Chelsey Dyer is an independent designer based in Oakland, California focused on helping small businesses, entrepreneurs, and makers develop thoughtful and distinguished visual strategies to build their brand and effectively communicate their services and work. In addition to working with clients, Chelsey self-creates beautiful stationery products that she sells in her personal shop and boutiques around the world. We love Chelsey's minimal but friendly aesthetic and typography-focused design work. We have been long time fans, and are so excited she is sharing her wisdom with us.
Tell me about your path to becoming a freelance designer.
Before moving to San Francisco in 2009, I’d spent my entire life in Texas. There will always be a special place in my heart for the Lone Star State, especially Austin (nice folks, spring-fed pools, and breakfast tacos — so good!), but creative opportunities were limited and I was curious about the world beyond. After college, I decided it was time for a change of scenery. I visited the Bay Area a few months after graduating, and it became immediately clear that this was the place I needed to be.
At first I wasn’t confident enough in my skills to apply for the design jobs I really wanted. So, for the first year, I worked odd jobs, which helped me find my footing and build the experience and confidence I needed to take the next step. One of my first regular gigs was the Bold Italic — an online magazine that highlights the experiences of people living in SF. That work was rewarding in a lot of ways: not only did it help me fine tune my style, but it also allowed me to build important relationships and collaborate with other creatives — like Jess Levitz, the creator of Freelance Wisdom (Hi, Jess!). Eventually I landed a full-time design job with Fitbit, where I spent the next couple years.
At Fitbit, I was finally able to work with a team, collaborating and learning from other creatives. As my confidence and skills grew, my job eventually transformed into a lead design role. Working for a rapidly growing startup allowed me to work on a huge range of tasks: brand strategy, packaging design, art direction, lifestyle photography and more. I wore ALL OF THE HATS and loved it. Though I was busy and burnt out, I would still take on freelance projects. I missed the variety and excitement of working with more than a single brand or client. I listened to my intuition and began researching how to make the jump and start a legitimate sustainable business.
In my past experience, freelancing was unpredictable and stressful. If I was going to jump into it again, I wanted to do it right. I took in all of the books/articles/podcasts/blogs I could get my hands on to better understand other freelancers’ processes, time management strategies and methods for staying sane while working alone. I created a game plan and lined up a few freelance projects to overlap my last month at Fitbit so the jump would feel less scary.
Once I fully transitioned to freelance life, it became more and more clear that this was the right decision for me. Sure, I panicked at times, but it seems like a requisite amount of stress and anxiety accompany anything worth doing in life. In my mind, I knew I wouldn’t be successful unless I created the space, time and opportunity for myself to really go for it. Besides, what the worst that could happen? “Failure”?
So far, it’s been a great run and I’m so appreciative of the trust and support I’ve been given by clients and colleagues I’ve had the opportunity to work with.
In the beginning, how did you attract your first good clients?
I’ve designed and sold my own calendar for the last seven years, and it’s played a big role in familiarizing a wider audience with my work. Not only does it incorporate my minimal approach to design, but it’s also organized into astrological months, as opposed to Gregorian ones, which makes for a totally different experience. My design work is subtle and thoughtful and my calendar reflects that.
Since making the jump, I’ve been fortunate to become close friends and colleagues with Sarah Schulweis of Anchor & Orbit, who works with some really dreamy makers, entrepreneurs, and small businesses that often need design work. She’s been my biggest advocate and supporter as a freelancer. It’s so important to nurture the relationships that push you forward. In Sarah’s case, I designed her website to help communicate her capabilities to current and future clients and show the value in working with her specifically. Not only does setting her up for success make me feel good, but it’s also mutually beneficial. If she attracts new clients and work, more opportunity will most certainly circle back around to me.
Do you have any tips for being your most productive?
1. Listen to how you’re feeling right now.
Know your habits. For instance, what time of day to you tend to be most productive? When do you hit a wall? Understanding how you need things to look before getting into your workflow is an integral part of getting stuff done. If I’m not feeling inspired, no amount of sitting on my computer, staring at the screen and clicking around is going to evoke some brilliant concept. If I need to take the afternoon off and come back to the work in the evening, that’s totally fine.
You can’t (and shouldn’t) to do it all.
If you find yourself pushing off certain tasks, first think about why you’re avoiding them. Is it something you specifically need to do? If the task at hand doesn’t require your particular expertise/skills, consider hiring someone else to do it. Delegating can help you create more space for the work you enjoy.
2. Create bookends for yourself to get things done.
I’ve tried out many methods to maximize productivity. Setting aside blocks of time has really helped me get things done more quickly. Two or three hour blocks seem to work best for me. It’s not so long that I go crazy and get distracted or lose focus, but allows enough time to get into the flow of a task and really accomplish something. My theory is, the more time I give myself to do something, the longer it will take to get it done. Setting aside a specific amount of time for a single task forces you to sit down, focus, get it done, and move on.
3. Done is better than perfect.
I’ve paid a lot of attention to my habits and what I struggle with. One of my biggest pain points has been overworking a project. I tend to nitpick and over-design when a project should be done. There's also this strange anxiety I get towards the end of projects. It’s like this tiny, counterproductive voice in my head telling me that if I delay completing a project, I can avoid the potential criticism and self-doubt that comes with putting work out into the world. Ultimately, I have to fight these thoughts and make the decisions necessary to finish the work and move on to what’s next.
What has been your greatest struggle as a freelancer so far?
The solitude, hands down. There is definitely a required amount of isolation that’s necessary to be productive, but spending most of your work day with little to no interaction with others can be a huge bummer. With that said, I’ve been very intentional about staying connected with the creative community around me. Scheduled co-work days with colleagues, regular freelancer happy hours, and weekday lunch dates with friends all help combat the day-to-day solitude.
What is your favorite thing about freelance?
Flexibility. The restraints of a normal job just doesn’t work for me or my creativity. I’m personally affected by the kind of work I do and my surroundings. Being able to decide where I physically want to be based on where my head is at on any given day is huge. Each of my days can look different depending on the project, colleagues, clients, and other life things. I can determine my surroundings, which really helps with my productivity and, more importantly, my creativity. With this flexibility, I’m able to create the right balance for my business and my well-being.
Sense of Accomplishment. Although it's extremely daunting to run a business and create products for people, there’s a huge sense of pride in accomplishing it entirely on your own. I feel responsible to and accountable for my clients which drives my self-discipline. I find so much motivation in the fact that other people are relying on the work I’m creating for them. Once a project is complete and my client sees the benefits of the work I’ve done for them, it’s extremely gratifying to know that I alone made something really important happen for them. There’s also a huge sense of accomplishment in creating the environment and opportunities for yourself to work and create in. You make every decision about what your days, work process and clients look like. Managing your time and daily life is an accomplishment in itself.
How do you continue to attract your ideal clients?
I think one of the most important ways to get the clients you want is knowing when to say no. There are a few important factors in deciding if a client is a good fit — timing, availability, possible exposure, and most importantly, how you and the client might work together.
Most of my clients approach me because they appreciate my specific style. This is important because, in general, people who recognize and value your work from the get-go will allow you to be the expert and make tough decisions without resistance. A baseline amount of trust makes the whole process a lot easier for everyone.
Do you have any tips for dealing with the nitty gritty business details?
Canned responses: these save a ton of admin time. Any emails I find myself writing over and over again (like communication with potential clients) have become canned responses that I can customize further if necessary.
Typeform: I use custom forms to gather all necessary project information from potential clients. These are extremely helpful for writing comprehensive estimates and help kick-start the project once they agree to work with you.
Teamweek: high level scheduling + estimating new project timelines
Todoist: project task lists, notes, reminders, daily scheduling, personal to-dos and anything else floating around in my head (everything goes in here...everything.)
Harvest: time tracking + invoicing
Calendly: scheduling client calls
Google Drive: project docs, file storage
Hire an accountant ASAP. Trust me, this will just make your life so much easier. I also keep a simple spreadsheet with tabs for each quarter to keep track of my income and expenses that I share with my accountant when tax time rolls around.
Since you are your own boss, do you have any advice for maintaining a work-life balance?
Take time off. I do my best to really unplug and enjoy my weekends. But time off should be relative to how you’re feeling – if you need to unwind and be done for the day at 2pm on a Tuesday, then do it. I think freelancers tend to overwork themselves because there aren’t any boundaries between our work and our life. You have to set the limits for yourself and allow the necessary time to let your brain rest, take care of yourself and nurture your personal relationships. These things support you in your work, so it’s important to prioritize them.
The 3 greatest attributes you need to be a freelance creative are:
Discipline, Enthusiasm, Resilience