger with a sweater on it back where you got it from, maybe things might fall, you have to really push things around. Anyway, so the clothes are cheap, and the experience is not great because everything does not look nice. But then you go into a high-end boutique, where everything’s very expensive, and they have, like, you know, when they have three of each item, or even just one of each item and their space, like, 12 inches apart from one another on their hangers, very minimal. And you go in there and already immediately feel intimidated, but seeing those things makes you think that they’re very nice and high quality. And hypothetically, the garments could be made by the same company and the same quality, but because of the experiential design, it may be a lot to do with the graphic design of the graphics themselves in the space and the brand, makes it feel higher end and as though it’s a higher price experience you’re paying for.

So, I wonder if that’s happening here too, where something psychological is happening in my brain with this micro-café, where I just feel like because it’s made by robots, it reminds me of a vending machine, it reminds me of a mall kiosk, so I feel like the coffee isn’t going to taste as good, I feel like I should be paying way less and that kind of thing. Is that on me or is that on the design of the experience? I think it’s both. I think it’s a problem that we have in society psychologically with and how we mark what’s a better experience and what we’ll pay more for. And I don’t know what True Bird’s coffee is priced at, I’m just thinking in my head, psychologically, I think I would assume that the coffee isn’t going to taste as good. And maybe in my dumb human brain, it wouldn’t taste as good because it’s coming from a robot at a kiosk.

Anyway, something to think about, but look it up. I’d love to know, or at least to have you take a look too, and think about how you would feel about getting your coffee from there. Does it matter to you? Are you just like, “I don’t know, it’s coffee?” And it’s weird because I definitely do sound like a coffee snob right now, but please know, I’ll drink any coffee. The coffee no one else will drink, I will guzzle it down, I don’t care. I love all coffee. If it tastes like an ashtray, I’ll drink it. If it’s single origin, I’ll drink that too, baby. Pour-over? Love it. That hazelnut coffee from Panera? Yeah, I’ll drink that too. Delicious. So, maybe that gives you a baseline for what kind of commentary I’m giving you, and what perspective I have. Alright, let’s move on.

A buddy of mine named Cameron Koczon, and Cameron is a partner at Fictive Kin, he makes some other products, like Teux-Deux, which is the to-do app that I use every day, he’s a buddy of mine, he’s a friend. I miss him terribly. Cameron has been doing this series off and on over the last couple of years called “Thanks for Making.” And with the series, it’s a YouTube series, what Cameron does with this series is he just highlights a few different things that people have made recently, and he talks about them and thanks the maker and kind of dives in really quickly into who made it and thanks them for making it. And it’s delightful. It’s very similar, he covers similar [types of things] things to the things that I talk about on this very podcast, in just highlighting interesting things that people are making and he thanks them for making it. And I just love that he does this because it means nothing for him, like it doesn’t really give Cameron any exposure I don’t think, there’s nothing in it for him. It’s just that he takes time to make something that celebrates other people and lifts other people up, and just gives a moment to thank people. And he’s thanked me before in one of his videos, and it made me feel great. We often work, we do, we work hard, you and I, and to just have a little bit of validation or to have somebody just say thank you is great. Nobody thanks me for making this podcast. Nobody, we don’t thank each other, we don’t often celebrate each other and lift each other up. And I love that Cameron takes the time to do this.

So, whether or not you want to watch his video series, we’ll link to it in the show notes, it’s either/or, your choice, but the goal here, I think, is to take the time to lift up and support other people. We’ve got a lot on our brains right now. I know you, you’re like me, because all humans do this, our brains are nearly filled to the brim thinking about ourselves and all of the choices we make and the impact we have and the thoughts, we’re just anxiety overthinking, and we don’t take enough time to think about other people because our brains are just so anxious about ourselves and what our actions are doing. I get it. Oh, do I get it.

So, let’s just maybe use Cameron as an example, I sure am, to take the time to celebrate other people, thank them for what they do for us, what they make for other people, even if it’s not for us, and take the time to lift other people up and celebrate them. We need this so badly right now, we really do. We really need to support each other and help lift each other up and thank each other. So anyway, Cameron’s Thanks for Making series is something that I just want to take the time to [say,] “Thank, Cameron, thank you for making.”

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Now, I don’t know that much about you. I don’t know everything about you, what goes on in your head, but I will say that almost every creative person that I know has this constant argument with themselves in their head about, “Should I freelance? Should I have a full-time steady job? Should I freelance and work for myself and maybe have it all?” Or, “I don’t know, that’s pretty scary, I’ll just, maybe I’ll just have a full-time job, so that that way, there’s no fear, and I have some more stability. Yeah” And I know, I’ve been a freelancer my entire career, and there have been a handful of times where that fear has gotten the best of me, or, I’d say, almost [got] the best of me. And I have applied for jobs, had interviews, gotten job offers and almost took them, it just keeps happening, because the fear gets to be so much sometimes of, “Where’s the next project going to come from? Has the world moved on without me and forgotten that I exist? Am I completely irrelevant? Am I actually adding anything useful to the landscape?” These are all the things that go on in my head constantly.

And I will say, now that I’ve been freelancing, you know, this whole time and never had a job, I think at this point, nobody would want to hire me, because I have no experience having a full-time job, so who would want this? I don’t know. So, now I’m kind of a lost cause, not completely, I’m sure if I worked really hard, I could get a full-time job. I know it would be very hard, it’s rough out there. So, I just want to kind of outline for you some of the qualities and features that I’ve noticed myself, having, or having to have over these last few years, as well as almost every freelancer that I know that has been freelancing for a while has. And I will also tell you some qualities in people that I know who have tried to freelance and immediately didn’t make it and went back to having a full-time job because they couldn’t take it; what those qualities are.

So, I think I have to start off by saying that being a freelancer is not better than having a full-time job. One choice is not better than the other, and if you are somebody who glorifies and infatuates anybody who is a freelancer, you don’t need to do that. There is no difference. One is great for some people, the other is great for other people, and that’s fine. Being a freelancer is not the end all dream for everybody. It just doesn’t work for everybody. It’s not for everybody. It shouldn’t be for everybody. Okay? So, I’m here to help you figure out if the freelancer path is right for you, which path is the best, because there’s not one that’s better for everybody. Right? Okay.

So, a huge component of this is the fear aspect, as I mentioned. When you’re a freelancer, you have to be able to withstand a certain amount of fear of the unknown, basically, of where the money [is] going to come from. Having to rely on people just constantly believing in you and trusting that you can do it and coming to you and asking you for something is terrifying. I will tell you that it is the worst part of freelancing to me, the fear aspect. And there have been times in my psyche where I let the fear take over, and it actually prevents me from taking action and from fighting for myself to succeed. And a lot of the people that I know that try to freelance and don’t make it that far usually let the fear overcome them, and it generally holds them back from taking action and from fighting for themselves, because it’s scary, I know. So, what I would say is, what you have to do is let the fear sort of push you, to propel you into action, to be the thing that motivates you to continue to fight for yourself. And having that mindset shift for me with the fear has been extremely beneficial. And sometimes, especially this year, this year is so hard, I definitely fall into the pattern where I let the fear take over for me, and some days, some weeks even, it just completely swallows me whole and I can’t move, I feel unable to succeed and to do much, and that sucks. So, sometimes I have to give myself a little pep talk that reminds me to let the fear push me forward. And as a freelancer, you also have to be so self-motivated, you have to be able to push yourself, you have to fight for yourself so much, you have to advocate for yourself every day, you have to remind the world that you exist, and provide services and be a salesperson for yourself every day, and that is exhausting. And a lot of people that I know that try freelancing can’t do it, that gets them. The constant sales pitches, the constant fighting for yourself, reminding the world that you exist, pushing yourself onto people constantly, it is exhausting, especially with social media, right?

Social media is such a great tool for marketing yourself, and to remind the world that you provide services and are, you know, available. It’s a great tool for a freelancer like myself, but it is so exhausting. It is so hard some days to remind the world that I exist. Some days, I just don’t want the world to notice me. I just want to fly under the radar. And it’s like a little casual dream of mine to just go away and not have anybody notice me and not have to remind the world that I exist for just little bit. But all I get is a vacation, I can’t do that for long because I have to rely on social media in order for myself to continue to get work. That’s just the way that my specific career works.

Now, do you have to have a lot of followers on social media to be a successful freelancer? No. There are many freelancers, my partner actually, he’s a freelance product designer, he doesn’t use social media, he flies under the radar, he just uses word of mouth, he gets his last client to recommend him to somebody else, and it works. So no, you don’t have to use social media, but for the type of career that I have, it works really, very, very well, and it’s the number one way I get new work now. Word of mouth is great for sure, but social media is also great. So, you don’t have to have a huge following or any social media presence at all to be a freelancer, but you do have to be able to advocate for yourself.

And again, those self-initiated deadlines, the self-motivation, the willingness to be able to act every day, to move forward every day, to get things accomplished daily throughout the day is so important. There are a lot of people out there, you know, I wouldn’t necessarily say the procrastinators of the world, but the people that really rely on accountability of somebody else saying, “I need this by noon, give it to me by noon.” And as a freelancer, you really you get to pick the day and the time, and you’ve got to stick to it whenever you say it to somebody else. And there’s nobody else who’s like, “I need it by noon,” you’re just kind of picking the day and the time, and you just have to allow yourself to be the person that’s setting that stuff for you. And that is hard, it is hard. But as a freelancer, you have to be able to uphold that schedule for yourself, which is a challenge as well.

So, you either need to stick to a routine, or you just need to be great at holding yourself accountable. And if you’re a person that loves stability and routines, then being a freelancer is actually really bad for you, because as a freelancer, you have to be okay with so many unexpected changes of plans, things getting thrown at you. Whenever I wake up every day, I don’t know what that day is going to look like because so many different things get thrown my way every day. And if you’re somebody who loves routines, it’s going to be an uphill battle trying to fight against all of those unexpected changes of plans, the uneasiness in your schedule. And it’s tough, it depends on what kind of freelancer you are. If you’re somebody who goes and works in-house on very long-term contracts that are full-time, it’s going to feel a little bit more like a full time-job, and that’s great. But if you’re somebody like me, who juggles, you know, six to 20 different projects and businesses and things you do at a time, ooh baby, no day looks the same.

So, again, I’ve talked about this in a past episode, but what I would say you have to do as a freelancer though, is kind of have that balance of stability of projects and paying opportunities that give you that sense of stability and structure. You have to have the balance of having a lot of that mixed with what I call strategic play, which is just exploring, being curious about your style, being curious about the type of work that you’re doing and services that you offer, in a strategic way to where it’s helping you work towards where you want to be going. So, it’s play because it’s fun, you’re experimenting, you’re being curious, but it’s all for a very intentional purpose of trying to get you where you want to go. And usually, for me, the strategic play portion pays me no money or very, very little money. Because usually it’s self-initiated projects, things that I’m doing all on my own without waiting for somebody to just trust me and believe in me to be able to do it, so it’s opportunities I’m creating for myself. So, there’s usually no pay involved, but I’m doing it very strategically and intentionally to try to get myself somewhere I’m, you know, want to be going and want to get paid for eventually. And I like to mix that with stability, because I need to pay my bills. I need to get rid of that fear, you know, the monster that’s constantly chasing me and allow it to push me forward into that strategic play zone of fun.

Ah, so freelancing, again, it’s not for everybody. And if all these things I’ve said to you, you’re like, “I don’t mind that. That sounds great. Yee-haw, I can get through that,” I think that’s the second “yee-haw” I’ve said in this episode. Hmm, I’m not mad about that. So I think, you know if this sounds like you or not, and if this sounds like a nightmare to you, then don’t be a freelancer, or freelance in your spare time on top of your full-time job if you want to. Yeah, that’s fine. It’s not for everybody. But I think this information is probably helpful for you, in case you’ve been curious about freelancing, or quitting your job and going freelance, or maybe you lost your job or got laid off, and you’re like, “Hmm, well, since I’m here without a job, maybe I’ll just become a freelancer now full-time,” and maybe this information has been helpful for you. So, that’s all I’m trying to do here is [go] past the glitz and the glamour of a freelancer’s lifestyle, and unveil the fact that maybe somebody’s just wrapped a present in Swarovski Crystals and beautiful gold leaf wrapping paper, and you unwrap it, Meg’s unwrapped it for you, and you realize it’s just a piece of garbage. I’m not saying freelancing is a piece of garbage. I actually, I am. It’s a piece of garbage that might be someone’s treasure. This a lot of metaphors. I’m also going for one person’s trash is another person’s treasure, so it might be garbage for you, or you might open it up and it’s someone else’s garbage that you find to be treasure. I am horrible at metaphors, at analogies, I’m terrible at it, but thank you for going on this journey with me. So, are you made to be a freelancer? I’ll let you decide. And, of course, this is one person’s subjective opinion on freelancing, so go out and seek other opinions too.

That’s it for this episode of Overtime. Wow, that was really a delight for me. Did you have a nice time? I really enjoyed your company. Thank you for allowing my voice to tickle your ear holes today. Let’s just take a deep breath and enjoy our last few moments together. [Deep breath] Thank you so much. If you want to continue the conversation on the internet, use #DribbbleOvertime, or tweet or tag me. My handle is @yourbuddymeg. Okay, bye here be next week.