Build a Creative Career on Your Own Terms
Build a Creative Career on Your Own Terms
How to leverage new skills to confidently freelance full-time: An Interview with Jillian Tranquilla
Been chewing on the exciting possibility of going freelance full-time? Then you’re going to want to hear from Jillian Tranquilla, a multi-talented creative who’s now offering web design services after completing the Squarespace Design Course.
We chatted with Jillian to talk about creative trajectory, post-grad client work, and reflections on making the big leap—read the interview below to learn more about how she transitioned from agency and in-house roles to full-time freelancing.
Meet Jillian Tranquilla, a Squarespace Design Course Grad and Full-Time Multidisciplinary Freelancer
“Hello! I’m Jillian Tranquilla, a multi-disciplinary creative out of Calgary, Alberta! I was born in 1993, baby! I’m an Aries, Cancer, Sag, and enneagram 4w3 (an Artist!)! My primary medium and focus is commercial photography; however, I also work as a graphic designer. Like many 1993 babies, we lived our afterschool lives on websites like Piczo and Neopets.
I think there’s something super special about the early 90s kids because I’ve found that a lot of us who started learning how to code our personal Neopets and Nexopia pages when we were preteens naturally have found our way to branding and web design in our adult years!”
Beyond the 16:9 Artboard: Upskilling with Squarespace
Could you share more about how you decided to learn Squarespace?
JT: I always knew that Squarespace was a third-party web builder that I wanted to explore. I spent the last half-decade working as a designer at a boutique and thriving digital marketing agency called Arcade Studios. I was hired as a Content Producer, a hybrid position where I operated as an in-house producer and photographer. Between photography projects, I supported design and eventually became a sr. designer on the team.
However, I was mostly executing social media graphics (think HEAPS of Instagram stories designs) day in and day out. Squarespace felt like the natural move for me to study, as it would allow me to service user-friendly websites to small-mid sized businesses and move beyond the 16:9 artboard. I was also super excited about the prospect of being able to design these digital storefronts (websites!) that could house campaign photos and video, copy, and graphics all in one intentional space.
On Becoming the Full Package for Clients
How does Squarespace design interact with your other skillsets?
JT: As a photographer, videographer and designer, I have foundational skills to help businesses cause visual impact. But now that I can design in Squarespace, I can offer full-scope marketing services to clients on different rungs of their journey! One of my favorite services to offer includes Brand Design, especially a service called Design Intensives. Design Intensives are a foundational service I offer to new and budding businesses that need to develop their overarching brand personality.
With intensives, we’re able to execute a full-scope brand identity in just one day! What’s so exciting about this is that it opens the door to web design as the organic next step. You loved your brand identity? Now, let’s apply it to your custom website! And with photos and video, on and on it goes. I just don’t touch the copy. Too much work for me, haha!
“Everyone comes to a freelance journey differently.”
How did you decide to go full-time freelance, and when did you know you were ready? Have you ever freelanced before starting the course?
JT: For me, this wasn’t my first time attempting to freelance, and there is so much I’m still learning as I go. My first attempt was a total flop; I had no idea what I was doing - and eventually, I just decided that a full-time agency job felt correct. After 5 years in an agency setting, with quick turnover and being siloed into a single lane, I felt like it was time for something new.
What was also incredibly expansive when working at an agency was being able to see so many brands come through our doors and move through similar stages of marketing (strategy, web design, collateral, ads, campaigns, etc). After watching that flow for a while, I felt like I had what it took to try freelancing once again. After another 2 year stint in-house at a slower-paced position, I decided it was time to take the leap. And I’m so happy I did! My first year was a building year, where I worked with some incredible retainer clients. Now that I’m in my second year, I’m taking things to the next level and launching my website and services to the public, officially!
Post-Course Reflections & Wins
“I’d say that before this whole journey, I felt like I wasn’t operating at my fullest potential—and now that I’m offering all these services that I'm both passionate and skilled at, I feel aligned and in my purpose. I just need to continue to find balance as I keep moving forward!”
What have you learned about yourself and your skills in the process of learning a new skill?
JT: I think I’ve had to learn the most about time management, capacity, and pricing. As a one-person show, I’m really eager to start working with subcontractors and a team. I’ve had a lot of late nights, numbers not quite adding up, and anxious days. But all of this has pushed me to find my growth edge! I’m hoping that I can learn to say no to more instead of spreading myself so thin, find a balance, and really claim the lifestyle that is possible with freelancing.
What aspect of the course was the most helpful for your success in the course?
JT: When taking the Squarespace Design Course, having access to the TAs in the Discord was invaluable. I don’t think I would have made it to the end of the course without knowing I could ask questions and get support. I learnt so much in proximity to the TAs’ problem-solving for me. I am also obsessed with the resource center. I try to go in there all the time, even though I technically hit trophy!
How have your new Squarespace skills helped you after completing the course?
JT: Completing the course has opened up an entire world of opportunities and possibilities! Everyone who is operating as a business (including myself) needs an online storefront, and Squarespace’s user-friendly interface means it’s appealing for new businesses who want to make an impact online. For me, I took the opportunity within the course to go full-out on my own portfolio website that could serve as a service funnel for my clients. Now that it’s complete, I know that whenever I meet an ambitious creative, I can feel confident that I can offer them a service like Squarespace Web Design, and I know it’s going to push them to the next level of their biz.
One of my first projects after completing the Squarespace Design Course was a fully custom online course on the Art of Directing Emotion in Film. I used the skills I learned in the course to lightly custom code the site, build out their course, and eventually sell it to the public. It’s rewarding to see a website not only create a splash in the industry but also lead to real revenue on launch!
Can you share what you’ve worked on after taking the courses?
JT: Since completing the course, I’ve worked on 3 bigger web clients. My first client was for the in-house marketing agency I helped create while employed for a beauty distributor. My next project was a 27-page website revamp for a local dance studio, and my most recent project was for two filmmakers launching their online course! In addition to this, I’m shooting campaigns, video work and doing ad-hoc design as well as now offering design intensives. The idea is to offer this full suite of services so that I don’t get too bored, see what sticks, and then refine from there. It sounds like a huge scope of services, but it keeps me nimble and always learning, which I absolutely love!
Advice for Aspiring Full-Time Freelancers
What advice would you give to someone whose goal is to freelance full-time?
JT: I would really stress the importance of building foundational systems. I think there’s lots of nuanced advice that comes with this, like not getting too deep in the weeds before starting. However, I think that being intentional in creating a streamlined structure is going to save you heaps of stress and time. At the very least, make sure you have all your contracts in one spot, etc.
I spent a lot of time building out my CRM (I am currently on Honeybook) so that when I get a lead, I don’t spiral with anxiety because the flow is overwhelming. My CRM allows me to flow through onboarding without batting an eye - and frees up so much time for creativity and to give my clients the headspace they deserve.
Is there anything you would tell your past self now based on what you know now about creative career paths?
JT: I would tell her that your ceiling of how much you make comes down to your people-pleasing tendencies. There are a lot of creatives out there who are willing to share and mentor you, and when it comes to finances, your ceiling is really set by your own limitations. Get around other freelancers, creatives, and business owners. A lot of the time, the nuances you are finding your way through have been navigated already by people before you. Don’t be afraid to ask questions and to learn from them! Also, become intentional about creating a culture of generosity and sharing.
There can be an air of competition, and if you’re not careful, that can create division and unnecessary stress for you and your business. Instead of seeing the other designer or photographer down the road as your competitor, look to them as an expander (someone who has created a life that you desire too) and take it as a sign that it’s totally possible! Ask them questions, and find ways to build them into your network. You never know how those relationships can push you forward!
Thanks for sharing your story, Jillian 🫶
Feeling inspired by Jillian’s dynamic journey to freelance? At ilovecreatives, we embrace all the twists and turns in our creative trajectories. No matter your starting point, it’s truly never too late to get up outta your lane to explore new ones.
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