Unmuted: From Pop Star to Powerhouse Founder

"Promise me you'll come back through butterflies."

Anna Sinclair sat beside her father, squeezing his hand in his hospital room. She reached for a tissue from the box resting on the table beside him. A box splashed in bright butterfly print. It would now be their symbol.

As stage 4 lung cancer claimed his final breaths, it was how she wanted to remember him. In that moment, her journey from rising pop star to founder to award-winning agency CEO finally made sense.

Because that butterfly also described her own life: a series of metamorphoses, each demanding she fall apart before she could become something stronger.

"I had to keep shaping who I was and chipping away at who was  really underneath it all, a girl who simply wanted to make the world a better place.”

Becoming Anastasia A

Anna was six years deep into a psychology honours degree when a serious relationship fell apart.

"Probably the worst, most horrible breakup of my life," she says.

So horrible, she left school and moved back home. Something her fiercely independent self never wanted to do.

"I was the first woman in my family to attend college and university. I put myself through school, got my big break in the city," she says. "It felt like I had hit rock bottom. I lost my degree, I flunked my dissertation. Everything I worked so hard toward felt like it was slipping away, like things couldn't get any worse.

Writing music became part of her healing journey, but it was also her loudest dream, ever since she was a three-year-old singing on the karaoke machine her dad bought her.

“I would play my music for my father, and he always reminded me I could do better, be better. I never felt good enough." So she poured herself into it.

After sending countless Facebook messages, Anna caught the attention of a successful radio programmer. The connection led to backstage access, introductions to industry players, and eventually a full-time rotation on Disney and Family Channel.

With Family Channel offering national exposure, Anna secured a manager, filmed her first music video, and earned the opportunity to operate her own label through Universal Music Group.

Her first Juno-nominated album set the tone, working alongside a team of 15 people, including stylists, choreographers, publicists, and musicians.

“We've all come from
the ugly worm to the
uncomfortable cocoon,
and now we're flying."

Anastasia A spread messages of positivity on screen and on tour. Songs like Kiss & Tell and Sparks Fly, and her performance of her song Believe at WE DAY, left a mark in ways she never anticipated.

"There were little girls and little boys DMing me, saying, 'I'm alive because of you.' I remember thinking, this is bigger than music."

But she also felt pigeonholed.

Almost 20 years old, Anna was discovering herself as an adult woman.

"There was immense pressure to say and do the right thing at all times because little girls were watching everything you did," she says. "But to labels, executives, and media, you had to be bigger than life. The brand had to be sellable. The constant pressure for the next hit, the next headline, the next opportunity was exhausting."

And pregnancy was not considered sellable.

Anna found out the hard way when she shared the news that she and her husband, Brandon, were expecting. It was the hardest stop of her career.

"No one's going to sign a pregnant pop star. How are you going to shoot a music video with a big belly? What if you love your baby more than this contract? All of those things that were said to me deeply rattled my cage."

And just like that, Anastasia A's microphone was gone.

Becoming Total Mom

Anna felt like she lost her voice when she lost that contract.

She and Brandon moved into his parents' basement while they figured out what came next. She mourned her music career while embracing motherhood. At times, it felt like two waves crashing into each other.

She was lost.

Then she attended a baby show in Toronto. When she got home, she dumped thousands of dollars' worth of gifted products onto the floor. I thought, wait a minute. Everything is for the baby. What about the mom?"

No one seemed to notice the gap. She couldn't look away.

"I couldn't stop thinking about how many ambitious, career-driven women were being left to figure it out on their own. Who was helping them? Not the mommy groups. And definitely not mainstream media."

Total Mom was born in 2018 to show women that they can be the CEO of their life and their business.

But while Anna was teaching people to honour their identity, she was losing touch with her own. "On the outside, I had it all together. I was scaling a business by 400 percent, winning awards, navigating a buyout, surviving a pandemic, and trying to hold everything together."

Anna spent years hiding her childhood as a two-time refugee, and her struggles with Premenstrual Dysphoric Disorder and PTSD. She buried the pandemic’s mental health toll and the injury that nearly left her unable to walk.

"I almost lost myself in the idea that I was the Total Mom, and then life happened. I felt like a fraud. What I was really feeling underneath was loneliness, pain, and fear. I was too scared of the stigma and of losing business to share that with the world."

It would take losing Total Mom to finally break free.

Becoming Anna Sinclair

At its height, Total Mom supported over 9,000 founders and generated more than 65 million media impressions through Canada's Total Mom Pitch and related programming.

One email changed everything.

A contract representing 70 to 80 percent of annual revenue was not renewed, which forced Anna to significantly restructure the business. She could have viewed it as a failure. "The truth is, if we don't fall flat on our face or get stung hard, we don't get better at building resilient businesses," she says. "It took shifting all of my beliefs around failure, accountability, debt, and letting go to discover an entirely new level of success."

Once again, Anna was back at square one, building something new with Sinclair Creative Agency.

Starting over wasn't easy. Keeping it going in today’s economy is even harder. "All the successes and recognitions I'd received were tied to Total Mom," she says. "It took trust, credibility, and proving myself all over again. Starting fresh in a male-dominated industry was a huge leap." 

She had an advantage this time: 15-plus years creating events and experiences in entertainment and branding. 

Still, something held her back. "It hit me that I felt shame around things that weren't my fault. I wasn't fully confident telling the world that one chapter had closed and another had opened, and I didn’t want it to discredit my talents and skills."

"And when he passed away, he finally said the words I had spent my entire life waiting to hear: 'Everything that you have accomplished today was because of you.' "

Losing her father was a massive awakening. So was finally confronting the things she had carried for most of her life. "I wasn't ready to face the ugly truth and the messy parts."

She is now.

"I can put my feelings, my experiences, and everything I've learned into helping clients. I can be in front of the camera or behind it. I can build brands, create experiences, dream big, and bring those dreams to life."

Becoming Free

Today, Sinclair Creative Agency produces award-winning events, campaigns, and partnerships for brands across North America. Canada’s Total Mom Pitch is returning for its seventh season, bringing back the "Mother of All Pitches" after taking a pause following her father's passing.

Both are part of her metamorphosis.

"We've all come from the ugly worm to the uncomfortable cocoon, and now we're flying. We're finding our mark, and we're leaving that mark on the world."

Anna is reminded of this every time she sees a butterfly, whether it’s a tattoo on someone's arm, an ad on a bus, a piece of décor.

She still keeps her father's butterfly tissue box. It reminds her of where she's been and who she's become. 

"Leading up to his death, I was always trying to prove myself," she says. "I just wanted his acceptance. And when he passed away, he finally said the words I had spent my entire life waiting to hear: 'Everything that you have accomplished today was because of you.'" 

Through the grief, those words brought release, freedom to be herself fully. A metamorphosis that shattered her and rebuilt her into something stronger. 

"That's what I think is so beautiful about a butterfly. Once it learns to fly, nothing can convince it to crawl again."