Lauralee Sheehan on the parallels between being a rock star and an entrepreneur.

Lauralee, Founder and Chief Creative Officer of Digital 55 explains how standing out from the crowd and maintaining an edge as a musician helped her achieve entrepreneurial success in digital media and STEM.

By Lauralee Sheehan

Rockstars and entrepreneurs are idolised in society because they are considered “exceptional,” and maybe even superhuman since they represent a small percentage of the population. Similar to musicians, entrepreneurs represent the risk-takers who humbly work towards their goals everyday, without ever knowing whether things will lead to success. They need to be all-in on whatever they’re doing and not be afraid to express abstract ideas. This kind of passion and commitment is inspiring to the public eye, and serves as the fuel that keeps me going everyday. Many assume that the rock star life couldn’t be further from that of a digital entrepreneur, but in my experience, the two are eerily similar and intertwined with one another. 

The Art of Continuous & Incremental Risk-Taking

During my early band days in the indie duo Lovely Killbots, we were essentially entrepreneurs — we had to build everything from the ground up from music to media (lots of modular development), experience design to marketing and social media and it was all about taking incrementally bigger risks. I learned a lot from the idea of building slowly and pushing further as you go and this meant building not only a band but a brand. 

Over time, this transformed me into a digital entrepreneur running Digital 55, a media agency focused on producing knowledge-based, social purpose content, edutainment and learning experience design (LX). It started off as a one-woman show, but things quickly grew and now I’m leading a growing core team of 6 people and an ever-expanding collaborator roster who work closely with us on our portfolio of projects. 

I’ve also been learning to maintain my edge as the company grows. As you grow it’s easy to forget the ethos of what you were trying to build, so I like to think about bands and labels that were able to always “keep it cool” no matter how much exposure they got or how the industry changed around them. 

“In a song, you have layers upon layers of concepts and ideas and I think building a business is the same.”

Follow the Rules to Break the Rules

Another thing that translated from band days to entrepreneurship is the idea of following rules and patterns to eventually break them. In music, you have boundaries you work within like time signatures and beats per minute (BPM), but from these boundaries you are able to create the art and abstraction of songwriting through melodies and lyrics, riffs and licks. 

I think entrepreneurs do a similar thing in terms of setting up a business, working within industry regulations and taking on a lot of responsibilities — but you have to colour in the lines first in order to paint outside the lines later. In a song, you have layers upon layers of concepts and ideas and I think building a business is the same. Recently, we wrote a song, Bliss and Nothing Less, that is about the Toronto indie scene circa 2008. We layered musical patterns, sounds, textures and lyrics and I think that idea is similar to how Digital 55 was built and continues to grow. It’s a little bit technical, a little bit abstract, a little bit badass.

Discipline Daily

Everything starts with daily habits. I’ve always considered exercise and fitness an important aspect of my life then and now. I exercise and walk daily to get my endorphins in. Pre-pandemic, I’d go boxing four times a week — this was my analog, no tech time.  I think getting physical and spending some time with your thoughts without the distractions of social media, tech and all other things that might allow you to avoid thinking about things that are uncomfortable, uncertain or not immediately satisfying is a huge way for me to dedicate some time for growth in my mindset. 

During my band days, performing in front of a live audience was a workout in itself — lugging gear, jumping up and down on stage and singing my heart out takes dedication and physical and mental stamina. Nevermind all the behind the scenes work that people don’t see, like rehearsing three times a week, using vacations to work on band strategy (and now business strategy), practising scales, listening to music constantly from a research and inspo perspective. If it weren’t for the grit, work ethic, and unending determination instilled in me from my early band days, I wouldn’t be where I am with Digital 55 today.

“I used to think that the most important aspect in running Digital 55 was to become known for producing fresh, innovative digital design and interactive media — but its true value comes down to the original stories we are putting out into the world and the content we get to produce.”

Standing Out From the Crowd with Social Purpose

Rockstars and entrepreneurs are educators who share diverse perspectives of the complex human experience and storytell in a compelling and provocative way. I used to think that the most important aspect in running Digital 55 was to become known for producing fresh, innovative digital design and interactive media — but its true value comes down to the original stories we are putting out into the world and the content we get to produce. 

Like a rock star, the meaning of the lyrics is what resonates in the hearts and minds of your listeners and gets you indie darling status. Whether I’m composing a new single or leading my team to produce digital content across subject matters, the intention is the same — to “leave everything on the stage” and tell a great story that leaves a lasting  impression that connects experiences, cultivates understanding, provides access to knowledge, and ultimately, to influence social change. 

It is arguable that the pandemic has shifted what society traditionally admired about celebrity culture — excess, glamour, beauty, and social influence based on “non-essential” talents. As a result of lockdown restrictions, people struggling to make ends meet, businesses being shut down all around us, and our world forever changed, the pandemic has humbled us all. Now more than ever, we’ve put a greater emphasis on older values such as community, local living, mental health, wellness, humility and the gift of time. Most recently, Digital 55 produced several digital courses with PowerED by Athabasca University: Navigating Extraordinary Times and Digital Wellness 101: Optimizing Your Time & Energy which covers the aforementioned values in the context of wellness during the global pandemic. 

Considering the rise of our dependence on technology which has only been accelerated during the pandemic, digital entrepreneurs and content producers are the new rockstars of our time. The public’s attention has now shifted towards what used to be seen as an unassuming group of brilliant nerds who live online — a.k.a. tech entrepreneurs.  Although I agree that tech has taken over our lives and will be the future of business and life in general, music will always have a place in my heart. 

It will forever influence how I show up as an entrepreneur and has a profound impact connecting with people on a deep and personal level in an inexplicable way. I’ve paid my dues in my past life as an indie-famous rocker, and I wouldn’t be who I am today, leading the award-winning team at Digital 55 if it weren’t for my rock star days. Being a musician taught me how to pour my heart and soul into projects that wouldn’t be understood by the mainstream, develop genuine self-confidence after experiencing failure, and adapt in an ever-changing digital world. These formative experiences shaped me into the fearless businesswoman that I am today, and I wouldn’t change a thing about it.