Lauralee Sheehan Of Digital 55: How To Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur

by Christina Gvaliant

Being a founder, entrepreneur, or a business owner can have many exciting and thrilling moments. But it is also punctuated with periods of doubt, slump, and anxiety. So how does one successfully and healthily ride the highs and lows of Entrepreneurship? In this series, called “How To Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur  we are talking to successful entrepreneurs who can share stories from their experience. I had the pleasure of interviewing Lauralee Sheehan.

Lauralee Sheehan, Founder and Chief Creative Officer (CCO), is a design thinker, a digital addict, but above all an artist. With years of experience working in digital dev and interactive media, Lauralee is a trailblazer in the digital space, pushing forward how creativity and tech intersect. She has led dynamic digital teams on various award-winning digital, interactive, learning, and research-based projects. Lauralee brings a fresh, authentic, and innovative approach to the design, digital media, original content, and learning space.

Fun Fact — She is an Indie Musician.

Thank you so much for joining us in this interview series! Before we dive in, our readers would love to “get to know you” a bit better. What was the “Aha Moment” that led to the idea for your current company? Can you share that story with us?

Lauralee Sheehan: I was at an education-focused conference in Austin and throughout the conference, everyone I spoke to was enthralled with my interdisciplinary background and my interactive media approach to knowledge-based content. It was an approach that was natural to me, but I did have an “aha” moment and realized how very valuable and disruptive this thinking could be for the digital learning industry and how massively technology was changing our relationship to content.

In your opinion, were you a natural born entrepreneur or did you develop that aptitude later on? Can you explain what you mean?

Lauralee Sheehan: I’ve always had a rebellious spirit but my aptitude for entrepreneurship was defined and cultivated throughout the years and through many different experiences from working in film to wanting to be a Rockstar, to working in interactive digital media and content producing. I do believe that being an entrepreneur is not an inherent natural state but actually emerges based on years of consistent hard work and behind-the-scenes sacrifices.

Was there somebody in your life who inspired or helped you to start your journey with your business? Can you share a story with us?

Lauralee Sheehan: A few years before I started Digital 55, I was working for a not-for-profit and had this amazing manager who ended up being a huge influence on me. She was whip-smart and creative in her thinking even in a more structured, systems-based environment. She gave me a lot of opportunities for education and leading innovation initiatives at the company. We had a conversation about career development, and she was so honest and real with me, by telling me that I should not try to progress at that company and that I needed to start my own thing. I will never forget that moment because that shattered any glass ceiling for me and opened up my thinking on impact, purpose, and power.

What do you think makes your company stand out? Can you share a story?

Lauralee Sheehan: It’s been so cool to see some of the stand-out differentiators that people give kudos for and call out often in terms of the interdisciplinary background the team brings to the table. It’s the music background and the ethnography and cultural anthropology background and the film background. It makes what we do more exploratory, edgier, and more complex because we are pulling from different disciplines. Drawing on these diverse backgrounds, we are able to disrupt and intersect different thinking to design authentic and engaging content in the interactive digital space.

You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

Lauralee Sheehan: I think the three for me are curious, disciplined, and conceptual.

Curious because I think you have to be open to exploring things you don’t necessarily understand and that is one of the things that truly make you an entrepreneur. You have to be comfortable with the unknown.

Discipline because you have to chip away at this dream of yours, day-by-day, without the accolades or immediate outcomes. I liken it to studying music. If you want to become proficient at an instrument, you have to pick it up each day and practice scales, learn chords and theory and during that process, there is a long period of time where you just suck … until suddenly you reach a level of expertise and prowess and when that moment happens, it’s awesome. The same can be said for building a business.

Conceptual because I think like an entrepreneur, you are probably going to be a visionary or a big thinker. Usually, all the little details are not your favorite and although you might have 1000 things on the go, you naturally gravitate to using your time and energy to vision the big stuff into reality.

Often leaders are asked to share the best advice they received. But let’s reverse the question. Can you share a story about advice you’ve received that you now wish you never followed?

Lauralee Sheehan: Right before I took my company full time I was working at a company with terrible cult-like workplace culture. It was so bizarre and I was told so many negative things about my leadership style which really affected me personally. So, although it wasn’t one piece of advice that I wish I hadn’t followed, the lesson I took away from it is “trust your gut”. If you think that the vibe is off, don’t feel like you have to blindly follow leaders that are not mentally or emotionally healthy themselves.

Which tips would you recommend to your colleagues in your industry to help them create a work culture in which employees thrive and do not “burn out” or get overwhelmed?

Lauralee Sheehan: I think this is so important and such a challenge in this digital world we find ourselves in these days. In tech, media, and content producing, burnout is always a risk because digital just never stops but especially now in these pandemic times. We were in a high screen-time industry before and now we’re just always on screens and always on crazy deadlines and dealing with sensitive content that takes it out of us emotionally. To try to support not burning out, flexibility is one of the main things we integrate into our culture. Flexibility in where we work, when we work, how we want to work, and not placing weird expectations on productivity. That looks different these days and that’s okay.

What would you advise other business leaders to do in order to build trust, credibility, and Authority in their industry?

Lauralee Sheehan: There’s this new framework of responsible business and I think that is key these days for leaders to build trust and credibility no matter what industry they are in. A responsible business is essentially one that benefits society and addresses negative impacts it might have on society, people and the planet. Business as usual is not a thing anymore because nothing is usual and everything is changing in terms of the issues the world is facing. People want to work for, buy from, and invest in businesses they believe in, and thinking about purpose and impact is the most powerful way to build credibility, trust, and value for your business.

Can you help articulate why doing that is essential today?

Lauralee Sheehan: Leaders have to understand this changing landscape and do some deep thinking on how to provide thought leadership in their industries. Don’t rest on the status quo when it comes to that as there is too much going on in the world on too many levels.

What are the most common mistakes you have seen CEOs & founders make when they start a business? What can be done to avoid those errors?

Lauralee Sheehan: I saw a company crash and burn quite dramatically because they took on large-scale projects without a perspective or understanding of what expertise and talent these projects needed in order to build and create. It was all sheen and sparkle on the outside in terms of the company’s big bold vision but in reality, there was no vision. I think you should be humble in growth and grow quickly but not too quickly that you put your team and your company at risk.

Ok fantastic. Thank you for those excellent insights, Let’s now shift to the main focus of our interview about How to Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur. The journey of an entrepreneur is never easy, and is filled with challenges, failures, setbacks, as well as joys, thrills and celebrations. This might be intuitive, but I think it will be very useful to specifically articulate it. Can you describe to our readers why no matter how successful you are as an entrepreneur, you will always have fairly dramatic highs and lows? Particularly, can you help explain why this is different from someone with a “regular job”?

Lauralee Sheehan: The highs and lows are hard to prepare for and wow, are they ever a real part of the entrepreneur experience. You have so much to shoulder in terms of responsibility, accountability, and liability. You are responsible for the livelihoods of your team, you are responsible for the sustainability of your business, you are responsible for the work you produce and also your social impact as a company, and sometimes that gets to be a lot. You never turn off and can’t walk away from things at 5 pm. It stays with you 24/7 and that is something that you don’t experience when you are working for someone else. There might be stress and there might be pressures that affect you but when you have to make tough decisions that could make or break your business, that is on a whole different level.

Do you feel comfortable sharing a story from your own experience about how you felt unusually high and excited as a result of your business? We would love to hear it.

Lauralee Sheehan: I think during our second acceleration phase, the highs really come when the team is absolutely killing it. There have been so many wonderful things said about what we produce and the thinking that goes into the process and I am always so proud of the team when I hear those things because I know it. It’s a testament to the talent in the team, and the next-level thinking that is brought into our approach but also about the trust we’ve built in our collaborations and how that allows us to be super free-thinking and innovative.

Do you feel comfortable sharing a story from your own experience about how you felt unusually low, and vulnerable as a result of your business? We would love to hear it.

Lauralee Sheehan: This is going to sound strange, but I’ve felt low and vulnerable as a result of my business when it comes to romance. Since becoming an entrepreneur, my dating life has been complicated and part of that has to do with the demands on my time of running the business. The more success you have the fewer people want to hang out with you in a romantic sense (or so has been my experience) and the qualities that help you succeed as an entrepreneur end up being a scarlet letter “E” in your personal life (I’ve been called aggressive, intense, standoff-ish, you name it). It brings up a lot of questions, as a women entrepreneur, about how far we’ve actually come when it comes to supporting, reciprocity, and equity.

Based on your experience can you tell us what you did to bounce back?

Lauralee Sheehan: Haha, still working on that.

Ok super. Here is the main question of our interview. What are your “Five Things You Need To Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur”? Please share a story or an example for each.

Lauralee Sheehan: 

Resilience — You are going to have good days and bad days, successes and failures, yes’s and no’s. Days where you feel like an absolute zombie because you are so exhausted and haven’t slept in what seems like years. There will be days when you feel like you have to fix everything for everyone as if you are some type of superhuman. And sometimes you might feel like you don’t have it in you but you have to get up, show up and work it out.

Grit — I started my business in the wake of my employer going bankrupt, from which I learned how to mobilize quickly to support our clients and provide space to continue those key relationships and build a new future. I’ve dealt with late-paying clients, with my own bills to pay and my team relying on me to get them paid. And I’ve had to move forward with my business and support my team, no matter what was going on in my personal life. No matter what successes or losses we came up against.

Purpose — This will keep you going and especially when we don’t quite know what the world is going to look like moving forward. To run a business in the world today, the purpose of what you are doing will keep you going. We circle back to our purpose constantly and it helps me make decisions for the business about what we will invest our time in and what we won’t.

Passion — This keeps you going and fits well with purpose. If you are not fired up about what you are doing, you will probably fold when things get rough or you are sacrificing other parts of your life and wondering if this whole entrepreneurial thing is worth it. And as much as it’s been glamorized on social media, it’s not. It’s insane hours and hard choices and big risks and insane amounts of responsibility.

Creativity — When you are feeling low, creativity helps you channel that lower energy into something else. They say art doesn’t come from happiness and there is something in that. Use the lows to spur free-thinking and channel that low vibe energy into something creative or innovative. Your mood will immediately start to pick up and I find that working on things creatively that are separate from the business (for me it’s music), also helps me infuse that back into the business in a really meaningful way.

We are living during challenging times and resilience is critical during times like these. How would you define resilience? What do you believe are the characteristics or traits of resilient people?

Lauralee Sheehan: I define resilience as putting in the time and effort to create your own stability and stay agile during any personal or societal shock. Resiliency helps you make micro-decisions every day that will start to build strength, grit, and determination. For instance, I was boxing 4 times a week pre-pandemic and that commitment wasn’t about getting into music video shape (although that is was a great secondary outcome), it was about carving time out consistently to work on a skillset or discipline that challenges you, takes you out of your comfort zone and changes you as a person. You start to see huge gains in this process, but it is not a stop and start process, it is something you have to continuously work at and show up for.

Did you have any experiences growing up that have contributed to building your resiliency? Would you mind sharing a story?

Lauralee Sheehan: I had a very complex and unstable upbringing and had to get used to very unstable situations often. This taught me to be very agile and know that there are variables in the things that happen around you that you have zero control over. Instead of letting this paralyze and terrify me, I was able to build internal strength to know that I could create new environments and new situations for myself with time and patience.

In your opinion, do you tend to keep a positive attitude during difficult situations? What helps you to do so?

Lauralee Sheehan: I tend to keep a positive attitude and sense of humor (which may be even more important). There are going to be one million difficult things that you have to figure out and approaching everything with a touch of humor and real talk helps not only your client collaborations but most definitely it helps your team and builds trust in company culture.

Can you help articulate why a leader’s positive attitude can have a positive impact both on their clients and their team? Please share a story or example if you can.

Lauralee Sheehan: This is key. They say that your overall vibe will have a great effect on people and especially when you are in a leadership role you have to be extra aware of it. We’ve all been in a room where someone was such a downer and able to drag the energy way down and it’s not how you want to show up for your team and your collaborators. It’s challenging to put to the back of your mind the big risks you are taking in the business or maybe something going on in your personal life but being totally present at the moment is game changing. I try to stay off my tech when someone needs my attention or has asked for my time to show respect to them. This means I’m not answering emails or tinkering around with distractions while we are speaking. I also try to support a totally open communication policy. We’re in a very deadline-driven space and digital truly never stops so that can be stressful, but the team is still human and sometimes we need to talk about how quickly we’re going to be able to get something done, realistically.

Ok. Super. We are nearly done. What is your favorite inspirational quote that motivates you to pursue greatness? Can you share a story about how it was relevant to you in your own life?

Lauralee Sheehan: “Life is what happens while you’re busy making other plans.”

This famous saying from John Lennon reflects a paradox in our lives. Although we like to live in the moment, we also continuously plan for the future. The beauty in this quote is not that we don’t have agency over what happens in our lives but there is something poetic in being open to things you haven’t planned for and know that might be exactly where you need to be.

This was very inspiring. Thank you so much for the time you spent with
this. We wish you continued success and good health!

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