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Ownr Success Story: Digital 55, a Digital Learning Agency

Digital 55 recognizes the power of design to shape and transform the world around us. In this interview with Ownr, Chief Creative Officer of Digital 55, Lauralee Sheehan shares her entrepreneurial experience and advice, and gives insight into her company’s goal of purposefully harnessing the power of design for good, to bring about social change.

What is Digital 55?

Digital 55 is a collective of award-winning designers, developers, researchers, and content strategists working together to create unique, innovative, digital interactive products and learning experiences. Our work is defined by our rebel spirit, rooted in interdisciplinary arts such as music, film, and design.

We recognize the power of design to shape and transform the world around us– and it is our goal to purposefully harness that power to design for good. Because we are passionate about social change (we call ourselves “rebels with a cause”), some of our projects have included subject matters such as equity, diversity and inclusion, human rights, leadership, and skills training. Some of our clients include Athabasca University, Ontario Human Rights Commission, Ontario Arts Council, and Healthy Start.

Digital 55 is based in downtown Toronto and operates in a decentralized film-based model, booking and curating talent on an as-needed basis and with a focus on project specs and client objectives.

Digital 55 Studio in Toronto with Lauralee Sheehan
Digital 55 Studio in Toronto with Lauralee Sheehan

What inspired you to set up a digital learning agency?

My dad was an entrepreneur so I’ve always had an interest in entrepreneurship. Throughout my career, I have started a few small businesses including Digital 55 but had always kept a full-time job and never quite made the full time leap into entrepreneurship

In 2016, I landed what I thought was my dream job running a design and dev team at a digital learning agency, but soon started noticing some red flags with the company. When they announced bankruptcy in 2018, I was crushed. But I made the decision to truly commit to my future. So the next morning, I put on my black dress and red lipstick and went into the office prepared to handle this experience with grace, class, and true leadership. I committed to wrapping up our clients’ projects in the most graceful way I could and made sure they felt valued and cared for, and sure enough, they began to ask me about my next steps. 

From there, I knew it was time for me to move Digital 55 into full-time operations. I took the leap and never looked back. 

Read more about why people want to become entrepreneurs

What do you love about being your own boss? What keeps you motivated?

Being your own boss comes with higher risks and far less free time, but ironically enough, it also comes with more empowerment and a greater sense of freedom that you just don’t get in other settings. There is definitely more stressors, but still, a great sense of individuality. I love that I get to decide what I am investing in and which clients to collaborate with, which is very empowering. 

I’m motivated by innovation and creativity and building the team with that in mind. Even if some projects are more challenging than others, there is something about being in a space of innovation that keeps everything exciting and interesting. 

What has been your biggest business success or earliest win?

2019 was a big year in terms of getting a big contract with a major client that has become the pinnacle to the business and moved us into a rapid scale and growth phase. So that was a huge win! But we have also been receiving grants for innovation and funding to go global which has changed everything for us. 

What do you remember about the initial days of Digital 55? When did you register your business with Ownr? Anything you can share about your experience of using Ownr to set up?

I started the business in 2015, through more traditional channels and as a sole-proprietor, but I didn’t know a lot about certain things when it comes to getting serious about starting a business. Over time, I found Ownr and was able to incorporate the company really easily through the Ownr platform. I was really intimidated by the process previously because it sounded really stressful, but Ownr made it such a seamless, easy, and transparent process. All the things you need to do are very clear, so it made the choice to incorporate really easy to make. 

What’s the hardest part of running a business of this nature? Is there anything you wish you knew before you started? Anything you would approach differently?

We are in the scale and growth phase of our business, which has been super tough. Starting up was really tiring, but scaling and growing is extra tiring. The risks are higher; there are more people invested, like collaborators and clients, and much more responsibility to make things happen. This phase has been a much more emotionally challenging one. 

Another thing that has been hard working in digital experience design and development is that the modular nature of the projects is complex. Scope creep and changes in scope are the norms, not the exception, and that can be hard to manage. You get excited at the beginning when you win a contract, but those early conversations change completely from what the project eventually becomes. 

I am getting better at having difficult conversations with clients early on or saying a hard no. There is usually a gap in information, especially on the tech side, so it’s very hard. You want to give your client everything, but the process as a developer is much more complex than what may have been agreed to on the contract level. So I’m learning to set boundaries with clients and feeling more secure in asking for more funds when scope does iterate or change drastically.

What does a typical day as an entrepreneur look like for you?

Things have been more routine for me, with a 9-5 schedule now that we have an office! It’s only been a few months since we moved in, but it’s become much easier to cut myself off from the business in the evening by having that separation of business and life. The office has a coffee bar in the front (with unlimited coffee), so I usually start my day off by chatting with the barista about life philosophy! 

My days usually involve a lot of meetings with clients or my team. These days, I tend to spend the mornings collaborating with my team and the afternoons are spent doing the creative direction, design or dev on projects. 

I also go boxing almost every evening which has been essential for my personal well-being as a business owner. 

Are there any tips you’d like to share with other entrepreneurs starting their business journey?

Be graceful with yourself because there are going to be really messy moments where it feels like everything is going sideways. During the startup phase, everything is a win cause you’re just happy to be in business but as you grow, you are bringing on more and more projects and people become invested in your company so it becomes harder to manage. There will be highs and lows, so go easy on yourself. 

Find a practice or workout that works for you to stay in shape, but also to enjoy the routine. Putting on my boxing wraps is such as small thing but it has become a ritual for me and it makes me feel like I can live outside my business too. These moments help you stay true to yourself and you can bring that back to the business, too. It’s important to remember to reconnect with yourself on a regular basis. 

What are your goals for your business?

This year, we want to continue to focus on experience design and do it by breaking apart subject matter or content that can help change peoples’ lives. We want to build experiences that explore important subject matter, that we can break apart and rebuild and keep creating more and more meaningful experiences that help people understand the world and make positive change.

Of course, we also look forward to further growth and providing more jobs and bringing on more talent to our team. 

Where can people learn more about Digital 55?


Instagram: @digital_55

Twitter: @digital_55

Facebook: Digital 55

Linkedin: Digital 55

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