UAC 88 | The Power Of Questions


A well-formed question is a gift to somebody. If it’s thoughtful, it allows people to have their own a-ha moments. Allison Trowbridge, the Founder and CEO of Copper Book Clubs, a book club platform and community-based company, talks about the power of questions. Allison shares her go-to questions on her own show and dives deep into why she feels asking questions is important to learn about people and building relationships. Learn about Allison’s book writing process, the impact of her book, Twenty-Two, and her advice to new writers out there. She also dives into how tensions are necessary for growth and shares her guilty pleasures and cornerstone habits.

Listen to the podcast here:

Allison Trowbridge: The Power Of Questions, Doing The Next Right Thing, and Living Like You’re Loved

This is a podcast all about learning how to live a good life. We’re doing that with each episode we release. We believe that learning how to live a good life takes having intention in the tension, as our mantra says. Life is full of tensions and we get to live within those. The goal is to live intentionally within those. This episode is an interview and it was an awesome interview, one of my favorites. I know I always say that, but it’s true. Before we get there, I would like to encourage you, if you haven’t yet, please leave us a rating and review on iTunes. This is by far the easiest and best way to help us out. You can scroll down on your phone, click that five-star button, write in a few words and Adam and I will even read it out on air. It would be super cool to share a little bit of what you had to say. That’s an awesome way to be able to support us as we keep pushing out this content and trying to continue building this community and promoting more human flourishing. That’s our goal as a whole.

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We had an interview with the lovely Allison Trowbridge. Who is Allison? Allison Trowbridge is the Founder and CEO of Copper Publishing House. She published her book, Twenty-Two in 2017 with Harper Collins and Thomas Nelson while completing an MBA at the University of Oxford. Allison became obsessed with publishing after witnessing a handful of books ignite the global anti-slavery movement where she worked for nearly ten years leading marketing, fundraising and international campaigns at the Freedom Fund, Not for Sale, and as a partner at an impact investment fund, Just Business.

She is a powerhouse, as you can tell from the bio. I absolutely loved the time with her. In some of the reference and background research that I did, a lot of the common themes I heard from other people were words like magic, spark and light describing who she is. From the moment I walked into her home, that rang true. She is a magical person and she has a spark that lights up the room. I experienced and witnessed that firsthand. This conversation was a true joy. She’s also a podcaster so we got to talk a lot about questions, asking good questions and the power of questions. We talk a lot about where she got her creativity from and what her background was like. We talked a lot about learning, reading, writing and human trafficking. We go through a whole slew of things and it was a fascinating story and conversation. I also got the chance to read her book, Twenty-Two: Letters to a Young Woman Searching for Meaning.

I have to say, I was a little bit self-conscious about my own writing after reading her book. She is a beautiful writer. It was well written and beautiful in her writing. I’m not quite as beautiful. I’m a little more efficient so I need to work on that. She has obviously read a lot and is a gifted writer. That’s a great book, especially if you’re a young woman reading this and want some encouragement about that season and stage of life. Even as a man, I enjoyed and benefited from it. She shares a lot of beautiful things in there. You’re going to want to read this whole interview because it is phenomenal and it will challenge you but also inspire you. Sit back, relax and enjoy this conversation with Allison Trowbridge.

Allison Trowbridge, welcome to the Up and Comers Show.

Thank you so much for having me. I’m so glad to be on the other side of the mic. This is fun.

It is nice to feel the receiving because sometimes when you’re giving, at least on the podcast end, there are so many technical details to tend to that it can be quite stressful.

I’m always thinking about questions. I love doing interviews on podcasts but it’s fun and relaxing to be the one asked questions. This is a fun change. I like it. I can get used to this.

Do you go by Allie or Allison?

I go by both. I also respond to, “Hey, you,” “That girl there,” “Al,” anything.

What has been the most bizarre nickname you’ve gotten?

One of my best friends, Jeannie, her mom calls me Alibaba. She only calls me Alibaba. I don’t think she knows what my real name is, but her name is Mama Mai. She’s become this personality and I am Alibaba. I love it. Feel free to call me Alibaba.

A well-formed question is a gift to somebody. It’s thoughtful and it allows somebody to have their a-ha moment. Click To Tweet

I don’t know if I should steal that. It seems intimate there. There’s something about nicknames. That’s why I love trying to give nicknames to people sooner rather than later because you have a closer bond. It’s weird.

When I was born, my dad wanted to give me a name that couldn’t be nicknamed. I don’t know why he thought Allison couldn’t be nicknamed but there you go. When I was five years old, I loved the concept of nicknames. I remember in the back seat of the car asking my mom what a nickname was for Allison. She thinks about it and says, “I guess it’s Allie.” I’m like, “Good to know.” The next day in kindergarten, the teacher goes around taking roll calls and calls an Allison. It was silent and she’s like, “Allison.” It’s silent. She looks at me and goes, “Allison?” I’m like, “My name is Allie now.” She goes to Allie and I’m like, “Present.” It was a self-ordained nickname when I was young. I agree, I love nicknames. I’ll nickname anything.

Was that out of rebellion or was that out of curiosity?

I don’t know. I loved the concept of nicknames. What are some that people call you?

I’ve had quite a few. My dad always called me T-man. I had that on my wall above my bed.

That’s cute. I like T-man.

It was a good one. It was fun. It’s how I know my dad. He always calls that and now I get T a lot. In high school, I nicknamed myself, Ya Boy, YB who’s a famous rapper out of the Bay Area. I was big into rap music so we can go both ways. You can give it to others and you can give it to yourself. Some were more proud than others but they are great. One of the things that we were talking about before that I would love to hear from you on is questions. One of the things I heard a lot about from some mutual friends how good you are at asking intentional, meaningful questions and how you create space for that with relationships in your life. We talked about podcasts being such an amazing arena for asking questions. I’d love to hear how you think about the use of questions or what the power of questions is for you.

A well-formed question is a gift to somebody. If it’s thoughtful, you can allow somebody to have their own a-ha moments, which is why counseling and coaching are so powerful. I love being able to ask people things and draw up the gems within them and allow them to even learn or discover something about themselves. Also, I’m insatiably curious and I love getting my head around who people are, what their stories are, where they come from and how they think about things. Another part of it is selfish because I feel that I already know what’s in my head. That, to me, is so boring because I know my own story. I don’t understand people who love to talk about themselves because I feel that there’s nothing interesting about that. I love getting to know people and dive deeper.

What are your go-to questions? What are the ones that you love asking the most?

My friend, Lane Wood, gave me a great one once. He loves asking people, “What are you excited about?” I’ve stolen that one from him, especially if I’m ever doing an interview with someone and I don’t know where to go next. It’s the best because it opens them up to think about what they’re passionate about and what they’re looking at towards. Usually, there’s a lot more you could ask from that. In general, things that are open-ended. I love asking people what books they’re reading.

You can learn a lot from that. It opens up our perception of their reality. At the end of the day, we’re always perceiving things and assuming things about the people that are on the other side of our eyes that we’re looking at or talking with. A question helps us maintain that open mind and also get a clear understanding like a more objective understanding. It’s so hard to always push for that. That’s why developing a habit of question-asking and question forward is a great self-practice because it helps us be more open-minded.

We also learn to listen. It’s over my bed and my room. It says, “Listen.” It’s a constant reminder to me to hear people and I love learning. People have so much to teach us and we stay at the surface.

For you, this is a big one because we all suck at this. In listening, how do you evaluate yourself on your listening in day-to-day life? What are your self-checks, self-talks or reminders that you use to be active in listening or being in present at the moment to listen or hear someone?

UAC 88 | The Power Of Questions

Twenty-Two: Letters to a Young Woman Searching for Meaning

If I’m thinking about what I’m going to say next, I’m not doing a good job listening. The temptation is to ask a question and already be forming where you’re going next instead of actively hearing, receiving, even taking a moment to pause and internalize. We jump in and cut each other off and we’re thinking about our own and the thing that we want to get out and communicate. There’s no growth in that.

There’s a tension there too because you also want to synthesize what they’re saying with what you already know. You also want to connect it to what you already know about them and you also want to connect it to the flow of the discussion. There are layers that are weird.

That is a good point. You do it when you’re podcasting. You do need to be thinking a little bit about what question you’re going to ask next.

It’s a different environment than normal but it is fascinating. What has been the most interesting question you’ve ever been asked or you ever heard? Is there any that come to mind?

My friend, Peter Smith, who founded a company called Blockchain asks every person that he’s hiring what their convictions are. That’s such a beautiful question and it tells you a lot about a person. It’s such a neat thing to bring into an interview. It shows you what’s at the core of somebody.

One of the questions that I read on a newsletter, and I use it with the young adults’ group I lead for an icebreaker question, is if you could safely eat any inedible object, what would it be? The cool thing about this question is on its surface, it doesn’t feel like it wouldn’t tell you much about the other person. When they answer and they describe what it was, it tells you about where their mind goes when it gets creative. It tells you about things that they’re interested in or things that they like already and how they compare it to other things in life. It’s usually the more innocent questions that don’t seem you can learn that much about people that are the ones we learned the most. It’s like fiction. It’s usually what we learned most about life, not necessarily nonfiction, which is fascinating. If there was an edible object that you could eat, what would it be?

It may be fun to eat clouds. That would be cool. Put your hand out and grab some clouds or eat a rainbow.

Insatiably curious, where did this curiosity come from? What were the origins of that?

If you love learning, you are curious by default. That’s something my parents instilled in me at a young age and it baked in creativity. That was at the core of how my parents raised us. They raised us to be always learning, reading and creating things. That combination makes you curious about the world and wanting to grow and discover. Books open up a lot of that too. Stephen King calls books a portable magic. When you’re a kid that’s reading, your world opens up. When you’re young, it’s quite small and it suddenly becomes global and otherworldly. Curiosity becomes innate to all of that.

Were there any specific examples, illustrations from your childhood of things that your parents did to encourage that or maybe activities that they had you guys do?

One thing I loved was when we went to the library every week and we checked out 40 books because that was the limit. If we finished all of them, we would go again and check out another 40. Usually, it’s 80 if we went twice. Bobby was the librarian. He’s my brother and favorite person. We read all the time. I won $500 in third grade for a summer reading award because I read so many books, which I didn’t know was not a normal thing. I didn’t even know it was computing. That was one and art was a big part of my childhood. We weren’t allowed to watch a movie during the day if we weren’t drawing while we watched it. My mom is an art teacher so my brother and I were always sketching and drawing. That made our brains inherently creative. I used to write books when I was little too. My mom would take construction paper and staple it into a book and draw a big square on each page. I would draw pictures in it and sit there. This is before I could write. I was four and I would dictate to my mom, “Now the dog jumped into the river,” and she’s writing them. I have these little books that I wrote when I was 4 and 5 years old.

Who is the better artist, you or your brother?

Me by far. That’s one thing I can definitely claim. He would say the same.

What form of art still gives you the most joy or life?

I love painting. I made a date with a friend to do it, a painting day. It taps my brain into a different place.

My sister has been diving more into her path as an artist. I have always enjoyed it. When I want to, it happens. It’s rare. There’s so much freedom and beauty in that. What were the books from your childhood that you look back on as having some of the most formidable impacts on you?

The first one that comes to mind is Goodnight Moon. I don’t know how that would have had a big impact on me, but I loved that book. What’s some more intelligent book than Goodnight Moon? I would make my parents go around the room at night and say goodnight to everything in my room, which shows you who had the power in that relationship. It’s was a 30-minute bedtime routine. I was good at delaying it. I loved the Narnia books. You wouldn’t have known Babysitters Club or any of those but there are so many of these good classic chapter books that were fun. One thing that I’ve always pursued in my life is wonder. Reading links us into and keeps us in a state of wonder and curiosity. It allows you to enter someone else’s story and experience their world, emotions, tragedies and hopes. I’m not a parent but I hope I can give that to my kids someday.

Without taking the time to stop and rest and just be, we begin to believe that our worth is based on our contribution. Click To Tweet

Reading has got to be, if not, up there in the top echelon of things that create wonder and curiosity. What other things have you found to help you in pursuing wonder and creating that curiosity for you?

Exposing yourself to creation is one. Being in nature and being near things that inspire awe like oceans mountains, under the sky, getting into places out of cities where you see a clear sky at night. That plays a big role. Another big one for me is people. I surround myself with people that I’m constantly learning from who spark and inspire ideas, creativity, who I want to be more like and emulate elements of their lives. The people that we surround ourselves with are everything.

I echo all of that in full unison. One of the things that people often said about you, in doing some research, they talked about how one person said that you’re a people collector in a good way.

They have lines and lines of people in the back closet.

I thought it was a funny verbiage.

I worked in anti-trafficking. I promise I don’t collect real people.

One thing that most people know you would agree with is, you’re good at gathering people and bringing intentionality to that time, but also surrounding yourself with great people. At an early age, who are your mentors or who was your first mentor? Someone that came alongside you in the journey of life?

My earliest one was my kindergarten teacher. It truly was. Her name was Mrs. Som. It’s funny when you’re five years old and somebody invests in you and believes that you’re special and have something to offer the world. As a kid, you live into that. We live in the words that people speak over our lives. That’s true as an adult as well. If you have mentors, friends and people coming alongside you that are speaking big things over you and believing those things for you, you naturally live into that.

A lot of people are always wanting to know how do you create that community that you want? How do you have those people in your life that you need? Networking is one of those things, especially here in LA.

I don’t love that word.

I hate it. One thing that another friend had asked was, “How do you network in an authentic way?” How do you think about finding a community in this stage of life?

UAC 88 | The Power Of Questions

I never ever think about networking and I wouldn’t go to a networking event because I’m about friendship, community and tribe. For me, it’s about being in places where I’m surrounded by like-hearted people. They don’t have to agree with me or think like me, but there’s a heart towards making an impact in doing some measure of good in the world and creating some greater change, the sense of coming alongside each other. I’m drawn to people that there’s both a depth of friendship but it’s also oriented towards the outside world and doing something in the world. It isn’t only, “Let’s be friends for our own benefit and our own enjoyment,” but rather, “Let’s build into one another’s lives so that we can go out and do more for the world.” Maybe that sounds too aspirational, but it is baked into all of my friendships. It’s this sense of how do we build into one another and support one another and do great things together?

That’s why I don’t think about networking so much as friendships and long-term relationships. It’s so important to identify what your tribe is, where they gather and being a part of those things. I don’t typically love conferences, but I love going to events, gatherings and conferences where that tribe of people shows up. I spent most of my twenties working on social justice issues. Finding people who are aligned towards that, have become decade long friendships, people who are still in my life and I still invest in. There’s this sense of running alongside each other.

That’s how we’re wired and created as relational beings. There’s some tension there. We all are somewhere on the spectrum. There’s a spectrum of even introverted to extroverted as a lot of ways we describe it, but needing time by ourselves, with God, others, our work and rest. There are always seasons and ebbs and flows. Where are you on that spectrum or scale of people time versus me time or individual time versus relationship?

I am a genuine ambivert. I always thought of myself as an extrovert. A mentor drilled into me the Myers-Briggs. He’s like, “You are an introvert that’s trained yourself to be extroverted. If you don’t identify how much you need time to be alone, think, synthesize, process and go out into the world, you are going to spin out and burn out.” It was insightful because I love being around people and if you leave me by myself too long, I go bonkers. If I don’t have time away, even at a big event, I need to step away and get a quiet moment to recalibrate and rev up again. It’s been learning and understanding myself and how badly I need both. I love having people around. My roommate and I joke about having alone time together where we love having people in the house but being able to go into a different room and be alone and that being okay. I feel that it gives a visual to what I need. I love having community, people, investing in people and being around people all the time, but if I don’t get those moments away and quiet time to think, rest, process, dream, get a vision, I’m vision-oriented and I need to get quiet to do that.

It’s interesting you bring up that point because making my mind into a threshold in a relationship where you can be together but be alone is a form of mastery. It’s awesome. When you’re comfortable with someone enough that you can both be quiet together, that’s a special relationship and it’s not every person. It’s a cool gift.

My closest friends, we do not have to fill the space. One of our best days is in pajamas half the day, no makeup, catching up on work and doing life together, not having to be on. Even when you’re working and there’s a sense of being on and bringing your best self, which is so wonderful. There are a time and place for it, but you’ve reached a depth of friendship when you can be completely off.

It’s so refreshing, especially in LA. What have you found as the rhythms for that? What are the things that you found that you need to prioritize to help you with that?

A big one is sleep. “News alert world, we do need sleep to be healthy humans.” I spent a lot of years running on no sleep and that was not wise. If I don’t get seven hours, I have to find time to catch up. I’m trying to do better at prioritizing that and taking care of myself in that way so that I can bring my best mental, emotional energy to whatever I do. Another big one for me has been Sabbath. I have to have a day out of the week where I turned my brain off. The big thing is, I’m not oriented towards work, email or doing or producing. There was a stage I went through in my mid-twenties where I was co-writing a book for a pastor of mine and it was about a year in my life where I intensified my normal work schedule to prove to them that me doing the book wasn’t going to detract. It’d be working ten-hour days. Get home, eat something and work on writing from 8:00 PM to 1:00 AM or 2:00 AM.

On weekends, I would get home from work on Friday night and work straight through the weekend and not leave the house until Sunday night to go to the grocery store. I still physically feel how burnt out I was at the end of that season. I have these flashbacks to being crumpled on the bathroom floor weeping. It all feels so dramatic and I had all these events I was producing and being so tired. I couldn’t lift a spoon to my mouth to feed myself. It doesn’t have to be that. It was funny, I submitted the book and went to church the next weekend. My friend, Dave Lomas was preaching and he talked about Sabbath. I’d always heard about Sabbath, but I never took it seriously. He laid at home about how without taking time to stop, rest and be, we begin to believe that our whole contribution or our worth is based on our contribution.

That is all based on our doing instead of creating space for authentic faith to take the lead and saying, “God, I trust you to move the needle on things and make things happen and open doors. It’s not all in my sheer exertion but rather the end goal is not how much I produce, but faith as a relationship, a being, a state of existing communion with God.” It was one of the deepest convictions I’ve ever felt of, “Here I was resenting God and my faith for being here. I am doing this noble holy work and I’m killing myself in the process,” and we become these martyrs and we don’t have to. The great irony is I realized I could spend two hours staring at a blank page feeling I was working and I was so burnt out versus if I’m rested and healthy, I can bang out a paragraph in five minutes.

This is such an important point. This needs to be heard over and over again because it’s so counterintuitive. This is something that came up in an interview that I was on a different guy’s podcasts. He brought the point that it’s not necessarily counter-intuitive, it’s counter-cultural. That’s because we’re getting our intuitions a lot of times from culture, which naturally happens. It’s a power of culture. It’s not necessarily good or bad but we have to recognize what is good and bad in that culture, intuition we’re getting and this pressure we feel to keep going and do more and be defined by what we do instead of who we are. They’re half-truths which make them even harder to recognize. There are so many great resources. Joe Rogan’s podcast with Matthew Walker was great. It’s two hours of pure sleep information. It should be non-negotiable for anyone reading and we have to preach this ourselves a lot.

The Sabbath one is the one that I’ve been super convicted of a ton too. When you’re not in a traditional 9:00 to 5:00 job like anyone nowadays, it can be hard for any of us to set aside a day. Sundays for me, I serve at the church’s coffee carts. Sundays are not Sabbath for me. Now was supposed to be it for me and I didn’t do a great job. I was convicted by that. There’s a great sermon by Tim Keller. It’s called Work and Rest. It was the most beautiful breakdown I’ve ever seen. Part of the thing he highlighted in there was this inner murmur of the soul, which is the voice of self-reproach. That’s the thing that is amplified when we don’t take a day aside. It’s saying, “I am not good enough unless I do X or I’m not enough until I do this.” That self-reproach is a voice that is fueled by not taking a Sabbath. It’s a self-dependence on God dependence and there are so many layers to this.

It’s the most freeing thing when you realize God is not waiting for you to get somewhere or do something for him. Click To Tweet

When I took the Sabbath, it was the most refreshing thing, experientially. You can’t even define it. It’s like, “Thank you. This was a blessing.” You were asking me about finding creative inspiration and it’s, you get so many inputs when you take space, dream, think and imagine. Go to an art museum, for a walk, listen to a podcast, and watch a great film to allow yourself to be exposed to great ideas, art, people, conversations and relationships. Those things fill you up and are the seeds of inspiration for the great work that you will do. If you don’t create space for those, you’re diminishing your ability to ironically produce at the highest level. I’m an Enneagram 3.

I was going to ask you about that.

Are you a three? I know one when I see one. I thought so. We have the same issues. It is a three, which is the achiever for anyone who doesn’t know that the Enneagram typing system. The great temptation of the three is to link who you are with what you do. We get into these cycles of achieving for the pure sake of achieving and getting runs on the board and we don’t even know why we’re doing it anymore. That links back to mentors for me. I finished grad school and I had a few mentors, one specifically who sat me down and explicitly told me to stop, take a break and take a full-on sabbatical for a couple of months. It was one of the hardest things I’ve ever done. It seemed the most absurd and counter-cultural. Imagine finishing an MBA and you have 350 Type-A students asking you what you’re going to do next and you say, “I’m going to rest. I’m going to take a break.” Everyone else has these high power jobs. It was difficult but the most game-changing thing. It was not easy. It was hard financially and emotionally. It was hard for a lot of reasons but it allowed me space.

At that point, I was at a level of tired that I had been burnout. I’d been up for a few years that I didn’t even know how to identify it because I had gotten so used to it and taking space to ground myself and get true rest, health and step away from what I was doing. I finally got to a place where if somebody gave me a livable salary and told me I could not ever work or produce another day in my life. To some people, that sounds great but as a three, that’s your worst nightmare. I would feel okay with it. I’m grateful for getting to live and do community. I feel loved in who I am and as I am not what I’m producing. That was a journey to get there because up until that point, you can’t even see it anymore. You have to keep doing.

That’s such an important thing to highlight because it’s not that we take this quantum leap into self-destruction. It’s these baby steps that add up into this wretched hole that we find ourselves in. We think that’s normal. When I was playing golf as an athlete, your career was based on your performance. I started seeing a direct correlation in real-time between the amount of sleep and recovery I had and the performance I could produce on the course. Not only from a physical but also from a mental standpoint but also the focus and the concentration. It became so evident to me that it was such a non-negotiable. If I wasn’t getting adequate recovery, it didn’t matter how much my output was, it was going to be limiting.

That lesson to me is priceless. It’s worth its weight in gold because now I can say with conviction, “I am going to be sleeping regardless of what my head is telling me about being lazy or whatever this is.” This is culture saying, “You need to work more than you sleep.” That’s not the right voice to listen to. I can preach that truth and believe it because of that experience. When you’ve been taking these baby steps into this hole, you don’t understand that there’s something outside of that hole. That’s such a hard thing to be able to convince people. It is worth it to prioritize and dig your way out of that hole to get to where the new normal is a level of optimization that you haven’t felt in maybe your whole life. It’s crazy.

I feel that I’ve got this little side ministry where I know burnout when I see it. I sat down with a friend and talked about her burnout. You see it. It simmers under the surface and there’s so much emotion wrapped into it. Sometimes all you need is someone else to give you permission to stop.

I have two questions. One is on the sabbatical. Think about that for the future, how would you apply that in your rhythms throughout your life ahead of you? Where are you on the spectrum of healthy to unhealthy and rest?

I would say take three months of truly stopping every seven years. It was funny because when that mentor told me I needed to stop, I said, “Can I sign another book deal and write a book on my sabbatical?” He’s like, “No.” How can I use this time and space for something? I have to be creating something and it’s hard to teach yourself how to be and being yourself and be okay with yourself. It’s beautiful and critical. I would say a big one like that every seven years. Something that I want to start doing and getting better at is, maybe once a quarter, taking a weekend away where I give myself a little mini-retreat to turn off and get into a creative headspace to dream, be in and rest and read. Even those little breaks are key and important.

We don’t need to save it all up for the once every seven years. Let’s also incorporate it in our daily, weekly or monthly life. It doesn’t have to be segregated into these boxes.

It’s also accepting limitations, which is difficult. I’m in a season work-wise of feeling like I’m in a full-on sprint. I’ve also prioritized getting sleep every night, regular workouts, a day off for Sabbath and time with community and still prioritizing community and not letting work take over any of those areas. I feel my focused brain time is output is higher than it’s ever been and it’s because of that. It’s fun to see your own ability to grow. It’s like a muscle you’ve worked on a lot.

Growth and seeing tangible processes are some of the most encouraging things in life. I don’t know of anything that’s more hopeful or helpful in life because it is that hope of growth. That’s fuel for us. There’s a great quote I heard and said a lot but it’s so good, “Forward progress is not a finished process.” I was like, “Praise God for that.” He’s never done with us and that we’re never done in life.

That was the moral story of my book so you don’t have to read it. The journey is in the destination.

UAC 88 | The Power Of Questions

The Power Of Questions: If you have mentors, friends, and people coming alongside you that are speaking big things over you and believing those things for you, you naturally live into that.


I want to hear more about that because I was reading a lot about that.

When I was in college, my favorite devotional is Oswald Chambers’ book My Utmost for His Highest. If they canonize that, I’d probably be okay with it. It’s so good. There’s a devotional on July 20th where he talks about how what we see as the journey God sees as the end result. In my early twenties, it struck me because I realized that in my whole life, I had always felt that God was waiting for me to get somewhere. I was going to wake up one day at 35 and have arrived. I would have figured out who I am, have my life totally sorted and I would be this finished product, not sailing into the sunset but it’s like, “Now I’ve got my life, I need to go.” I’m not 35 yet, but when I talk to anyone who is, they agree that’s a complete myth.

Culture can make us feel that we’re supposed to get somewhere and supposed to hit a point in which we have to pass this imaginary finish line. One of the greatest gifts is if you realize that the process is the end result. I imagined for the first time that God is outside of time seeing my life all at once. Not as being with me in this linear line. It’s the most freeing thing when you realize God is not waiting for you to get somewhere or do something for Him. You don’t ever arrive. It’s this more of a state of being and being in process. It’s a life-changing discovery.

We never stop learning it or never at least stop preaching it to ourselves as well. It’s not necessarily a natural default response. It’s an intentional chosen response.

I have to catch myself in it all the time because when you are driving hard towards goals and certain things, I have to check myself in and remind myself to be present and grateful for a season of churn of uncertainty, growth, goals, dreams, sprinting and all of the hard work. It’s easy to get in the mindset of, “Once I pass this point, I’ll be happy. I will be okay.” We have a tendency to build our lives around that, “Once I graduate, get the job, meet my person, get married, have kids, have grandkids and retire.” Suddenly you’re like, “Once I died.” We set life up in these goalposts that are not a thing.

Twenty-Two: Letters to a Young Woman Searching for Meaning, that is your book. It’s great. It doesn’t go away. Talk to me about what you learn from the process of that book because it is about the process of life.

I could easily say it’s the hardest thing I’ve ever done was writing that book. It was emotionally challenging. It took so much grit. In some ways, you learn that you’re stronger than you think you are. It’s a marathon to finish something that but also, it’s something that I felt such a strong conviction had to exist in the world. It wasn’t that I didn’t care, but I wasn’t worried about the outcome of it as far as the reason why most people write books will be for a platform reason, professional reason or, “I need to write this book to establish my career as a consultant in this area. This book will let me do that.” This book for me was like, “I will feel like Jonah running from God.” Not to be dramatic about it but I felt that it was such a strong conviction. It came from when I was graduating college when I was 22. I pulled an all-nighter with one of my closest girlfriends and it was gripping.

If only there was a book that spoke to the season of life. I feel that there’s never been a better moment in history to be a young person in your early twenties. There’s also never been a more challenging time where you feel these pressures to do it all, be it all, have it all, have your life figured out, solve global poverty by the time you’re 30 specifically young women but all young people. All of these things feel debilitating and you lose the ability to be present and enjoy the process. I made a commitment back that whatever I did career-wise, I was going to write that book someday because I so badly felt that I needed it and needed that guidance. For me, it was a piece of my life mission that was so rewarding to see it brought to life but honestly, I had night terrors before it came out. It was scary.

I want to dive into a little bit of that. From that initial seed, what was the amount of time before you started creating that book or moving forward with that process?

It always sat with me from when I was 22 that I wanted to do it. Back then, I was like, “I’m going to write it now.” I’m so glad that I got busy with work and there’s not a book that exists that I wrote when I was 22. I was not in a place where I should have been writing a book. Fast forward to five years, I had been thinking a lot about the idea of mentorship, the role of mentors in my life and of younger people I was mentoring. I was sitting with that. I was on a business trip in London and extremely jet-lagged. I sat up in bed at 6:00 AM and it downloaded into my head. I saw the book and it was a series of letters that I write to a character.

I joke about it and it was like CS Lewis meets Little Women but no demons. It was a Screwtape Letters type of format. From that point, that was when I felt I saw it and saw the vision for it. From that point on, it was like, “I need to start moving, making a plan to leave my job and start moving forward with doing a book proposal.” I never had any doubt about it that it was going to get done because I felt such a strong conviction. It was almost like someone else’s going to write it. This book needs to exist in the world. It began the process from there.

What was the timeline from start to finish? How long and what was the lowest point of that journey?

Funny enough, writing the proposal took a bit of time and talking to agents. It took nine months or so. I signed with my agent, wrote a sample chapter and shopped it around so it was another six months. Once I had the contract, I don’t like saying it, but I only gave myself six months to write the book because I got the contract with only a sample chapter and the outline. The bulk of it is you have 1 or 2 months where you’re like, “I have to write a book.” For whatever reason, that takes two months to sink in and you’re like, “I’ve got four months to write a book.”

Life is short. Make the biggest, most significant impact that you can. Click To Tweet

Truth be told, I wrote the bulk of the book in three months. In a full-on, I hate my life, intense, somewhat depressed sprint which probably involved poor planning on my part, but it was also how life worked out at that time. From there, it was working with my editor and we’d go back and forth. She would hand it back with light edits and maybe fix this paragraph and stuff like that. I would come back and rewrite whole entire sections, add new chapters, and move huge pieces around. I was doing these intense deep dives and rewrites. She’s like, “You didn’t have to rewrite all that.” I’m like, “It’s not good enough.” That was intense. I would say a year all in of writing and editing before it was shipped off and goes into copy edit.

What was the lowest point of the whole book process for you?

The lowest point was when some beloved friends of mine gave me their home in Long Island to write from because I was living in New York at the time. New York City is the worst place to write a book from because you try and carve out a day and three people text you that they’re in town for the weekend or something. There’s always an event or there’s always something. I was not doing well in staying focused there. I left and forced isolation. It was dead of winter so it was snowing. I was all alone at this house in the cold in the winter. I had gone through a bad breakup and I came down with some form of I don’t know if it was pneumonia. It was a level of sickness where at one point, I laid on the kitchen counter for about an hour because I couldn’t move. I tried to call a doctor to get medicine but I had no voice. I couldn’t speak to ask the doctor. It was not good and I lost a couple of days of writing off of that. I would say that would be the low point.

They make great stories looking back to it.

I do think that there is an element of how our bodies respond to stress. If we’re not managing it well, they wage a strike against us so that we’re forced to stop. I was carrying so much emotional, mental, physical stress that my body shut off on me.

It’s not only physical stress or emotional, but it’s physical, emotional and mental. It’s all three. Everyone experiences different forms of that. When you combine all three, they all play a factor in a system overload. Stress is ultimately a fear response and it’s affecting the nervous system. That’s a temporary state, not a prolonged state that our body can be in. It’s amazing how our bodies are designed but we don’t listen well.

The formula for staying healthy and balanced is so simple and yet when you have something looming, it feels impossible.

What are you most grateful for in the book?

I get messages a couple of times a week and I get handwritten letters sometimes from girls who’ve read the book and them sharing the impact that it made on them is unreal. It’s 100% why I wrote it. The fact that it would do that for one person but that it would do that for many. It’s not like it was some crazy bestseller or anything like that but the depth of impact it had on a number of young women’s lives was my why.

Carl Rogers said, “That which is most personal is most universal.” If we write from my place of the most personal for us of what that itch that you can’t help but scratch, that’s the thing that’s going to reach most people because it’s universal. It’s an experience that we all relate to. Usually, we get those flipped around which is sad, but it’s cool to hear that testimony of it. How would you encourage young or first-time authors or writers? What would be the encouragement you would give them or the pieces of advice you’d give to anyone starting, embarking or in the middle of that journey?

We get caught up on the idea of writing only for publishing or getting published and thinking that it’s not valid or worthwhile if it doesn’t get that endorsement. That’s a huge mistake. For one, if you get into a regular rhythm of writing, it’s one of the most beneficial practices. A good friend of mine, Allie Fallon, has a site called Find Your Voice. It’s all about building in daily practices of writing in your life. She’s taught me a lot about the health and mental health benefits of it. There are all these great stats about people’s salaries going up X amount.

The writing in and of itself has the ability to know yourself and process your story and be able to understand what’s going on in your world. That is one of the most invaluable things and the ability to share ideas and documents. There are so many ways and places to share ideas beyond a book, whether it’s writing on medium, blogging or writing something for your own friends and family. There’s so much value in that. The neatest part of being in the rush to the finish line of writing the book and having a deadline is once I was so attuned to writing all the time, you start getting ideas and inspiration everywhere. I would say probably anything that anyone has ever underlined was something that came to me half asleep in bed at night, on the subway, walking down the street or talking to a friend where I would dictate it into Evernote and save it.

I would have all of these one-liners and I would write around them. It’s attuning yourself to inspiration. I’m not doing a ton of writing at the moment and I want to get back into a rhythm of frequent, if not daily writing. When I’m not in a rhythm of writing all the time, I don’t get those flashes of inspiration in the same way. To a young writer, the best thing to do is to start doing it and see it as a way to serve. If you see it as a way to serve people and to both write for yourself, to know yourself, write as a way to bless and serve other people and share ideas, there’s always going to be avenues that open up for that down the road. Whether it’s a publishing deal someday or simply sharing something with someone in the smallest way but the way that you said it and give them an a-ha moment.

UAC 88 | The Power Of Questions

The Power Of Questions: Allow yourself to be exposed to great ideas, art, people, conversations, and relationships. Those things fill you up and are the seeds of inspiration for the great work that you will do.


I’ve definitely found that out when I was in the mode too. You’re in a mind or a mode of thinking that produces these amazing breakthroughs that you’re talking about. It reminded me of a quote I heard. Graham Duncan said, “People are like musical instruments and the range of notes they can play is dependent on the range of tensions that they’ve learned to hold.” Which is speaking more to life but it’s also true in writing in the sense that it’s an open loop. You haven’t closed the loop. Since it’s still open, you’re holding this tension of an open loop. Throughout everyday life, the subconscious is working on it and it brings together these amazing connections.

I love that you talk about tension because that’s one of my favorite topics. I will credit Andy Stanley on this when I heard him speak on it at Catalyst years ago. It always stuck with me. He talks about how tension is something that we have in our daily lives, in business and work. We’re always trying to alleviate and get rid of tension. The tension is good, needed and important. We need the tension in our company, “Do we spend money on hiring new people, marketing the product or anywhere in life?” Everywhere you look, there are tensions. He used the example of a church, “Do we build a new building? Do we pour money into ministries and outreach?” Everywhere you look, there’s tension. If you’re constantly trying to alleviate it, you miss the benefit and the brilliance that comes from that tension. If you think about human beings and what makes mammals so special is the opposable thumb. The opposable thumb allows us with our index finger to create tension, which allows us to use a tool to do everything else that we do. If you don’t have tension, you can’t have anything else. I haven’t heard of that before. It was fascinating. Andy Stanley is on that one. I wish I could say I made that up.

Have you ever heard of the book, How We Got to Now?


You’ll love it. It’s great. It’s how six innovations have shaped the modern world, but it’s using similar ideas of one key integral part that massively shapes society at large. The breakthroughs that it brings are interesting. Let’s stick on tension a little because I love this. It is our mantra, “Intention in the tension.” Having intention in that tension is our role in life in a lot of ways and it’s daily. What is the greatest tension that you’re living in? What’s the tension on the front of your mind in daily life for you?

The biggest one is probably how to spend my time. I feel constantly in tension around whether it’s in friendships and relationships and wanting to invest in so many people all at once. It tensions around because I’ve lived in a lot of different places. I have a community and a lot of different places and wanting to both invest and grow in communities and places like New York where I’ve lived previously but also to be present and invest deeply here. That’s tension. Wherever I am, I’m missing someone. That’s a tension that I’ve had to accept. I’m never going to be able to live in the same place as all the people I love. That’s a hard one to embrace. The tension of building a business and everything needing time and energy poured into it, knowing how to spread that out and what things to wait or defer on and how to prioritize. That’s a lot of tension.

The more conscious we are, the more we find them everywhere which is like, “Why won’t you go away?”

By realizing those tensions, back to the instrument quote, those are what allow us to play. If the strings on a guitar don’t have tension, you have no music. I feel the tension everywhere in my life and I embrace that because that’s stretching even though it’s not always comfortable, but it allows the best sound.

One of the things I always say is, “There’s tension but it’s a beautiful tension and life is a beautiful dance.” Dance is something that has a lot of tension in it. There are usually multiple people moving and it’s going to an external sound. There’s space that you’re taking up. You’re trying to create a movement around that there’s a lot of tension there but it’s so beautiful to experience it and it’s done well. That’s life. It’s amazing. It’s this beautiful dance, which is such a beautiful tension. Speaking of dancing, I hear you’re into ‘90s R&B. Is that true?

Was that Kristen who said that? I went to a ‘90s R&B bar with her once. That’s incredible. Who isn’t?

Let’s touch on your career path because you have lived in many places and have done many things. Give me the 30,000-foot view of college to now and we’ll hone in on a few pieces of that.

I spent most of my twenties working in anti-trafficking. I had the privilege of being the first employee of what became a significant organization in the anti-slavery space. It was a wild ride to get to be a part of helping to build a social movement. When I started working on the issue, no one knew what modern slavery was. I was the friend you didn’t want to bring to a cocktail party because I’d shut down every conversation when somebody asks me, “What do you do?” I’d say, “I work on slavery.” They’d say, “We dealt with that in 1800. It’s not a thing anymore.” It was an incredible ride to get to be a part of building that social movement and working in that organization. I was a partner for a while in the Impact Investment Fund and worked with a firm in New York to deal with supply chains and transparency tied to preventing trafficking and human rights abuses.

From there, I went to Oxford and did an MBA over there. I initially had wanted to do an MBA in City Business because being for so long in the nonprofit space, I saw a lot of nonprofits struggle to find sustainability because they didn’t run like a business. There was this sense of, “If I’m doing something good, that ought to be self-justifying and we’ll be okay.” Also, because I felt there needed to be more of better business acumen there. I decided to go to business school. I had it as a dream for a long time. Around the time when I was writing the book, I was thinking about life regrets that I had which were so funny. I was sitting around thinking about what do I regret in life. I was reflecting and I regret that I never went to business school because I had been a dream.

When you are doing things you love that serve the world, there’s naturally going to be good that comes out of that. Click To Tweet

At the time, I was 29. If that’s my biggest life regret then what the hell am I doing? I had to go so I turned around and application in a month or something and took whatever tests I needed to take. I applied on a whim. It’s not the traditional, “I thought about it two years in advance,” as smart people do. It was an incredible and formative experience to do that. I published the book while I was there, which I don’t recommend. They told me at Oxford that nobody had ever done that before. I was like, “That’s strange.” I learned why because I’d have final exams and spending out edit. It’s 7:00 AM and I have final exams at 9:00 AM on private equity. It was a challenge leading to burnout. After, I took some space and time and led me to start a company. That was quick.

Thirty thousand is a tough level to get to. It was great. In that, there’s so much that you did. The first question is, what did you want to be when you grew up as a kid?

The President of the United States.

When did that dream change?

Who said it changed? I’m kidding. As fun as politics looks now, I’m good. I asked my mom as a little kid, “What’s the biggest job in the world? Where can one make the biggest impact?” She said, “Being the President of the United States.” I was like, “Great, done.” Life is so short and I’ve always had this drive to make the biggest, most significant impact that I can, which is part of why I love writing. I love that it lives beyond you and you can share something with someone in perpetuity that you don’t have to be there. That something can affect someone’s life and you can create something that blesses somebody is so mind-blowing and cool to me. The drive was towards what could make the biggest impact.

In the journey after college, how did you think about the next step wherever you were in that career path? In those ten years, was there ever a time where you knew beyond the next step of where you wanted to go?

When I was 22, I created a twenty-year life plan and I’ve executed against it.

She was like a robot, a classic three right there.

I’m kidding, I never did that. I have no idea. It was much a joke. I hadn’t had any plan to go into the nonprofit space at all. When I was 21, the founder of that organization spoke at my college and there was a documentary film made on the organization and on anti-trafficking. I found out the director needed some help so I started. I made them a website and was packaging DVDs and shipping them off. I packed boxes in their living room. It’s so funny because there was no big plan. This was a cause that I cared about and I wanted to help and be a part of it. They saw how much work I was doing and they were like, “What are you doing after you graduate?” I was like, “I have no plan. I don’t know.” They said, “Why don’t you come work for us?” I was like, “Great, it sounds good. It’s the only job offer I have so let’s do it.”

It was organic in that sense. A lot of times we put so much pressure on ourselves to have a formulate plan instead of letting your passions lead, running at them and trusting the process to evolve as it’s meant to. When you are doing things you love that serve the world, there’s naturally going to be good that comes out of that. Whether that impacts your career or it’s a place for you to drive joy and meaning in your life. It’s so important and so many people are focused too much on, “I need that dream job.” For me, “I want to be a part of this.”

It’s being a part of the journey. That’s also what that book I brought up. He highlights that point of how we got to now. It’s a point that there are always 2 or 3 quantum leaps needed to get to where the innovation needs to be. It’s never one big leap. It’s usually a few smaller leaps that get us to where we need to go. The same is true in any career path or on any journey in life. It’s not necessarily about knowing what ten steps down the road is. It’s about knowing what’s your next step and how can you make that step well. Now you can be faithful to where you’re at in that journey. The end will take care of itself in a lot of ways.

My mom says, “Do the next right thing.”

That’s sound advice. I will say though, on the point you made that I love that you’re highlighting the letting the passions lead. In that, there’s also tension. It’s not passion and having a passion be the thing that drives us isn’t necessarily sustainable or isn’t necessarily the whole picture. How do you think about the tension within, letting your passions lead but also doing things that you don’t necessarily want to do in light of that passion? Even the tension within that thought. Flush that out a little bit for us.

UAC 88 | The Power Of Questions

The Power Of Questions: If you see writing as a way to serve people and to know yourself, there’s always going to be avenues that open for you that down the road.


I didn’t want to be packing boxes. It’s what’s needed to be done. It’s not to say that you’re always going to enjoy exactly what you’re doing but it’s going to be oriented towards something that you care about or believe in. I’m also a big believer in being wise and still paying the bills. There’s this push to go out and pursue a passion and forsaking all else. Adam Grant writes about this well in his book, Originals. There’s this myth that the startup founders that succeed are the ones that go all in and both feet first. He had the chance to invest in Warby Parker because they were a couple of his students and he told them no because they all had day jobs and he’s like, “This is a passion and something you guys are obviously pouring a lot into, but you’re hedging so I’m not going to bet on you.”

He would have been a billionaire if he had done that at the time. Out of that regret, he wrote the book Originals, where he studied and realized that the people that made the biggest innovations had a steady income. Even TS Eliot worked at a publishing house until he was 50 as a writer. It’s important if you are driven into creative passions and finding the stability that can be something where you still have meaningful contributions but you’re not always depending on your art or your passion to pay your bills.

It’s stability and sustainability.

They’re such sexy words. Dependability is my new favorite one.

The next place I’d love to hear from is on business. What led you to start a business and what is your goal for this business?

We haven’t launched yet so we’re technically in stealth mode. I can say a little bit, but I can’t say a ton. The company is called Copper and we are building a platform for book clubs to connect people in meaningful communities and to use books as the gathering point to bring people together. It was funny because I didn’t anticipate becoming a tech CEO. It’s not where I saw my journey going but it’s become the natural right next thing. I started out with the vision of wanting to improve the publishing space. I saw a lot of authors become frustrated by the process. In that time that I took a sabbatical after grad school, one of my professors from Oxford reached out to me a couple of times and said, “You should do something in the publishing space. This industry needs to be disrupted and you can do it.” Her name is Rachel Botsman and she’s a phenomenal thinker and writer on the collaborative economy and on the real trust plays in society.

She kept giving me that little nudge and only because I was taking the time and space to have that sabbatical. It was a light bulb moment out in the country in England and I was like, “No,” and shrugged it off. I had that light bulb moment of, “I do need to do this. She’s right.” Entrepreneurship is so much around problem-solving and continually holding things loosely and continuing to drive into what is the core problem that you’re solving and how do you do that? Are you doing it in the best way possible? I initially incorporated it thinking I was going to start a publishing house to make all these innovations that I wanted to see. The further I got in it, I realized that even if I was successful in it, I wasn’t going to transform the space. It would be like a drop in the ocean, so to speak. I came back to, “What is it that I’m trying to solve for authors?” I realized that what makes it so hard to publish a book is the shameless self-promotion you have to do.

I’m sure you know the joy that feels like. You pour your heart and soul into something that’s meant to be of service and you turn around and have to hawk it on the street corner. It feels incongruent and out of entirety usually with the why, why you did it and why you write a book to serve people. It came from me saying, “What could I build to serve authors and publishers and create a platform that served, improved the space?” Malcolm Gladwell writes about network effect in his book, The Tipping Point. That had always stuck with me about how these books are going viral out of nowhere was because they would go from one to many to many. That’s network effect so I got to thinking, “How can I create network effect for authors and do it in a way so they don’t have to travel nonstop on a book tour, speaking in front of half of them to a room of fourteen people in order to sell copies of their book? There has to be a better way.”

It can’t be Amazon that’s the only way to discover books. There has to be a more community-driven approach. It’s so funny. I set out to solve those issues in publishing and process for authors. I realized that we have this as a society, a huge loneliness crisis where half of Americans are lonely and the UK appointed a minister of loneliness in 2016. That’s becoming its own health issue where we’re relying on social media to replace in-person and real-life community. We’re not designed for it. Truly our mental, emotional, physical health is suffering. As a result, they now say being lonely is equivalent to smoking fifteen cigarettes a day which is insane. That doubled me down into how do I create a community and serve authors and publishers in the process? That’s through book clubs. We’ll hopefully launch soon so stay tuned. It’s a lot of the why.

If we shift our perspective to say, “It’s not about this breakthrough idea that we hang onto with a closed hand. It’s about having this breakthrough idea lead us to the next breakthrough idea, which keeps innovating as we iterate it through what’s needed.” It’s because you never know the core until you start working to try and find and define it in a lot of ways.

It’s also having a lot of smart, wise people speak into it. I’ve had people say, “This is such a great idea. How did you come up with it?” I’m like, “I didn’t. I started moving towards a problem that I saw and kept adjusting what I was building in order to better serve those needs and allowed people who are a lot wiser and had more experienced than me to speak into it and shape it.

That’s something we can all do wherever we’re at in life. This is something I love doing with any ideas that I’m sitting or stewing on. It’s giving it as much air as possible. Talk to as many strangers, friends, acquaintances, anyone. If it’s something you believe in, there are two positive things that could come. They could either refine it by giving you good feedback, advice or affirmation. Two, they’d take it and bring it to the world for you. Both of those are good things because we can’t do everything. Be open-handed with it.

We’re relying on social media to replace in-person, real-life community, and we’re just not designed for it. Click To Tweet

I did a photoshoot and met these two people. I met them and we ended up having some good conversations that led to me sharing this big vision I’ve been having and getting to share it. If they’d taken the road, amazing. If they helped me take the road, amazing. If nothing happens, at least I get to flush it out a little bit more with new people. We all have the power to do that, which is cool. Before we end with a few one-offs, I want to touch on human trafficking. The big question is, I don’t know if you want to focus more on America or the world but whichever one you feel strongest about, what is the state of affairs now? How has it changed over the last years?

One of the reasons why I became so passionate about publishing was I saw books ignite the anti-trafficking movement. Back in those early days, 2007 and 2008 where nobody knew about this issue, around that time, a few years before. Through that time, there were a handful of books that were published on modern-day slavery, all in quick succession. I watched the greatest, whether it be, funders who would read the books and pump hundreds of millions of dollars into the space to politicians, celebrities, thought leaders, activists, soccer moms, high school kids, you name it. People would read these books and genuinely become informed, go out and do something, and be activated to engage in some way. That’s what created a bigger social movement around the topic. That is where a lot of my passion for the space derives from because I see the power of the written word to move the needle on some of the biggest and most pressing issues of our time.

As far as the current state of affairs goes, it looks like the number has gone up because the reporting has gotten better. They estimate around 46 million people in slavery. When I was working on the issue, the estimate was 27 million. That’s because their reporting has gotten better. I have been so encouraged not only to see the mass awareness that’s happened, how many people have gotten engaged and supporting anti-trafficking organizations. What many people don’t realize is when they hear the word human trafficking, they think sex trafficking. More than 80% of all trafficking is in the labor industry and in the supply chains that touch our lives every day. The consumer awareness that’s growing around thinking through where our products are made and who’s making them. The sweater I’m wearing, the cotton in it was grown somewhere and somebody picked that cotton. If it was picked in Uzbekistan, it was probably from child labors so it’s beginning to connect those dots.

I remember in 2009 and 2010, we had built a website called Free to Work where we were analyzing companies and their supply chain transparency. I remember a donor saying to us, “Companies are never going to care about this issue. This is truly a lost cause. You are never going to be able to make a difference in this.” I left lunch with a friend who’s built a company called FRDM. His name is Justin Dillon and his company maps the supply chains and the risk profiles of major corporations and his clients include Target, Boeing, SAP and Virgin. To see companies like that coming on board and caring about their supply chain and legislators caring about it and passing laws. The California Supply Chain Transparency Act was passed a couple of years ago. It requires companies doing revenue over $100 million doing business in California to disclose their supply chain. It practices monitoring and transparency. Those have a significant change in impact. I’ve been so encouraged on the corporate side and to see the innovative models coming out.

I had the privilege of working with the Freedom Fund out of London in New York for about six months before I went to grad school and to see how they do this hotspot model. It’s where they engage all these local actors to work with 12 to 20 different local community-based organizations, legislators, law enforcement, local government and everything to eradicate slavery. They’ll be able to eradicate and to liberate an entire village in India. It’s absolutely incredible. Seeing these innovative high impact approaches being done and how far we’ve come in ten years, I have an enormous sense of optimism and hope. If you look back through history, we are actively in what could be called The Fourth Abolition Movement. To see history happening and being written is pretty big.

What do you see as the biggest need at its core? If we had to strip away all the layers, what is the core component that is at the root? It’s hard for something this big but in your understanding of this space and what’s going on, what do you see is at the core?

The challenge of it is that there isn’t a lynchpin in it because it does sit at the intersection of so many other social issues with poverty being at the core of it. What a lot of people don’t realize is, the reason people are exploited is economic and people are vulnerable to that because they don’t have jobs. If there are no job opportunities, people are vulnerable to being taken advantage of, exploited, trafficked and enslaved. Creating economic opportunity for vulnerable communities is probably at the root of it because you personally are not vulnerable to trafficking because you have a job, generating income and can sustain yourself. That’s not the case for many people in the world. That’s why so many people are vulnerable to it, specifically women and children. That would be at the heart of it. As far as what we can do about it is not only having an awareness but it’s truly caring. Caring about who mined the mica that’s going in your eyeshadow or the chocolate in the dessert you ate. As consumers, we usually don’t care. If we don’t care, it allows bad actors to act with impunity and that’s on us. It’s when good people do nothing and don’t ask questions to bring it full circle on our interview.

The pushback is we can’t care about everything. The more important pushback even on that is, the more you care, the less you’ll obsessively consume. We consume way more than we need on all fronts, whether it be information, actual goods, standard goods, food, you name it. We are always consuming. Caring helps us curb our consumerism, which is a good thing that we need to even personally. It works in your favor, not in your detriment and that goes back to intentionality.

A general curiosity and an awareness of it as far as if you see someone that looks like they can’t walk away asking questions. To truly take this interview full circle, it’s being curious and being aware.

Speaking of being curious, what is the next book in your heart?

I’ve got a couple. I’ll tell you one is a fiction book which is fun. That one is a pure passion project. That one is still a few years out. It takes place in Oxford. The whole book takes place within a two-hour class and the whole storyline happens through flashbacks.

Are you in the process already?

I have some of it that’s written. I have a few others that will probably come out that are non-fiction books that I’m toying with. One I wanted to do on wonder. I have a few other concepts.

UAC 88 | The Power Of Questions

The Power Of Questions: A lot of times we put so much pressure on ourselves to have a formulaic plan instead of letting our passions lead and trusting the process to evolve as it’s meant to.


Me as well.

I have one being in our 30s. It’s a follow up on the Twenty-Two.

That’s funny, it’s similar to how I’ve been thinking about the next book because mine was the Quarter Life Perspective so 25. I’ve been thinking about the first 30 years as my next subtitle. What’s the belief you formally held that you no longer believed to be true?

The world is black and white. That’s the message that I would want to write in that 30s book. When I was in high school in my teens, I had all the answers. Things were pretty black and white and clear. The older you get, the journey of life is learning how to embrace the gray, uncertainties and tensions. Instead of pursuing, having all the answers, learning how to ask good questions and being okay to sit with the discomfort of not being able to resolve at all.

What do you wish you knew more about?

In general?



It might be fitting with the current season of life.

Maybe. You never know.

What is your guilty pleasure?

I’m going to say coffee because I always feel that I always have these existential moments of, “I should not drink coffee. That’ll be so incredible.” I’m like, “Why? It’s so wonderful and brings me so much joy every morning.” I would say coffee, red wine and popcorn.

Those were all great. I would throw dark chocolate in there too.

That’s not guilty.

It’s pure adult joy. What are your cornerstone habits?

Instead of pursuing having all the answers, learn how to ask really good questions. Click To Tweet

I’ve been thinking a lot about this and trying to develop a good morning routine. I’ve always fought against routines. One of the ways I’m reframing it is thinking about rituals. There’s so much hydrating every morning when I first wake up. What are yours?

Mine are definitely bookends so having bookends for the day in the morning and evening. I’m always starting and ending my day in the Bible and God’s word. I’m starting with some and having those in place. Other ones are checking in usually once a week on a weekly vision time or journal time. Priming for prioritizing presence with people. Consistently committing to time for reading, outside extracurricular reading. Exercise and sleep are a non-negotiable for me. Those are some of the cornerstones for me.

Those are great. I like yours better. I’m hydrating. Community staying priority is a big one. Sleep, consistent exercise, being in places and consuming content that inspires me and challenges me to grow.

What do you say is your favorite form of community?

Sitting around a table with a small group of people and going deep on meaningful subject matters usually with a glass of wine or whiskey.

What’s your favorite whiskey?

I like bourbon. I like Laphroaig whiskey. Have you had that?

I haven’t.

It’s good. It’s peaty.

I’m a big Rye guy. I like something a little bit more bitter like Campari. Have you ever had Campari?

I love Campari.

Campari is one of the things you either love or hate. There’s nothing in between.

Negroni is my go-to.

UAC 88 | The Power Of Questions

The Power Of Questions: The temptation of technology is to make us more self-sufficient and independent, and while both of those are great, it’s a lie to believe we don’t need each other.


Campari soda is nice too. What books have had the biggest impact on you personally?

Man’s Search for Meaning. That was my subtitle. I added meaning in there because of Man’s Search For Meaning by Viktor Frankl. That is required reading for life. That’s a big one. Another one has been The Art of Gathering by, Priya Parker which I highly recommend. It’s helping inform the way about the company. It’s sweet because our team has been going through it as our own book club. We did a book club meet on it which is wonderful. There are so many areas of life that it applies to and how you think about bringing people together. That would be another big one.

I’m going to have to check that out. If you were to give a TED Talk, what would you speak on?

I’ve wondered about this. It’s a fun one to think about because I wouldn’t give a TED Talk until I felt I had one zinger that I wanted everyone to hear. At the moment, I would say, “Journey is the destination,” because that’s what Twenty-Two was about. When someday I do give my TED Talk, I want it to be on the next big idea. I don’t know yet.

Life will unfold it which is exciting.

It’s fun to dream about, though.

Something with the format of TED, which is the most refined form of a keynote has to be some core truth that is in your bones. That’s the only way it leaves an impact.

I don’t know what the title would be but it would be around the community, how we need one another and how we’re hardwired for relying on each other and existing with one another. The temptation of technology is to make us more self-sufficient and independent. While both of those are great, it’s a lie to believe that we don’t need each other. Also, comparison culture. That one needs to be beaten down with comparison culture.

Which is defeated largely by the community in person.

Completely and venerable authentic community where you see the difference of seeing someone’s Instagram and catching up with them. Everything looks perfect and polished and you talk to them in person.

Even the negative side of anything social is like, “Are you going to say that nasty comment when they’re standing right in front of you to your face?” No. You’re going to see them as human beings. It’s not that you’re not only going to say it, but you’re also not even going to think it, because you’re like, “This is a human like me. They have feelings, thoughts, desires and beliefs like me.”

Live like you’re loved. Click To Tweet

It’s bringing humanity back. It would be somewhere in there.

Last question, if you could send a morning text reminder to every up and comer out there, what would you say and why? They get this text message from you every morning.

I would say, “Live like your loved.” If you know that you’re loved unconditionally, you can go out and do anything and take any risk because your worth and your value is not in your achievements or failures and whatever comes of those. They’re all going to take you further in your journey. The fact that you are loved is unchanging and you can’t earn it.

Praise God for that. Allie, where is the best place for people to find you and connect with you and see what you’re up to?

It’s on Instagram and my handle is @AllieBridge. I would say the same for Twitter, but my Twitter got hacked by a Russian bot and I have not been able to get it back so don’t follow the Russian bot. It’s sad.

That’s crazy.

That’s okay. One social media is fine for me at the moment.

Thank you so much for this time. This has been a treat and there are many good things to think about and be reminded on.

Thank you for having me.

For everyone reading, we hope you have an up and coming week.

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About Allison Trowbridge

UAC 88 | The Power Of Questions

Allison Trowbridge is the founder and CEO of Copper, a platform helping people gather in meaningful community through book clubs.

She published her first book, “Twenty-Two” in 2017 with HarperCollins / Thomas Nelson while completing her MBA at the University of Oxford. Allison fell in love with the publishing world after witnessing a handful of books ignite the global anti-slavery movement, where she worked for nearly ten years leading marketing, fundraising, and international campaigns—at The Freedom Fund, Not For Sale, and as a partner at an impact investment fund, Just Business.

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