Meg O’leary
One of the best parts of my job is meeting people who are passionate about what they do. In doing so I’m not only learning about their business. I am learning about their lives; who their kids are; what their hobbies are, etc. Bits and pieces of their personal story is woven into their professional one.
This Second Act Interview is the first since the pandemic, and I think we can all agree that the pandemic changed the way we work, where we work, and the work we do. If you’re reading this, you likely know someone who turned their career upside-down and right-side-up again since 2020. Those stories are in large part due to accommodate school, child care, older loved ones, etc. effected by the pandemic. But a few of them—like this one—are about something more: reevaluation, and following a passion.
So without further ado, we would like to introduce you to…
Name: Meg O’Leary
Education/Training: BA in Marketing, MBA in Management, Pediatric Sleep Certification through the Center for Pediatric Sleep Management.
First Job/Career: Prior to starting my own business, I worked at American Express for 15 years. During that time I held various marketing and business strategy roles. I was both an individual contributor "doing the work" and also a people leader, managing large global teams.
We haven’t had many conversations about what came before A Restful Night, but I have been able to piece together that you were quite accomplished in your field. Can you share some of your achievements from your “First Act”? I feel like my whole career at American Express is a highlight. The beauty of working at a company like American Express is you gain so much transferable experience. During my tenure there I worked in new product and program development which has helped me think about how to mold and shape my own business. During one role in Consumer Travel, I worked on a lot of branding and marketing development which helped me build a creative eye. My last role, prior to leaving corporate, was in a B2B function in business travel where I learned about sales, how to generate leads and how to work a pipeline—this experience by far has been the most instrumental in helping me grow and scale my own business.
When did you decide it was time to leave your full-time job to pursue A Restful Night? Did the Covid-19 pandemic play a factor at all? Yes! Like many the pandemic put a lot in perspective and really gave me the opportunity to take my career in a different direction. When the pandemic hit I was working in business travel and the sector basically shut down. I was furloughed for several months and then went back to a business strategy role which was quite intense. At the time I was 6 months pregnant and knew that the hours and demands of a corporate job, coupled with taking care of my family during a pandemic weren't feasible. I chose to take a departure package and left the company willingly and happily with many memories and great friends to take with me! After having my 3rd baby, I took a few months off and then knew I needed something more. This was when I started to soul search and realized entrepreneurship could be in the cards for me. After some really productive conversations with my husband and mentors, I went ahead and took the steps to get certified as a sleep consultant and start to build my newest baby ... "A Restful Night".
Have you found any similarities between your first career and your new one? As I mentioned above there are so many things I've taken forward from my American Express career into being a small business owner. I was always known as being a flexible, nimble employee—"give it to Meg she'll figure out how to get it done". This is the truest statement in my current job since every task or problem that comes my way I literally need to figure out how to solve it on my own!
“My proudest accomplishment is for sure the 200+ families I’ve supported and the 85+ five star google reviews that commonly use words like “life-changing,” “confidence,” “life back”. To know I’m changing the lives of families makes working hard each day so rewarding.”
How is business going so far? What are you most proud of? It's been incredible! I am just about to hit my one year mark in September and the momentum only keeps growing. I never imagined I'd be where I am in just a year. Since launching A Restful Night I've launched my brand and website (thanks to Studio Eighty Seven), built an instagram following of nearly 2,500, hired another sleep consultant to support me and am on track to more than double my initial revenue goal. My proudest accomplishment is for sure the 200+ families I've supported and the 85+ five star google reviews that commonly use words like "life-changing,” “confidence,” “life back". To know I'm changing the lives of families makes working hard each day so rewarding.
If you could go back in time, would you pursue A Restful Night from the start? I don't think I would have had the knowledge or skills to know how to launch a business successfully had I not worked in various roles beforehand. I also think being a mother of three young children makes the work I do more meaningful and gives me real life, relatable experience to pass along to the families I support. I truly believe I'm in the right place at the right time!
Do you have any advice for someone thinking of pursuing their “Second Act”? I always say if something is equal parts scary and exciting it probably means it's a good idea. Go into things with eyes wide open and be calculated about where you invest and what risks you take but don't let perfection get in your way of trying something new!
