As a group of women working towards common goals for STYLE Canadas brand and business, we understand the value of peer support in the workplace. So, after our last Supper Club at Soho Housewe decided to bring like-minded women in business together and feature them in an ongoing series: #LeadingLadies. Here’s hoping that we’ll see you at our next Supper Club. Keep your eyes peeled on our events page for more details.

Photo courtesy of Michelle Esteban.

Michelle Esteban – Entrepreneur, event planner extraordinaire, world traveller, wife and mother

Location: Toronto and Curaçao

Industry: Hospitality

Professional title: Founder and Owner of The Occasion 

SC: What led you to pursue your career?

ME: Style, creativity and design enticed me. I love to take a clean slate and create dreams for events and experiences that I know will last a lifetime. As an event planner, my job is never the same twice and it does not involve sitting at at desk for long periods of time. Plus, you can literally work from anywhere.

SC: What has your career path looked like?

ME: As a teenager, McDonalds was my very first job. Working as a cashier for only a few short months until I convinced my boss that I would be better suited to plan the birthday parties. I started out in many different roles: executive assistant, marketing manager, communications manager… but I always enjoyed the different aspects of events.

SC: What is The Occasion?

ME: The Occasion is a global, luxury boutique event planning company that focuses on experiences and design.

SC: Your work-life includes a lot of travel with your children and husband. What’s that like?

ME: My husband is also in the hospitality industry which creates some beautiful conversations at the dinner table. Our travel is intense and when you have three kids in the mix it gets a bit more interesting (and makes for a great reality show!). A lot of sacrifices and compromises are made with our schedules but this is why family time is so important when we are all the same country.

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Trust in your friends and they'll have reason to trust in you~ • • • NOLAN. NOLE. Happy Birthday! Felix Cumpleaños! • • • Such an amazing human in every way. The support and the deep conversations with him is undoubtedly some of the best I've ever experienced. Some of my quotes, my LOL moments, my style consultant and my photography director, we are truly beyond blessed. Now if only he would authorize my Tik Tok account then I could continue to embarrass him…😊 • • • #happybirthday #april #boymom #birthdayboy #quotes #style #son #fashion #travel #instastyle #instafashion #fashioninspo #simplestyle #menwithstyle #family #lovemyfamily #caribbean #proud #streetstyle #stylelove #lifestyle #beautiful #melanin #styleinspiration #styled #ourstyle #styledbyme #love #me

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SC: What is the biggest lesson you’ve learned in your career to date?

ME: There have been quite a few lessons, but I would say knowing that my only competition is me.

SC: What obstacles have you overcome to get to where you are today?

ME: Deciding to start The Occasion was a no brainer, as I have worked so hard for so many years for some of the biggest tech giants in Canada, with little or no sleep to prove how amazing I was in this field. I remember flying from Maui to Rome and upon arrival, after over a day of travel mixed with a major time difference, I met with owners, executives and took notes. Then I had to be available for calls back in Canada. I have never felt exhaustion like I did at the time but also never felt so excited to be in the position I was in. It also reminded me that I was the biggest power negotiator but the lowest paid every where I went during this trip.

SC: What’s your biggest strength?

ME: Many would say its finding a great pair of shoes for an amazing deal but seriously, I believe it is seeing the best in every situation, personally and professionally. Pouring rain? Wow, I cannot wait to see the rainbow! Flight delayed? There is a reason for the delay and we are being saved from something or someone….

SC: What’s your biggest weakness?

ME: My biggest weakness is procrastination. I try to make things perfect, which causes delay. This is a constant work in progress and it drives me crazy. I’m aware of it, which is the first step… right?

Photo courtesy of Michelle Esteban.

SC: How would your friends describe you?

ME: I think the first thing that my close friends would say is that I am stylish, funny, light hearted and caring. Firecracker, motivational and have extremely high standards and expectations. They would also say I hold stress and emotions privately. Few make it to my inner circle but my outer circle does not exclude anyone. I have absolutely no time for ignorance and small minded people.

SC: How would your colleagues describe you?

ME: My colleagues would tell you that I like to work hard and have fun while working. Most of all, they’d say I am a true professional who is ambitious, a visionary, a trailblazer, and trustworthy.

SC: If you have one goal for The Occasion and one goal for yourself, what would they be?

ME: There are many goals for The Occasion. The first one that comes to mind is for the company to be one of the most sought after event companies globally. Whether it be for a company incentive celebration, a product launch, Fashion Week in Paris, the opening or closing games of the Olympics, a wedding celebration or the grand opening of a hotel, I would like to have the opportunity to bid. For myself, my goal is to continue to grow and learn so I can provide opportunities to my community.

SC: What are some personal career and business milestones you’re proud of?

ME: No matter how big or small, I am so proud of many things that myself and The Occasion have accomplished. Having a Top  Chef competition in Jamaica with two of the most famous chefs in Canada and two of the most famous chefs on the island, then immediately having the food brought to the tabes of 120 guests. Having a beautiful dinner at the Vatican was not too bad either.

SC: What advice would you give your 18-year-old self?

ME: Don’t date that guy! Seriously, it’s going to be ok. Slow down. If it as meant for you, it will not pass you. You will loose some friends, but don’t worry. They are teaching you how to be a better human. You will walk in a few blizzards in Alberta with no socks trying to be cool but, don’t do that – it will hurt really bad when you can feel your toes. That dream of you owning your own company and traveling the world? It’s not a dream. It can happen to a little Jamaican girl. Dream bigger because that dream did not scare you. Also, stop worrying about what people have to say about you. Opinions are not facts.

SC: From one Black, female entrepreneur and business owner to all those out there, what message would you like to send at this time?

ME: The past few months have been heavy for so many and especially for those of us in the Black community. I know with darkness comes light. However, do not quit. Stay focus and remember your why. It is easy to get lost in the heaviness of what’s going on around us, but we have to remember that every experience, good or bad, is one we leave with knowledge. We are in a place of opportunity, hope and awareness to move forward. If individuals are not extremely bothered and saddened by the injustice today, then they are not listening. Know these are not your people. Focus on the many who are now open to listen, to change, to let us sit at the table and give us opportunities. Please use this new awakening and go back and pitch to that company, that brand, that boss. Use your voice to let everyone know that you are qualified and that you are a badass. We will continue to lead with love and kindness.

Photo courtesy of Michelle Esteban.

STYLE Canada

STYLE Canada

STYLE Canada is a lifestyle destination that inspires modern Canadians to dress stylishly and live fully.

2 Comments

  • Avatar Ricardo Esteban says:

    Thank you so much STYLE CANADA for showing this fantastic ‘in and out’ of one of the most amazing women I have been blessed to meet, learn from, love and being loved by.

    As a husband, it is an honor and a privilege to have incredible Michelle’s soul beside me… She simply makes me a better person with every single one of her pure heartbeats and I cannot feel more proud of my wife, my soul mate, my inspiration, my life friend, my best alive poem, ‘mi amor’.

    To the ones that have had the magic opportunity of having become part of Michelle’s dreams… Congratulations…! To the ones who will have this amazing opportunity soon… You will discover and understand why Michelle is a unique diamond and always winner bet, professionally and personally.

    Ricardo Esteban

  • Avatar Suzanne Spencer says:

    What an amazingly inspirational story. I love the advice to your 18year old self… will have to share with some young ladies I know, and hope they take notes! But seriously, we need more of this zest for life, the passion in all that you do, and especially looking for those rainbows when situations seem bleak. This story also reminds us to raise the standards, get uncomfortable and dream bigger and prioritize quality time with those that you love. #inspiration #beautifulblackwoman

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