Krista Monson on Curiosity, Courage, and Turning a Life Well Lived into a Living Legacy Posted on August 10, 2026August 7, 2026 By Kekeletso Nkele, small.news Assistant (small.news) — On August 5, 2026, Krista Monson, Founder of Sincerely Yours, joined our small.talk to share how a career spanning dance, theatre, Cirque du Soleil, and Madison Square Garden led her to her most personal work yet — helping people preserve their life stories as living memoirs. Krista joined Silver Lining Founder and CEO Carissa Reiniger to speak about the power of curiosity over fear, the courage it takes to listen inward rather than seek outside validation, and why she believes the biggest gift we could give every small business owner is to stop calling what they do “work” and start calling it contribution. Q: How has your career formed over all these years to arrive where you are now? A: I grew up in Edmonton, Alberta. As a young person, I was a performer and dancer. I also pursued a degree — not as a backup plan, but because I was passionate about learning. I fell in love with the French language. In Western Canada, French immersion was rare, so I stood out for my interest. Learning a new language opened a window into other cultures and new ways to understand and express oneself. I earned a degree in French as a second language, returned to performing for a while, and then began my professional journey as a choreographer and producing director. My work took me across Canada, from Halifax to Vancouver. The highlight was choreographing the opening and closing ceremonies for the 2001 IAAF World Championships in Athletics — the third largest sporting event in the world and its first time in North America. This was a huge challenge and introduced me to a new genre — blending sport with storytelling. Around that time, my husband, a musician, and I had a one-year-old son. I loved the city and the growth it offered from a theatre perspective. I was teaching at a college, but even at 30, I didn’t want to be a big fish in a small pond. I craved new experiences, so we took a leap. At the airport, I ran into a family friend whose daughter was on the Canadian Synchronized Swimming Team. She remembered reading about me in our hometown paper and thought I’d be a great fit for Cirque du Soleil. Top Stories Two Mexican Banks Direct Capital Toward Renewable Energy and Nuevo León’s Small Businesses Two of Mexico’s active commercial lenders announced financing initiatives in the final days of July targeting distinct but strategically significant sectors of the economy — renewable energy infrastructure and small business growth in the country’s leading industrial state, reports Mexico Business News. New Zealand Labor Unveils $1.56 Billion Small Business Package — With a Significant Trade-Off at Its Core New Zealand’s Labor Party has released a small business policy package — costed at $1.56 billion over four years — as part of its 2026 general election platform, reports Business Desk. From a Mother’s Recipe to Myanmar’s Modern Trade: How Royal Manizawta Reinvented a Family Balm for a New Generation In 2007, a mother in Yangon received a formulation from a traditional medicine doctor in Taiwan—not as a business plan, but as a remedy for her own daughters, who suffered from skin rashes and allergic reactions to conventional analgesic rubs. Q: Do you feel like it was hard to evolve? A: I get bored quickly — that’s one thing I’ll say honestly. I love new challenges. In French, impatience means excitement to do something next. I always like trying new things, and I don’t rest in one place for too long. Some people do, and that’s great. But I like to go to places where I can help figure things out. The evolution wasn’t something I planned. It wasn’t “I’m going to reinvent myself next year.” It happened by invitation — but it was never random either. Q: What prompted you to start this business? A: I created what I now call Sincerely Yours Memoirs — a service for individuals, and a separate offering for founders, leaders, and what I call unicorns. What I’m dedicated to doing is helping people, primarily older adults, recreate their life story in the form of a living memoir or personal documentary. It’s both a service and a product. The service is clearing the space and making time for an authentic, unhurried conversation — someone gently and quietly filmed in their own home. Then I edit that footage and create something cinematic: a living memoir for them to watch with their families now, and for their families to hold onto forever. The path to it came through burnout. I was working for Madison Square Garden during COVID and had been asked to curate an international theatre conference — a full 24-hour online event with speakers across four pillars. A good friend in Belgium and I were tasked with sourcing international speakers, and one of the people I approached was Gilles Ste-Croix, co-founder of Cirque du Soleil. He agreed, but preferred an interview format rather than a solo session. We pre-recorded it so we could manage the connection and enrich it visually — floating in a photo of George Harrison when Gilles mentioned meeting him, for instance. Afterward, I found myself replaying the recording. Not for information, but for something harder to name. Watching him, I noticed not just what was said but how it was shared — the pauses, the expressions, the feeling of a life being remembered aloud. I realized I longed to hear the voices of people I had lost in the same way. That clarity became my new direction. Q: What do you find the most concerning or worrying right now? A: For small businesses, what worries me is that the next generation — young people just beginning to take risks and try things — is being deterred from listening inward. Deterred from asking what makes them curious. We ask big questions: What do you want to do in life? What’s your passion? Those are hard to answer. But “what are you curious about?” — that’s a question people can actually begin with. And that curiosity is what leads to healthy small businesses. I worry about stifling it. About young people feeling they need 18 million others to validate an idea before they act on it. Risk-taking is inherent in small business, and I feel it is less and less encouraged. That concerns me. Q: What do you think the opportunity is right now? A: Two things can be true at the same time — and the opportunity lives in that reality. The old model — work somewhere for 45 years, retire, and if you have regrets at 65, well, at least you provided for your family — that schema is being disrupted. The expectation that you must have your life defined by 25 and stick to it is loosening. There’s far more agility now. That agility can also lead people to seek outside validation instead of staying true to themselves. So alongside the opportunity, there’s a need for courage — just as much as curiosity. Really understanding your own vision, and being willing to start small. That combination is where I see the real opportunity. Q: If you had a Magic Silver Wand, and you could use it to make one thing true for every single small business owner in the world right now, what would you use your silver wand for? A: Change the word “work” into “contribution.” Coming from a freelance background and becoming a mother, I was always navigating that binary question people put to women: are you working or not? As a freelancer, the work came in waves — a month-long project, two weeks, a gap, then another. I was immune to that conversation because my contribution was constant, even when a contract wasn’t. If we called what small business owners do “contribution” instead of “work,” I think it would change how they see themselves — and how the world sees them. Q: How do we support you? A: What I’m learning, including through Silver Lining, is to find ways to connect directly with people. The medium I really work with is the live voice — conversation. When I actually get to talk with someone, that’s when something shifts. Most people’s first instinct is: “My life is too ordinary. I’ve never been on camera.” I understand that. But when we talk, and they realize it’s simply a conversation — not an assessment, not a test — the resistance softens. One woman I worked with, quite an intellectual, said: “Oh — you’re not here to evaluate me. We’re just talking.” And that was exactly it. So the best support is any opportunity to talk about this work — not because I love what I do, but to help others understand what a living memoir can mean. That’s where it begins. Do you want to shop small? Check out our new buy.small Marketplace! Latest Stories
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New Zealand Labor Unveils $1.56 Billion Small Business Package — With a Significant Trade-Off at Its Core New Zealand’s Labor Party has released a small business policy package — costed at $1.56 billion over four years — as part of its 2026 general election platform, reports Business Desk.
From a Mother’s Recipe to Myanmar’s Modern Trade: How Royal Manizawta Reinvented a Family Balm for a New Generation In 2007, a mother in Yangon received a formulation from a traditional medicine doctor in Taiwan—not as a business plan, but as a remedy for her own daughters, who suffered from skin rashes and allergic reactions to conventional analgesic rubs.