Follow Your Arrow: Web Developer Cee on This Freelance Life

The concept of ‘freelancing’ is an interesting one — especially right now, when so many folks seem to be quitting their jobs and going solo. The word itself comes from days of old, when mercenary knights — those with no allegiance to this lord or that queen — would pick up their sword and fight for anyone who paid them, conjuring in my mind images of sword-wielding free-folk who roam the country, doing as they please.

The reality of freelance work/life these days is a little different from my fantasy! Freedom is awesome, but it brings its own challenges. There’s the fact that you have to motivate yourself from the moment you get up to the moment you decide it’s time to knock off. And there’s the fact that ‘knocking off’ doesn’t always seem to work. There’s the fact that you get to choose who you work for (or with, as many of us prefer to say). There are the dry spells… and then frantic, stressful weeks of deadlines and client demands. And, of course, there’s the secret knowledge that you’re totally, utterly winging this thing.

But for many — myself included — its a way of working that truly fits with who we are. In this Follow Your Arrow interview, we hear from Autostraddle’s very own webmaster, freelance web developer Cee Webster. (Yes, that’s her name!) Cee’s the person who makes such awesome things as A+ subscriptions actually work, who ensures you can read Autostraddle on your mobile, and who keeps the whole website running smoothly for readers and writers. At the same time, she designs, builds and maintains sites for a whole bunch of other clients – because that’s how freelancers roll.

In this frank interview, Cee shares lessons from 15 years of solo working, including time management, winging it, and her very first client… who’s still with her today.

Cee Webster, freelance web developer, Dapper Digital

Age 36, Portland, OR

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Hey Cee! Can you describe your business?

Dapper Digital makes custom WordPress websites for small to medium sized businesses and organizations. I’m a freelancer, and a sole proprietor.

How would you describe your approach to business? Are you super smart and professional, a big planner, are you just totally winging it?

I’m winging it, and have been since the beginning. I try things and if they work I keep them, and if they don’t I try another thing.

What does a typical day look like for you? Do you have a routine? What is your workspace like?

Routine is very important to me. I usually get up around 8, respond to emails and figure out my day plan. Then I make a coffee and get to work coding. I take a break for lunch and possibly the gym, then come back home and work until dinner. Often I work after dinner too. I spend on average around 30-40 hours a week working on Dapper Digital. My office is the master bedroom of my house. I have a wall of desks and two windows and a beanbag chair with a low table. It’s by far the messiest room in my meticulously organized house.

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When did you know that this was what you wanted to do? And what were your early goals, your first steps? 

I discovered web development while in art school around 1998. Coding was love at first sight, but it took me another year or two to realize it could be a career. I built a site for my dad’s company and used that as a portfolio and I started freelancing right away. I got my first client about 15 years ago and they are still my client today.

The first 5 years or so I did a mix of freelancing, traveling, and working full time for agencies. I think the longest I held out at an agency was a little over a year. I’d save up and take off for 6-12 months and travel and freelance during that time.

I hated the structure of working for corporations. It felt so sluggish and full of internal politics and hierarchy. I don’t do well in those situations — I deeply dislike being managed. And I hated having to be somewhere every day at a certain time, and felt like I did not have control over my life.

I went full time freelance 10 years ago.

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Why do you do this? What makes you spring out of bed in the morning? What’s the best thing about the work you do?

After all these years I still really enjoy coding, solving problems and creating websites. I thought I’d be tired of it by now. The best thing about the work I do is that the technology constantly changes, you have to keep learning, and the problems are often very different so it doesn’t get boring. And I have so many years of experience now that the endless frustration I experienced early on rarely enters my work day now.

I can’t put into words how much happier I am to have control over my time and how I do my work. I love that I can take off time when I don’t have work to do or can work from anywhere with my laptop. I can rent out my house and travel the world while working which is really amazing.

And the worst?

Dealing with clients can sometimes be difficult. When websites or servers break it can be very stressful and there’s no one else who can help or offload the work to. Keeping up with my inbox is impossible. Sitting all day inside is not great for my body and I’ve had on and off wrist issues since college.

What are the key challenges you face in your work? What are your tactics for overcoming these?

It’s hard to focus on learning what I consider the less interesting parts of running a business — taxes, marketing, sales. It all needs to be done and if I want to continue to work alone I need to do it, but it’s not fun for me. I find reading about the subjects I don’t like more tedious than talking to people about them, so I tend to ask folks who know about these subjects instead of reading.

It’s impossible to keep up with my email.

Sometimes I get overwhelmed with my to-do list. I have a white board and often when it’s really full I can’t even look at it without a mild amount of panic. If I notice I am feeling that way I try to break it down into micro-tasks and get those done. Once I start doing that I can usually get back on track.

How do you approach time management?

I work hard when I have work, and I make sure to take time off when I don’t, and get away from the computer and do something physical or outside.

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And what about work-life balance? Has your social/family life been impacted?

I think working for myself has been very good for my work-life balance. I can take off hours during the day to have lunch with friends, or take off a Friday to go camping for the weekend much easier than if I had a 9-5. Thankfully I like my work so I don’t have to worry about working too little. I think I’d still do this even if I wasn’t getting paid.

On the other hand, I’m on call if anything breaks for several of my clients. Being on call doesn’t stress me out, but it has sometimes gotten in the way of things I’d rather be doing.

How do you market your business?

I don’t market my business at all really. I see this as a huge area which needs improvement. I don’t even have a logo for my company!

How does being LGBTQ impact on your business (if at all)?

I don’t think it has impacted my business other than the clients it might attract. No one has ever said anything to me about being queer. I think being more MOC has maybe helped people trust my tech knowledge or opinions more, which is really lame.

What’s your hot tip for queer women who want to start their own business?

Don’t be afraid. Your fear can be your own worst enemy. If you want something, make sure the want overrides the fear.


You can find Cee at dapperdigital.net, or on Twitter @ceeweb.

Beth Maiden is a tarot reader and writer based in Machynlleth, mid-Wales. She has two cats, a hot builder girlfriend, far too many tarot decks and not enough coffee cups. She's really into bread, the colour red, camping and brand new notebooks. She'd love to cut your hair, read your cards or hang out with you on her blog, Little Red Tarot!

Beth has written 111 articles for us.

23 Comments

  1. I loved this interview. Learning more about the inner workings of Autostraddle is always fun! I also appreciate seeing people who have consciously planned out their work to be a good fit for their lives.

    And as someone who just closed a business where I worked a very structured 60 hours per week for the last ten years, I appreciate the sentiment that it is okay to take a break and have down time when there is less work.

  2. This so resonates with me. 15 years ago I was also a college art student, but I went to work in the tattoo industry for a while and wound up in a corpate office forever until I couldn’t stand it another day, and now I’m back in school learning web design and coding! It’s great to read about someone who has been able to succeed on their own doing what I hope to be doing one day. Gives me real hope! Thanks for sharing. :)

  3. I am strongly considering freelancing, or at least switching from permanent full-time to medium-term contracting. The main thing holding me back is fear about how I’d find clients. How do you find clients, Cee/others?

    Also I say this every time I can – I really appreciate all the work you do to make Autostraddle great, Cee!

    • Hey @dina, I can’t speak for Cee, but as someone who does freelance web design too, I’d say two things bring me work:
      1) Word of mouth/quality work – make sites for people you know, and things can really grow from there if they like your work. Know that there are always many, many people looking for a sound web designer they can rely on, so just *be awesome* and they will love you. Show up, do the work, answer emails, do a great job.
      2) Know your niche and SEO your own website that way. With my first business, I made a page saying that I was a feminist web designer, and got several clients who were specifically Googling for exactly that.
      Works for me!

      • Thanks for that! I guess it’s tricky because I’m not a web designer, but a technical writer, so therefore my work is a little more… obscured, I guess? Also, I can’t use most of the work I’ve done as samples because it’s an IP risk!

        I kind of want to branch out into copywriting for this reason, but it’s tricky getting the experience.

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