From Combat to Calm: Resilience, Grit, and Mindfulness with Jon Macaskill


What happens when a Navy SEAL turns mindfulness teacher?
In this powerful episode of The Unbreakable Mission, I sit down with my friend Jon Macaskill—retired Navy SEAL commander, speaker, father, and co-host of Men Talking Mindfulness. We dive into his journey from the battlefield to breathwork, and what he's learned about real strength through transitions, setbacks, and self-discovery.
Jon shares deeply personal stories—from childhood challenges and military pivots to divorce, fatherhood, and launching a mission-focused podcast that’s changing lives.
We talk:
- Resilience, grit, and the walls that test us.
- Why mindfulness isn't soft—and how it's forged in the fire.
- How being a father has revealed more about him than the SEAL teams ever could.
This episode is a masterclass in owning your story, eliminating excuses, and redefining what it means to lead.
Your mission: Reflect on one internal struggle you've been avoiding. Write it down. Then take one action today to face it head-on.
Text me what stood out to you from this episode—just hit "Execute - Send a Text" on your app.
Let’s execute.
See More about Jon: https://podcast.unbreakablemission.com/guests/jon-macaskill/
Text the word "Mindful" to 33777 for more information about what Jon is working on and how you can connect.
Men Talking Mindfulness Podcast - https://mentalkingmindfulness.com/
Thank you for listening!
I'd love to invite you to share any feedback or insights with me dan@danw.us
To your success!
Dan
Dan Woerheide (00:02.101)
Welcome back to this week's episode of the unbreakable mission. I am well, I'm a little nervous, but no, actually, I'm really excited. I've got my friend, John McCaskill with me and John's journey from leading in combat to leading through mindfulness is impressive to say the least. It's rare. He's taken everything that's forged him in the seals and now helps others tap into resilience, presence and purpose. This
I believe is going to be a powerful conversation that you're going to want to be a part of. John, thank you so much for journeying with me.
Jon Macaskill (00:41.234)
Maybe it will be journey. Yeah, Dan, happy to be here, man. It's been a while since we've seen the one another. I was so excited when you reached out and invited me on the show. So, uh, definitely excited about what could be a journey together. So let's do it.
Dan Woerheide (00:56.565)
Yeah, absolutely. Well, I want to say it is a pleasure to have you here. I mentioned before we started, but I believe your work history itself and who you are as a person exemplifies the mission that I am all about. Extreme ownership, eliminating excuses, excuses and relentless execution. You have experienced all of that. Would you agree with that?
Jon Macaskill (01:25.07)
Yeah, when you put it that way, yeah, I hadn't really thought about it, but yeah, it's, it's been, an adventure. mean, since, since we met, you know, we were working in the coworking space together there in, in Norfolk and, you know, both working on what our future was going to look like after the military. And it has been, it has been everything and more, you know, lots of, lots of pivots along the way.
Dan Woerheide (01:52.367)
man.
Jon Macaskill (01:54.851)
But all in all kind of heading roughly in the same direction. So, I'm happy where I've landed so far. and I say so far very intentionally because I'm sure that there's going to be more adventure in the, in the future. So yeah, this is part of it, right?
Dan Woerheide (02:08.753)
So it's exactly that's exactly how this has come about, right? Some pivots and natural progression into the next thing. And we never know what's around the corner. That's beautifully said. So here's what I'd like to start, if you don't mind. I'd love for you to share with us a time that you hit a wall and what it took to break through those barriers for you. Can we start there?
Jon Macaskill (02:18.349)
Right.
Jon Macaskill (02:35.054)
Yeah, I'm trying to think of a single time I've had a lot of walls. the, yeah, let me start kind of chronologically. I've got three that are popping into my mind, since you've asked that question. And, and one of them is probably not what you would imagine, but, I was born in South Africa and moved to the States when I was seven years old and
Dan Woerheide (02:39.543)
Ha
Dan Woerheide (02:49.633)
Perfect.
Jon Macaskill (03:03.232)
In South Africa, the academic year starts in January and ends in December. So, you know, I had just turned seven when I moved in August of 1984 and the school year in the States starts in August. moved to Louisiana. And so my parents thought, well, he's had six months of schooling, first grade. Let's just put him into the second grade. And so I went into the second grade and I struggled.
Dan Woerheide (03:06.924)
Mm-hmm.
Jon Macaskill (03:31.503)
I don't even remember how long I was there in second grade, but I was struggling. I was definitely hitting a wall as a seven year old. And my parents then decided to take me out of second grade and put me back in first grade. So now I've spent a little bit of time as a South African new kid in the school with a strong accent, developing friendships in the second grade. Now I'm uprooted from the second grade and put in the first grade.
Dan Woerheide (03:58.838)
Yeah.
Jon Macaskill (03:59.139)
Which everybody's like, well, kids are resilient and kids are resilient, but it was also, I don't want to use the word traumatic, but it was, it shook me a little bit, right? I've developed these friends now they're going to make fun of me because I'm being quote unquote held back when they didn't really understand the situation. And then I was put back in the first grade. So now all these kids are also going to make fun of me because they're like, this guy's older than us. He's being held back.
And, and I was, I was made fun of for being the South African kid for having an accent and then for being held back. But the reason I tell you that is that actually for years in my mind, I resented my parents as a seven year old. I've resented my parents for it, but I think it ultimately ended up making me more resilient. had to bounce back from that proverbial wall, if you will.
Dan Woerheide (04:45.505)
Yeah.
Jon Macaskill (04:56.718)
Um, and then I also, I believe that I was more mature, even though now I was only six months, seven months older than my classmates. I was more mature. Uh, I had some schooling behind me. So if you've ever read Malcolm Gladwell's book, the outliers, uh, I ended up being one of those outliers because I was actually essentially a year ahead of my classmates almost academically. And so that set me up for success in the first grade, whereas second grade, wouldn't
Dan Woerheide (05:12.908)
Mm-hmm.
Jon Macaskill (05:26.37)
Wouldn't have been. So that was my first wall. I, I think that I can remember. and it seems fairly insignificant, but I think that it did actually change the trajectory of my life quite, quite significantly. the, the second one was, when I was in, in high school, I had done really well academically and athletically, and I applied to go to the Naval Academy.
Dan Woerheide (05:42.593)
Yeah.
Jon Macaskill (05:55.943)
And I got denied initially and I was upset at the Navy. was like, well screw you Navy. Then I'm going to go enlist in the army or do something else. I see that face. well then, then, then I decided, well, let me do some research on this. And, you know, I was, I don't know, 18, almost 19 years old at the time and
Dan Woerheide (06:20.417)
Mm-hmm.
Jon Macaskill (06:24.174)
I found out that from the enlisted ranks in the Navy and the enlisted ranks in the Marine Corps, there's a certain number of people, and I'm sure same for West Point. There's a certain number of people who can be picked up from the enlisted ranks and go to the Naval Academy. And very few of those billets are picked up every year. And so I was like, well, you know what, I'm going to go an alternate route. I'm going to enlist in the Navy.
See what happens and if I get picked up for the Naval Academy, that's great If not, then I'll still be serving my country in the service of my choice And I'll give you a little wink there so So Ended up going into the Navy put in a package to go into the SEAL teams as an enlisted guy then also Simultaneously or almost simultaneously put in a packet to go ROTC and then another package go to the Naval Academy
Dan Woerheide (06:59.915)
Have we taken you in the army?
Jon Macaskill (07:19.154)
And I did not hear back from SEAL training. I got selected for ROTC and I got a secretary of the Navy nomination and accepted at the Naval Academy. now it was between ROTC and, and the Naval Academy and ended up choosing, what one of my master chiefs in the Navy later said. He was like, you chose the lesser of two evils. I don't know. I don't know that I chose the lesser of two evils. think, I think the Naval Academy was pretty evil, but.
Dan Woerheide (07:47.298)
Fair enough.
Jon Macaskill (07:48.003)
But it, but it was great. and the reason I tell that story is, that initial, denial of getting into the Naval Academy, it could, I could have taken it two ways. could have just been like, well, screw you. I'm, I'm going to go a completely different route. But then, then I did some research and I stayed with it. And I think that tenacity, paid off and, I wish that I could just say that I inherently had that tenacity. think that was instilled in me.
from my father and then from my coach. was a track and cross country runner in high school and my coach had really instilled a lot of that in me. And then the third one that pops into mind and it's certainly not the last wall that I've hit and I'm sure there's many more that I will hit in the future. But I was married previously, Dan, I think you know this about me, but I was divorced. And that divorce,
Bless my ex-wife's heart. was with me when I was in the SEAL teams, when I was on deployment and some of those deployments were really rough. Uh, you know, we lost a lot of good guys and, uh, she knew them, she knew their families, she knew their kids. Um, and when I came back from that, that deployment or my first deployment where we lost a lot of guys, um, I could not really connect with her and it took me years.
trying and her years of trying to connect and we never quite fix things. So we ended up getting a divorce and, to me, I felt like an utter failure. I don't think now anybody who gets a divorce is necessarily a failure. At the time I did, I, I quite honestly, I judged other people and then, and then I started judging myself for what did I do wrong? What could I have done better?
And after years of therapy and counseling and mindfulness and meditation and some deep introspective work, I realize now that I was not a failure. I mean, I may have had some failures in that marriage, but I am not a failure because of it. That marriage ended up being a failure, but that doesn't mean I am a failure. And I'm remarried now. My ex-wife is remarried. I think we're both on a much happier path.
Jon Macaskill (10:12.246)
you know, I don't have children with my ex, thank goodness. and I'm certainly, not judging people who get a divorce, who do have kids, but, for, for me, did not. So we were blessed in that respect and, and now, you know, I'm remarried three kids, with my wife. Now my ex is remarried and she has a kid. and I think we're both better for it. So those, in a quick.
thinking those are the three walls that popped to the front of my mind.
Dan Woerheide (10:42.947)
I can absolutely appreciate the reframing that has taken place in some of those. And I don't know that I did it justice, so I'll make sure to mention that, you know, today's work, I think it sounds like a lot of that may have contributed to the work you're doing today. So you are a co-host of Men Talking Mindfulness, and you've got a lot of work around, we'll call that a project mission, because you've got a lot
Jon Macaskill (11:01.74)
Absolutely.
Jon Macaskill (11:08.044)
Yeah, it's a passion project for sure.
Dan Woerheide (11:10.655)
It's a lot more than just a show happening. I know.
Jon Macaskill (11:13.846)
Yeah, yeah, absolutely. We are. It's, it's a, it is a mission. it, started small. so the, mean, much like most podcasts, but we started in 2020, at the beginning of the COVID pandemic and, my, my podcast cohost and I, we were just friends who would touch base on the phone once a month, once every couple of months. And I, he's a yoga instructor and his business completely disappeared like overnight.
Right in March of 2020. so five years ago, almost to the day that since we're recording and, and I saw that, and then I saw that he was taking his courses online onto just onto Instagram. He wasn't even doing anything really formal just on Instagram. And I reached out to him. said, Hey man, let's, let's do something where we're basically having these phone discussions about mindfulness and meditation and try to bring it to more people.
Because I feel it's important that other people hear about what I consider to be life changing and quite literally life saving practices. And so we just started with Instagram live, you know, quite, quite literally with the two of us with our phones in front of our faces. And, you know, we had like five listeners, but yeah, yeah, exactly. It was, it was super small and, simultaneously I was doing the podcast with the nonprofit that I was working with and you actually helped me, cause I.
Dan Woerheide (12:29.706)
I remember that.
Jon Macaskill (12:40.846)
I even know that at the time I didn't know that you could record video on zoom. Actually, I think it was even before zoom. think what Skype is what I was using for that podcast for that nonprofit. But anyhow, with, with, men talking mindfulness, we started small and then we ended up, realizing, know what? There's more, there's more here. It's, it's deeper and specifically it's, it's changing. It's changing a lot of people's lives, but.
75 % of our audience, Dan is men. I mean the name men talking mindfulness, you would imagine that it is largely men, but, but we've started hearing it towards men. That's not how it started. It started with men talking mindfulness. It was just two men talking, but now a lot of men have reached out. lot of wives, spouses, friends have said, Hey, you know what? My husband needs this. My, boyfriend needs this and they've turned their, their significant other onto the show. it.
It's changing lives. got a text this morning. I mean, I won't name names, but I'm just going to read a part of it. If you don't mind. Uh, let me see where it is. So he says,
Dan Woerheide (13:45.205)
Yeah, absolutely.
Jon Macaskill (13:55.533)
You're one of my role models. starts with how you live your life. and it talks about, I'm going to skip some of it, but he talks about how will my podcast go hosts. I, he says from this extended connectivity, I've seen people start their meditation journey after hearing about all the benefits from your show. have normalized basic breath work to start meeting at meetings at work. I've had some hard ass dudes open up about their mental health struggles.
after witnessing my vulnerability, which is inspired by your journey and your show. So, I mean, and we get messages like that regularly. And now, now I can, I can't not do the show, right? My, my podcast cohost and I can't not do the show with people listening whose lives are being changed. So it's absolutely, it's, it started as a passion project and now it's a, it's a mission.
Dan Woerheide (14:46.625)
That's so powerful. And I think, so let's go back for a minute if you don't mind. Thank you for sharing that message or the parts of that message. And it's wonderful to know that people's lives are being changed, right? Because we can have a passion project and we can share our mission that we're on. But when we start seeing the results in real life, right? It takes time, I know that. But when we start seeing those results, it's...
Jon Macaskill (14:52.355)
Yeah.
Dan Woerheide (15:17.483)
I want to use the word rewarding, but it's beyond that because it's not rewarding to me specifically other than to know that I'm sharing something that is serving people well and serving them in a way that they might not be getting elsewhere. that to me, well, it's definitely rewarding to me, but I think that's how we contribute to creating better relationships and better people in the world. You that's how you change the world.
Jon Macaskill (15:36.931)
Sure.
Jon Macaskill (15:45.199)
Absolutely. That's what I was going to say right there. That's how you start to change the world. you know, Dan, that's probably the same heart of service that we're doing this mission with, right? The podcast that we do and the podcast that you're doing now and everything else that you're doing, behind the, behind the scenes with this podcast and everything else. I think that started with the hardest service that we.
Started the military with right? That's that's why we probably went into the military was to serve I know that some people join because they want their college paid for because they want x y or z and that's that's great more power to them But I can tell after having discussions with you you join for something else and there's no judgment for joining to pay for your Your college. I mean, I got my college paid for right? But the there was a greater calling there
Dan Woerheide (16:34.839)
Great. Yeah.
Dan Woerheide (16:40.246)
Absolutely.
Jon Macaskill (16:40.534)
And that calling was also something we couldn't not do. And now after retiring there, that heart of service continues. And, and I love to see that, that it's growing in you and, and it's going to, it's going to grow in the people that you inspire and touch.
Dan Woerheide (16:57.463)
Thank you so much for that. appreciate it. And this, yeah, you you talked quite a bit about some of the journey that you've been on and I want to dig in a little bit, but, you know, it's unfolded with lots of mistakes and lots of, I won't call them failures. I've just called them, you know, lots of trial and error of finding what actually feels most aligned. And I'm going to say it was, is it David? It's Coggins, right? I'm trying to think off the top of my head.
Jon Macaskill (17:17.144)
Yeah.
Jon Macaskill (17:26.082)
David Goggins, yeah, Goggins. Yeah. Yeah.
Dan Woerheide (17:26.997)
Yeah, off the fly. you're familiar with who he is. And I was inspired by something I heard him say on one of the podcasts I listened to. And it's one of those like it's not Goldcast. It's not Goldcast, but it's one similar that I listened to. It's just a motivational with a series of clips. And this mission was actually inspired by some words he said. And I'm going somewhere with this. But he said that, you know, the foundational piece that
Jon Macaskill (17:49.441)
Okay.
Dan Woerheide (17:54.079)
allows people to succeed in seal selection is the shared struggle. And so I'm sure you've spent quite a bit of time answering questions about what it's like to serve in the seal teams and what it's like to command or lead seal teams. I'm really interested in touching on that a little bit, but more interested in sharing how the transition from that environment, which is
Jon Macaskill (18:01.486)
Mm-hmm.
Dan Woerheide (18:23.201)
high risk, high impact, potentially high reward, real life ownership of that situation that you're in and eliminating excuses into serving people through mindfulness and meditation and the work you're doing today because that, we've talked about this before in a previous show that I did, but that's a tremendous shift in my mind. Help me see this one.
Jon Macaskill (18:46.822)
Yeah. Okay. There's, there's a lot there. So if I forget, if I forget something here, Dan helped me, you know, just kind of give me a little prompt, but, okay. So David Goggins, the kind of the shared, misery, if you will, kind of the shared struggle, right? never heard that before, but I, I would have to say that I agree. you know,
Dan Woerheide (18:50.177)
Sorry. We're good.
Dan Woerheide (19:01.079)
Yeah.
Jon Macaskill (19:11.054)
I'm still in the text thread with some of my first platoon mates. There's like 20 of us in this text thread going back and forth and we give one another, give one another grief about X, Y, or Z. every once in a while we'll get a picture of the beer log, which is, know, back in the SEAL teams, if you screwed up, you have to buy a case of beer. And there's still people, including myself, who haven't paid up on this beer log from, from 18 years ago or something. Uh, so we'll give you one another grief, but, uh,
But we are also there to support one another. And in this text thread, just last week, we were going back and forth about this one particular training mission that we were on. And it was up in Aberdeen, and it was raining and it was cold. And, and I remember, going up to my, one of my buddies as we were getting out of the Helo truck, right? We didn't have a helicopter, so we had a truck and we were simulating a helicopter and,
He was in the back of the truck, the back seat. I had been in the bed and I went and opened up the door and he was like, how is it out there? And I said, it's suck suck fast 2005. And every once in while I'll still get a text from him that just says suck fast 2005. And we'll both laugh because that, that commiserating in that actually made us laugh and we were able to get through that training weekend. but yeah, so there's definitely a, a,
Dan Woerheide (20:22.582)
Yes.
Jon Macaskill (20:40.626)
shared struggle there, whether it's with a training weekend or on the battlefield or mission planning or long nights with very little sleep. There's, there's a shared struggle, literally, but then there's shared struggle metaphorically, right? The, lose brothers together and that strangely bonds the rest of us together even more tightly. I mean, that, that is a struggle as well.
And then as far as, you know, leading guys on the battlefield. And I want to be clear here for those who, Hear the word seal team, you know, the seal team is by, by doctrine is essentially the battalion size element. And, I never led a seal team, not the battalion size element. I was of rank to lead one, but I, quick vulnerability.
Dan Woerheide (21:32.759)
Fair enough.
Jon Macaskill (21:38.275)
Vulnerable moment here, Dan. ended up getting in trouble in the Navy because my sister's ex-husband battered her. And, and I sent him a barrage of text messages that basically told him what most brothers would tell a guy that did this. And, and he took these text messages. So this was not my proudest moment nor my smartest moment. He took these text messages and sent them to NCIS.
Dan Woerheide (21:55.467)
Yes, sir.
Jon Macaskill (22:04.934)
And you can imagine how that went. I ended up never commanding a SEAL team per the doctrine, but I led men on the battlefield. So from a platoon to a troop, you know, different size elements, but never the actual SEAL team. But from leading men on the battlefield, leading full organizations, know, men and women outside of the battlefield, but still supplementing or supporting rather, the, who were on the battlefield.
Dan Woerheide (22:06.782)
No,
Jon Macaskill (22:33.346)
To doing what I do now, I guess it comes back to what I was talking about before. It's the, the hardest service. People think that there's a huge dichotomy between, okay, seal special operator and now mindfulness and meditation teacher. They're really not that far out from one another. both, I'm wanting to serve in both of them to there's a particular mindset that I think you have to have.
as, a mindfulness teacher, you, you, you want to give back, then also so many of the, the warriors that we all know in, in essence practice mindfulness without calling it that, you know, situational awareness, tactical awareness. when you're on the battlefield, you have to be paying attention to where your people are, where your assets are, where your support is, where your radio is, who you're talking to on the radio, what channel you're on.
Which radio you're on, you know, you remember times when I had three iridiums on me, right? Or not, not, not, not three iridiums, but, shoot. Now I'm spacing on the name of the radio. Anyhow, three, three separate radios, small radios, right? And then an iridium cell phone and, that you have to have awareness. But then also when we were on the shooting range, people would like, just breathe, right? Just breathe. And we would do some box breathing on the shooting range to calm our heart rate down, calm our respiratory rate down.
Dan Woerheide (23:32.535)
I don't know.
Dan Woerheide (23:53.004)
Yes.
Jon Macaskill (23:58.351)
So there was some mindfulness learned there and if you look at some of the ancient warriors, mean you look at the samurai, the Spartans, they practiced some form of mindfulness, they certainly didn't call it that, but they practiced some form of mindfulness and or meditation before they went on the battlefield so that they would be present, so that they would be aware. You you see
Some of these, you know, football players before a football game that they're, they're getting super amped up and they're bumping chests and you know, that's great, but that's going to get them amped up for a little bit. And then, then they're really not going to be the player that you want on the field. You want somebody on the field who's very aware of what's happening. You've seen the other side of that same coin where you've seen quarterbacks, you know, different, different key players on the field meditating. Right. And this has become more and more prevalent.
And those are the guys that do really well. They know what is happening on the field. It's not just about that one particular play. They know that play. Then they think operationally and take things strategically, like not how are we going to win this play necessarily, but how are going to win this play? How are we going to win this quarter? How are we going to win this game? That's who I want next to me on the battlefield is how who's going to win this battle and then ultimately get us off the battlefield and win the war. so yeah, I think.
ultimately it's not that big a leap between the two and then I'll peel back the onion. One, one more layer is that mindfulness and meditation helps you to be, more compassionate. And I think that's a piece that a lot of special operators actually are. They just don't, you wouldn't imagine it. So what I mean by compassion is they see the people that they're working with as actual people, not just objects.
And when they're leading them, they see that those people have their own struggles and they have their own battles that they're fighting internally. when, when you're aware of that and you can lead through that, I think that's, that is mindfulness. That is a way of living. And so I've basically carried what I learned in the SEAL teams in a different way or under different names.
Jon Macaskill (26:16.146)
and just carried it forward and continuing the same mission just in a different way.
Dan Woerheide (26:21.495)
that I thank you for clarifying and for sharing all of that. You clarified a couple points and we're a bit vulnerable. I've not heard that story, so that's outstanding. I'm curious from those experiences, right? Is there one theme, could be one thing even, that stands out to you that allowed you to not just be successful on the battlefield, but beyond mindfulness and into being an entrepreneur?
Jon Macaskill (26:29.294)
Yeah, yep.
Jon Macaskill (26:52.59)
Hmm.
If I if I could say two and and they're they're two of the ones that I speak on when I go up on stage and I speak it's it's about resilience and grit and I know You know many other seals. I mean David Goggins talks about that Jocko willing talks about the You name any seal they're gonna be talking about resilience and grit if they're And you name any seal they've written a book about it, right?
Dan Woerheide (26:58.155)
Yeah, absolutely.
Dan Woerheide (27:20.329)
Absolutely.
Well, most of them.
Jon Macaskill (27:24.704)
Right, right. And I mean, all jokes aside, I mean, I know that's true. So there's a reason though, right? So people, when they give me grief about being a SEAL and they're like, Hey, have you written a book? Well, one, I have it's, it's very short, but yes, I have. And yes, it's about the same themes that many other SEALs talk about. But there's a reason that we talk about that is because it is instilled in us and it's helped us to be successful as SEALs on the battlefield, as administrative leaders, as
leaders within our families, our communities, and then later as, as entrepreneurs, coming back to how we started this conversation, the walls, you know, as an entrepreneur, you're going to hit many walls. You're going to have to pivot. You're going to have to bounce back. I mean, that's the very definition of resilience is getting knocked down and then getting back up. And I'll take it one step further is it's getting back up when you don't have to, it's getting back up when people don't expect you to, right? As, as an entrepreneur, if you get knocked on your ass,
And you lose all your money people are like, know what? Just go get a job. You'll be all right. Well, that's that's true. And I have respect for people who do that. But and maybe that's what you got to do to continue on your entrepreneurial journey is you got to set a foundation. It's kind of a safety net, whatever bottom line is you get back up when you don't have to. And then and then the resilience piece or sorry, the grit piece.
You gotta keep grinding and and when I say grind, I don't mean waking up at 4 30 a.m. And taking a picture of your watch. I love jaco. I love them. But as a matter of fact, we're having them on our show next week. But I'm not talking about that. Yeah, okay, we'll get there. So I'm not talking about that grind. I appreciate that that grind to a point, but I think it's also unhealthy if you get too far down that grind path. And that's actually what I want to talk about with jaco next week is
Dan Woerheide (29:00.279)
Nice. I submitted a question for that, so.
Jon Macaskill (29:18.958)
Is, that a dangerous mindset to be propagating? I think there is value in that as an entrepreneur, absolutely putting your, your, your, you know, your head down and, continuing to grind, but eventually you've got to take a break. And, and I think the grit is actually grinding, then knowing when
knowing when to take a break because there's actually going to be a positive return on investments on investment. If you take that break, right? If you continue to grind, grind, grind, you're going to hit that diminishing returns or even negative returns. It ends up eating into your business, eating into your entrepreneurial journey. Whereas if you take that break every so often, I mean, you got to sleep, right? you got to rest. Now I will caveat that with don't rest before you need it.
and, that's where laziness comes in. And that, that to me is laziness when people rest and I'm not talking about sleep necessarily. I'm talking about resting. Okay. Hey, I'm taking a step back because I'm tired, quote unquote. Are you really? No, you're just lazy. But now if you truly are tired, if you truly are exhausted, then it's time to take a rest reset and then come back stronger. So I think resilience and grit are the two things.
Dan Woerheide (30:37.236)
Absolutely.
Jon Macaskill (30:40.3)
that carry over from the military and special operations that are required within the entrepreneurial space.
Dan Woerheide (30:50.083)
That's I think that's wonderfully said and I couldn't agree more. I know I was fortunate enough in the army to have been brought into leading as a master resiliency trainer. you know, training other trainers was where I had had left off at. And that world brought in positive psychology and mindfulness and started putting a name on the things that we as leaders in the military were learning, but didn't have a.
Jon Macaskill (31:05.123)
Yeah.
Dan Woerheide (31:19.479)
specific name for it other than whatever we nicknamed all of these things that To be real, you know when we're you know, we're in a platoon format and we're going through some of these trainings It's like this is kind of silly Right, but it was practical and it worked and that's why they you know continue to instill those different disciplines in Everyone that comes through and I couldn't agree with you more it it those two things resilience
which is really what the Master Resiliency Program was built for, but then grit, the ability to continue to drive through the hard stuff. And I just posted on my social media personally, at the time of this recording, it was yesterday, about that topic, right? You don't get results from going to the gym and lifting weights. You get results from turning off the snooze and getting out of the bed.
and going to the gym in the first place. It's the hard work that you have to put in to get the results that you desire. So I love that. John, I don't know how long we've been on here, but I love this conversation. So I have one more question for you. it's really about, again, I think people, it's easy for people to ask about the things that are intriguing. And as a former SEAL, it's easy to,
Jon Macaskill (32:18.381)
Right.
discipline.
Jon Macaskill (32:25.997)
Right.
Jon Macaskill (32:31.054)
Ha
Dan Woerheide (32:47.123)
ask you about that stuff. a mindfulness expert, it's easy to ask you about best practices, but I'm really curious about what's something that you rarely get asked about that has fundamentally shaped who you are and how you show up today.
Jon Macaskill (33:03.468)
hands down being a father. yeah, I, I wish that I could say that, seal training was the hardest thing I've ever been through. And it was definitely hard. I will say being an entrepreneur is, is harder because there's just so many unknowns and, it's all on, on me as my, as I chose being an entrepreneur. but then I'll say the hardest thing that has definitely made me who I am is, is being a father.
Dan Woerheide (33:05.036)
Mmm.
Jon Macaskill (33:33.679)
Let me rephrase that. I don't think it's made me who I am. I think it's revealed to me who I am. And some of it, I will admit, some of it is ugly. It's not what I thought. Like, you know, I love my kids. I adore them. I have an eight year old, a six year old, and a soon to be four year old. And they push my buttons and they try my patience. Thankfully,
Dan Woerheide (33:40.791)
But that's good.
Jon Macaskill (34:02.4)
I am a mindfulness and meditation teacher. I, yes, I may lose my temper, but I don't lose it to the point that I could, although my eight year old would probably disagree with me. But, yeah, parts of it are ugly, but then other parts of it are, tender, nurturing, caring. there there's pieces there that I've
never felt before like I love my wife. I adore my wife and you know my my ex-wife before that but man my kids they are my pride and joy and there's there's some things that they will do that will just light up my world and then there's other things that they will do that will really test me but I found myself you know brimming with pride over some things and then
crying because of some of the things they've said. Like my eight year old one time, this was two or three years ago. she came up to me. So I've got two little girls with a little boy in the middle and my eight year old, she must've been six at the time. She comes up to me. She's like, Hey daddy, when, when you die, are they going to bury you next to me? And I S I said, sweetheart, first off,
I hope they're not burying me next to you. If, if, if we're going to be buried next together next to one another, I hope it's the other way around because I'm older than you. I, you know, chances are higher that, that I'm going to die before you. And she said, well, who's going to die before, before, between you and mommy. And I said, well, chances are probably high that I'm going to die first. I'm five years older than mommy and I'm a man and we traditionally have shorter lifespans.
And she said, so does that mean I'm going to die after my brother? And, and man, just thinking about my kids dying, first of all, it's terrible. And then for her to ask such a deep question, said, sweetheart, I want to stop this conversation right now. I'm getting sad. And she said, I'm not kidding. said, daddy, it's important to talk about death.
Jon Macaskill (36:23.086)
It's something that happens to us all. you know, simultaneously I was like, Holy cow. I'm so proud of you for being so deep, but at the same time, I'm so sad to be thinking about these. So, sorry, that was a long anecdote to tell, but, uh, that is the, the parenthood being a father has shown to me that I'm a completely, I don't want to say different, but,
Dan Woerheide (36:25.527)
Wow, that's profound.
Dan Woerheide (36:32.257)
Yeah.
Dan Woerheide (36:40.535)
That's okay.
Jon Macaskill (36:53.024)
I am, I'm a deeper person than I even thought that I was, you know, 10 years ago. And I thought, I thought 10 years ago I was pretty deep. Ask me in another 10 years, I'll probably be even deeper. Yeah.
Dan Woerheide (37:02.639)
It will continue to progress in my experience. I was going to say I can 1000 % relate. I remember that that moment in reflection, you know, when I had my daughters, that I would say has really contributed to shaping who I am and how I show up for people today because I if I had had boys life would have been different.
Jon Macaskill (37:30.121)
Hahaha!
Dan Woerheide (37:30.847)
Like my mentality around treating people one way versus another completely changed. It shifted and it was recognition of how our world shows up sometimes. And I didn't want to be a contributor to what I didn't like to see.
Jon Macaskill (37:46.711)
Yeah, no, hear that. know, I think, you know, I'm blessed to have both a boy and two little girls. And, and I think that I'm actually going to be a better boy dad for my son because I'm also a girl dad. so it's, yeah, it's, it's, it's working. It's working.
Dan Woerheide (38:01.036)
yeah, what a wonderful setup.
Dan Woerheide (38:05.953)
Yeah, I'm curious. So your daughter was a deep thinker at, we'll say six years old. Is she still at eight, one of those deep thinkers? Yeah.
Jon Macaskill (38:11.852)
yeah. my gosh. Yeah. Yeah. One more anecdote and then I'll spare you anymore. she said the other day, you know, I was, was getting upset with my, my six year old, my little boy, cause he was, he's a six year old little boy. mean, he's doing what he does. And, my eight year old, she comes up to me. She's like, daddy, if you had a cup of water and you were to spill that cup of water,
Dan Woerheide (38:19.34)
Go for it.
Dan Woerheide (38:26.743)
Mm-hmm.
Jon Macaskill (38:40.75)
Would you ever be able to get all that water back into that cup? And I said, no, had no idea where she was going with this. I said, no. She's like, well, that's how your anger is. Your anger. You will never be able to pull it all back and put it back inside you. There's always going to be little parts that are with us. I was like, right.
Dan Woerheide (39:06.561)
That is deep, wow.
Jon Macaskill (39:08.526)
I don't know where she got that if she made it up but man talk about humbling Yeah depth man and and those kids are mirrors They show you truly are more so than anything else. So yeah, she's she's very deep very she's an old soul. I love her to death Yeah, she is
Dan Woerheide (39:13.409)
Hmm.
Dan Woerheide (39:16.756)
Absolutely.
Dan Woerheide (39:28.107)
She's gonna go places, my friend. I imagine they all will, but just those two stories, it's just mind-blowing. That's incredible. Love that. John, I am so grateful for you spending this time with me. I know, what's the easiest way for people to find you is to text the word mindful to 33777.
Jon Macaskill (39:37.198)
I couldn't believe it, man.
Jon Macaskill (39:53.794)
That's correct, yeah.
Dan Woerheide (39:55.019)
That'll give them your link tree and access to all the cool things you have. What's up? Thank you. What do you have on? I'm just you have anything on the near future agenda that you are are super excited to unravel?
Jon Macaskill (39:58.201)
You got it. You nailed it, man.
Jon Macaskill (40:10.978)
Yeah. Yeah. So Will and I, we've, we've developed a mindfulness and meditation course. It's, it's online, but it's live. It's not virtual or sorry. It's virtual, but it's not recorded. It's us live. so we were doing that periodically. We've got another one coming up next month, starting in April. Will and I, I've, I've just joined a group.
I don't know if you're familiar with wild at heart, but the book written by John Eldridge, we've got John coming on the show next week and, I've just joined a wild at heart retreat. yeah, there's, there's a, there's a lot that's going on that we're excited about. We, our podcast just got picked up by a network called the valor media network. So, it's, it's out there on YouTube on, that channel.
Dan Woerheide (40:39.575)
there.
Jon Macaskill (41:00.344)
we did have our own YouTube channel and still exists, but we're putting all new content on the valor media network. And we're super excited about that. It's growing very fast. yeah, lots of things on the horizon, that, that we're, we're excited about others. Others are still coming.
Dan Woerheide (41:15.783)
I love that teaser. Awesome. Any anything else that I didn't cover that you were hoping to share today,
Jon Macaskill (41:17.516)
Hahaha
Jon Macaskill (41:23.084)
No, man, I think we've unpacked a lot here in what, 50 minutes. So pretty impressive. Great questions, man.
Dan Woerheide (41:25.281)
Yeah. Hey, thanks so much. Again, I'm grateful for you spending time with me. It's always good to connect with you and see you. maybe this time we won't let as much time lapse. It's my fault. I'll own it right there. So hey, good to see you. And for all of my listeners, thank you so much for joining us today. Do me a favor.
Jon Macaskill (41:38.276)
All right.
Jon Macaskill (41:44.696)
You too, Dad.
Dan Woerheide (41:51.019)
They, at the top of the app that you're watching this listening rather, wow. I'm all over the place today. Wherever you're listening to this, if you're listening from your favorite podcasting app, it says send the host a text, click on that link, send me a text. It's anonymous unless you share your name and what you have going on in your world, whether you have a podcast or something else you're working on. If you want to share that and get a shout out in the future episode, do that, but click that link.
Jon Macaskill (41:57.399)
Hahaha!
Dan Woerheide (42:20.447)
and tell me what's one thing from today's conversation that stood out to you. I appreciate you and until next week, stay strong, eliminate your excuses and let's work on that resilience and the grit that we talked about today.

Jon Macaskill
Mindfulness Coach
Jon Macaskill (pronounced Muh-KAS-kill) is a retired Navy SEAL Commander turned mindfulness teacher and leadership coach. During his 24-year Navy career, he served in multiple highly dynamic leadership positions, from the battlefield to the operations center and the board room. Jon's unconventional yet highly effective style of teaching leadership is fueled by his passion for helping people and organizations become the best versions of themselves. He takes what helped him excel in his professional life and heal in his personal life and now shares this through mindfulness coaching, grit and resilience training, and keynote speaking, all in the pursuit of helping others achieve their full potential.