Home » Interview with a Freelancer – Tyler Hakes of Optimist

Interview with a Freelancer – Tyler Hakes of Optimist

A lot of people in the creative industry are passionate about it because not only do they get to do what they love, but they also have the freedom to make their own schedule. Being a creative freelancer is something I know that I, and many others, have always aspired to. I wanted to talk to someone who has been in the industry to get to know what it really takes to not only be your own boss, but be successful at it. I interviewed Tyler Hakes who took his freelance work experience and created a content marketing company, Optimist, which is a collective of freelancers:

What is your line of work?

Writing is my main focus–both copywriting and content. But my background is in marketing, so, for many of my clients, I am actually managing content marketing as a service versus just cranking out words. 

Do you have any formal education in this field?

I have a B.A. in Journalism from the University of Iowa.

How long have you been a full time freelancer? 

I left my job to go full-time at the beginning of 2016. So, I’m approaching my one year anniversary. Before that, I had done a lot of freelance work on the side for a few years just for extra income but hadn’t really pursued it seriously. 

What’s your favorite part of being your own boss?

It’s really cliche, but it ultimately comes down to freedom. Not just being able to work in your underwear or whatever most people think of when they think of the word “freelance”, but having freedom over the work that I do, the people I work with, and also just my entire life trajectory. I can pack up and move wherever I want, whenever I want. I can take a Monday off if I don’t feel like working. I can fire a client if I don’t like the work that I’m doing or if I don’t believe in their mission. 

I get the freedom to align my work with my own values and not just work a job to pay the bills, but actually do things that give me purpose. I feel really fortunate for that. 

What’s the hardest part of being a freelancer?

For me, it’s probably shutting off work. I’ve always been a bit of a workaholic and even though I don’t have to work full-time hours at this point, I still tend to default to filling my time with something to work on. So if I’m sitting around at night watching Netflix or it’s the weekend and I have nothing planned, I’ll tend to catch myself thinking about work or even checking Slack or Trello all the time. 

One of my goals is to try to separate my life a bit more, get out from in front of the screen and capitalize on the free time that I have now that I am freelance.

What is your workspace situation?

I have a home office that I use most days. Sometimes I get a bit stir crazy and seek out a change of scenery at a local coffee shop or go somewhere to get some lunch and end up working there for a few hours. 

When I’m working on creative projects, especially, I find that getting out of the house can help me focus my thoughts and come up with better ideas.

How did you build your clientele? 

With a lot of luck, mostly. 

I started by using sites like UpWork and landed a few great clients from there, some of whom I still work with from time to time. After that, I started to expand my search and use things like Reddit’s /r/forhire and traditional job boards that have filters for freelance/contract positions. 

But I also hustled a bit and got creative. I set up Google Alerts for hosted job software pages (like greenhouse.io) that contained the words “freelance” and “writer”. I scoured sites like Angel.co, which have listings for jobs, but sometimes have contract/freelance work. 

Now I pretty much have a steady stable of clients with most of the work being on retainer. So, I rarely look for new opportunities at this point. If I do, I generally use Reddit or UpWork. 

What is the most important information to gather from your client? 

As a writer, the most important thing is usually the voice and the tone of the writing. So, I try to really understand how my clients want things to “feel”. I’m a big fan of using either real people or fictional characters as a reference point. It helps me kind of “get into character” when I sit down to write for different clients. 

So, a few weeks ago, I had a new client and I proposed that we use Ron Swanson (from Parks & Rec) as the persona for their brand. They really loved the idea and we passed around clips for a few days. I love when I get to have fun with work like that. 

If my role is bigger and I’m managing content, then it really comes down to their goals for the site. Most people do content marketing because they want to grow traffic, but the way that you accomplish that can vary a lot depending on the kind of business it is, their target market, etc. 

Thanks so much for taking the time to do this interview! Do you have any final tips for aspiring freelancers? 

My biggest tip is: Just do it. Take the plunge. I contemplated quitting my job to go freelance for 6-8 months before I finally did it. I thought it would be scary. But, I found quite the opposite. I’ve never been happier and more motivated in my life. And I think it’s hard to “build into it” in a lot of ways. At least for me, being in the do-or-die situation of having the hustle for work really motivated me and pushed me to make it happen. I didn’t have that same feeling when I was just freelancing on the side. It was always just something extra, so I didn’t have the same motivation. 

Oh, and raise your rate. Seriously. You probably aren’t charging enough. 

I don’t know about you, but I found this interview incredibly helpful. I think all aspiring creative freelancers should take his advice. Check out Tyler Hake’s new content marketing company, Optimist!

What are your favorite parts about being a creative freelancer?

|| the chaotic creative

  • Bonnie McConaughy

    That’s a lot of helpful information. As someone running a blog + business, and starting work as a freelance writer, I also find it difficult to shut off work. I will take a break and then feel inspired again and start working. Sometimes I really have to force myself to stop and do something purely for fun!

    • I’m so glad you thought so! I’m not a freelancer yet but I definitely feel the same way, it’s hard to turn off work. Having fun is essential to a creative career, but sometimes it’s the hardest part!