003C. An Interview With Matt Thieleman on How to Build Character

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Key Quote

“What are the habits that actually move you toward the life that you want?” – Matt Thieleman

Episode Summary

In this podcast episode, we delve into the captivating journey of Matt Thieleman, who became the CEO of Pilea, a coaching network with an ambitious mission to connect every founder in the world with a coach. However, Matt soon realized that his true path lay elsewhere, prompting him to make the difficult decision to step down.

As Matt navigated this challenging period, he leaned on his coach, friends, and fiancée, discovering the importance of self-care and cherishing time with loved ones. He also faced the difficult task of upholding Pilea’s values, even when it meant letting someone go with a compassionate heart.

Join us as we explore Matt’s transformative experiences, where each choice he made contributed to building character and moving towards his goals. After leaving Pilea, Matt took two months for introspection, which led him to pen his insights in a book called “This is Coaching.” Through this process, he gained a clearer understanding of his purpose as a coach.

In our conversation, we discuss the link between character, habits, and striving for one’s ideal life, as well as the significance of balancing masculine and feminine energies. We also touch on the power of curiosity and dialogue in becoming better humans.

So, tune in to our podcast episode to learn from Matt Thieleman’s inspiring journey of self-discovery and growth, and remember to always sign off with love.

Full Transcript

[00:00:00] Wesley Jackson: Can you relate to this?

Picture yourself having joined a new company as the CEO. This company aligns with your personal mission and you believe that this is what you’ll be doing for the next 10 years. However, a few months down the line, it has become clear that you were in fact wrong, and it’s time for you to move on to something else.

But how can you tell in the first place if the work that you’re doing is aligned with building your character or not? If it isn’t, then what do you do now? How else can you build character other than through your work? Where do you go from here? You’ll find all this out today through a story from Matt Thieleman, transformational coach, speaker, advisor, and visionary.

In today’s self-help podcast episode, you’ll learn about how to build character, how it relates to habits, and how these two powerful forces influence our lives.

Welcome to Surviving Humanity: A Self-Help Podcast, where we shift your perspective to help you overcome the obstacles in your life.

We are Wesley Jackson and Andrew Gilley, and we hope to foster a sense of connection and community over our common struggles while providing you with the tools to overcome them.

As always, our FacebookSubreddit, and Twitter are the best places to go for community connection, and support. Links to, these are in the show notes.

Let’s get started.

So Matt, do you have any stories that you’d like to share that are related to how to build character?

[00:01:13] Matt Thieleman: So in 2021, I joined Pilea, which is a coaching network that is focused on supporting venture-backed founders. I joined the team as CEO, and the decision was in support of one of my main missions in the world, which is to connect a coach to every founder in the world.

When I look at broadly our culture, and I look at the companies that have made a big impact in our culture the last handful of years, a lot of them have been small startups that have grown to be now massive.

When I think about the massive impact that especially these tech companies have on our culture, I think about if we can support their leadership, their CEO, in creating a culture and becoming the leaders that will build more supportive and loving organizations now when they have 10 to 20 employees, then what could happen when they have 200,000 employees? So, that’s a really meaningful mission for me.

So, I had the opportunity to join this company as a CEO, thinking it was gonna be a 10-year trip growing and building and scaling this company that is completely devoted to my own mission, that I did not found.

So, the building character part was not only me being CEO, but the fact that a handful of months into the job, I realized that it was actually not what I was meant to be doing for the next 10 years, and made the tough decision to pull myself out of that position and then rediscover what is next for me.

[00:02:21] Wesley Jackson: Wow. So that must have been a really hard decision for you to make. What were you seeing, hearing, feeling, and thinking when you were going through that?

[00:02:30] Matt Thieleman: The crux of what had me leave was that the co-founder and I are amazing friends. And work really well together. When I was in that position, we were essentially bumping heads in a way that wasn’t effective.

It was no longer gonna serve the mission or the business. What I had to do was take pause and say if I’m really committed to this mission and if I’m really committed to the success of this business, what’s actually the best thing here, where would I fit in and what actually needs to happen in order for the business to have the best opportunity to have the success that we’re looking at to have the impact we’re looking at?

I was lucky enough that I was able to craft the values that Pilea lives, and they’re actually very close to my values. So, I started to look at them and one of them is to be integrity. For me, integrity means living the things that I speak, so I really looked at if I’m committed to this, how can I best support this? And it started to become clear from that lens it’s actually not with me continuing to be in this sort of relationship that isn’t working.

One of the other primary values of myself and Pilea is be leader. For me that means having challenging conversations and making challenging decisions in pursuit of something bigger. I chose in those moments to say, “Okay, great. This is gonna be really challenging and this is what has to happen.”

[00:03:35] Wesley Jackson: So, you mentioned it a little bit already about how you took a closer look back at your values, but how else would you say that you have found a way through this period in your life?

[00:03:45] Matt Thieleman: The first thing is: I’m a coach. I stand for coaching. I have my own coach. So that is number one.

My coach at the time was extremely helpful even through that whole year in continuing to point me to – so I have a history of… I can give all of myself in pursuit of a mission or in service of others, and she did a really wonderful job of saying, “Yeah, great. You’re thinking about everyone else, and also where’s Matt? And actually the best way to serve everyone is for you to serve Matt as well.”

So, her input through the whole process was extraordinarily helpful.

I have an amazing group of friends who know me and know my values, so having really challenging conversations or just conversations where I could say, “This is really hard.” And they would sit and say, like, “Yeah, I get it. It sounds really hard. You don’t have to change. You don’t have to make a decision. I’m not gonna give you advice. I’m just gonna be here with you in the midst of this challenge.” was just so incredibly helpful for me.

And my now fiancée was also really supportive and actually, it took her a bit to be supportive, which was really interesting to me in that when I’m clear on a decision – so, by the time I realized I need to step away from CEO, it was clear and there was no faltering.

She makes decisions in an entirely different way than me, it takes her longer, and she sifts through kind of the pros and cons more. And so she was like shocked that I could wake up in a weekend and be like, “Yep, it’s clear.”

And she was like, “How are you not like wrestling with this for two or three months?”

For about a week, it was actually challenging between the two of us cause I felt like she wasn’t supporting me. But what it created was really more depth and understanding between the two of us. And like a willingness to say like, “Oh, she doesn’t get me, I don’t quite feel supported, but we’re still here together and we’re in it. And we’re gonna still be committed to our relationship and to our own depth.

Even in the tough spots, we found ways to come together more.

[00:05:20] Wesley Jackson: That’s great.

I’m really curious. I want to dive deeper into this concept of what your coach mentioned, which is “serving Matt.”

What did that look like in your case?

[00:05:29] Matt Thieleman: So, back to my partner – she works weekends, so she works in healthcare. She works three 12 hour shifts and then mostly on the weekend. And that was challenging for me schedule-wise to spend any time with her. What I ended up doing was taking Thursdays off every week just to spend time with her, so I could have that part of my life where I at least got to really dedicate time to her.

We live in beautiful Colorado, where we both really love to hike and get outside, so lot of those Thursdays were spent just getting outside together.

It was like, one, make sure that my relationship continues to be strong and two, get outside and get into nature and find recovery that way. And then the third, I continued to take care of my body, so I joined some places where I could get in sauna, get massages; it was really like taking care of that aspect of me as well.

That was where I succeeded. Where I didn’t always succeed was simply advocating for myself within the context of the business at Pilea, talking with the other leadership folks and saying “Hey, this is what’s working. This is what’s not working.”

That was where my coach continued to point, “Hey, there’s more opportunity here for you to really advocate.

And the wonderful thing about leading an organization that’s committed to transformation and coaching is that we have a tremendous opportunity to build that from the top down or from the bottom up, like inside-out.

And so she constantly was like, “Look, if you’re actually in service to these values as an organization, you as CEO have to advocate for them. You have to stand for them more than anyone else or else you’re not gonna be an integrity out in the world.

I can’t say that I always nailed that, but it was always a place for me to look at. Like, if we were really committed to these values that we have, how might we act as an organization?

[00:07:02] Wesley Jackson: It sounds like you had to ask yourself a few very big questions during this process. I’m curious also, how would you say this whole experience changed your perspective in regards to what it takes to build character?

[00:07:14] Matt Thieleman: I remember that one of the last things that I did as CEO, even after I knew that I was stepping away and some other folks on the team knew, was I had to let someone go on the team. In that moment, I said, “Look, like I know that I’m only here for another couple of months, but right now this is still my job. So, I’m gonna take that on and I’m gonna do it with courage and I’m gonna do it with an open heart and I’m going to really own the responsibility of that decision.

So, when I think about character, I think about the willingness to do what feels is an integrity with us, to stand up as a leader, especially when we don’t actually have to. That’s the crux of it, it’s like – I’ll speak for myself. I know that I’m offered opportunities to take the easy way out, to not have a difficult conversation, to survive life or just hold on. And I think character is developed by saying, oh yeah, that’s an option and I’m gonna choose what I think will move me toward where I want to go, especially when it’s really hard and scary.”

Letting that person go is one example.

Then, just continuing to lead and being really thoughtful about how I left the organization was, another point for me of constantly showing up every day and saying, “Yeah, I could just skate out, but I’m not going to, I’m gonna complete with love.”

And lastly, I, the co-founder and I went through our own sort of coaching – like couples counseling – as we split as a way to clean up and clear anything that may have been in the way for us having a relationship going forward.

All of those things were challenging, all of those things could have been avoided, but I think character is doing them.

[00:08:30] Wesley Jackson: Ooh, I love it. That’s quotable right there. Speaking of quotes, something that you said really reminded me of an earlier episode that I recorded with Kyle Golding on unethical advertising.

He said that, “Doing the right thing is always the right thing. Doing it when it’s hard is even more important.”

So, with that said, I’m curious as to where your journey went after Pilea? What did that look like?

[00:08:53] Matt Thieleman: So, I exited Pilea at the end of December of 2021. I took off January completely. So, I just allowed myself a month to play and that turned into taking about two months off. During that time, still working with my coach, taking this time off, and it’s a pause in order to give space for something else to come.

I knew that I’d be moving back into coaching. I knew that the mission of Pilea was still really important to me, and I knew that something else was gonna happen. I wanted to get really clear on who I want to be as a coach and as just someone in the world.

That time off culminated with a trip to Hawaii. That’s where my fiancée and I got engaged. It was really amazing. I remember landing in Maui and we walked outta the airport and my whole nervous system relaxed, probably for the first time in more than a year. I was so stressed. I was carrying so much.

At the end of that trip, we had to get up really early for a flight home. It was like 4:00 AM, still dark. I don’t get up in the dark. I get up with the sun. This is not usual for me. My eyes open and inside of me there was a voice that was like, “You’re writing a book.”

And I was like, “Okay, great, cool. How or when?”

And it was like “This year.”

And then, I wrote a book out April 4th of this year. It was just channeled, the outline of the book was channeled through me in about five minutes.

I got out of bed, I told my fiancée, she was like, “That’s crazy. Maybe you should wake up at 4:00 AM more often.”

I got to the airport and I wrote 80% of the outline, and then I just started writing. In about five or six months, I completed the book and have since then gone on to the publishing process.

So, what happened was I allowed for space in my life so that something new could come. What also happened was more clarity on who it is I am in the world and who I’m here to serve.

So, I got really clear that, while yes, my mission is to support founders and people up to huge things, I’m also here to serve coaches, because the way that I think about it is it’s great if I get a coach for every founder in the world, but if those coaches aren’t all really amazing coaches, if they’re not all world class, then it’s not gonna make that much of a difference, so let’s uplevel the level of coaching around the world.

I think from that place is where the book came. So the book is called This is Coaching. It is the book that I wish I had when I was an early coach and is also the book that I plan to return to, even as I continue my experience as a coach, because it reminds me of what are my values and who I am, it reminds me of what my job is every day, when I wake up and choose to be a coach.

[00:10:56] Wesley Jackson: Wow. It sounds like you were really struck with inspiration since, like you said, you allowed for that space in your life and you really slowed down and gave yourself the time needed. Let’s change gears here a little bit though, and I want to know how would you say building character is related to habits?

[00:11:12] Matt Thieleman: This reminds me of a conversation I had with a friend yesterday who was asking about my relationship to systems and structure. And I avoid it often. I think many of us do. I say, do them because they work.

There are a lot of well-intentioned self-help folks who will say like, “This is the ideal morning routine, blah, blah, blah.” And we can get in the place of what should I do? It’s the same when we’re building a business – should I be on Facebook or whatever.

What is it for anyways? Why are you even asking that question?

So when I think about habits, I think about what are the habits that actually move me toward the life that I want? And that is the tangible things. That’s the experience of life, and that’s living my purpose.

So first of all, get clear on that. And then secondly, if you’re like me, you’re not going to want to stick to those habits on a regular basis. Generally, that seems to be human consensus. We want to avoid structure. We rebel against it.

Character is waking up and choosing to take a look at where do I want to go and what am I doing this for? And then asking, “What is this step that will move me there?”

And then doing it. Not always, and not perfectly. And part of character is being willing to have compassion for ourselves when we’re not perfect. I would say it’s a pretty low character person who just constantly beats themself up.

That’s also a place to look. But yeah, like being willing to stick with stuff that we know will move us forward even when we don’t want to.

[00:12:22] Wesley Jackson: I want to know, would you say that the goal needs to serve as the foundation below the habit, or do you think that the habit is what gets you to that goal?

[00:12:32] Matt Thieleman: I’ll offer my model since we’re using a cool foundation metaphor; and so I think for me, a “what for” is the foundation of everything.

We could call it our “why”, our purpose, our mission, our values. That’s the foundation. If I’m going to jump, I need something to jump off of, and for me, that’s the primary thing that we can jump off of. And then we jump into: “What is the life that I want?”

We’re actually, going through the three steps of coaching that I offer in my book, which is: “Where do I wanna be? Where am I now? And what’s in-between?”

So habits are what’s in between. They’re simply the steps along the way.

My friend Jonathan Fields has a concept of support scaffolding.

As we move up the chain, what are the systems and structures that hold us so that we maintain a high level? So habits are these little steps that we can incrementally place to keep us at a higher level, and then we can build other pieces of support around that.

[00:13:18] Wesley Jackson: Support scaffolding. That’s an interesting one, I’m gonna have to look deeper into that, I haven’t heard of that one.

[00:13:23] Matt Thieleman: He has a great podcast episode on it. I’ll see if I can share it with you.

[00:13:26] Wesley Jackson: Great. So, let’s blow this topic up a little bit. How do you think this story of yours, where you’re attempting to refine your character and build upon it, is related to larger problems throughout society and why is this important?

[00:13:39] Matt Thieleman: When I hear folks complain “There is no dialogue today, there is no willingness to see the other side.”

The first thing that I think is: “Where can I get more curious about the other side?”

And again, there’s so many conversations about the polarization of politics, the polarization of all kinds of viewpoints today. To me, a tremendous test of character is saying: “I stand here and am I willing to look at the other side, holding onto my values and willing to look over there and be in the really challenging perspective, trying to understand them while holding onto myself?”

So, in the context of my decision to step away from this position, it was in the midst of a lot of conversations that were really challenging. It would’ve been a lot easier for me to just hold on and withstand and survive the experience. I actually think that if I hadn’t chosen to leave, nothing would’ve changed. So, my invitation for anyone is if you’re in a place where like you, at your heart and soul level, know that it’s not the thing for you, just ask yourself, “What’s here for me to say, what’s here for me to understand?”

And also to my point of being willing to look at the other side, to say: “What’s over there that I’m not seeing?”

If I really can’t understand this position or someone else’s perspective, where can I get curious? That’s where I would have folks start. It’s a very basic place to start, but I imagine a whole lot will open if that willingness is there.

[00:14:51] Wesley Jackson: I agree completely.

“Where can I get curious?”

I think that’s a really great way to phrase it, and a really, seemingly simple question on the surface, but it can open up, like you said, all kinds of possibilities and opportunities from there. What would you say then at the end of the day, is the moral of this story and what can we all do that are listening to become better humans in response to all of this?

[00:15:11] Matt Thieleman: I did not expect that leaving this position that I had attached so much of my identity to, that I thought was gonna be a long-term place for me, I did not expect that leaving that would create then the opportunity for me to share something like a book with the world that was not at all how I thought life would go.

I find that I often have and my clients often have a lot of fear about leaving something that we know we have a fear about what might be next. And when we have that, we try to either hold on or control the way that we exit.

And what I got to learn here was my willingness to be in that liminal space, to be in the place of nothing, was what allowed what wanted to come next through me.

The last several months I’ve been really thinking about this idea of balancing the yin and yang in life, the masculine and feminine, right? So, getting clear on this is a goal that I have, and also allowing for openness and energy to come through. To me, it’s a deep spiritual practice. I certainly don’t have it mastered, but, to me, that feels like the way toward a successful life for me and something that I’m really excited to continue to investigate.

[00:16:15] Wesley Jackson: I love it. You’re speaking right to my heart there with the Taoism. So, before we go, Matt, if you had to choose what is your one tip for surviving humanity?

[00:16:23] Matt Thieleman: For surviving humanity?

[00:16:24] Wesley Jackson: Yeah.

[00:16:25] Matt Thieleman: It’s gonna be the signature of my emails, which is love. I sign off with love with a period. And so it is both I’m offering you my love, and an invitation, a demand, a command for you, an assertiveness that says, “Yeah, that’s why you’re here. Go love.”

[00:16:38] Wesley Jackson: I love it. Go out there and love people.

Thank you to our guest, Matt Thieleman. Matt is a transformational coach, speaker, advisor, and visionary who partners with leaders and changemakers to unlock their purpose and share their unique gifts with the world. You can find his latest work at goldenbristle.com, which includes his newly released book, This is Coaching.

I found Matt’s approach to coaching and character development to be a lot more holistic than usual, and I really appreciate his focus on values and integrity in particular. We highly encourage you to check him out if you’re interested in learning more about how to build character.

Tune in next Tuesday for our monthly newsletter episode, where we’ll share the top insights from this month’s Surviving Humanity articles and other personal development tips.

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Links to our Patreon and the challenge can be found in the show notes.

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