April 1, 2019

“I just woke up and said, ‘I’m going to be victorious.'”

Michelle Osbourne
Michelle Osbourne

Meet Michelle

My name is Michelle Osbourne and I’m turning 45 this September. I’m originally from Toronto (born and raised) and moved to Quebec City 5 years ago. Around the age of 38-39, my partner of 12 years said she was no longer in love with me and wanted to move on. It was hard but things had been tough for a while. I think it just took one of us to have the courage to let it go. So it was nobody’s fault, it was hard at the time, but looking back it was the right decision. Three months later we sold our house and I moved into a 700 sq foot apartment. I had a huge huge job in Toronto, a great life, lots of travel, money, and things and now I’m in this little apartment, sleeping on a blow-up mattress and not knowing where I was going to go.

One morning I just woke up and said, I’m going to be victorious, I am not going to be a victim. I started a blog called 40×40 at the age of 39 and I said I’m going to do 40 things I’ve always wanted to do by the age of 40. I completed about half of the list. But the purpose of the blog wasn’t to finish all 40 but the process of what I gained doing all these things. After that blog, I was on top of the world. I started to create this dream life on my own. And that’s how my midlife reinvention began. Things I thought I couldn’t do but felt forced to do –  because now I had put this blog out there telling everyone I was going to do it — made me feel courageous and powerful and it gave me the strength to do things I never thought I could do. At the beginning of the blog, I went on vacation by myself which was on the list and I ended up meeting my partner on vacation. I was really happy being by myself, really for the first time in my life since I was 14 years old, and so I wasn’t looking for a relationship. But, you know how love works. We dated long distance (she is from Quebec City), visiting one another until we decided that I would move in with her for a year to see if we liked each other enough to stay together. After a year we decided I would give up my job and move to Quebec City because she would have lost her seniority if she had moved to Toronto.

You must know French to live in Quebec City and I did not know French. I started my life from scratch. I enrolled in school from 8 AM to 4 PM, five days a week. I did that for a full year and got a certificate from the University. Now I’m fully bilingual and can have conversations but I would have had to have another ten years of French to be able to get a job at the level I was at in Toronto. I even tried to get a job at Target and they said my French wasn’t good enough! So I decided to reinvent myself and use my skills from being a communications, administration, and governance professional working with presidents and doing big things. I thought I would use that to recreate myself and offer my services. And now I have a successful business helping companies reinvent themselves and coaching entrepreneurs on social media. And, I do it all in English!

I wouldn’t have been able to do any of this in my 20s or 30s. Those are the figuring it out, impressing other people, trying to look good years. It took me having those experiences to be clear about what I could offer and what I would accept in return.

Now I have a new blog called, Uncomfortable Bliss, all about the bittersweetness of having to reinvent yourself and all of the challenges that come with that and how it’s wonderful at the same time.

The biggest part of the journey has been about being courageous, because I’m sure a lot of people were like, “Michelle, are you crazy? Why would you want to start at zero again?” I thought, “what do I have to lose? I can stay in Toronto and do what I’ve always done or I can embark on this adventure and have something really amazing happen”.

I think a lot of people focus on what if something goes wrong but don’t focus on what if something goes right. I decided to focus on what if something goes right. And if it doesn’t then I’ll move back into my amazing apartment and I’ll get an amazing job back in Toronto and who cares!?

What would you say has been the biggest shift in your life since turning 40?

After 2 years together, at the age of 42, we decided we would have a baby and that I would be the one to carry the baby, which is a conversation we had to have because we’re both females. It took us less than 6 months for me to get pregnant which was a huge surprise because of my age. I now have a 2-year-old perfectly healthy, strong, and magical being in my life.

That was a big shift! First of all, I couldn’t have had her before that. I just mentally wasn’t there. I was having a great time waking up when I wanted to, traveling when I wanted to, doing what I wanted to when I wanted to. So my whole life, since I was 5 years old I said no children, I’m not interested. I just want career and travel and that’s it. And at 38 when my marriage was breaking up I started feeling it and I said to myself please don’t feel this because your marriage is on the shits and finding someone who you connect with and want to have a baby with after 40 is like a needle in a haystack. And it’s funny how the universe works. I truly believe that I’m living this life because I was able to take a moment for myself and enjoy being by myself and celebrating myself. I think a lot of times, when you’re searching too hard and you’re desperate and you want, want, want that’s when it doesn’t come. I had such a good time just enjoying myself that my life filled with all of these things because I made space for them.

When do you feel you are most powerful?

I feel most powerful when I’m being authentic. And it doesn’t matter what I’m doing.

When I first started blogging, I was doing my checklist but I was also like “should I do it like this person? Or should I do it like that person? Or this is what people are looking at so maybe I should do it like that.” So even though I was doing this blog and loving it I still wasn’t 100% authentic. Now when I’m on my social media or taking pictures or showing myself in my bra and panties with cellulite and my boobs hanging out and I just feel like this is me and this is how I feel inside and you’re seeing how I feel inside on the outside.

So I’m powerful when I’m feeling proud, talking about what I want to talk about, not feeling nervous talking about how I’m a queer person with a child. Now I celebrate it. I don’t think I ever hid it but I wasn’t as vocal about it as I am now. Because it’s a big part of my life. I have to raise my child, who is biracial – in a city that doesn’t like people of colour or anglophones – with two moms who are interracial. So now I have to have the power and the strength to raise a child in this environment. Hopefully, when she becomes a certain age it won’t be so bad but I think about these things, so if I’m not authentic with myself how can I teach her to be authentic? Every day I think about how awesome it is that I get to live my truth and be authentic about it and I feel like a superwoman. I put on my red lipstick, and I have my bald head, and I feel like I have superpowers.

What are the top three most important things to you right now?

My daughter, myself, and the life I’m creating with my partner and my child.

When I was younger it was all about my career and how much I can do and now it’s all about how do I make sure I live in this space of peace and love?

How do you make sure your actions are aligned with what’s most important to you?

It’s tough. My life is such a balancing act. I’m an entrepreneur trying to do my own projects and also trying to make sure I have space for my family and it’s difficult. Just learning how to be present for my family while still being able to be okay to say I want to do stuff for myself too.

There are times when I recognize that I’m spending a lot of time doing my stuff and I’m not paying enough attention to the other side and then I just stop. Sometimes I just stop. I don’t do any of my projects because I just want to spend time with my family. And then I’m like, okay I’m going to take a little time today but I’m going to schedule it in my day and the rest of the time I’ll spend with my family. But I don’t really have the answer because I still figuring it out. Just like so many women are trying to figure it out.

I really thought I would stay home with my daughter until she was at least 3-years-old but I missed working so much. Not that I didn’t love my daughter but I missed having something for myself. I went through the struggle between being a stay-at-home and a working mom and I had a breakdown. I asked myself should I feel bad for wanting something for myself? And the answer is no because I can give her so much love and support it’s ridiculous and I think there is still room to give stuff to myself. But, I don’t know exactly how to balance it. I just do the best I can.

That’s another reason I’ve set up my work so that I can call my own shots. Because if she’s sick I want to be home. If I don’t want to go into the office I don’t want to feel guilty about it. So if I can’t work like that in my life I won’t take the job anymore.

What seeds are you planting today for the future?

All I want to do is speak my truth and have a voice and help people get inspired by my story and my journey.

What advice would you give someone who is interested in redesigning midlife?

I have six steps that helped me redesign my life:

  1. Embrace minimalism.
  2. Learn and practice Emotional Intelligence.
  3. Do things by yourself especially when you’re afraid to.
  4. Move (if you can) somewhere where no one knows who you are so you can start fresh.
  5. Experiment more sexually.
  6. Remember that nothing lasts forever (the good and the bad).

I think the biggest part is not to care what other people think. You can either be nervous about what everyone is going to say and live with regret or get over what everyone else is going to think and shine and have this amazing life. You kind of have to shit or get off the pot. There are times when I wonder what people are thinking about what I’m doing and then I get myself out of it right away.

So get out of your own way and go for it and if it doesn’t work, it doesn’t work. That’s when you go to plan B and plan C and plan D because so much of time plan A doesn’t happen the way we think it will.

How can people connect with you and your work?

People can visit my website michelleosbourne.com and follow me on Instagram at @uncomfortable_bliss.

Welcome to my Power Profiles Series

Here I introduce you to powerful midlife role models in our community. May these stories inspire you, motivate you, and show you what is possible.

Sara Smeaton Coaching SS-177 Photo by Marina Dempster
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I'm here to reclaim the term 'midlife' and embrace the power these years offer us.

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1 Comment

  1. Sarah Lang on July 23, 2019 at 9:15 AM

    Holy cow!!! What an inspiration you are, Michelle!! Fabulous story and interview. Thank you for sharing your truth with us.

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Sara Smeaton Coaching SS-177 Photo by Marina Dempster


Sara Smeaton

Sara Smeaton is a certified professional coach and facilitator who partners with people in their middle years to help them grow and thrive personally and professionally. She works privately with clients in Canada, the US and the UK.

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