We were lucky to catch up with Anna Sinclair recently and have shared our conversation below.

Anna, appreciate you joining us today. How do you think about spending on things like coffee when times are tough?

Reflecting on my journey, I realize how my initial reluctance towards spending on self-care and indulgences was deeply rooted in a ‘don’t spend’ mindset. At the outset, I failed to grasp the significance of investing in my well-being and how it directly impacts my confidence and professional growth.

In the first few years of my business, I was far more apprehensive about spending money of specialty coffees and self-care-related spending. My mindset was quite different and I truly didn’t comprehend yet how much treating myself and investing in self-care was important.

This “don’t spend” mentality actually led me to even not pay myself and I now see how important it is to reinvest in my lifestyle, and quality of living and contribute to the ongoing feeling of abundance. For example, I didn’t realize that my money mindset was hurting my confidence and the more I avoided treating myself to things, the more I subconsciously felt like I was not advancing with the business enough to do so.

In hindsight, I see how a money mindset played a part in my growth and that when I shifted my thoughts around investing into expenses that brought me joy, that the confidence also brought results and the return on investment was always much greater! For example, a 6 dollar Starbucks has brought me hundreds of thousands of when that coffee hits right, I feel fabulous and ready to close a sale!

I know it sounds ridiculous but that rings true for trips and massages…my CEO trips do wonders for the company’s bottom line. I always come back from my CEO trip with a massive return. Why? I think the entire trip reminds me I am successful, making it happen and pushes me to do/ask and create amazing returns.

In essence, my journey has taught me a valuable lesson: investing in self-care and indulging in small luxuries isn’t just about personal satisfaction—it’s about nurturing a mindset of abundance and empowering oneself to achieve greater heights. By embracing this philosophy, I’ve not only elevated my confidence and productivity but also witnessed tangible returns in both my personal and professional life. As I continue to evolve, I remain committed to prioritizing self-care and investing in experiences that enrich both my well-being and the success of my endeavours.

Anna, love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations?

So my name is Anna Sinclair. I am an award-winning entrepreneur, angel investor, and CEO of Total Mom Inc, a professional network & platform supporting women founders to start and grow their businesses with a 65M annual reach serving 25k+ members.

My journey began in the entertainment industry, where I was signed as a pop singer to Universal Music Group and Disney, and worked as an actress and casting director. Transitioning from entertainment to entrepreneurship was pivotal to my success. I lost a major record deal because I was pregnant and essentially in response, started an organization that focused on equality and support systems to women juggling motherhood and their business.

Total Mom started as a festival for moms -the first of its kind in Canada and then evolved into a professional entrepreneur platform that empowers women personally and professionally through our events, programs, business summits, and initiatives aimed at supporting mothers in starting and growing successful businesses and curating a lifestyle that’s unique to them.

Coming from humble beginnings as a two-time immigrant and refugee, I started my entrepreneurial journey by establishing a small business in my husband’s parents’ basement with a newborn. Today, I proudly serve as the CEO of an award-winning company that collaborates with major brands across North America.

My professional community network and online e-learning platform has a strong focus on enhancing social and financial capital for working parents. Over the past five years, my commitment to women’s empowerment has earned me recognition as one of WXN’s Top 100 Most Powerful Women in Canada, solidifying my position as a leader and influencer in the Canadian business landscape.

I am also the founder of the Canadian Women Entrepreneur Industry Gala (CWEs), a groundbreaking event that brings together industry leaders, founders, creators, and media to create opportunities for women. Through my visionary approach and disruptive mindset, I strive to ensure that more women have a seat at the table, revolutionizing the gala experience and fostering inclusivity within the industry.

With a wealth of experience working with over 350+ brands, I possess the knowledge and expertise to guide projects from conception to execution. Through my firm, Sinclair Creative Agency Inc., I provide consulting services to individuals and consumer lifestyle brands, specializing in branding, business strategy, content marketing, and asset development.

Can you tell us about a time you’ve had to pivot?

I learned quite a lot about pivoting and taking big leaps from the pandemic. The entire situation from 2020-2021 was eye-opening for me. We were on this upward trajectory, dreaming big about taking our festival on a cross-country tour. But then, bam! The world hit pause, and suddenly, our plans were dashed. Events were cancelled left and right, and we found ourselves staring at some serious financial challenges.

I’ll be honest, going back to the drawing board wasn’t exactly what I had in mind. But you know what? It ended up being a blessing in disguise. It forced us to get creative, to think outside the box, and to dig deep into what mattered most. I thought we’d be brainstorming ways to dig ourselves out of debt, but instead, we found ourselves asking a bigger question: How could we step up and support our community during this tough time? It was like a lightbulb moment.

The support poured in, not just from sponsors, but from our entire community. It reminded me why I started this journey in the first place – to make a difference, to uplift others, and to show that even in the toughest times, we can come together and thrive.

Looking back, I realize that sometimes the biggest challenges can lead to the most profound growth. The pandemic forced us to pivot, to adapt, and to find strength we didn’t know we had. And in the end, it made us stronger, more resilient, and more connected than ever before.

How did you put together the initial capital you needed to start your business?

When it comes to funding my business, it’s been a journey of sacrifice, determination, and a deep commitment to our community. Instead of drawing a salary for myself, I made the conscious decision to reinvest every penny back into the business, particularly focusing on initiatives and programs that served our community. This approach not only allowed us to keep our overheads low but also provided the flexibility to pivot, innovate, and grow.

While I wouldn’t necessarily recommend forgoing a salary to others, it was a personal choice that aligned with my values and motivations. You see, for me, success isn’t measured solely in monetary terms. It’s about making a meaningful impact, creating opportunities, and fostering positive change within our community. And I found that by prioritizing the needs of our business and community over personal financial gain, I was able to achieve a sense of fulfillment and purpose that far outweighed any monetary reward.

Of course, there were times when I needed additional capital to fuel our growth. In those instances, I turned to small loans and bootstrapping, leveraging my skills in design, marketing, events, and sales to generate revenue and support our endeavors. It was a testament to the resourcefulness and resilience of our team, and I’m grateful for the opportunities that came our way.

Looking back, I wouldn’t change a thing. The journey may have been challenging at times, but it’s been incredibly rewarding to see the impact we’ve been able to make and the lives we’ve been able to touch through our work. And for me, that’s worth more than any paycheck could ever be.

Contact Info:

• Website: www.sinclaircreativeagency.com
• Instagram: @annasinclair.ca
• Facebook: https://www.facebook.com/AnnaSinclair.ca
• Linkedin: https://www.linkedin.com/in/annaasinclair/
• Other: www.annasinclair.ca , www.totalmom.ca , www.totalmompitch.ca , www.cwegala.com

Image Credits
ASHLEY KLASSEN