Episode 97: From Surviving to Thriving: How to Build the Courage, Confidence, and Long-Game Strategy Your Consulting Practice Needs

Season #1 April 10, 2026

What if the slow, frustrating stretch of your consulting practice — the one where the pipeline feels empty and the revenue isn't where you need it to be — is actually your long game paying off? Rachel Wexler knows exactly what that feels like, and she'll show you how to recognize the seeds you've already planted.

In this episode, host AJ Riedel talks to Rachel Wexler, Executive Coach and Leadership Consultant at Rachel Wexler Leadership. Rachel brings more than 20 years of cross-functional leadership experience in education and edtech to her coaching and advisory practice, where she works with leaders and organizations on interpersonal dynamics, team performance, and sustainable growth.

Why You Should Listen to This Episode

If you launched your consulting practice expecting to replace your income faster than everyone told you it would take — and now you're wondering what you're doing wrong — this episode is for you.

Rachel Wexler is three-plus years into building Rachel Wexler Leadership, and she speaks with unusual candor about the gap between expectation and reality: the no's that outnumber the yes's, the promises that don't materialize, the perfectionism that keeps you planning instead of doing, and the slow-burning relationship-building that eventually turns into real work. She also talks about what it means to expand your practice model intentionally — moving from coaching into blended coaching, consulting, and advisory work — without losing focus or chasing revenue that doesn't fit. This is a conversation about playing the long game with your eyes open.

What You'll Learn in This Episode

Why It Takes Longer Than You Think — and What To Do About It: Rachel shares the hard truth about income replacement timelines and why the conventional wisdom she ignored turned out to be right — plus the mindset shift that helped her move forward anyway.
How to Build Thicker Skin Without Losing Your Heart: When you are the product, every unanswered email and unfulfilled promise can feel personal. Rachel explains how she learned to depersonalize rejection and stay energized through the slow seasons.
The Long-Game Strategy That Actually Builds a Pipeline: Rachel describes what "over-investing in opening doors" looks like in practice — and why conversations that don't convert immediately are still worth having.
When and How to Expand Your Practice Model: Rachel walked her practice from pure coaching to a blended coaching, consulting, and advisory model — not by planning it, but by following what clients needed. She explains how to recognize those signals and respond without scope creep.
How to Stay Focused When Opportunity Distracts You: Rachel gets honest about the challenge of staying pointed at a consistent North Star when interesting — and potentially lucrative — opportunities keep pulling you sideways.
The Daily Habits That Keep a Solo Consultant Centered and Energized: From getting enough sleep to building in-person connection into every day, Rachel shares the practical routines that help her stay present, sharp, and sustainable.

Listen to These Key Moments

[00:28] What Thriving Really Means — Rachel shares a story from her mid-20s about her parents insisting on celebrating life's moments — and why it took her 20 more years to understand why they were right.
[06:14] Rachel's Path to Self-Employment — After more than 20 years running product and strategy teams in education and edtech, Rachel describes what finally pushed her to make the leap — including a milestone birthday she used as a non-negotiable deadline.
[16:17] The Challenges of Building a Practice From Scratch — Rachel gets candid about the reality of income replacement timelines, learning to handle rejection, and why she couldn't circumvent the advice she was given no matter how hard she worked.
[20:57] Evolving From Coaching to a Blended Model — Rachel explains how her 360 coaching process organically revealed consulting and advisory opportunities — and how she learned to navigate those without compromising her coaching work.
[30:03] Over-Investing in Doors and Playing the Long Game — Rachel talks about what it feels like when a door reopens after a year of silence — and why planting seeds, even without immediate return, is a real business development strategy.
[34:00] Is Your Practice Delivering the Lifestyle You Imagined? — Rachel shares an honest answer to this question, including how she structures daily in-person connection to stay centered during weeks that are wall-to-wall Zoom.
[38:16] Where Rachel Sees Her Practice in Three to Five Years — Rachel describes her vision for doubling revenue through collaborations, deepening coaching work, and building a thought leadership platform — and references Will Guidara's concept of continuous 10% improvement.
[44:10] The Biggest Challenge Ahead: Staying Focused Without Losing Momentum — Rachel names the two competing forces she expects to face as she grows: keeping all the plates spinning while staying true to a consistent North Star.
[45:23] Books and Resources That Have Shaped Rachel's Practice — Rachel talks about Brené Brown's work — specifically Dare to Lead — and Priya Parker's The Art of Gathering, including Parker's concept of the "magic question" that unlocks genuine connection in group settings.

Resources Mentioned in This Episode

Dare to Lead: by Brené Brown
The Art of Gathering: by Priya Parker
Unreasonable Hospitality: by Will Guidara

Rachel Wexler is an executive coach and leadership consultant with more than 20 years of experience leading cross-functional product, strategy, and learning design teams in the education and edtech sectors. At Rachel Wexler Leadership, she works with leaders and organizations on interpersonal dynamics, team performance, leadership development, and organizational change. Her practice blends executive coaching — including in-depth 360 processes — with consulting and advisory work that helps leadership teams communicate more effectively and work better together. Rachel also conducts research on women leaders through her project JUUL (Joining and Empowering Women in the Exploration of Lived Experience) and hosts the interview series Full Picture Leadership.

Connect with Rachel on LinkedIn: linkedin.com/in/rachellevywexler

Website: rachel-wexler.com

Instagram: @rwexlerleadership

Episode Transcript

Rachel Wexler — Full Interview Transcript
Thriving Through Podcast, Episode 97 | Air Date: April 14, 2025

What Thriving Means
AJ: Rachel, welcome to the Thriving Through podcast. I'm delighted to have you on the show with me today.
Rachel: Thank you, AJ. It is such a pleasure to be here.
AJ: The podcast is named Thriving Through, so the first question I like to ask my guests is: what does thriving mean to you?
Rachel: That is such a good question. We do a lot of surviving. I often tell this story about when I was in my mid-20s, and my parents and I had this conversation about celebration. I was young and optimistic, and I thought my parents were making a very big deal of an event that didn't need so much pomp and circumstance. They said to me, almost in unison, 'Life is hard, and so we need to celebrate all those moments.' I was very judgmental in the moment and thought, it's not hard.Twenty-some years later, I can say to you: yes, life is hard. And too often, people are surviving, and they are not thriving. I see thriving as that moment where you're not just getting by, but you are feeling really good about what you are doing. You believe in what you are doing — and that can be in one's personal life, in their professional life. Hopefully it is the combination of them. It is feeling as though somebody really understands what they bring to this world, and that they are giving, and they are receiving, very much as a cycle. And that leaves them feeling a sense of fulfillment and joy.
AJ: I love that definition. My goal in life is that I want self-employed consultants to have fulfilling consulting practices. Profitable, yes — we need profit to build wealth. Sustainable, that's important too — but fulfilling is the most important thing.
Rachel: When I wish people a happy birthday or Happy New Year, I always use the word fulfilling. Fulfilling isn't just that you are giving and not receiving. It's not just about being profitable. It is being able to feel like you are giving something and you are receiving — and I think that is thriving.

The Neuroscience of Celebrating Small Wins
AJ: I want to go back to the story you told about your parents and celebration. One of the things I do in my coaching calls is that we start out by having everybody share a win. It can be a small win or it can be a big win — even a teeny-weeny win. And then we do something they think is stupid until they get used to it. I have them do jazz hands, or a woo-hoo, or just throw their hands in the air like they just don't care for ten seconds. To celebrate the win.There's actually a neurological reason to celebrate, because when we do something like that, it triggers dopamine. Our brain goes, oh, I like that feeling, I want more of that. So then the brain goes out and tries to find other wins. Your twenty-plus-year-old self didn't know the importance of celebrating, but your parents were really onto something — I take it all the way down to the teeny-weeny wins, not just the big stuff.
Rachel: That advice is so salient, because in our respective independent consultancies, we're always focused on those big wins. And if that's the only thing we're celebrating, we could go a long time without one. It's funny — I am probably better at getting my clients to celebrate the smaller wins than I am myself, because the minute I feel like I've been celebrating, it's already on to the next thing. But celebrating those wins, big and small, is really important. It helps us, it fuels us for the next thing.
AJ: Yes, because what we're doing is hard. Being a self-employed consultant, being the CEO of your own business, chief cook and bottle washer, and salesman and everything — that's hard stuff. We need to feed ourselves, and not just food.
Rachel: Exactly. We try to make it so it's not just food.

Rachel's Path to Self-Employment
AJ: Tell me: what was your path to becoming a self-employed consultant?
Rachel: My path to being a self-employed consultant really came after more than 20 years in industry. I started my career as a consultant, and then had been running product and strategy teams, largely in the education and edtech sector, for the better part of 20 years. I really enjoyed what I was doing, because I was not only intellectually challenged, but there was also a fulfilling aspect — I liked the people I worked with, and we were working really hard on programs where the learner, or the learner's organization, was benefiting from the educational programs we were designing.In the last work I was doing, which was in the workforce development sector, we were designing programs that had the potential — and ideally the likelihood — to break generational poverty. To help someone who hadn't been helped by the public education system previously. That was really amazing at the end of the day.I also really enjoyed walking into a room and gathering the context. Some people look at a balance sheet to size up an organization. I've always been the person who walks into the room and sees how people are interacting with each other — and I can pretty quickly connect with individuals and really understand what is going on. Some people I worked with really appreciated that part of me. There was one person who used to tell others, 'If you don't know what's going on with your team, send them to Rachel, she'll tell you and help you figure it out.'
Rachel: When my youngest was about three — I have three kids, who are all teenagers now — I had been parenting pretty intensely for about eight years, and I felt like it was time to do something for myself. Not to go out to dinner with friends or go away for a weekend, but to really have an opportunity to learn. Somebody recommended taking an executive coaching graduate certificate program, and I did some research. For me, it brought together three things that really interested me: business and business context, people and internal motivation and learning, and lifelong learning — because that's what I was doing in my day job, designing learning programs.That was actually eight to ten years before I set out on this journey. I share that because for people who are considering this path: it's not an easy decision. We leave a salary, benefits, and all the things that come with that. We leave a place that we are accountable to, and we take that need for structure and put it entirely on ourselves. It took me a long time before I had the confidence and the courage to take that risk — and that was not because I didn't have the support of a loving partner who is an entrepreneur at heart. I had colleagues who also thought this was where I should be. And yet, I needed to believe enough in myself.So truly, I talked about it for years. I had many different plans. I would talk about it all winter, with this idea that I would take a few months off in the summer. I had saved a little fund of money to support myself without income for some bit of time. And every spring, I would find a reason to stay in my job.Finally, during COVID, I left my job and took on a few other projects, planning to also launch my practice. And I avoided everything that scared me and dove into the projects I was running. Then I had a milestone birthday, and I decided I had to make this leap before that birthday, or else I would live with regret. I could never get over the hump on my own, so I used that milestone — arguably meaningless in terms of the content of the work — as my absolute barrier.
AJ: Thank goodness for milestone birthdays, right?
Rachel: Now I really should celebrate every single one.

The Challenges of Building a Practice from Scratch
AJ: Tell me a story or two about some of the challenges you faced in building your practice, and how you've overcome them.
Rachel: One of the things was that some of the best advice I had been given, I thought I could circumvent. One milestone I had was to replace my income. People said it's going to take you at least three years to do that. And I thought, no way — I can work harder, I will do whatever it takes, it's going to take me maybe six months, then a year.The advice was pretty true. It certainly wasn't going to happen in six months to a year. And I thought, gosh, I'm doing this work that some of the people who know me best had been really pushing me to do, and felt so confident that I was ripe for this consulting practice. And I believed that, therefore, I'm going to figure this out faster than anybody else. The reality is, it takes some time to really get one's footing. And that is everything from setting realistic milestones to pitching yourself and your business, to listening to everything around you, and then aggregating that learning and iterating. It's a constant cycle of continuous improvement — really, product-market fit.And when you are the product, you also have to learn how not to take things personally. It didn't matter how many times people would say, you are going to have a lot more no's than yes's — I thought I was going to beat those odds. The reality is, you have to develop thicker skin, probably, than ever before. Really not take things personally, whether that's somebody not responding to an email or somebody saying, 'I'm going to make these introductions for you,' and then it doesn't happen.Oftentimes, people have so many things on their plates. They want to help you, but maybe that sounded like a great idea on the side of a soccer field on a Saturday afternoon, and by Monday morning they have a pile of deliverables. This genuine offer that they made on a beautiful Saturday afternoon is relegated to the bottom of their list — and that really isn't personal. That's been something I've also had to get used to.
AJ: And it's really important — the empathy you show in understanding that it's really important to you, but not so important to someone else, because they have so many other urgent things.
Rachel: And we learn lessons when things don't go well. It's really when things don't go as planned that we learn. The past few years have been full of learning.

Evolving From Coaching to a Blended Practice Model
AJ: You evolved from a primarily coaching model to a blended coaching, consulting, and advisory model. How did you know it was time to expand, and what did that shift require of you?
Rachel: One piece of advice I had been given was, 'Rachel, don't let the idea of a perfect plan constrain you.' Those who know me best know that I'm a perfectionist at heart. As a working mom, we learn how to accept something less than perfect — but I could easily get stuck working so hard on a plan that I don't actually do the work I'm intending to do.When I launched my practice in February of 2024, I wanted to offer some blend of coaching and consulting. But people who knew me knew that I had started my career as a consultant, and at different points in my career I had worked as an independent consultant. I didn't want this to be another version of one of those chapters. I really wanted the consulting work to be adjacent to coaching.I felt a need to really reposition myself — which was a risk, and continues to be a risk — as the product of my leadership experiences, but choosing to focus on people, interpersonal dynamics, and growth. I viewed it very much as the pendulum needing to swing all the way out toward coaching before it could fall somewhere back into a consulting model.One of the things I do when I start a coaching engagement hired through an employer is conduct a 360 exercise. I speak with somewhere between seven and ten colleagues — peers, managers and executives, people who work on the client's team — and I try to develop a really good picture of how this person shows up, where their growth edges are, and what legacy relationships might be acting as constraints. That becomes the heart of the coaching engagement.In doing that, when I'm coaching a leader, I end up speaking with a number of people on the executive and leadership team. I get a pretty good sense of what is going on. And so, when I speak with the CEO or other executives, I can bring an objective lens to that leader's attention. In the throes of these 360 exercises, it became clear to my client — not necessarily the person I was coaching, but the person who hired me — that there was more I had to offer. Doing some coaching as well as consulting or advisory work was a way to really tap into more of what I bring to the table.Some clients said, 'Thank you, this is really helpful, keep coaching this employee.' Others said, 'Could you help in these other areas?' And oftentimes the answer was, yes, I can help you do that. With a number of clients, I've figured out ways to extend the relationship and bring an objective, experienced lens to the table — opening up lines of communication and rethinking ways of working among leadership teams.
AJ: Your coaching mechanism — the 360 — helped you see where there were problems or issues separate from your coaching that you could add value on for the client.
Rachel: Exactly. And I like being seen as an extension of their team, not so far removed that there's a veil between us. Really connecting with my clients enables them to trust me and to trust the spaces I create, where they can be vulnerable and take risks they wouldn't otherwise take. That helps build long-standing relationships.I don't view this as transactional — I'm going to do this project and then I'm out. I may not work closely with someone for several months, and then they may have a question and call me back in. I'm interested in building long-standing relationships, and I think that becomes one of the filters that people notice about me.

Over-Investing in Opening Doors and Playing the Long Game
AJ: When we talked earlier, you talked about over-investing in opening doors and playing the long game — and now you're starting to see those early conversations come to fruition. What does that feel like?
Rachel: When somebody comes back after I haven't spoken to them in over a year and says, 'I was thinking about you the other day' — the very human in me gets really excited, because it means that at some point we did connect. We did have a meaningful interaction. And they just didn't need to act on it in that moment. But when the moment arises, it's human nature. We like to feel that we matter, that we said something of value.When that door reopens, it is somewhat exhilarating. In the context of big wins and small wins, sometimes it's that reopening of a door — which isn't revenue. It's just someone saying, 'I want to reconnect, I have some follow-up questions.' But that's a small win, because that door is reopening.We plant a lot of seeds as independent consultants. Sometimes, at the end of a week, I feel like I'm just tired because I feel like I'm on all the time. Whether that's at a board meeting, or in a client meeting, or sometimes even in the grocery store — there is a bit of always being on, because you don't know when somebody is going to ask a question, or whether somebody's been reading some of my posts and comes up to ask about something I wrote. You want to make sure that in that moment, you're not sitting there thinking about all the stresses of the day — that you can open that conversation and be ready to go.
AJ: That's a big challenge. How do you manage that?
Rachel: Something I've never really been good at, but that I'm finding more and more important, is making sure I get enough sleep. We are all fresher, happier, and more agile when we've had proper sleep. I think the other thing is just trying to stay centered and making sure that I'm living my values and being true to myself. When I say I feel like I have to be on, that is being the best version of myself — not being someone I'm not.

Is the Practice Delivering the Lifestyle You Envisioned?
AJ: Is your consulting practice delivering the lifestyle you dreamed of when you made the leap?
Rachel: I would answer that in a couple of ways. We are all our own worst enemies, and my DNA is to work really hard. It would be very easy for me to be constantly working and not making time for anything else, because I haven't reached all of the big goals I have for myself. And then I have come to learn: I made this decision, I've taken a lot of risks, I've given up a lot of things in order to have this practice and this lifestyle. If I don't figure out what I need and live into that, then I'm really not achieving my goals.I'll give you an example. I have a number of clients I meet with in person, and I have clients spread across the country. Some days I can be on Zoom all day long, and that doesn't feel great for me. What I have learned — only because I've gone through periods where I haven't been able to achieve that balance — is that on days that are end-to-end Zoom, I need to either make a coffee date with a friend, or go for a walk with a friend or colleague. Something every day that gets me out and with somebody in person.I play tennis rather competitively, and so tennis has become a really good outlet — I can get a workout and be with people I really enjoy at the same time, so it serves a double purpose. That is my key for staying centered and maintaining a certain balance. That doesn't mean I'm not working from 5:30 to 7:30 in the morning, or that I may not work at night or on the weekend. But I do try to build in a little bit of time every day so that I'm not sitting at my desk from sunrise to sunset.I also recognize that because I'm my own boss, I can and need to prioritize certain things. It's important to me to be at my kids' games and school events. It doesn't mean I will make it to everything, but I do try to make it to the things that really matter.
AJ: That's the beauty of being a self-employed consultant and coach — those are some of the benefits.
Rachel: And if I'm not taking advantage of them, then why am I doing this?
AJ: Exactly — you might as well have a job where you get a steady paycheck.

Vision for the Next Three to Five Years
AJ: Where do you see your practice in three to five years?
Rachel: In three years, I'm hoping it's doubled in revenue. Which doesn't always mean I'm working twice as hard — it could mean I have some collaborations that expand my scope and purview, and it could bring in different types of work. I always said I wanted my practice to be some combination of consulting, coaching, and thought leadership.I hope this long-game strategy continues to play out, and I have more organizations that I'm working with on an ongoing basis, so that I have a more regular group of projects and initiatives at any given time. I also see an evolution of my coaching practice, which comes with more years in the business.On the thought leadership side, I would love to do more speaking — some keynote speaking based on my experience as a coach, as a leader, and as a researcher who interviews leaders and shares themes from those conversations. I would love for that part of my work to also expand.Last year, I had multiple clients who were all independently reading Will Guidara's Unreasonable Hospitality. He was the partner at 11 Madison Park, which became the number one restaurant in the world — and he was the head of the front of the house. In an industry where great restaurants have historically been synonymous with excellence in the kitchen, one of the things he said in his book was that excellence isn't just doing one thing really well — it's about doing a set of different things, and doing everything continually ten percent better. When I think about the three-legged stool I always envisioned when I started Rachel Wexler Leadership: where do I want to be in three to five years? I want to be a little bit better every year on each of those three dimensions.

Biggest Challenges Ahead
AJ: What do you think are the biggest challenges you're going to face in achieving your goals?
Rachel: Continuing to cultivate new clients while also doing the work — that's part of being everything: the wait staff, the bottle washer, the everything. So one challenge is how can I keep all of it going, and then figuring out what I would outsource and who are the partners I'd like to bring on to help support a growing scope, while being really mindful of scope creep.The other challenge is going to be how to continue keeping things interesting without getting too excited about everything and not staying true to a specific anchor. How can you be responsive to inquiries that come in while also staying pointed at a consistent North Star?
AJ: That bright shiny object — going after things that maybe are not quite aligned. They would be good money, but they're not aligned. That requires discipline.
Rachel: Even naming them, I'm taking notes as we're talking, because as I say these things I'm thinking, I need to remember this — whether it's a sign on my desk or a list I keep going back to, to stay true to why I'm creating what I'm creating, how I'm creating it.

Resources That Have Shaped Rachel's Practice
AJ: What is one book, podcast, or resource that has been invaluable to your consulting practice?
Rachel: Personally — and even something I share with my clients — I am a Brené Brown devotee. I just love listening to her. I love knowing that we all have a softness inside of us, and that's okay. Sometimes it's naming what we're afraid of, being vulnerable, talking about what we carry with us as a way of entering this world. If there were anything I could do, I'd say I want more of what she's doing. My favorite of her books is probably Dare to Lead — though that's a hard question.
Rachel: Another person I really enjoy is Priya Parker. She wrote The Art of Gathering. One of the things she does that I love is what she calls a magic question — different from a standard icebreaker. Her magic questions are democratic in nature: everybody wants to answer, and they want to hear what the other person is going to share. And someone has to take a risk in answering.One of my favorites is a question I used long before I knew it aligned with her magic question construct: 'What was your first job, and what did you learn from it?' Sometimes you can unlock someone because it brings them back to a place before they were a leader of a multi-million dollar organization — before they went to college and entered a new world. You really understand how someone entered the world and incorporated those early learnings into who they became.Priya Parker's work is so interesting. In many cases it's about how do you bring people into a space, get them to interact and contribute, and build something together that has never been created before.

How to Connect With Rachel
AJ: How can listeners connect with you if they want to learn more about you and your work?
Rachel: I always love when people want to connect. I post regularly on LinkedIn — I find that it's a real way to start conversations. I often share things I've found in conversations with clients. Without ever divulging who they are, I share in my work how people are often surprised to know that there are other people like them, facing the same types of challenges, held back by the same internal or external hurdles. That's a real way of helping people feel human.On LinkedIn, I'm Rachel Levy Wexler. On Instagram, I'm rwexler Leadership. And I have a website — rachel-wexler.com — where I also blog.When I started this work, I was also doing some research on women leaders. The project is called JUUL, which is an acronym for Joining and Empowering Women in the Exploration of Lived Experience. Some of that material I share on social media and on my blog.I've also recently started an interview series called Full Picture Leadership, where I talk with leaders about a high-stakes moment when they thought they had all the information they needed, and then realized they hadn't seen the full picture. That will become content for my blog and LinkedIn. There are plenty of ways to reach me, and I love when people come with questions and really interesting situations to help think through.
AJ: Wonderful. For those of you listening and watching, all of the links will be in the show notes at ajriedel.com. Rachel, thank you so much for being my guest — and for those of you listening and watching, until next time, keep thriving through.
Rachel: Thanks, AJ!