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Sustainable Leadership Through Self-Awareness with Kevin Bailey

Sustainable Leadership Though Self-Awareness with Kevin BaileyLeadership requires a marathon mindset. You can’t take on everything yourself and sprint to the finish because there is no finish line. If you’re doing your job right, you keep supporting your people so you can achieve evermore goals together.

Kevin Bailey is currently CEO and Co-Founder at Dreamfuel, and it’s not his first time in the C-Suite. But success can come at a price if you aren’t prepared. Something Kevin learned the hard way in his very first leadership position, a post he ended up leaving due to burnout.

In this episode, Kevin shares his story of stepping down after pushing himself to the point where he no longer enjoyed the work. Listen in to hear about Kevin’s positive mindset techniques for creating a sustainable leadership approach. Along the way, you’ll learn how a leader’s energy can make or break an organization.

After You Listen:

Get your copy of Coherence by Dr. Alan Watkins

Connect with Craig:

Learn more about ClearPath Consulting and Coaching:

Download Craig’s 10 Rules for Better Meetings

Key Takeaways:

  • A negative mindset spreads through a company to the client. Develop techniques to stay in a positive head space
  • Organizations reflect the virtues and vices of their leader, so be aware of how you show up
  • To avoid burnout, focus on setting your team up for success instead of taking on the brunt of the work

Things to listen for:

[01:58] Lightening round with Kevin

[03:35] The weight of leadership

[05:30] Having the right mindset

[07:56] Setting a vision and bringing it to fruition

[09:27] Adopting a marathon mindset [11:24] Advice Kevin would give to his younger self

[12:48] Creating balance so you can work better, longer

[16:07] Craig’s takeaways

Full Transcript

[00:00:00] Craig P Anderson: Welcome to the Accidental Leader Podcast, the only leadership podcast that shows how today’s successful leaders develop the competence, competence, and calm to lead their team and organization to success. I’m Craig Anderson and my career journey is a tale of accidental leadership. I started out with a degree in English and a growing comic book collection, and my plan was to be a high school teacher, but what we plan and what happens aren’t always the same thing.

A college job turned into a career in education finance. An entry level in my alma mater became over time increasing leadership roles in Fortune 500 companies, including many national leadership roles. As that chapter closed, I spun off a business from a large operating not-for-profit, and grew that into a successful business that was named a great place to work in Indianapolis.

Over my career, I learned a lot of leadership lessons the hard way I created this podcast so you don’t have. Kevin Bailey, welcome to the Accidental Leader Podcast. Thanks for coming on today. You’ve got a great leadership story that I know a bit about and I really thought you would be a great guest to be on.

But before we get started, you are the CEO and co-founder of Dream Fuel. Can you tell us a little bit about the work you do at Dream Fuel?

[00:01:17] Kevin Bailey: Dream Fuel is a mental performance platform. We mainly help sales teams and executive teams, as well as math elites achieve their maximum potential by developing a mindset that empowers them to consistently perform at their very best.

So a lot of people get tripped up by their own thinking and. We kinda help them stabilize that. Everybody on our team has a background in neuroscience or psychology, and there’s just a lot of good stuff out there now that you don’t have to suffer your way through your career. You can, we call it like perform like a professional athlete, you know, in whatever your vocation is.

[00:01:52] Craig P Anderson: I love it. Well, the way we always kick off the Accident Leader podcast is with our lightning round three questions about leadership. So we’ll jump right in and see how this goes. So one, what is the best leadership book you have ever read?

[00:02:09] Kevin Bailey: I like a book called Coherence by Alan

[00:02:11] Craig P Anderson: Watkins. And who is your leadership crush?

Jesus. Okay. . I love it. No, because there’s a lot to be said there and I don’t know that we talk about him as a leader as much as we do, as about this kind of Christian figure. I’ve been

[00:02:26] Kevin Bailey: watching that chosen, I think it is, you can see his leadership. It took a lot of a bunch of rag tag people that were, yes, you wouldn’t call them, they weren’t the Pharisees, you know, they weren’t, they weren’t the, the top of of society and he taught them how to create a revolution that changed humanity in a lot of good.

[00:02:44] Craig P Anderson: That’s great. I love trying to find those opportunities to find leadership in ways we don’t think about it. Cool. Last one. In 10 words or less, how would you define leadership?

[00:02:53] Kevin Bailey: Enough faith and a future vision that you’re willing to do whatever it takes to lead through it and keep people aimed in the right direction.

[00:03:02] Craig P Anderson: I love it. I think so much of a leader’s role is casting that vision and then keeping it in everybody’s focus. So that’s a crucial piece of leadership. Well let, let’s jump back a bit. Let’s talk about, so you’re currently CEO and co-founder at Dream Fuel, but we all had that first leadership role.

So what was your first big leadership role?

[00:03:24] Kevin Bailey: CEO Sling. when you were in that role, how do you rate your performance overall? When you look back at it, how do you feel about it now?

I thought I did a pretty good job. I had, I struggled at a certain point, but I’d say for the majority of the time when I was in CEO position, I think I did a great job all the way through when I stepped out of that CEO position.

And then I think I recognized that I kind of hit my capacity for leadership at that age and experience.

[00:03:52] Craig P Anderson: When you think about going into that CEO role, what surprised you the most about leadership? That you didn’t expect? The pressure

[00:04:00] Kevin Bailey: and how much it challenges you at your deepest levels. You know, when you have like a hundred, a hundred families depending on you and stuff like that, and a lot of things outta your control, it’s an incredible amount of pressure.

And that’s if you’re successful, right?

[00:04:14] Craig P Anderson: And I don’t know that people realize what that feels like if they’ve never sat in that chair.

[00:04:20] Kevin Bailey: Normally you’re just responsible for yourself, and then you are responsible for a family. And then if you’re successful as a leader, you get responsible for a whole lot more people, at least their livelihoods.

[00:04:31] Craig P Anderson: And when you think about that, how do you see most leaders viewing? Do they view it that way? That I’m actually responsible for the lives of all these people that I employ?

[00:04:41] Kevin Bailey: I think it’s more like a subconscious felt thing than it is a conscious. I think that they feel it, you know, cuz you’re constantly having to deal with performance and sometimes you gotta let people go.

And in those moments you become very aware of the gravity, but more at a subconscious level I think from

[00:04:56] Craig P Anderson: that role. What was the biggest leadership lesson you learned? The

[00:05:01] Kevin Bailey: mindset’s really important.

I mean, as a leader your energy is kind of what cultivates forward moving among your team or backs, slid. A hierarchical organization, if you’re the leader, your energy sort of sets the tone. So when your energy is lagging or slacking or anything like that, your whole team feels it. You do it long enough, you can create real problems in your company.

All the way down to your customers. You know, like, uh, you look at companies that are failing, their leaders are normally in a terrible head space. That terrible head space gets given to their whatever directors, VPs, down to their frontline team, then down to their clients. Then it all rolls back up to the top again and creates this kind of cyclical process of negativity.

[00:05:49] Craig P Anderson: And it goes back to what you said in your definition of leadership, that you’re setting and casting that vision for everyone to go forward and they kind of rally around that. And if you’re losing faith in it or you’re just tired, or it shows, people see that the leader sets the tone for the organization in ways, I don’t think they always realize.

I worked in an organization once where the leader was a great guy, but he was very shy and he would go up the elevator every day and because he was shy, He would not talk to anybody in the elevator and it wasn’t an intentional effort, but that really cast appall when people felt like they didn’t see a lot of energy come out of him.

And that’s just a very indirect way. I think a leader sets a tone. It’s very interesting. Sure.

[00:06:33] Kevin Bailey: Organization tends to reflect the virtues and vices of the leader. Yeah. Very interesting. You always see that play out, you know, based on people I hire and the the culture.

[00:06:43] Craig P Anderson: Yeah, so there’s a lot to be pulled away from that and how people can align with the leader.

And do you see that in that first leadership role, your leadership team rise and fall with kind of where your Headspace was at?

[00:06:55] Kevin Bailey: Well, I had two business partners, so it was really a trifecta and I certainly saw our team rise and fall with our energy. Yeah, very good. We had a ton of positive energy and really

[00:07:06] Craig P Anderson: drove it.

So now tell me about your current leadership role. What does your role encompass with Dream Fuel today?

[00:07:14] Kevin Bailey: Yeah, so I’m a co-founder of Dream Fuel. Anna Aurora is my co-founder, as well as my wife. Ashley is our cfo, so it is another trifecta team, but we also have some great team members on board as well, different coaches and operations people.

But yeah, my, my role is as a CEO and my job is to help set vision and do what I said, you know, stay strong. Get it done. Keep the energy up throughout the journey. Practice great mindset techniques.

[00:07:44] Craig P Anderson: and, and I may know the answer to this question, but when you think about the lessons from your time at Slingshot to applying that today, what has changed in the way you lead?

[00:07:56] Kevin Bailey: Time has changed a lot. When I founded Slingshot, I had, I had no family and I was just had all the time in the world and I always. You could say in the past a little bit of a perfectionist, and I think I was more than willing to monkey things into place and do a lot of heavy lifting, and in this situation, I don’t have the time to do all that.

So there’s gotta be a lot of, there’s a lot more faith I think, involved in championing of

[00:08:25] Craig P Anderson: my team. Do you find yourself now in more of a delegation mode than you used?

[00:08:30] Kevin Bailey: I mean, I delegated there and you know, at some point I obviously had to, we got pretty large, but I was just a lot more in the weeds. How

[00:08:37] Craig P Anderson: does that feel today to kind of not live in the weeds of the organization, making that transition good


[00:08:42] Kevin Bailey: bad?

You know, I mean, sometimes it makes me uncomfortable cuz I don’t have, you know, I’m not, I’m not in it as much as I was before. Sometimes it feels very freeing. How

[00:08:52] Craig P Anderson: does that influence the way you hire and the way you kind of guide the team?

[00:08:58] Kevin Bailey: Gotta hire really motivated, talented people, you know, and then give them the tools they need to succeed.

I think it’s giving me a better lifestyle, you know, . Um, and that’s really important, especially to finish the, the hero’s journey, to see it all the way through. If you’re burning really hot and you burn out, which is what happens at Slingshot, basically, then you business is not gonna be successful. So little more of a marathon type of mentality.


[00:09:28] Craig P Anderson: is interesting though from the hero’s journey perspective, and when I think about what your business does, part of the hero’s journey is to have the guide and in some ways is your current business providing the guide?

[00:09:39] Kevin Bailey: We are guides to a lot of leaders. Yeah. Was

[00:09:41] Craig P Anderson: that, as you thought about that from a leadership role, do you find even today that there’s a guide in your hero’s

[00:09:48] Kevin Bailey: journey?

Sure. I have like three coaches, different areas like in product and marketing and mindset. And obviously being a coach myself, coaching a lot of high performance leaders through their quests, I’ve definitely recognized the value I’ve had with them. And then it’s like, well, I need, I need that too. I can’t always be that for myself.

[00:10:07] Craig P Anderson: The leader who brings that guide or that coach in can some ways take some of that pressure off, or even help you self-regulate to maybe call you on the things when you’re going too far in one direction. I would imagine for. So if you could go back in time, I love science fiction stuff. So if you could go back in time to yourself as a younger leader, what piece or pieces of advice would you give that would be most helpful

[00:10:33] Kevin Bailey: to you?

I would’ve just taught my former self better how to ground and stay. And equanimity through the journey and stay in it. Cuz I chose to step out of the CEO role and I think that was a bad move. I mean, it was necessary for where I was at psychologically. I just had a kid I was in burning out and I was in a weird place, but that wouldn’t have happened.

The burning out stuff if I had. Taught my former self how to stay grounded, how to stay in equanimity through the ups and downs so that I could have stayed in that place and ultimately got done what needed to get done in that business. I thought I could just solve everything by like bringing somebody else in to do what I was doing, but there was something special that I was doing and I needed to keep doing it.

And sometimes the, the hard way is the right way. And I, I thought I could buy my way into a easier situation.

[00:11:24] Craig P Anderson: It’s interesting cuz I’ve heard some people say a lot of times come to the older generation of leaders will say, boy, if I could go back, I’d have more lifework balance and I would do different things and then contradict that thought and say, but if I hadn’t grinded poor English, if I hadn’t grinded so hard back then, I wouldn’t be in a position today to be so wistful about it.

But what I’m hearing you say is, Actually, if you had taught yourself and had that equanimity and more balance that might have made what you were doing even sustainable longer than and made you stronger for it and more successful.

[00:11:56] Kevin Bailey: Yeah, for sure. You gotta do what you gotta do. You can work as smart as you can, but.

I think it wasn’t so much heaven. Hell, both states of mind grinding a flow state, both states of mind. It’s not about how hard you’re working, it’s how much you’re enjoying the work. So I got into a psychological state where I wasn’t enjoying the work anymore. I loved working hard. It was never a burden to me.

It’s all about how you approach the work and the physiological states you’re in while you’re doing the work. Are you in flight or are you in fight? Are you in freeze or are you in focus? Completely change. So, That just means people are working in flight.

[00:12:32] Craig P Anderson: So it’s kind of the law of polarity. There’s working hard, but it’s either grinding or you’re just enjoying it.

And as you said, in the flow state, both of those are very busy states, but your mindset that you wrap around it is what I hear you saying, the differences. Yeah,

[00:12:47] Kevin Bailey: but it’s not just your mindset. I mean, you gotta look at it from all dimensions of your psychology, so principally your physiology. So the signals in your body is your heart racing?

How does your stomach feel? Are you sweating? Those kind of things, all the physiological signals, you can regulate that with breathing among other things. Then your emotions. Your emotions are just basically, if you think of like your physiology, so heart. Different impulses in the body as instruments. The emotion is the song.

So the physiology comes together to create this emotion. And then you have emotional regulation as well as physiological regulation. And then you have feelings which are your interpretation of the song. So I could say you have sweaty palms racing heart and a stomach that’s turning, and you could say, well, that’s anxiety.

Or you could say that’s excitement. You could feel differently about that emotion. And then above emotion, you have thoughts. So to me, a mindset is a state of being where you are regulating all four of those dimensions, physiology, emotions, feelings, and thoughts. And if you can master that, then you can put yourself into flow state very easily and hold it.

[00:13:55] Craig P Anderson: Yeah, and I’ll always remember something you recommended to me many years ago was a breathing app that I still use to this day that just kind of gets you focused and settled, and that mental to mention to leadership is part of what we’re talking about here, is getting yourself in the right flow state and the right mental state to be successful and sustainable.

Kevin, if people wanna learn more about you, what’s the best way for them to follow you?

[00:14:18] Kevin Bailey: Yeah, they can just go to dream or email or just Kevin Bailey on Lincoln. Awesome.

[00:14:24] Craig P Anderson: Well, Kevin, thanks so much for being on the Accidental Leader podcast. I appreciate it. Thanks, Greg. As always, on the Accidental Leader Podcast, I like to give three takeaways from our interviews, and I like to frame them in the key leadership areas of confidence, confidence, and calm.

Kevin talked about confidence, especially in how your confidence and your attitude passes through you to the rest of the organiz. How you present is going to impact your people. So it’s really important to think about how you are presenting to your people and the level of energy that you bring every day in competence.

Kevin talked about how in this current leadership role he is doing far more delegating and staying out of the weeds of the organization. And that level of competence is built by hiring the right people on the team who bring the strength so that you can stay out of the weeds of the day to day. And then finally, calm.

Really had a great conversation around the mindset that you have and how you can regulate through breathing and paying attention to your emotions and taking care of yourself. So how you take care of yourself and how well you monitor and regulate yourself really drives to that calm to keep your stress levels down so you can be sustainable as a leader.

So, thanks again to Kevin for great interview today. Lots of great insights for all of you. Are you an accidental leader looking to. A great place to start is by leading better team. If you’d like help with that, go to to download my 10 rules for better meetings.

Your team will thank you and you will feel a lot more confidence, competence, and calm in your next leadership team meeting. Thanks for listening today, and remember that leaders aren’t born, they’re made. You can go from accidental leader to the greatest of all time leader. It just takes confidence, competence, and calm.

We’ll see you next time.