Experiments: Building Self-Trust and Confidence Through Small Shifts
- Kim Meninger
- 12 minutes ago
- 22 min read
In this episode of The Impostor Syndrome Files, we talk about experimenting with your own growth. My guest this week is Jen Wilson, a coach and consultant whose nontraditional career path has taught her that confidence doesn’t come from perfection; it comes from trusting yourself to handle whatever happens next.
Jen shares how she built her career through unexpected twists and turns, including co-founding innovative schools, burning out and then reinventing her work on her own terms. We explore why self-trust matters more than fearlessness, how small, low-risk experiments can rewire long-held patterns of self-doubt and practical ways to pause, observe your triggers and create new neural “tracks” that support courage and authentic action.
About My Guest
Jennifer Wilson is a consultant, coach, educator, activist, and author. She founded New Leaf Coaching and Consulting in 2006 to partner with world-changing organizations, such as The Obama Foundation and NRDC, that are committed to social and environmental justice. As an abuse survivor, she uses both her pain and resilience to support others in their own healing.
Jennifer earned a Masters in Counseling and Educational Psychology, leading to a career in community social work with youth and families before holding multiple roles within K12 public schools and higher education in Wisconsin. After co-founding two high schools serving marginalized urban youth in Milwaukee, she shifted her focus to working for transformational change within higher education and the nonprofit sectors to ensure that future generations live on a healthy planet in just societies.
Jennifer has had a lifelong love affair with words and writing. She had her first byline in 4th grade, reporting the 4-H club news for her local paper, and the first book she bought with her own money was Roget's Thesaurus. When she's not reading or writing, she heads outside for inspiration, across her home state of Wisconsin and around the world.
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Connect with Jen:
Book - Waking Up to Your Worth: https://consultnewleaf.com/waking-up-to-your-worth-ten-touchstones-for-overcoming-imposter-syndrome/
Website: https://consultnewleaf.com/
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Transcript
Kim Meninger
Welcome, Jen. It's so great to have you here, and I'm excited to get started. I'd love to start by inviting you to share a little bit about your background with us.
Jennifer Wilson
Thanks, Kim. I'm really happy to be here with you as well and with all of your listeners. So my career has been a zig-zag, zig-zag, zig-zag, not a straight line of any kind of way, and I never could have predicted the twists and turns that it's taken. So my careers began. I got a Master's in Counseling straight out of college when I was young and wasn't sure what I wanted to do, but I discovered in graduate school that I loved teenagers, and that came as a shock to me, because I didn't necessarily like teenagers very much, and I just recently been one, but I fell in love with working with these teenagers at a high school in the South Minneapolis schools. It can still picture their faces and their names to this day. So I started getting involved in youth work. So I did juvenile crisis counseling, some community based social work, case management for youth who were adjudicated and also had alcohol and drug diagnoses and their families, and I just became really involved in their worlds. And then a friend of mine said, Why don't you work in the schools? That's where the kids are. Just finish up some courses, get your license to do that. You can have my job. I'm going to be dean of students. And let's, let's work together, because you're already doing this work. So I did that, and I fortunately, was hired into an alternative school where staff went by their first name, and it was just this warm, welcoming environment. I didn't know that not all faculty was like that. So I became an alternative school person myself, and then I started working in regular public schools, and started to see this real disparity between how people like me were fortunately for, for myself, public education or traditional education worked really well. For me, I could book learn, I could take tests, I could do all the things. But that's not for everybody, and we don't do a good job of supporting folks. So I started to get really interested in, who are we losing, who are we missing? And it turned out to be people who were different, people who were too fill in the blank, too queer, too nerdy, too whatever, too not athletic, and also students who had been incarcerated or had illness or had to help their families or parents themselves, nontraditional students. So I co-founded a couple of schools in Milwaukee, and from that experience, I learned how to take things from an idea into reality. So that was kind of, this is all to say. This is what prepared me to be a coaching consultant, which I am today, at the same time, way back before coaching was so well known in the Midwest. Anyway, it was kind of still a joke on a sitcom. I fell in love with it. I had a coach, and I made really big life changes with the support of a coach, and I didn't need therapy. Well, I did. I had plenty of that, but I also when I was well enough, I was like, I'm well and I'm doing okay. I don't need therapy, but I want support, and coaching seemed to be the thing. So I got training, oh gosh, maybe like 2530 years ago, and have been practicing ever since. So all of this kind of culminated at a moment when I burnt myself out completely. I was working 14 to 16 hours a day starting this school because I had two jobs. It was the school counselor and also doing administrative work in the evenings. And it just all came to a head, and I had an opportunity to take a job from a company on the East Coast doing some online and Virtual Teaching. This was way back before we even had zoom, that I was involved in that world too. And I said, Where do I have to live? And they said, you can live wherever you want. And my light bulbs all went off. And I thought, here's my chance to move out west to Oregon. I'd gotten into mountain biking and hiking and rock climbing and things, and that's, that's just a place that I just love. Person I was seeing at the time, had a brother there. He wanted to go. It all lined up. So I quit my job, sold my house, and was ready to go. And in two weeks, he said, at Christmas, before Christmas dinner with his family, he said, I don't want to go. A week later, the company said we didn't get the grant. There's no job. We're so sorry I had no home, no relationship, no plan and no job, and didn't know what I was going to do, but I took a pause, I crashed in some friends, open apartment between tenants, and figured out, what am I going to do? So I sent one email to everyone I knew, saying, I'm consulting and coaching. Here's topics that I care about and know something about. And like magic, things started to come in, and it's been that way for 20 years.
Kim Meninger
Wow, that's amazing. Oh my goodness.
Jennifer Wilson
So that was a lot of those kind of a lot. That's the highlights of the story. But I think as. Shared that because people often say or will have a belief that I made a decision to start my business in this very planful, thoughtful, safe way, and it wasn't that way at all.
Kim Meninger
I'm glad you said that, because I do think and you started with the zig, zig-zagging, right? I think there is still a belief that if we're not following a very clearly defined, linear path, that we're doing it wrong, right?
Jennifer Wilson
Yes, my friends, my friends who cared about me, some of them got on board pretty early, but some continued for I'm not kidding, like a whole year to send me job openings. And at first I would just say, oh, you know, thank you. I'm doing okay. And then after a while, I started saying, Did you want me to pass this on to other people? I wasn't sure what you wanted me to do with this, because they were just so worried for me, because being self-employed to them seems so scary.
Kim Meninger
That's true. And I wonder too, because you mentioned kind of falling in love with teenagers, and when you started your, your coaching and consulting business, were you making a shift in the population that you were serving too, and how did that sort of feel, to expand who you were focusing on, or maybe even do Less work with teenagers?
Jennifer Wilson
Oh, that's such a great question. So at the beginning, in the first few years, one of the schools that I helped start, I saved one of the best jobs for myself, so I led experiential education trips. So I was taking young people from the city out to see the stars and the night sky in a place where there was no light, teaching them to cross country, ski and paddle and camp and canoe, because nature and being out in it is everyone's birthright. And unfortunately, a lot of people, especially black and brown people, aren't, don't feel welcome or safe in a lot of our natural areas in Wisconsin in particular, maybe that's true everywhere. So it was a social, social justice issue for me. So that social justice is kind of at the heart of everything that I was doing. So when I was doing direct counseling with students, I felt I was having an impact, for sure, but I started getting interested in doing systems work like I we don't have a young person problem. We have an adult made system problem, I think. So I thought, well, that's where I can make young people's lives better on a larger scale. So that's where, that's where the school development came in. And through that process, I started working with other groups of educators around the state who are interested in starting schools that did things differently as well. So that was part of my consulting started out in the K 12 world, and also continuing to work some with teenagers through this program that I'd created. But over time, we had some political shifts in Wisconsin, and public education took a real hit with act 10 during Scott Walker's tenure, and I began to see that I could not be as effective as I used to be there, and I shifted over to working with nonprofits. So that's my current focus, and has been for the last 15 years, I would say, is working with organizations that have missions to make life better for everyone in an equitable way.
Kim Meninger
So what do you see as the challenges that are kind of most prominent or top of mind with people that you're working with? What do they come to you for? What are you helping them to address?
Jennifer Wilson
I love that question. I think, I think the most universal question that people bring to coaching and consulting, but we'll focus on coaching for a bit, is, how can I know that it's going to be my decision is the right one and how it's going to go before I make the decision? That's like trying to see around the corner before you get to the corner. So sorry, we can't.
Kim Meninger
You're right. Everybody wants a crystal ball, right?
Jennifer Wilson
Yes, yes. And this belief that there's a right decision, a friend of mine a long time ago said there's not a right or wrong decision, it's just the one you make and then what you do with it. And I thought, you're totally wrong. I didn't believe her. I didn't want to argue. I'm like no other clearly, some bad decisions you can make, and that's not what she was saying. Yes, you can make bad choices, but I do believe she's what she said is right or correct. I should say to not use the word right, but when we make a decision, we don't get to know how it's going to turn out, but we do get to trust ourselves that will respond to whatever happens next. And so I think that's one of the things that that I think folks often struggle with, is understanding that. When the imaginary thing, if it even happens, which nine times out of 10 it doesn't, but when it happens, that you'll be able to trust yourself to act in your own best interest at that moment.
Kim Meninger
I love that you said it that way, because that is something I say a lot too, when I talk about confidence. Is a lot of people, when I asked them to define confidence, will use terms like fearlessness. Essentially, what they're saying is that I can walk into a room and feel brave and feel in control, and I, you know, I feel so good about myself, and I always push back and say, you know, that's not really a realistic definition of confidence. Confidence is really about self-trust, as you just described it. It's really about trusting that no matter what happens, we can handle it, we will figure out the next step forward. And I think that if we can make that adjustment, we can take leaps of faith a little bit more intentionally, or maybe more courageously.
Jennifer Wilson
I love, I love that you just use the word courageously, because courage means doing something in the face of fear. If there's no fear, then it's not courage That's right. And courage comes to the root of the word. I'm a word geek. The word core is French for heart, so it's, it's heart, it's heart LED. It's coming from your heart, even when afraid, especially when afraid.
Kim Meninger
Yeah, yes. And you know, you were talking to about people wanting to be able to see around the corner. And I think that we oftentimes want to feel the confidence first. We want to ready ourselves right like I want to. I want to have all the answers I want to, you know, and certainly, there's a fair amount of due diligence that can be done before certain decisions. I'm not talking about being impulsive and throwing caution to the wind, but at a certain point, you really can't know what the outcome is going to be until you do it. And I know that aligns with the what I often say too, which is confidence follows action. It's not the other way around, like you can't wait for confidence to show up and then do the thing you want to do, right to your point, like it's, it's in the face of fear, you do the scary thing, and then you build confidence on the other side of that.
Jennifer Wilson
Yes, yeah, one of my favorite questions is inviting someone to and invite you to do it right now, if you want to, and anyone listening, think of it something that you're proudest of in your life, that you did just one thing. Do you have something in mind?
Kim Meninger
I would say, probably leaving my corporate life.
Jennifer Wilson
Was it easy or hard? It was very hard, yeah, so never have I asked that question. Had anyone say I'm proud of this and then that it was easy? Never, I suppose it's possible, but usually, almost all the time, in my experience, people say something that was, that was hard and scary, and so that proves, you know, kind of supports your point of saying that the confidence follows taking the action like, Wow, I did that even though I was afraid, not I'm not afraid. I'll do that.
Kim Meninger
Exactly, exactly. Yeah. And I want to bring imposter syndrome into the conversation, because I want to understand how it shows up in the work that you do. Is this something that you see often? Where do you see it?
Jennifer Wilson
It is rare for me to have a coaching client in particular who doesn't at some point use those words. In fact, someone just did last week. Two people did the last week. So, so people use these words to describe a set of feelings of, um, some common thoughts are, I'm in over my head, or they're going to find out I don't actually know everything that they think I know, or I thought I could handle this, but now I'm not sure, or at some point, somebody's going to discover that I'm just kind of making things up as I go. And I believe that, yeah, all of that's true for all of us. And then we often kind of project on other people that they know what they're doing, even though I don't. And that comparison, I kind of call it Junior High syndrome, feeling very self-conscious. And like one day, I lived out in the country, so I had to get dressed for school in the dark. And I got to school, and I looked down I had a black sock and a navy sock on, and I know the kids. These days mismatch their socks on purpose, and it's cool back then it was, I was mortified. I don't think I learned all day, because I was just like, someone's going to notice my socks. And that level of self-consciousness is part of imposter syndrome, I think. And I think when we can relax in that trust, if you think about a time when you're when you're like the most at ease, hanging out with friends, laughing, you probably in that moment not feeling self-conscious, so that letting go of ego and focus on like, how am I appearing and looking and trying to manage that and self-trust, which then lets you enter flow and a different state of being that people can feel around you is, is part of that shift from imposter syndrome to confidence?
Kim Meninger
I think, yeah, you know, and I often encourage people to think about, what is the difference, as you're describing between the situation where you feel completely relaxed, you're not self-conscious, you are yourself, and things are going really well in those moments when those thoughts start to creep in and you start to get really anxious and, and really think about like, what are the underpinnings of those situations? Because the better you understand what the you know components are, the better you can prepare and anticipate what might trigger you in the future. And also, are there ways in which you may be able to recreate some of the positive conditions that appear when you are feeling more relaxed?
Jennifer Wilson
Yeah, I love that idea of anticipating, of being like a social scientist, imagining, you know, sitting there with your field, field notes, and taking observing yourself like a scientist, saying, What are the conditions? What's happening? Ah, and getting really curious and getting to know yourself at that level, and then being able to anticipate, okay, so I've got this thing coming up. Here's how I likely might think or feel that is going to get in my way, and then being prepared with and here are three things that I can quickly internally do on the spot that will help me return to my state of balance with myself.
Kim Meninger
Exactly, exactly. So are there common ingredients that you see in the people that you work with for common ingredients, about common ingredients, that lead them to feel this way, to struggle with imposter syndrome?
Jennifer Wilson
Oh, for the struggle part, yeah. I think sometimes, for, for a lot of people, it's these feelings are old. They're not brand new. They didn't just like pop up at the promotion time that there are mentors of mine, Robert gas and Judith and Sarah have this metaphor that I just love. If you've ever been cross country skiing, Nordic skiing, there's a machine that makes tracks in the snow that you can glide along in really easily, and your skis fit in it, and they take you a certain way, and but if you step out of those tracks into the snow and forge your own trail, it's hard going. So our neural pathways can be like that, like if we associate certain experiences and ideas with an emotion, for example, like any someone criticizes us, we feel shame. Boom, those are connected. And the more that that's repeated, the stronger that track gets carved in the snow. And the idea of shifting out of those tracks and making new connections is something that I think people really do well. When they begin to see like, oh, there's an automaticity to these self-doubts and thoughts and they're not real. They're based on connections that were made some other place in time that aren't even about now. So beginning to like become aware of that pause between something happening in the world and the space we have between that in our response or reaction, we can react reflexively, or we can pause and become aware of our own thinking, enough to know that there even is of space there, and to, to think something new and practice that over and over.
Kim Meninger
I'm so glad you brought that up, because I am a big proponent of the pause button. What you're saying too is really important about this not being necessarily a new thought, but one that has been with us for a long time, and I think that because we're creatures of habit and we're very overstimulated in other aspects of our lives, we're not necessarily slowing down long enough to examine what am I actually telling myself in these moments? What's the story I'm telling myself and. Where is this coming from, and does it serve me, right? Because I do think that a lot of this is rooted in early childhood, when we don't have the sophistication to be able to process information or feedback in the same way that we do as adults. That you know, we have a far less power and agency over our own lives, and so we we feel a lot more anxious. We use different coping mechanisms to navigate our lives, and then we kind of just perpetuate those as opposed to updating them with, with new ways of approaching challenging situations.
Jennifer Wilson
Yeah, I love that word updating. I often say, you know, I'm Jen 5.6 and, and so you mentioned pausing and taking time. So in the book I wrote, waking up to your worth, 10 touchstones for overcoming imposter syndrome, there is an entire chapter called Making space, and it's something that is not rewarded currently in our US culture. In fact, I wrote a blog post called busy is the new fine. How are you? I'm busy, so busy, and it's almost like, you know, I was up to 11. I did the baking, and then I did this, and I drove carpool, and I've got 10 reports, and we're almost like, bragging, yeah, and what are we bragging about? What's the prize? So I have developed a reputation among my friends and colleagues as a person who lives in balance, and so I need to continually practice that in order to be integrity with myself and for that to be true. So I think making that space is where we begin to even understand that we can listen to that voice in our in our quiet voice that knows and knows it knows within us, but pausing and not being busy, some can sometimes lead to actually feeling and that might be uncomfortable. My belief is that a lot of our busyness is to distract ourselves from feeling discomfort or pain. And questioning our thoughts can be uncomfortable or painful, and if we can make friends with the idea that it's okay to feel uncomfortable, which is not a message we usually get, and to develop our tolerance for feeling uncomfortable, then that's the pathway to an expanded world for ourselves of more flexibility, more joy, more options, more confidence, more self-awareness and, and self-trust.
Kim Meninger
I that's so beautifully said, and I wonder too, because you make a really important point, that it does generate a lot of discomfort, especially if this isn't something that you have done before, if there is a disconnect right between you know how you want to feel or think and how you're actually feeling or thinking, right that can that can create a lot of, of stress. So is there anything you'd recommend for kind of getting more comfortable with the uncomfortable?
Jennifer Wilson
I'm so glad you asked that. I am a big fan. I'm guessing you are too of small shifts leading to big results. So one thing I often ask in coaching is, how could you so, so you feel this way and you want to feel that way, or like you feel anxious and unsettled, and you want to feel more at ease and more confident. How could you feel 10% more at ease? What's one thing that might help you feel 10% more? And usually people have an idea of that and like, oh, well, actually, this would help me feel a little better. Great experiment. So the answer to your question, I think, is experiments. So looking at it that way, okay, the next time this comes up, don't have the expectation that you're just going to not feel those feelings and power through and just be different. That doesn't work. But what if you went in and said, okay, I'm going to feel, you know, the anxiety or whatever, but I'm going to experiment with trying this thing I thought to do and see if it makes me 10% less anxious? Sometimes you discover it does. Sometimes maybe it didn't. Maybe that wasn't the right thing, but maybe it made you feel 60% better. So looking at it that way, as just see what happens. Try the thing, see what happens. And eventually people come up with this set of shifts and tools that just like someone learning to play basketball, nobody get picks up a basketball and can just dribble well the first time they pick it up, you. You, you try it, and then you try. Oh, if I hold my hand this way, it works a little better. Oh, if I push a little harder, it works a little better. So it's these small shifts that allow us to then get really good at dribbling the ball. And it's the same way with our thoughts. One of my favorite little parables is the Akito master. A student said, Master, you never lose your balance. And the master says, I lose my balance all the time. I just recover more quickly. So the goal isn't to get ourselves to a point where we never feel these feelings. Feelings are okay. They come up. It's what how we respond to them in ourselves that makes the difference.
Kim Meninger
Yeah, that's really powerful and, and I want to go back to the experiment piece too, because I'm a big proponent of this as well. I think it's a really great practice. And I wonder if you think that even adopting the mindset of an experiment makes your relationship to the task a little different, right? Because, I think so often, especially those of us who are perfectionists, or who, you know, really tie our identities to our performance in some ways that making mistakes, or, you know, not, not having everything fully baked can feel really anxiety provoking, but just the mere notion of it as an experiment kind of creates a little bit of emotional distance between you and what you're doing, and might free up some, some ability to, to do it a little more lightly.
Jennifer Wilson
Absolutely, I had this experience with experiment when I was in my late 20s, and I write more about this in much more detail in my book, but briefly this, I didn't have a lot of self-esteem for a lot of reasons. I just lacked self-confidence, even though I was doing well to the outside world, performing well at work and all of these things, I just didn't I felt like I had to change who I was to fit in. I didn't know how to relax and be myself and develop friendships in an authentic way, because I was always trying to figure out who someone else wanted me to be and be that way to fit in, and I noticed it wasn't working. Really wasn't helping me win friends. In fact, it was annoying to people. And I started to really see that. And then I was like, What do I do instead? And I had the great fortune of going to a place that that called Diana's grow with mentors of mine, Cynthia Jones and Patricia storm and many other people in that community who, the first time I went, nobody knew me, so I went to this week long event out in the woods. And I didn't have the expectations of people saying, you know, this is who Jen is. Jen is this, this and this. And having to fit those, I relaxed and was a person that was joyful and fun and funny and confident and all of these things. And I decided I am going to make sure, I'm going to do everything I can to figure out how to have that person match who I am in my back home life. And so I started with experiments. I started really small, like, really small. And I think that's the place the way to do it. Like, when someone said, Oh, do you want to go to this movie in the past, I would just say, sure, because I wanted to be with that person and be their friend. So I'd go to the movie even if I didn't want to see it. So I started with just saying, I don't think I want to see that movie. What do you think about this one? To that sounds so small. But to me, it was, like terrifying. It really was. And then someone said, Oh yeah, that sounds fine. And we went and nothing bad happened. Or maybe they said, I don't really want to see that one, but how about this one? And it just worked. It worked its way out. And when I started having opinions and expressing them and being myself versus being who I thought someone wanted me to be. My relationships all shifted and changed and grew and deepened. So that's my lived experience with experimentation and how important it was to me to make small shifts that had such big impact.
Kim Meninger
I love that on so many levels, because I think I can totally relate to exactly what you described, having moved every couple of years when I was a kid, so I always felt like the new kid who was trying to fit in and always aim to please and trying to read the room and see what are the expected behaviors and often miscalculating, because people don't necessarily want a friend who always says yes to whatever they want, right? And just as you're describing, you kind of lose yourself in the process. But also to, to the, the level of experimentation that you're talking about, it's so small but so powerful that it's easy enough, and I get that easy as a relative term, but easy enough for us to find ways to do that in the course of our every. Day, work lives, personal lives, and really start to notice some shifts. It goes back to the whole idea of, you know, confidence follows action, right? That when you realized that the whole world wasn't going to collapse when you proposed a different movie, yeah, your, your brain updates accordingly, and now the next time that happens, it's not as scary as it used to be, right?
Jennifer Wilson
Those new tracks are being laid in the snow, those new neural connections of thinking and feeling are being made. So how this translates, I think, to the people's careers in the workplace. Right now I have a client who's experimenting with not going into a meeting, assuming the worst and armoring up, but to go in with a more relaxed mindset, 10% more relaxed, 10% less armored up, just to see if anything bad happens. So it's not like you said before so beautifully, that it's not about the performance. He's not going to reflect on how did how well did I do? It's what happened. So it's about what's happening and noticing versus grading the performance. And I think that's really important part of experimentation too.
Kim Meninger
Yes, I love this so much I and I feel like it's very practical, and something that you know, again, anybody can try out. Gosh, in the interest of time, I feel like I could go on and on with you, Jen, but because you've mentioned your book a couple times, and I want to make sure that people who want more of what we're talking about, talking about know where to find you and anywhere else that you want to point people to. For people listening, where can they find you and your book?
Jennifer Wilson
Thanks for asking. My company is called New Leaf Coaching and Consulting, and that can be found at consult new leaf dot com on the web, and there's a link there for the book. You can also find my book on Amazon, and again, it's called Waking Up to Your Worth, because we already have worth. We're just remembering. So waking up to your worth not making yourself worthy. And the subtitle is 10 touchstones for overcoming imposter syndrome. And each chapter has a theme, and at the end of each chapter are very practical things to do, because it's one thing just to talk about all these things. But what do you actually do if you actually want to address this? So there's exercises, suggestions, resources all throughout the book to try.
Kim Meninger
That's fantastic, Jen, and I'll make sure the links are in the show notes as well. Thank you so much for being here. I really appreciate the conversation.
Jennifer Wilson
You're so welcome. Thank you for inviting me. I've had a wonderful time talking with you, and yes, I could have talked five more hours. It's just been a delight.
