My first encounter with Jamie and her work was through a piece she wrote for The Billfold on Medium about how she asks for tips on all of her creative writing. It was one of those reads where you find yourself nodding your head more aggressively the more you read. So I read more of her writing and found myself connecting to every word. I had to reach out and learn more from Jamie herself. Jamie Varon is a freelance designer, writer and multidisciplinary extraordinaire. She is confident and self-aware in a way I haven't encountered in anyone else, and so her answers about what it really means to do creative work are honest and come from a refreshingly different perspective. Enjoy!

Tell me a little bit more about what you do and what that involves?

I am very much a multi-disciplinary when it comes to the type of freelance work I do. I tried doing solely freelance writing, but there’s something about writing when I just really need to say something, that’s very appealing. It puts too much pressure on it for me to try and make all of my money off of it. At least for now.

So I’m writing, and I have design clients and some consulting clients on retainer as well. I’m just scraping things together in the best possible way. It’s good. It’s nice to be able to write for a few hours and then shift my focus to something else.

Have you always been interested in writing? Or was that something that you stumbled on after trying a few different things?

In the back of my mind I’ve always thought, “I’m going to be a writer one day.” It was that romanticized version of a writer. When I was a kid, I loved both writing and reading-I always have. When I went to college I decided not to major in creative writing, which was a weird decision, because if you’re a writer you want to learn how to write really well. I just didn’t want this thing that I loved to be critiqued in that way. I feel like creativity is just something that’s really weird to be critiqued on.

So while I was doing design I would just write on the side. I’m 30 now, and when I was younger there weren’t as many opportunities to get your writing out there. It’s a different world now. You can put your writing on the internet and people can read it. That wasn’t even available. I put myself on MySpace [laughs], no one was reading that.

So once I started seeing more opportunities, I started putting my stuff out there. It’s been an evolution in a way. I’m also very practical. I never wanted to be a struggling artist. I always had to balance finances with doing the things that I wanted.

How did you end up freelancing and being self-employed? Why do you choose to stay that way?

I’ve been self-employed since 2009. Mostly doing design work. A couple of years ago, I got a job as a staff writer at a website called Thought Catalog. I did that for a year and from there I left to go freelance. I didn’t even know what I wanted to do with my writing, but I had a feeling from my time at Thought Catalog that I had something that people were connecting with. That was so cool. I just felt like I really needed to explore that, but had no concrete plans of what that would look like.

One of the things I noticed about your writing is a lot of it has this underlying message of changing your mindset and the way you think about things. My question is, how do you personally know when it’s time for you to try something new or to take on a new challenge?

That’s a really good question. I think it comes from a combination of things. If it’s been awhile since I’ve felt inspired and there’s just nothing happening, I know it’s time for a change. I really think that when things are meant to happen, they come to meet you. It’s not like magical fairies, but when you make a decision that feels really right, things end up happening.

For me, that’s always been a guidepost. If it seems like a wasteland of opportunity, I know that something isn’t working. Because when I set myself on the right path, in my experience things have just happened. Not that I don’t have to work hard, not that I don’t have to go out and get things, but I get yes’s more often. I get people coming to me. I get those serendipitous and synchronistic moments. I look for those and I notice those.

It’s important to note the difference between that and happiness, though. I don’t necessarily base it off of whether or not I’m happy. My happiness just isn’t something I can really stake anything on because it goes up and down all the time, as is life. But I look for where things are lining up, and if nothing has for some time, I know it’s time to change something.

What would you say are the biggest challenges that you face right now with your work?

At the moment, the biggest challenge is that I’m at a bit of a crossroads, where I have to start thinking about making money. Obviously I think about that now but I have some other opportunities where I can do different things. Unfortunately, that means my focus is always split in ten different directions all the time, and everything is the priority.

So my biggest challenge is looking at this thing that I love and how I’m going to take it more seriously. What does that even look like and what’s even possible? It’s strange because I feel like I’ve gone past the point of self-doubt. It’s not a matter of whether or not I believe I could do it. I think I could get there, there’s just a lot of options and I’m faced with this decision paralysis.

It’s a good problem to have, but it can be anxiety inducing. I’m already a pretty high-strung person, so every day when I wake up and I’m not sure what I should be focusing on-that’s a challenge. I want to be set off, I want to go and really dig my heels into something. I’m just not sure which direction to go in.

Do you have a particular structure or routine that you follow that helps your days or your weeks be the most productive?

When I’m very clear on what needs to get done each week, definitely. Sometimes I’m waiting for my week to fill out and I don’t know. Those are the most stressful weeks because I know something is going to happen, I just don’t know what. When I know, I can develop a routine that gets me in the right mindset and mode.

Right now, I’m working on a book and I’m also in this weird transition phase and I’m not writing every day, even though I feel like I want to. I know enough now to know what my ideal routine would be if I was actually clear on what I was doing each week. I just need to be in a place where I can actually execute on that.

On the flip side of that, I think routines and productivity tips are great, but if they cause you more stress because you feel like you can’t uphold them perfectly, they are getting in the way. It’s not even worth it, because the thing that’s supposed to help you relieve anxiety and stress is causing you the most frustration, just because you can’t perfect it. That’s not the best way to go about it. Don’t make yourself miserable just to stay on a routine. It’s supposed to help you. If it’s not helping, wait until it’s going to be helpful to you.

What are the main tools you’re using right now in your current workflow?

Honestly, I’m so back to basics. I feel like I have all this high-tech stuff and I end up being the most productive using my paper journal, my paper planner, and my highlighters. My meditation is my productivity booster. A lot of tech always seems to just muddle the simple things that I need, which is to journal, empty my mind, and have a very clear idea of what my week is about.

Do you ever experience periods where you feel disconnected from your work and what you love about your work? How does that manifest for you? How do you continue to create during those times?

I don’t think I recognize burnout until I’m out of it. I’ll get to a point where I can look back and think, “man I was absolutely burnt out.” In hindsight, I’ll think that I should have given myself a bit of a break and been kinder to myself. I’m trying to close that gap. I’m trying to see when I actually need to rest as it’s happening. Usually, I’m so hard on myself, I’m sure everyone is. I don’t give myself that.

The other part that I’m trying to understand is the difference between when I’m resisting something and when I’m procrastinating. When I’m just afraid and when I actually need to rest. There seems to be a very fine line between the two.

Burnout is one of those things where sometimes you need to rest completely and take a break, but sometimes it means you just have to put your efforts into something else. It’s difficult to see the difference and there’s no “one-size, fits all” approach.

In the second instance, where you’re emotionally burnt out on something, it’s not going to help to sit in the bath for a week. Sometimes the only thing that’s going to cure it is to actually do something. Finish your project or just put your time into something else.

Sometimes you do need a real physical break though. When you’re self-employed you always feel like there’s more you should be doing. You’re your worst boss. You don’t give yourself days off, you have to work 12 hours, you’re awful to yourself [laughs]. I’m trying to learn the difference between just needing to give my brain a rest from making decisions and when I need to just sit in the bath for a week.

What aspects go along with being a freelance writer that you don’t think people realize until they do it themselves?

Writing is a very, very romanticized profession and people have high expectations for how it’s supposed to go and how it’s supposed to be. I encourage people to figure out their own path, instead of holding themselves hostage to these expectations. I know that when I started, I had this very romantic view, like “I’m a writer now!” As if that means something. But you make it mean whatever you want.

I think it’s important to take it slowly too. One thing about freelance writing, especially right now, is that people will pay you for your most personal stories. I have given a lot of people advice to be very careful about what they reveal because of wanting some sort of notoriety. What you write is going to be on the internet for a very long time, and it’s very personal. I think that’s something to take into account, because we are in this time of complete vulnerability and you can say whatever. But, you need to take care of yourself too and make sure you’re not revealing everything when you are not ready to.

In the earlier days when you were first starting to write and publish online, before a lot of people were reading your work and responding to it, what kept you motivated to keep going?

I feel like I was motivated to say a lot of the things that I hadn’t let myself say for years. I got to the point where it was now or never. That’s totally arbitrary, but for me, it was now or never. Say the damn things you want to say. That, to me, was really motivating. It was purifying in a way. I just had so much that I had kept inside and never said, I needed to get it all out. That served as my motivation, at least initially.

Two years ago, I had a job where I had to write every day. That pushed me in a lot of ways. It was this question of, “can I do this? Is this possible?” I got to the point where I’d rather know if I have something and if I can do it, than spend my life not knowing out of fear of trying.

Why do you do what you do? Why is it meaningful to you?

When I was a teenager, I felt very alone. I often thought, “Nobody thinks like me. Nobody is like me. I’m the weird one all the time.” I think I still have a little bit of that person in my mind, but now I think, “Other people must feel this way too.” The more I share and the more I see people connect with my deepest stuff that I didn’t think anyone would connect to--it emboldens me. It’s almost healing to share it and to see other people feeling the same way.

It’s like, “Wow. I don’t feel alone in this anymore.” There’s nothing that I feel like I can’t say to someone now. There’s nothing I feel hidden about. Which is crazy, because when I started writing, I didn’t realize how much I had kept in. How much I wasn’t saying about how I really felt.

That’s been the guiding force because I like how I feel when I don’t have to hide anything. I love how it helps other people feel less ashamed. They see someone, and it doesn’t even matter who it is, just someone else that’s talking in a way that they think. The more people read my stuff, the more I find this to feel like a responsibility. I have something that I’m willing to talk about that other people aren’t. It would be really stupid not to use that gift.

It’s strange because the more people read my writing, the more humbled I feel by it. I originally think I started writing with this desire to be well-known, a bit of ego. But, the more people read my stuff, the more humbled I am by it, which I mean, of course that would happen.

Who would you want to see on Ways We Work?

Mari Andrew - She's a brilliant illustrator and writer.