small business

Lindsay Pruitt

We could not be happier to chat with Lindsay Pruitt this week! Lindsay is the WordPress Developer behind Made to Thrive, a small front-end development studio that partners with graphic designers to build beautiful, easy-to-use WordPress websites for creative small business clients. With 5 years of freelance experience and nearly 100 websites under her belt, Lindsay has a wealth of knowledge to share. Oh and did we mention she is a mother of two?? Yep, she's doing it all, and she made time to talk with us. Thank you for chatting Lindsay!

Tell me about your path to becoming a freelance web developer.

I actually fell into web development completely by accident. I finished my college degree in Business Management without having any idea that I had a knack for computers, coding, or an eye for design. After college, I got married to an Air Force pilot and we moved from California to Mississippi. Being so far from family, I decided to start my first blog to keep my family and friends up to date on our adventures, which then led me to playing around with my blog design and discovering that I had a natural ability to pick up web code. With a little encouragement from my husband, I decided to go back to school for web design & development, and everything just fell into place from there! 

In the beginning, how did you attract your first good clients?

Getting a steady client load definitely didn’t happen overnight. I spent a solid 2 years working for free, building small websites & blogs for friends and family to build my portfolio, while also working my 40+ hr a week “real” job. Once I had a decent portfolio in place, word started to spread organically and the clients/projects began to come my way. Then after another year of working both jobs, I was finally able to transition solely to freelance web development.

Do you have any tips for being your most productive?

For me, it’s about focusing all my attention on one task at a time. I actually book up my calendar a little differently than most others in that I code one website from start to finish before moving onto the next. Because each website is so different, I’ve found that its more productive for me to throw my whole self into one project at a time. The outcome is that I finish the website faster and with fewer mistakes than if I try to bounce between projects and clients. Another thing I do that helps is turn off my email and social media while coding. Stopping to read an email can really throw my productivity into a downward spiral! 

What has been your greatest struggle as a freelancer so far?

Definitely the comparison factor. It’s easy to be hard on yourself in such a saturated market of talented designers and developers. At times I have gotten stuck focusing on what others are doing or how successful/creative/skilled I think they are in comparison to where I am, which then distracts me from my own goals. Comparison is a simple trap to fall into and can be detrimental to your business, making you question whether you’re “good enough”. Focus on your own path, and assess business growth on your own curve/timeline! 


What is your favorite thing about freelance and/or web development?

Aside from the fact that I am obsessed with the job itself (seriously though, sitting down with a coffee and coding for 4-5 hours is my happy place), I love being completely in charge of my schedule. In the past while working corporate jobs, I felt like I was on this hamster wheel waiting for the weekend to roll around, feeling smothered by the routine. Being able to work on my own schedule and work from any location has been the most amazing shift. It keeps me from feeling “locked in” which ultimately makes me way more productive.

How do you continue to attract your ideal clients?

Since I’m strictly on the development side of things, its a trio of choosing the right designers to code for, who have the right clients, who have the right projects. For a while I was just taking on any project that came my way, and my portfolio reflected that. It was not cohesive and there was no clear vision for what type of client I was trying to attract. So I decided to start asking myself 3 questions with each new project inquiry: 
- Is this project something that I’m personally interested in/inspired by?
- Will this project grow my skill set, teach me something new, and/or challenge me as a developer? 
- Are the client and designer both kind people and fun to work with? 
If the answer to any of the above is no, then I decide to turn down the project and wait for a better fit to come along. Once I started being intentional about the projects I took on and following those 3 guidelines, my portfolio began to reflect that and my business benefited so much! 

Do you have any tips for dealing with the nitty-gritty business details?

Since I originally went to school for business, I was a little bit over confident when I started freelancing and thought that I could easily do it all myself (accounting, taxes, marketing, drawing up contracts, etc). I learned the hard way that hiring both a lawyer and an accountant should be non-negotiables in getting your freelance career off on the right foot. I now have an amazing lawyer who has given me confidence in my client contracts and my LLC business setup, and an awesome accountant who makes sure I’m getting my quarterly taxes and yearly taxes done just right. Since hiring them, it’s been such a load off my plate, one that I didn’t initially even realize was there! On a daily basis though, I do my own bookkeeping (via Xero) and invoicing (via Pancake App) which helps me stay on top of everything and keep business organized. 

Since you are your own boss and a momma to two little ones, do you have any advice for maintaining a work-life balance?

Becoming a mom right as my business began to really take off (and now having two little ones) has been both the hardest challenge and biggest blessing. I was so worried that my business would suffer after I took on my new role, but surprisingly it turned out to be the best thing for it! My time now is much more limited so that means that when its time to work, I’m forced to be super focused and productive. Having babies has also helped me to balance my work and family time because now I don’t have the option of working straight into the night like I used to in my pre-baby days. So overall I guess my advice to freelancers that may be nervous about how kids will affect their work life is: don't stress about it! It will all work out just fine and your business may even benefit from the new work/life balance that the little ones bring. 


The 3 greatest attributes you need to be a freelance creative are:

Passionate, Organized, and Authentically kind.

Connect with Lindsay

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Chelsey Dyer

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.

Photos by  GhostFoto Graphics

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.
calendar_astrology.jpg

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

Connect with Chelsey

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Vanessa Wade

Vanessa Wade is the owner of Noirve Design Studio, a boutique design firm based in San Diego, CA, focusing on brand development and website design for small businesses. She has a knack for small details, clean and modern design. Vanessa loves collaborating with individuals who appreciate simplicity and strive to work hard. Since venturing out on her own 2 years ago as a small business owner, she has never worked harder, but she wouldn't trade that hard work for anything! 

Tell me about your path to becoming a freelance designer.

After relocating to San Diego right after college I worked at an advertising agency where I was able to build up my portfolio and soak up as much experience as I could in the design and marketing world. After work each night I’d come home and work on freelance projects to make a little bit of cash on the side and found myself way more excited about my freelance projects than I was about the work I was doing during the day. Eventually one night after a few glasses of wine I had a chat with my husband about what the next steps for me were in my career. For years I had talked about wanting to work for myself full-time but I had always been too scared of failing. I was finally in a place where I felt like freelance work was coming in slowly but regularly and like I could really try this freelancing full-time thing out. I think just realizing what that failure would mean really opened my eyes. If I failed I could just go out and get another job, not a big deal! So the next day I gave my notice at my job and spent that month reaching out to friends, old clients, and posting on my blog regularly to prep for the chaos that was to come. That was exactly two years ago. :)

"I think just realizing what that failure would mean really opened my eyes. If I failed I could just go out and get another job, not a big deal!"


In the beginning, how did you attract your first good clients?

Blogging had helped me a lot when I was first starting to get the right clients. I was blogging a ton about my design projects, my life, my process and was also able to use blogging as a creative outlet to try different styles of design. This is where I was really able to grow and learn, and I think eventually potential clients were able to see this.

Do you have any tips for being your most productive? 

Definitely setting specific hours for work and writing a to-do list daily for myself. Some days are easier than others but if you don’t get everything done in one day don’t beat yourself up about it. Just get it done the next day! 

What has been your greatest struggle as a freelancer so far?

Not taking feedback the wrong way! My feelings used to get SO hurt if my clients didn’t love something right away and I think stepping back and not being so attached to the work has helped me grow. Also learning to ask the right questions when a client is giving feedback has helped tremendously.

"Learning to ask the right questions when a client is giving feedback has helped tremendously."


What is your favorite thing about freelance?

I’ve met a lot of friends in San Diego who are working for themselves as well, and being able to meet up with them for coffee in the middle of a weekday to collaborate, discuss ideas, or even just have brunch, is the best. It really makes the long hours worth it.

How do you continue to attract your ideal clients?

Word of mouth! When you go above and beyond to do great work for your clients they’ll continue to pass your info along. 

Do you have any tips for dealing with the nitty-gritty business details?

Invest the money in a lawyer to write a solid contract for you. When I first started out I had used a contract I got off google and my current contract has saved me in so many ways. You definitely want to ensure you’re fully protected if a client tries to add more work onto a project that was never discussed or if a client tries to push a deadline out. Protect yourself!

The 3 greatest attributes you need to be a freelance creative are:

Drive, communication, being nice.

Get Social with Vanessa

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