Five Things I Learned Leaving Television For Entrepreneurship

Written by Dawn Chubai, Live Shopping Strategist

Dawn Chubai is an award-winning broadcaster (Breakfast Television & The Shopping Channel), and founder of Live Selling School. After generating more than $250 million in live sales and spending over 40,000 hours on live television, she now helps brands harness live shopping, video commerce, and on-camera communication to drive growth.

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I had built the kind of television career that, from the outside, looked difficult to walk away from. I was an award-winning broadcaster and national television host for nearly 25 years across two major Canadian broadcasters (Breakfast Television on CityTV and The Shopping Channel). I had recognition, credibility, tenure, a high income, and a career I had worked incredibly hard to create. By most conventional measures, I was still succeeding.

That is what made the decision so complicated. Career reinvention is often portrayed as something forced upon us by a layoff, a failure, or a sudden ending, but sometimes nothing is visibly wrong. You are still performing well, still being paid, and still admired for what you do. Yet beneath all of that success, you begin to sense that the life that brought you here may not be the life that will carry you forward.

I was not disillusioned with television or ungrateful for what it had given me. I was beginning to wonder whether everything I had learned could be used in a way that was no longer dependent on one role, one employer, or one platform. The safest decision would have been to stay where I had security and continue benefiting from everything I had earned. Instead, I chose to find out whether the experience, instincts, and expertise I had developed could create value in a business of my own.

This is not a prescription for anyone else’s career. It is simply what I learned when staying began to feel less like choosing my future and more like holding on to my past.

1. I had built the career I thought I was supposed to want forever

For nearly 25 years, success looked exactly the way I had been taught it should. I was on television, people recognized me, and my presence could bring a genuine sense of excitement to a room. There was something special about arriving at an event and seeing how much it meant to the organizers that “Dawn from Breakfast Television” was there to cover it.

I attended high-profile events, appeared in society pages, dined in beautiful restaurants, and had access to experiences that were easy to interpret as proof that I had made it. I enjoyed the recognition and would be dishonest if I pretended otherwise. Being known opened doors, created opportunities, and allowed me to be part of some extraordinary moments.

What fulfilled me most, however, was what that recognition could do for someone else. My coverage could bring attention to an event, give a business credibility, support a cause, or help a public relations team deliver the exposure it had promised. I wanted the organizer to feel that my presence had mattered and that the invitation had produced something valuable for them.

I loved being able to use my platform to make other people feel seen and to shine a light on the work they were doing. Over time, I began to understand that fame itself was never the destination for me. It was most meaningful when I could use it in the service of someone else.

For years, I assumed I was supposed to keep wanting more visibility, more recognition, and more evidence that I had succeeded. Eventually, I realized that what I wanted most was not simply to be known. I wanted to be useful. Recognition created access, but creating value was what made that access matter.

I wanted the experience to become the next thing

As I began thinking about the next part of my life, the question was no longer whether my television career had been meaningful. It absolutely had. Television shaped me, challenged me, and placed extraordinary people in my path. It taught me how to connect with an audience, communicate clearly, and build trust quickly.

My years at The Shopping Channel (Canada’s version of QVC or HSN) added another layer. I was no longer only communicating with an audience, I was watching people make buying decisions in real time. I learned how to translate product features into meaning, anticipate hesitation, create urgency without losing trust, and help someone feel confident enough to act. The sales were measurable, but so were the human behaviours behind them.

That experience became the bridge to what I do now. I began to realize that the most valuable part of my career was not simply that I had been on television. It was what decades of live broadcasting, and especially live selling, had taught me about communication, trust, and commerce.

For years, the platform and my contribution had been intertwined. I created value through the audience, cameras, and credibility of a major broadcaster. Eventually, I began to wonder what might be possible if the expertise itself became the focus.

The misalignment was not that I no longer valued television. It was that I had become increasingly interested in taking what television, and The Shopping Channel in particular, had taught me and applying it beyond one program, one network, or one product at a time. I wanted to shape it, own it, and share it more directly with founders and brands.

2. Nothing was wrong, but something no longer felt right

One of the hardest things to explain about this transition is that there was no single dramatic moment when everything fell apart. I was not running from failure. I was still performing well, meeting targets, earning bonuses, and benefiting from the security of a long-term career.

Even when my personal circumstances changed and maintaining the role required commuting from Vancouver to Toronto, I held on. I had worked too hard to reach that point to walk away casually. The job represented years of effort, sacrifice, and achievement, and I felt a responsibility to protect what I had built.

The people around me could reasonably look at my situation and wonder why I would ever leave. I had tenure, a dependable paycheque, and a professional identity that people immediately understood. The conventional advice would have been to stay, appreciate the security and “milk it for all it was worth.” Yet something in me kept resisting that conclusion.

Success can become a holding pattern

Eventually, I had to ask myself whether I was staying because the career still represented my future or because it validated my past.

That was not an easy question. My identity had been tied to being chosen by broadcasters, networks, and decision-makers for a very long time. Their approval shaped the opportunities available to me and, at times, influenced how I measured my own value.

I began to realize that I was not simply preserving a job. I was preserving a version of myself who still relied on an outside institution to determine what came next.

The career was not wrong, and it had not suddenly lost its value. What had changed was my sense of what I wanted to build next. I could see that staying indefinitely might preserve the identity I had worked so hard to create while leaving too little room for the ideas, ambitions, and contributions that were beginning to emerge.

That is a complicated kind of ending because there is no villain and no obvious crisis. There is only the growing recognition that what once fit beautifully may no longer fit the person you are becoming.

3. I had to separate my expertise from the platform that first amplified it

When I first considered entrepreneurship, part of me assumed that the visibility, credibility, and relationships from my television career would naturally carry me into the next chapter.

Those things gave me a valuable foundation, but they could not define the new work for me. I still had to explain the idea, establish my authority in a different context, and prove that the knowledge I had built could create value independently of the role people already associated with me.

That was humbling. I had spent years building a strong professional identity, only to find myself explaining a new vision in rooms where people did not yet understand the opportunity I could see.

I was no longer simply the television host people recognized. I was becoming a founder, strategist, educator, and advocate for a developing form of commerce that many businesses had not yet explored.

I also had to release the belief that the fame and professional relationships from my past would automatically build my future. Being known for what I had done did not guarantee that people would immediately understand what I wanted to do next.

The platform was the classroom, not the source of my value

The shift came when I understood that television had been the place where I developed my expertise, but it was not the owner of that expertise.

My ability to communicate belonged to me. My understanding of trust and human behaviour belonged to me. My experience watching people make buying decisions in real time belonged to me. The instincts I had developed through years of live broadcasting and live selling did not disappear when I stepped outside the studio.

The platform had been the classroom, but the education was mine. That realization allowed me to stop seeing entrepreneurship as a complete departure from my past. I was not discarding everything I had built. I was taking the most valuable parts of it and applying them in a way that gave me greater ownership over where they could lead.

I no longer needed my former title to be the entire explanation for my value. The career had given me credibility, but the expertise behind that credibility was what I could carry forward.

4. I could see an opportunity that the existing system could not fully hold

As the media and retail worlds continued to change, I became increasingly interested in what was happening at the intersection of video, commerce, and human connection.

I could see that consumers were not simply looking for more content. They wanted better ways to understand products, see them in context, and feel confident about what they were buying. Research now supports that instinct. PowerReviews found that 60% of shoppers always seek out visual content before making a purchase, reinforcing the importance of helping customers see and understand a product before they decide.

To me, live shopping was not merely another platform or passing trend. It was a new expression of something I had spent my career learning firsthand: people are more likely to act when they feel informed, connected, and able to trust the person guiding the experience.

The more I explored that possibility, the more I understood that my vision would never be fully developed within the limits of my existing role. Traditional television has given me an extraordinary foundation and a powerful way to reach people. What it could not give me was the freedom to take everything I had learned and apply it directly across different founders, brands, platforms, and emerging technologies.

If I wanted to help move the idea forward, I needed the freedom to test new approaches, work with different businesses, teach what I knew, and build a body of work that was not dependent on one employer or one paycheque.

This was not about rejecting television. It was about recognizing that the next expression of my work would have to be something I built myself.

You can build around an idea people do not yet understand

This was perhaps the greatest leap of faith. It is much easier to build a business around something the market already understands. People know what a publicist does, what a personal trainer does, and what a traditional marketing agency does. The live shopping strategy was far less familiar.

I had to become comfortable explaining the opportunity before many brands were actively looking for it. I had to trust the patterns I could see, the data that supported them, and the experience I had accumulated long before the market offered widespread validation.

That did not mean assuming I was automatically right about everything. It meant being willing to test the idea, gather evidence, and continually refine how I served the people who were ready to explore it.

The business was not built because everyone immediately understood my vision. It was built because I understood it well enough to begin.

5. The first new proof showed me my expertise could stand on its own

There is a strange period in entrepreneurship when the achievements from your previous career are highly visible, while the evidence supporting your new direction is still very small.

One of my first brave steps was putting myself forward to speak at the Social Pacific Conference. I was entering a space where I was not yet widely known for the work I wanted to build. Later, I sold my first Live Shopping course and signed my first one-to-one client.

Those moments were different from the public milestones of my television career. They were quieter and far less visible, but they answered a question I urgently needed answered, would someone invest in the knowledge, frameworks, and experience I had built when they were no longer packaged inside a familiar television role? The answer was yes.

Those early milestones proved that people would pay for what I knew, what I had built, and what I had experienced firsthand. They showed me that my expertise could create value independently of my employer and that the next chapter did not have to depend on reminding people where I had once been successful.

New evidence gave my experience a life beyond television

That first course sale and first private client gave me a different kind of validation. It was not the validation of being selected by an established institution. It was the validation of creating something myself and having another person see enough value to invest in it.

Entrepreneurship required me to develop a new relationship with proof. In television, proof often came in the form of ratings, renewals, awards, sales targets, and recognition. In business, proof could be one person saying yes, one client achieving a result, or one idea working well enough to repeat.

Those quieter wins helped me stop comparing the early stages of my new business with the peak of my former career. They gave me evidence that I was not simply walking away from something. I was building something.

They also confirmed that my experience could have a life beyond television. The work I had done for decades had not disappeared. It was becoming the foundation of something I could finally own.

What I now understand about potential before proof

Many of the most meaningful opportunities in my life began when someone saw qualities in me before I had the experience or formal credentials to prove what I could do.

Someone believed I would be good at something, gave me the opportunity, and allowed me to grow into it. I responded by putting myself around people who knew more than I did, watching closely, asking questions, learning quickly, and executing.

The confidence did not always come first. Sometimes I borrowed belief from someone who could see the possibility more clearly than I could. Action then gave me evidence, and the evidence eventually became my own confidence.

Today, I recognize a similar pattern in the brands I work with. A founder may not yet believe live shopping could work for their business because they have never experienced it. However, I can look at the product, the customer, the founder’s knowledge, the demonstration value and the available data and recognize when the ingredients are present.

That belief is not a guarantee, and it is not empty encouragement. It is an informed assessment based on experience, evidence, and pattern recognition. My role is to help the brand turn that potential into something measurable through strategy, preparation, and execution.

In many ways, I now offer brands what other people once offered me, an experienced perspective on what may be possible before all of the proof exists.

This is not a story about telling everyone to leave

I am not suggesting that feeling restless means someone should resign from a successful career or that entrepreneurship is the right next chapter for everyone. I am not a career counselor, and I would never pretend that my path provides a universal answer.

I also did not leave because television had become meaningless to me or because I suddenly rejected the recognition that came with it. I left because I had begun to see another way to use everything the career had taught me, and I knew I would have to build that opportunity myself.

I can only share what became true for me. Staying had started to feel more frightening than leaving because I could see that I was protecting the person I had been rather than making space for the person I was becoming. I knew I had more to contribute, and I no longer believed the existing structure would allow me to explore it fully.

Perhaps someone reading this is experiencing a similar kind of misalignment. Everything may still look successful from the outside. Nothing may be visibly broken. Yet there may be a quiet sense that the future is asking something different of you.

That feeling does not always require a dramatic decision. It may simply deserve your attention. You do not have to know exactly where it will lead before you begin asking what it is trying to tell you.

What leaving television made possible

I did not leave television because I had failed there. I left after building a career I was deeply proud of, learning from remarkable people and developing expertise that continues to shape everything I do.

The decision was not about rejecting the past. It was about refusing to remain dependent on it. Leaving allowed me to take everything I had learned about communication, trust, selling, and human connection and use it to help founders become the trusted influence behind their own brands. It gave me the freedom to build around an opportunity that many people did not yet understand and to work directly with businesses ready to explore what was possible.

I once thought my large reach would be my greatest asset. Today, I know that meaningful impact does not always require the largest audience. Sometimes it comes from helping one founder see a possibility, giving one brand the confidence to try something new, or helping one person stop outsourcing the trust only they can build.

Television gave me a platform through which I could create value for others. Entrepreneurship gave me ownership over how I could use the expertise behind that value, who I could share it with, and what I could build from it.

Today, I help founders and product-based brands explore the potential of live shopping, shoppable video and founder-led selling. To learn more about how brands can stop outsourcing trust and become their own influence, visit Live Selling School.

Follow me on Facebook and LinkedIn for more info!

Read more from Dawn Chubai

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Dawn Chubai, Live Shopping Strategist

After spending more than 40,000 hours live on television and generating over $250 million in sales, Dawn Chubai now helps brands apply the same principles that drive successful live selling to modern ecommerce. As the founder of Live Selling School, she works with businesses to leverage live shopping, video commerce, and audience engagement to compete in the trillion-dollar social commerce economy.