It Sucks, but I Love It: Finding Joy Through the Tough Stuff

Air Force veteran Josh Mason shares his journey of military transition and personal growth on this episode of Exit Buddy: Veteran Stories to Guide You. From cybersecurity to teaching, entrepreneurship, podcasting, and building a chicken coop, Josh showcases the power of creativity, networking, and embracing challenges with a stoic grin. He reveals how strategic outreach on LinkedIn and a willingness to tackle the tough stuff led to unexpected opportunities.

Chapters

• 02:09 Josh’s Pivot to Cybersecurity and Teaching
• 06:50 Transition Journey and SkillBridge Internship 
• 08:29 Networking Creativity Lands a Job
• 15:06 Entrepreneurial Ventures Post-Military
• 20:18 Embracing the Suck with Stoic Strength
• 25:43 Parting Advice on Cybersecurity Careers

Key Takeaways

• Embrace the Uncomfortable: As Josh says, nothing’s going to be as uncomfortable as basic training or being deployed was—civilian transitions are just another challenge to conquer. Get creative, step out of your comfort zone, and approach new opportunities with curiosity.
• Network with Purpose: Leverage veteran communities, LinkedIn, and online platforms. Your next opportunity may likely come through your connections, not traditional job application processes. Veterans take care of veterans.
• Continuous Learning is Your Superpower: Whether it’s cybersecurity, entrepreneurship, or building a chicken coop, approach new challenges with a learning mindset. Your ability to acquire and apply new skills is your greatest asset.
• Create Your Own Path: The civilian world isn't prescribed like military life. Be willing to craft unique opportunities, whether through internships, side projects, or unexpected career pivots. Your creativity is your competitive advantage.

Follow us for more veteran stories to guide your transition journey, and text this episode to a fellow service member who’s navigating their exit. Until next time, keep finding ways to endure and enjoy the tough stuff!

Visit us at https://exitbuddy.buzzsprout.com to learn more about the show.

Have feedback or questions for us? Email us at ashleyjones.creative@gmail.com.

Transcript

Kathleen Smith 00:47 Hello everyone, and welcome back to Exit Buddy: Veteran Stories to Guide You. I’m Kathleen and I’m joined again by my amazing co-host, Rachel. Rachel, what’s the mood in the studio today?

Rachel Bozeman 00:59 Just like it is outside—sunny and wonderful. Thanks for asking, Kathleen. This has been your weather report, but we’re not here for the weather. We are here to learn and hear some stories, and I heard we have somebody pretty incredible in the studio today to join us and share their stories. So are the rumors true, Kathleen? Who’s here?

Kathleen Smith 01:21 We’re thrilled to have Josh Mason, an Air Force veteran of 10 years of service. He’s worn a lot of hats, from aircraft commander to cybersecurity roles to being an instructor and even an entrepreneur, I think, more than once. Josh, welcome to the show.

Josh Mason 01:40 Hey. It’s great to be here. Thanks for having me.

Rachel Bozeman 01:43 Well, we are so glad you’re here. So I’m just going to jump right in, Josh, if you don’t mind. And so, as Kathleen mentioned, you’ve worn quite a few hats. Heard you wore ‘em pretty well. Out there, lots to choose from. So let’s dig into your cybersecurity career in the military, because I understand that’s really where you discovered your true passion—teaching. So tell us how you were able to pivot from cyber warfare to your role at the Air Force Special Operations school.

Josh Mason 02:09 Yeah. So I had been a pilot for about seven years. Some family stuff changed and pivoted into cyber warfare, and once I got there, started looking actually at teaching opportunities long before I wanted to be a pilot. I wanted to be a teacher. And finally, life had slowed down enough—both me and my wife were pilots before, and she had medically retired from the Air Force, and being at cyber warfare, I was not deploying as often, not busy as often as I was when I was flying—and yeah, looked at opportunities to teach. And finally, my commander said, “Hey, there is the Air Force Special Operations school right across the parking lot. You can go, and there’s a billet over there. Go teach, and if it doesn’t work out, you can come right back over here, and we’ll have a job for you still as a flight commander.” But I loved it. They loved me, and I got to teach and finish out my Air Force career at the Special Operations school.

Kathleen Smith 03:16 It’s interesting because it sounds like you have an inspirational story of having support through your transition. And I know a lot of people sometimes think that they’re not going to get support from their leadership during their transition. So I understand you have an interesting story of how your major board sort of impacted your transition timeline, but you had really supportive leadership that sort of helped you through your options. So can you talk to us about how that all came about, and how a SkillBridge opportunity popped up during that?

Josh Mason 03:54 Yeah, in the military, when you go to a board—at least for officers, usually it’s for major and above—you have two opportunities to meet that board if they don’t select you. Then, according to law, you have six months, and then you have to leave the military, and it’s an involuntary separation. It’s not punitive. It’s not bad or anything. It’s just what the law was, in order to not have everyone stick around always. When the paperwork comes through for all that, it actually comes from your O-6 commander in charge and gets delivered by your squadron commander. So at the Special Operations school, our commander is actually the Commandant for the Special Operations school, and sat down with me for a meeting, said, “Hey, here’s this letter. I’m not delivering it. I have an idea what it’s for, just because of the time of year, but I don’t know what’s actually in it. It’s for you from the colonel.” So opened it, read it, and I was like, “Okay, so it says I’ve got six months. December 31 is my last day in the Air Force.” He’s like, “Okay, I thought it might be that, in which case, there’s some things that you’re gonna have to figure out in that time.” And I hit him with, “Okay. I was thinking this might be a possibility. I’ve looked into SkillBridge. If I can get an internship, is it okay if I do that? Like, you’re not going to have a lot of time to do that. Got all this out-processing. They have to do TAPS, all that stuff, plus finding a new job, getting ready to move—all that.” But if you need to, yeah, you have our support. Basically to us, there’s not a lot you can do as an instructor. I knew what the schedule looked like for courses, what we’re going to be able to deliver, when we were going to be teaching. I wasn’t going to be super useful to them because of all those other things I had to do anyways, knowing that I didn’t want to leave, but I didn’t have a choice at that point. He knew that there wasn’t really any fighting it, and there wasn’t any point in trying to make my life difficult. And so knowing all those things, he knew that the best thing to do would be to make my life as helpful for me as possible. That’s one of those things that you hope you get a commander that understands that and supports. But yeah, I reached out to some veteran tech groups, found some folks on LinkedIn and on a coding Slack community, and found SixGen, the company that I ended up interning with, and chatted with them, asked about an internship, did a couple interviews, got the paperwork going, and learned a lot there, and yeah, that actually ended up leading into my first job when I got out of the Air Force.

Kathleen Smith 06:50 So I’m just going to pipe in here before Rachel asks her next question. It sounds like you ended up creating your SkillBridge internship program by just doing the reach out, crafting it within your head. And we’ve actually had another guest who did that exact same thing. And I just wanted to applaud you for having the wherewithal to do that. And the extra gumption—I mean, that probably got you outside of your comfort zone. Is there any advice you would give to somebody who might want to consider doing that themselves?

Josh Mason 07:26 Yeah, it’s the advice I would give anyone getting out of the military. The civilian world is not prescribed. If you were 18 and you signed a piece of paper and you showed up with boot camp and you kind of just did what your orders told you to do—you moved to this place, you went to the school, you did this job because it was what was placed in front of you—and then you get to the end of your career, and you finally have to go do something new. It’s going to require some creativity to be a civilian. There are plenty of jobs sure, where you can just show up, do a job, and leave. If you want to thrive, creativity is going to be helpful. The ability to look at a situation, figure out what I could do—this, that, or the other—do a little bit of problem-solving from experiences that you’ve seen in the past, reaching out and getting advice from others, and at this point, searching the internet and asking the AI a little bit if you need to, is going to go far. It’s worth doing, absolutely.

Rachel Bozeman 08:29 And I’m so glad you mentioned creativity, because I think it’s a perfect tee-up to this next question, which is about—I think everybody’s favorite topic—networking. And I understand that you have a really good example of where you were able to leverage your creativity and your networking to kind of cut through that noise, if you will. So you shared that as you were out there, kind of in this new spot, applying for all of these different positions—kind of that spaghetti approach, just throwing some stuff out there, seeing what’s going to stick—but then you were ultimately offered a job from one of those that maybe wasn’t the one that you had applied for. So tell us how that networking and creativity really played into your first job outside of the military.

Josh Mason 09:11 It’s actually worked really well. I haven’t had a job since the military that I’ve applied for. In the past six years, all the jobs that I’ve had have either reached out to me or I’ve posted that I’m available on LinkedIn, and people have reached out to me. The first one, it was from SixGen. I was working on a project. Had connected with some of the co-workers there, finding out about LinkedIn, followed some folks on YouTube. I recommend watching a bunch of videos about how to utilize LinkedIn. Well, some of them might be worthwhile. A lot of them might be repetitive. Eventually you’re going to hear some good advice. The advice that I’ve got for you is find the people who you’re interested in meeting. Find the people who have the jobs that you’re interested in. If you’re paying attention to this podcast, probably a veteran, or you’re in the military, and eventually you will have the veteran status. Find other veterans, because we take care of each other. We know what it was like and where you’re coming from, and that was what I bet on. I’m an Air Force Academy grad. Found a Naval Academy grad who was a bit older. He was working as a contractor from a company that some of my co-workers at SixGen had worked at, and he posted on LinkedIn that he had just gotten the role of VP for education on this contract, and asked around, saw what the contract was, and then I was in Maryland—near where I was looking at living, because I had a clearance and cybersecurity experience. And so it’s Maryland, Tampa, or San Antonio. That’s where you get if you want to make money in those jobs with those credentials, and so reached out. Said, “Hey, congratulations on the new job. I’ve heard good things about your team. I’m over here at SixGen. He said, ‘Heard what your team does, and you all do great work as well.’” I said, “Hey, I’m getting out of the military at the end of the year. I’m currently doing a SkillBridge internship. If you all need someone who could do project management, let me know.” That was the conversation, and I’ve still got it on LinkedIn. And he said, “Send me your resume. Here’s my email.” So I sent him my resume, and that was kind of it. It was like, “Okay.” And then the next day, I got a phone call from the recruiter and said, “Hey, got your resume from Al. Are you interested in being an instructor?” I was like, “Oh, yeah, sure. I could be an instructor. What does that look like?” There’s subject matter experts who have created the content. You just need to be able to deliver the content. I was like, “Oh, okay. Just need the books. Teach the books. I could do that.” And I got to teach Marines. That’s easy.

Kathleen Smith 12:01 Oh, watch it.

Josh Mason 12:07 I taught hundreds of Marines. They’re amazing.

Kathleen Smith 12:10 They need more than crayons.

Josh Mason 12:15 Crayons and energy drinks, and they did amazing work.

Kathleen Smith 12:18 They do amazing work.

Josh Mason 12:23 They are some of the best students I had, and they’re fun to make fun of.

Kathleen Smith 12:37 I’m married to a Marine. I’ve heard all of this. Anyway, we digress. Go on.

Josh Mason 12:47 It was all through networking. A lot of that I learned from the same veteran groups that I got the SkillBridge internship from, some of the same friends I met through there. I’m still friends with. I actually got a text message this morning from my buddy Stefan. We’re on a group chat together. And yeah, we’ve known each other for six years now, met in a Slack channel, and Dale Carnegie’s How to Win Friends and Influence People. So same principles.

Kathleen Smith 13:18 Yep, all good stuff. And yeah, it’s—I think I’m going to have to do an entire episode on okay, there are the in-person conferences, there’s a VetCon, actual. There are all the key communities, then there is all of the Discord groups, and there are all the Slack groups, and there is VetSec Con coming up in October, and so on and so forth. So the one thing that I think is just absolutely amazing is there are a lot of those groups out—even our producer has a beer hall right down the street from her, where they have Monday night fire chats for veterans. So I want the audience to know you’re not alone. You can find—you just have to put your little effort in. You can find a group online, in person, ongoing, one time a year. There are plenty of support groups out there. You will find your new tribe, and they will help you find other tribes. So and there are enough of the veterans and veteran groups on LinkedIn that you don’t need to go searching every other social media. It can be your platform. So enough about my soapbox on networking and social media support, because I want to talk about your other passions, and it sounds like you have another passion for entrepreneurship, which kudos to you. There’s a lot of people who are entrepreneurs, and they either idea people or they’re entrepreneurs, and they actually fulfill their idea. So how does the military prepare you for entrepreneurship, and tell us about some of your pursuits?

Josh Mason 15:06 The military, it can and it can’t. It all depends on who you’re around. There’s being from the Air Force Academy and being a pilot, kind of surrounded by a lot of other officers, in that sense—especially in the Air Force, I don’t know, it always felt like there were a lot of forward-thinking, “What am I going to do when I grow up?” sort of officers. So the idea of “I’m going to buy these houses every time I PCS, that way when I retire, I’ve got all these retired rental houses, so I don’t have to do anything now. I just I’m a landlord for all these military folks all over the country.” One of the guys who recently reached out to me on LinkedIn, he’s about to retire. He’s been running a web development company since since I knew him in like 2012. Yeah, he’s been making websites. I remember planning to deploy with him back when he was an instructor or evaluator navigator, and he would have two laptops on either side of the computer that we were planning on, and he’d be coding over here, talking to a client, and then also mission planning for the flight. And then he’d get up, and he was a weapons officer as well. And so you get up to the board and be like, “Okay, so you’re gonna work on this, and you’re gonna work on that, and you’re gonna make this chart, you’re gonna work on this thing, right?” Then be like, “Okay, in half an hour, we’re gonna rally back up, go over this thing.” He’d sit back down, like fix something on the website, finish something on one of the charts, and then also like hit up his client, and so like being surrounded by folks like that kind of led to a mindset of, “Well, what am I doing to expand things?” So my wife and I, we both got our MBAs. My wife got hers years before I did, but hers had a focus in entrepreneurship. So we started a bookkeeping business. At one point we had some rental houses. Yeah, eventually. Now, I’ve got a couple podcasts. I have—I wrote two books this year. One’s about to come out in a couple of weeks, actually. And I’ve got a couple nonprofits that I run. One’s New Village. We help people who are starting out in cybersecurity. And I just realized last weekend, I think, like 90% of my staff are veterans, because the Venn diagram for cybersecurity and veterans looks very, very circular.

Rachel Bozeman 17:36 So you just have a couple things going on. It sounds like just a couple, just a few things going on. Well, I do want to go back. You mentioned it—that some of the podcasts that you’re on, and you also mentioned a friend that you’ve had for the last six years or so that you found on a Slack channel, and I think there might be a correlation between that relationship and some of the podcasting. So tell us a little bit more about how you were able to kind of that friendship forged, and now here you are on the other side of the microphone doing podcasts.

Josh Mason 18:08 It’s very true. That first friend, it’s Stephan Someroth. I started my first job, got on LinkedIn, and his big thing was, has been to pay it forward—you know, share information on LinkedIn and do like vlog-style sharing. And as I found other folks on YouTube, LinkedIn, Twitch who were sharing things, I’d tune in and try to help here and there, and eventually made friends with the folks who were doing that work. And finally got the confidence to stand on this side of the microphone and get a decent enough camera and share what I had learned from other folks and from my own experience.

Kathleen Smith 19:01 We’ve been very fortunate to have one or two other podcasters on our show. And I remember when I was told that I was well and told that I would be doing a podcast—my staff ganged up on me and said, “You’re doing a podcast, and you’re our talent.” And I was like, “No, no, I’m not gonna do it. It’s not my comfort zone. I’m gonna get out.” So this ties into one of your LinkedIn posts I saw the other day—that people should be feeling confident about doing something that they haven’t done before, so getting out of their comfort zone. And the one thing that I end up chatting with several veterans about is they really like their comfort zone. They really like their uniform and their rank and where things go. But it sounds like your advice is more—try. Find something that’s outside that safe zone, something that’s new, different, maybe a podcast, maybe something technical. So tell us a little bit about this sort of mindset of trying something new, and how that’s going to help someone in their transition.

Josh Mason 20:18 Yeah, and it’s not unlike some of the other things that we do—especially in the military, we put ourselves through hard things and find ways of enjoying it. I remember this old cartoon. It’s old only to me because I’m old now. It’s like the army—it’s like in the field, covered in dirt, and just like, “It’s hot out,” and being like, “Man, this sucks. I love it.” And then like the Navy, like just being like wet—like on the side of a boat, like in cold, and like a parka, and being like, “Man, this is cold, but it’s beautiful, and I love it, and it sucks.” And then like a Marine, just like covered in mud, and like a swamp, and like with a snake, like on their shoulder, being like, “Man, I love how much this sucks.” And then like Air Force dude, like in a hotel room, being like, “Man, this sucks. The airport, the air conditioning is out,” and, “Yeah, you’re welcome,” yeah, but there’s—I’m also a stoic, and there’s just a principle in stoicism of we put ourselves through hard things in order to understand what it’s like to get through the hard things, because you’re going to run into something that’s hard, and you’re going to have to face it and deal with it, and being used to that practice of dealing with something that’s hard and difficult and getting through it is good for us, and that’s kind of the point of basic training. That’s kind of the point of physical fitness. It’s kind of the point of just random ruck marches and being in the field, just even if you’re not getting good training out of it, it’s for the sake of “this is going to suck, and you’re going to be fine with how it sucks,” because eventually stuff’s going to suck around you. You just have to be fine with it and deal with it. And so we lift heavy weights, and your body hurts, and you run and you want to puke, and you do things that aren’t fun, and sometimes we just gotta embrace the suck. And I’m sure I’m not the first one who has said that around this audience. I don’t know the post that I shared to Kathleen—I built a chicken coop. I didn’t want chickens. I’ve got an eight-year-old and a 10-year-old and a very highly influential wife—aka, I said, “No, we’re not like, no, let’s not get chickens.” And so we got chickens. And so like, “What are we going to do?” So then I gotta like build a chicken coop. It’s like, “Well, yeah, okay, I guess I’m building a chicken coop.” Like, “Well, then I have fun with it then.” And so I went to Home Depot, and I like rented a tractor, because apparently, if you have a couple hundred bucks and a driver’s license, you can just rent a backhoe. And yeah, no special license, just driver’s license and money. That’s all they care about. So you rent a tractor, you move some dirt around, you go buy some lumber and a nail gun and some wood, and you just build a coop. And I’m still recovering from some carpal tunnel. No harm, no foul. Well, I guess chickens—yes, it looks cool. I’m proud of it. It’s fun. But yeah, I’ve never built something like that, all the way from like dirt to—I don’t know, I feel safe standing underneath it, like it doesn’t shake, so like I feel good.

Kathleen Smith 24:30 Yeah, still standing, and your chickens are, and your chickens are still laying eggs, and that’s all good. So no, yes. So stoicism is a really powerful, foundational thought process, and the phrase is attributed to Marcus Aurelius, but also advocates as well. So yes, along with a few others, the obstacle is the way. So just understanding that—like, hey, it’s not going to be all comfy out there, but it’s actually fun to be challenged and see what you can really accomplish. So Rachel, what are we?

Rachel Bozeman 25:10 Hard to follow that—she’s got great quotes. And I was just going to give you some more like floor plans, because you can put chandeliers in the coops. I’m just throwing it out there, Josh—like it’s possible you can. You can do so many things. Your wife and I will exchange numbers. I’ll give her full ideas. It’ll be great out there. But now that I’m giving you ideas, you’ve already shared so many great tips and tricks with all of those transitioning veterans and veterans out there. Do you mind if I ask just for one more tip or trick that you might share—just some parting knowledge that you can share out there with our friends?

Josh Mason 25:43 Yeah, it’s hard to think about what do I want to do when I get out of the military and have a solid concept of what that can look like. I run Noob Village, a nonprofit about helping people who are starting a job in cybersecurity—or who are like transitioning careers. And it’s a strange career field, because the jobs are obscure, and no one’s really sure what they look like until you get into them. And it’s really hard to tell how to start, even myself. There’s a lot of jobs where, coming out of the military, I looked at, “Okay, do I need to now like start here at like entry level at the beginning?” Or there’s a lot of things where they were like, “Well, you don’t have the experience to be in these jobs, but you’d have to like basically take a huge pay cut to be at these jobs.” And I didn’t want to do those jobs either. And being a like 35-year-old captain who had been a flight commander—basically running—I don’t know, would have been working former under the people that were under the people that I was working had working for me when I was a flight commander—would have been like, “This is weird.” And so yeah, it’s very, very strange. The thing that worked for me was eventually understanding that it’s less about having exactly what that job description looks like and finding like thinking of it in the military terms—of “this leads that leads to that leads to that”—because that’s too often what we always think about as a civilian. That’s not how everything works. Obviously, it’s hard to become a leader without some sort of experience, but if someone’s a veteran, they’ve got a level of experience, and often they have a level of hard-earned experience that goes way beyond the years spent doing anything else. And if you’re able to take that, dig in, do some hard work and learn—especially a specific skill—dig in, and like I said, even Marines can learn cybersecurity, these concepts. Well, frankly, cyber is also not that difficult. We just—it’s words that people make complicated. My new book is Cybersecurity Beginner’s Guide. The whole point is to kind of cut through some of the jargon.

Kathleen Smith 28:39 Everything is cybersecurity. Everything is cybersecurity.

Josh Mason 28:44 Yeah, exactly. And if someone’s been in the military, they probably know more about cybersecurity than a lot of cybersecurity professionals. And that cyber awareness challenge once or twice, you’re probably good. Yep. Yeah, be able to know enough to give guidance to a lot of companies on what they could do better, and being able to ask around, being willing to say, “I don’t know what this looks like,” and be open to looking vulnerable and being a little uncomfortable. Nothing’s going to be as uncomfortable as basic training was. Nothing’s going to be as uncomfortable as being deployed and getting shot at was. Nothing’s going to be that uncomfortable as a civilian, unless you’re like my neighbor and you do septic work. The guy has his own septic company.

Rachel Bozeman 29:36 Josh, be careful what you ask for. You could get goats and miniature donkeys, and chickens. Like, there’s so many opportunities out there. Be careful.

Josh Mason 29:45 I’ve had goats give birth in my backyard. It’s not that weird.

Kathleen Smith 29:48 Well, Josh, you’ve shared a lot of your story with us today, including farmyard animals, and so I appreciate that very much. Thanks for joining us today. Thanks for responding to my weird outreach on LinkedIn, because you never know what’s going to happen when someone contacts you on LinkedIn. I’ve had some weird ones, but it sounds like you’ve had a lot of really great ones. So thanks for joining us today.

Josh Mason 30:17 Of course, thanks for having me again.

Kathleen Smith 30:19 It was really great hearing Josh’s thoughts on getting out of your comfort zone and sort of trying something new. And I really like that. That’s a recurring theme that we hear a lot of is that breaking in, doing something new, is really going to help you when you’re trying to do your transition and through your transitions that you will do throughout your career.

Rachel Bozeman 30:44 There was so much goodness in there. But I think what I really took away from there that resonated with me was just leaning into the networking. And I know we talk about it a lot, and we hear a lot of great things, but I just appreciated the creativity that went alongside the networking that he mentioned—whether it was going on YouTube and watching different videos, that might give you that that may not be something you’re comfortable with, is knowing how to utilize LinkedIn appropriately. Guess what? There’s probably a YouTube video, and we found out today there’s multiple ones, so get out there and check them out. So that’s it for today. Pass this episode to your fellow service members. Hit follow for more stories and keep blazing your trail. Exit Buddy out.