Every so often, you hear someone speak and immediately feel a connection to their message. That’s how I felt listening to Amy Swift Crosby during a breakout Q&A session at Liberty Road’s event in Los Angeles. She answered every question with such honesty and thoughtfulness that it made me step back and think differently about my own brand, not just how it looks, but how it feels and why it exists. Amy has spent her career helping brands — from BVLGARI to Barre3 — find their true voice, blending creativity with soul in a way that feels rare and lasting. She’s also the co-host of The Brandsmiths podcast, where she shares her gift for storytelling and strategy. It was clear to me right away that Amy belonged in our Seen series — not just for the incredible work she does, but for the way she moves through the world with intention, wisdom, and heart. I’m so excited to share a little more about her story with you.

Q & A with Amy:

1. What are you most proud of so far in your life, and how does it make you feel?

I’m most proud of my two girls, Fiona and Poppy. They make me laugh, they make me think - and part of it is just because kids force self-reflection, self-discipline, self-awareness of habits and patterns. As hard as the teen years can be for adults, I’m having so much fun with them. You really start to see who kids are becoming as they grow, and somehow it can feel like something you “did” to help those good qualities come to life in them. The truth is that some of it you probably did do, and some of it is just who they are, but creating a home and life that nurtures qualities worth having, I guess that feels like an accomplishment in this modern, complex world. It makes me proud of us as a family that we can have so much fun together, too. I wonder if enough credit is given to the “work” that is family life? It is hard work, but I find it to be noble work. I think “fun” has been the core value I’ve tried to nurture, because when you can laugh about it, you can get through it. 

2. What has been a challenge you’ve faced in your life, and what did you learn from it?

I’ve faced a few challenges. I’ve lost a business from Covid, and I’ve had cancer. Our house burned down. I lost my voice for 10 months due to tuberculosis. But I have also been given the chance to land on my feet, each time, which you can’t really anticipate much less orchestrate. Surviving hard things comes with its own reward. You get to live through to the other side. The net learning is that a few annoyances add up to too much. 

3. What is an important and unexpected change you’ve made in your life?

 One change is doing one-on-one work with people, versus exclusively brand strategy and writing projects. I’ve taken on private coaching clients in the past few years, and it has been really satisfying and personally challenging. My clients are the most interesting people, who are so brave and candid about their vocational challenges and goals. Some are very successful in the world, while others are making a pivot from one life to another. They inspire me, and I wish I had started dividing my work into these two worlds earlier, because brand work is my vocation and skillset - I love doing campaigns. I’ve been grateful to work with some of the most iconic brands in the world, with their teams, and a lot of brilliant minds. But a compliment to that is the intimacy of one-to-one, knowing someone’s life and helping them navigate it using the principles of brand strategy, which run pretty deep into the human condition. 

4. When did you first feel truly “seen” and understood for who you are, rather than how others perceived you? 

I started to feel truly seen when I started my newsletter, which consists of personal essays about work, life, and the human experience. Each time I publish something, I feel vulnerable - exposed. But I also feel connected to the people who reply or comment that it resonated with them. That’s my most personal work. www.amyswiftcrosby.com.

5. In what ways do you feel more authentically yourself now than ever before? 

I’m not really sure what change, but I think time peels the layers of “effort” away, slowly but perceptibly. You’re not “trying” so hard, you’re “letting” the information, signs, or instincts find you, guide decision making. Priorities become clearer. Desire is obvious, lack of desire even more so. I think I’m a lot more interested in things outside myself as I age, too, which maybe makes a person more curious and interesting? Hopefully!

6. Is your life what you thought it would be? Why or why not?

 I hoped my life would go this way. I worried a lot in my twenties if I was worthy of a marriage, a partner, of becoming a mother, of making a living as a writer. All those things have been labor, but they have come to fruition. I still have goals and aspirations, but those were my big concerns as a young woman (so basically, pppfew!) You plant seeds, take huge leaps, take risks, do stupid stuff, and feel profound disappointment. Some swings work out, some don’t. But you hope things net out in the progress category. 

7. What advice would you give to your younger self?

 I would say “yes, there will be curveballs. But you have everything you need to get through them, and your life will be more magical than you could ever imagine. Now go back to sleep.”

8. What wisdom have you gained that could only come through living these years? 

That sometimes there are no silver linings, and once in a while there are. You can create the conditions for good things - from your health to your friendships to your work opportunities - but you can’t muscle through everything with any guarantees. But mostly, find the funny people and keep them close. And if you want good advice, ask friends who aren’t beholden to keeping the peace and agreeing with you. 

9. What do you want your legacy to be? 

I don’t like to think of myself as someone with a legacy. It seems too self-serious. I hope anyone who survives me thinks, “What would she do or say in this situation?” Because I think I tend to take an unconventional view, where convention or platitude tends to be the default mode. I’m not a contrarian, but I don’t always go with the flow of zeitgeist. It can be dangerously flawed.

10. If you had to identify with one of the Mini ID Gold Medallions, what would it be and why?

I’d say STARGAZER. A cosmic gift is the best gift.

You can find out more about Amy on her website and Instagram.