Angela O'Brien, Featured Business, March 2025
The Lenovo Pro Community is pleased to spotlight Angela O'Brien and Esteem Lingerie & Esteem Bra Fitting Academy as the featured business of the month. In successful business for nearly 20 years, this family run business has thrived through industry shifts, recessions, health challenges and a natural disaster. Angela herself is the epitome of positivity, resilience and focus. She's found an incredible groove as not only a business owner but also consultant, educator and parent. Keep reading to learn more about Angela, the business, her advice and look forward to her featured video dropping later this month!
About Angela
I call West Kelowna, located in the beautiful Okanagan Valley of British Columbia Canada home. While I have lived and travelled in many beautiful places in Canada and around the world, I love the ability to live in a small city that has all the amenities yet is surrounded by a nature-scape that has mountains, forests, lakes, rivers and agriculture. My husband, two daughters and three cats and myself share a small farmhouse that sits on a working vineyard. We have a passion for gardening so in the summer months outside of work you can usually find me covered in dirt working in our vegetable garden. The winter months I amuse my self with reading, taking courses and knitting. We are so fortunate to live in the region we do, it takes very little effort for us to get out into nature whether it is for a hike or swim!
Day-to-day Operations
If you meet me in person at a networking event and ask me what I do? I will smile brightly and tell you that I’m a Professional Bra Fitter! To the vast majority of my customer’s, I’m the person who educates them on bras, how they should fit their unique body and matching up the right underwear to their needs. The intimacy of what we do working with women also leads to a fair amount of knowledge sharing and personal coaching on self esteem and body confidence. Behind the scenes I’m a founder and co-owner of Esteem Lingerie, a full-service lingerie boutique (brick & mortar store) and Esteem Bra Fitting Academy, an online education platform designed to support lingerie boutiques with training, development and business consulting & coaching. As managing partner of the lingerie shop, I’m responsible for all management, purchasing, bookkeeping, marketing, HR and regulatory compliance for the day to day running of boutique. My other job is designing and producing the training courses for our education company as well as educational content for our YouTube channel. I also consult and advocate for small businesses.
How did you start your business?
Starting Esteem Lingerie was a happy accident. By the time I was in my late 20’s, I had already spent a decade working my up in the insurance industry, first in sales, service & underwriting and finally working my way into training & development. I had come to the point where I was achieving significant success however, I was struggling with burnout, and I wasn’t happy in a restrictive corporate environment. I’ve always had an entrepreneurial spirit, and I always knew that I wanted to work with women helping them develop their health and self esteem.
At the time I was living just outside of Toronto, I was newly married and had just gotten what I thought was my dream job with a large insurance company. Within 3 months, I realized I was working in a toxic work culture and I wasn’t suited to living in urban sprawl. So I decided to quit my job and take a complete leap of faith to move back to my home province and start fresh. That’s when I got a phone call from my mother who was busy opening a high-end lingerie shop. One of her business partners had backed out of the venture and she asked me to join the partnership.
We started with a vision, an empty space and we built everything ourselves; from the actual store (my husband was our contractor and head builder) to creating all the systems, policies and procedures. We largely self-financed and opened the door starting from customer one and bra one. We have been in business and consistently growing for 19 years. We have created a destination boutique that is renown for our education and quality products and service.
Q & A
How long have you been a part of Lenovo Pro and what is your favorite Lenovo product?
About six months ago, the Canadian Federation of Independent business (CFIB) notified its members of their strategic alliance with Lenovo Pro. As a long time Lenovo customer, I signed up for Lenovo Pro right away. As for my favorite Lenovo product? It is my Lenovo Legion Laptop. My husband is a printer/copier tech and loves to refurbish ThinkPads that have been retired from businesses and give them to people who can’t always afford a computer. For many years, we invested in new technology for the business. However, it was a proud day when I finally got to purchase my Legion, even though I’m not a gamer. The clarity of screen and images is ideal for all of the marketing and video work I do.
How has using your Lenovo equipment helped you accomplish things in your life?
For me technology is a tool, not a toy. I consider all my technology to be an investment, and our Lenovo equipment has always been the most reliable, compatible equipment with the best value for our money. As a bra fitter, I work in one of the most non-technical/analog environment there is. Bra fitting is all about working one on one with humans. Right from the inception of our business, we understood that if we didn’t leverage technology effectively to run the business, we couldn’t do the work with the customers and run the business profitably. When we opened the business two decades ago, “our technology” required only one person to do all the “back-room” business functions whereas it was common for lingerie shops who didn’t embrace technology to require 3-4 full time people to do the same work. Our technology has also allowed us to grow the business and manage everything that life throws at a business far more efficiently and effectively. This overall has allowed us to not only grow the business but also achieve a pretty amazing work life balance -something that isn’t always easy for entrepreneurs.
What do you enjoy most about the Lenovo Pro Community?
I really don’t enjoy social media and scrolling through the internet, falling into rabbit holes. Conversely, I recognize the incredible creative power and educational opportunities when like-minded people converge to work with each other. I have a couple of communities that are my “go-to's” for quality information and Lenovo is my first destination for technology, and I can the see the Pro Community being added to the destination list for technological information and innovation.
What was one of your greatest successes in your professional life? What was one of your greatest challenges in your professional life?
I combined these questions because my greatest challenge of my professional life has also become one of my greatest personal successes which has transformed my business and its success.
Seven years ago, I was on vacation with my family and on the last day of our trip I had a freak slip and fall accident that resulted in a catastrophic brain injury, this injury and my lack of willingness to prioritize my health resulted in the brain injury robbing me of my ability to speak and read. My ability to synthesize knowledge and to speak in public have been the cornerstones of all my careers, so this was one of the most life changing and devastating blows to face. In addition, at that time I also held a mindset that working harder & longer will always prove to be the best strategy for success regardless of the fallout to my physical and mental health and relationships.
In order to recover, heal and re-train my brain, I had to do the exact opposite of what I had been trained to do my entire life in order to be a success. I had to pace myself and effectively plan how to spend my limited energy. Ironically, the technological tools that had facilitated much of my life were temporarily banned for me as I couldn’t handle “screen time”. Thankfully, after several years of various therapies and a complete reconstruction of my life and how I spend my time, energy and money resources; I have a vibrant, largely satisfying life that is quite often downright joyful.
The biggest success that came out of this challenge was being able to simplify our work environment, putting greater priority on our customers. Using technical tools to free up human resources to be human. Since embracing this mode of working, keeping focused on why we do what we do and how it contributes to our value position, we have become more productive and profitable. Being able to provide a work environment for my staff that doesn’t ask them to leave their humanity at the door, rather we embrace the creativity and collaboration that comes from pacing instead of constantly pushing.
What is one piece of advice you've received along your journey that has helped you?
There are two words in western culture that often we are asked to remove from our vocabulary as children… “Why?” and “No”. Being able to ask Why, not just once but sometimes repeatedly is the required curiosity that allows us to question, resource, learn and develop discernment. Without figuring out our “Why” our lives are driven by everyone else. The respectful “No” is what allows us to focus in on the activities and people that keep us fulfilled and lead a purposeful driven life.
The Why is what allows us to simplify!
What advice would you give to others?
Know that our culture and media love fairy tales. But being a successful business owner is more about resiliency and your ability to learn and grow. And it usually doesn’t resemble the fairy tale. Your journey is yours, make sure you keep at least one golden hour everyday that is about your growth, development and allows you the space to reflect on how you want to spend your time, energy and money. That continuous investment in yourself is what pays back dividends.
Connect with Angela
Thank you for being such a valued part of the community, Angela and congratulations on being March 2025's Featured Community Member!
Esteem Lingerie
Website: www.esteemlingeriegroup.ca
Instagram: https://www.instagram.com/esteemlingerie/
LinkedIn: https://www.linkedin.com/company/esteem-lingerie-group/
Esteem Bra Fitting Academy
Do you have any questions for Angela about her journey, interests or advice?
Please leave your questions and comments below!