Breaking Barriers in Aviation & Turning Passion into Nonprofit Purpose

In this episode of Exit Buddy: Veteran Stories to Guide You, retired US Air Force pilot Jessica Ruttenber shares her remarkable journey navigating—and ultimately transforming—the world of military aviation. Jessica recounts battling physical and cultural obstacles to become a pilot, and how she advocated for lasting policy changes at the Pentagon. She discusses her transition with SkillBridge, the mental gymnastics of leaving military service, and the importance of documenting injuries and seeking mental health support. Jessica also reveals how following her passion took her from a corporate role to founding a nonprofit that empowers the next generation of aviators. Her story is one of resilience, advocacy, and purpose, offering insights for anyone facing career transitions or striving to create meaningful change.

Chapters

• 01:53 - Jessica’s Fight to Get into the Cockpit
• 07:30 - Advocating for Women Pilots at the Pentagon
• 10:41 - Transitioning with the SkillBridge Program
• 13:07 - Finding Purpose with Level Up Aviation
• 15:38 - Importance of Documenting Injuries for VA Benefits
• 17:36 - Connecting with Veterans Post-Service
• 19:38 - Advice on Addressing Mental Health

Key Takeaways

• Break Barriers with Persistence: Jessica’s story of overcoming obstacles, like the half an inch in height that stood between her and her aviation dream, reminds us that determination can rewrite the rules.
• Safeguard Your Future: Let your ego go and document your injuries now, as this is critical for obtaining VA benefits and the support you deserve down the road. Be sure to prioritize your emotional well-being in addition to your physical health, and reach out for support when needed.
• Find Your Passion and Mission Post-Service: Transitioning out of the military can mean a loss of identity and tribe, but finding a new mission is essential, just as Jessica did with her nonprofit work. Don’t be afraid to pivot toward what truly inspires you.
• Build a Network of Exit Buddies: Surround yourself with others who have already navigated the transition to civilian life. If you don’t know where to start, find someone online from your unit. Even if you haven’t talked to them in several years, Jessica encourages you that they will be happy to share their experience with you.

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 lifting others as you soar.

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  00:43  

Hello everyone, and welcome to another episode of Exit Buddy: Veteran Stories to Guide You. I'm Kathleen, and I'm flying solo today in the podcast booth. Rachel, I'm really looking forward to having you join us again. I'm excited, as usual, to sit down and chat with somebody else that I've met through my network, wanting to share another really unique, wonderful story about veterans and their transition. So today we are joined with Jessica Ruttenber, a retired US Air Force pilot. Now, we've had a few pilots on before, but Jessica has turned into a program manager who's now leading Level Up Aviation to empower young aviators. Jessica, welcome to the show. 

Jessica Ruttenber  01:29  

Thanks, Kathleen, thanks for having me.

Kathleen Smith  01:31  

No worries. So you fell in love with aviation watching the Blue Angels. I know I've watched them in the San Francisco Bay area all the time, but you watched them as a kid, and later faced some barriers as a woman entering pilot training. Take us back to those early days in the military and your fight to get into the cockpit.

Jessica Ruttenber  01:53  

Growing up in Pensacola, Florida, that's where the Blue Angels are stationed. My dad took a job there as a butcher working in the commissary, worked his way up. So I would go to the beach on the weekends. My mom was an amateur photographer. She would try to get these pictures while they did their practices. And that's where my love of aviation started cultivating. However, it's the 1980s and Kathleen, you might know this, but maybe some of our, let's say, younger listeners might not. What was so interesting about the 80s was I could not fly a jet like that because women were excluded from combat in aviation and on the ground at the time, and it wouldn't be until 1993. But later on, a few years later, in middle school, it had a female mentorship day when they took young women into the room in middle school and introduced us to different career fields. And that's when I saw my first female pilot, and I was like, what? This is an option. I didn't realize that in my Catholic old-school family that this was an option for me. So fast forward, I get to college. I can't meet the medical right away, so I commissioned a cyber, but I get really determined that I'm going to get in that cockpit. And it's after 9/11 now, I've deployed. I come back. I am getting my private pilot's license. I'm trying to meet a crossover board, and I'm telling them I'm getting my private license. I'm doing all this work. It's several years. I get several waivers for my eyes, which is the reason I was disqualified because I had astigmatism, and I finally passed a medical physical, and I go to put my package in, and I'm accepted, like just before I'm too old to apply, and I get to cross over to be a pilot, but on my first day of pilot training, I get pulled out of class and told I was failed my physical again, and I'm confused, and I'm in my all-male pilot training class trying to explain to the flight commander who pulled me out that my eyes are fine. The waiver went through, but they're like, no, this time, you failed for your height. They measured me at five foot three and a half inches, and the requirement was five foot four inches. So literally, there's a half an inch between me and my dream. And I'm just devastated, but I'm also very stubborn, so I go around the country seeking an exception to policy and waiver before we have the process that we have today, and go to different aircraft. I went to Little Rock Air Force Base, got measured in a C-130. I went to Charleston and South Carolina, got measured in a C-17 and so on and so on to show that I could actually reach the controls and safely fly the aircraft. And then when I got into the KC-135, I fit that one, and I was allowed to resume pilot training. And I thought, that's it. Okay, I'm in. I'm going to be a pilot. I'll fly whatever. Let's go fast forward, 15-16 years later, I'm in pilot in the Pentagon, sitting in a meeting with the Chief of Staff of the Air Force discussing barriers to women in aviation, and they're still discussing height issues. And I'm like, dude, it is like 2018-2019 in my mind. Of course, I wouldn't say dude. I would say, sir, why are we still talking about height issues? So something that impacted me is still impacting women two generations later, and that's why I found out that 44% of women do not pass the standing height, compared to about two to 3% of men for being too short or too tall. But usually it's too short because the average height of a woman is five foot three and a half, which is what I am. But it also disproportionately affects minority women, because when we design aircraft in the 60s, it also was only using one body type, and different ethnicities have different heights when it comes to our torso and our legs, even though we're the same standing height. So often, minorities will fail the sitting height. Because an African American, if you're a black woman, 74% of you will fail the sitting height based on the hip-to-eye ratio. Looking outside the cockpit, even if we're the same height, passing your torso is too short to fly compared to someone who's Caucasian.

Kathleen Smith  06:32  

Fascinating. And I know that we're going to want to tackle that earlier or later, but we might not have enough time. But talking about tackling, I want to hear about how you advocated for women pilots at the Pentagon, tackling issues like pregnancy waivers. It looks like you touched. We talked a little bit about aircraft design. Tell us about that experience and what it was like inviting yourself to the table, because this is a lot of the work that you did on your own personal time. You talked about getting measured in the various different aircraft. I can understand that in the corporate world, in the corporate civilian world, we're sort of comfortable, well, no, I'm comfortable pushing against barriers, and I'm comfortable calling people dudes and things like that, and sort of proving them wrong. But I'm sure that there was a secondary barrier for you doing that in the military. You want to share a little bit about that?

Jessica Ruttenber  07:30  

Yeah, absolutely. The reason I found out about the height issue was because I was there about pregnancy and flying. I invited myself to the table through some very interesting ways, through politics and getting allies to invite me to the room. Since I was the subject matter expert, imagine that being in a room full of mainly men who have never had babies, most of them not pilots, making decisions without even medical providers about our bodies. But what it really came down to was I experienced a lot of barriers once I decided to start having children, and I didn't perceive any barriers even my height at the time, because I didn't know the statistics. I just thought I was a shorty because everybody around me was taller than me, but I didn't know I was the average height of a woman, so I just thought I was a shorty, but I was flying a Boeing 737, and when I decided to have children, I wanted to continue to continue to fly, because it was safe for me and for my fetus. But I was getting a lot of pushback, and there was some waiver process, but it was difficult to navigate. It was a very short period. It was a lot of bias. And quite frankly, people just didn't want me in the cockpit because they didn't feel comfortable, because it was biased, and I worked through that. I worked through the stigma after having the baby, thinking that I took my foot off the accelerator, and all sudden, my stratifications. And even though I was performing just like I was before, the maternal bias was setting in that I wasn't fully committed. So I moved on, and years later, I make Lieutenant Colonel, I noticed this starts happening to the women aviators behind me, and I'm like, okay, now this is a problem, because before, when it was just me, I had my own imposter syndrome, but now it's becoming a problem from the women behind me. So I started advocating. I didn't know what I was doing. I just went on these Facebook rants. Eventually, over time, I learned to extrapolate data studies and sell it to the Air Force, that it is a retention problem, that the amount of flying hours that we would get back. I had to sell it to them, not because it was a women's issue, but it was the thing that we needed to do for foundational readiness. Readiness to be lethal, and both things can be true. Because why would you want somebody sidelined for a year to have a child when they could be flying the majority of the time? So I presented that to the Pentagon, because eventually we try to work at a lower level. Yeah, fast forward, it needed to be the Chief of Staff that said, we're going to do this. So eventually, after working my way up to enough people that knew enough people to get into that meeting, who went to college with this guy who has a daughter at the Academy, I get invited to these meetings, and I'm sitting in the back of the room listening to the conversations, and that's how I got started with advocacy.

Kathleen Smith  10:19  

Sounds great. And thank you on behalf of all of the women out there who want to continue their dreams of being pilots and being in aviation. But let's sort of switch gears a little bit and talk about your transition and your first civilian role. How did you get involved in a SkillBridge Program, and how did it help you find your footing in your transition?

Jessica Ruttenber  10:41  

I had no idea what SkillBridge was until about a year before I was going to make the decision to retire, a friend told me about it. So that was the most interesting thing, because we have TAPs programs, all these transition programs, but this wasn't very well advertised, and I was in Washington, DC, which is a lot of companies if the region that I was in that wanted to hire, so it was the ideal time versus getting out and retiring in another location that didn't have as many companies, because literally across the street from the Pentagon, there's Boeing, there's all these other companies that I've been doing work with in the Pentagon, working in my portfolio. That makes it an easy walkthrough, and I found out about it, and I would highly recommend this to anybody who is thinking about transitioning, because basically, what you're doing is, six months prior to your separation or your retirement, you're going to intern for a company, and SkillBridge will help you find that company. You're not necessarily going to be on your own, and the military will continue to pay your salary while you intern for this company, and ultimately to get a job offer when you retire. You don't have to accept it. You could say no, thank you and walk away, but it's a phenomenal experience. They teach you how to interview. I was awful at interviewing, because I never really interviewed for a job in the military, because my records went ahead of me, and my commanders are the one that ultimately make the recommendation, so they gave me a lot of skill sets. The only problem I see with SkillBridge is that your commander has to approve it, so if you're in a critically manned career field, there's potential that you might not be able to do SkillBridge.

Kathleen Smith  12:21  

I'm glad you added that last point, because a lot of people think that it's a slam dunk to get into SkillBridge, but you do have to work with your command structure to be able to get into the program and have their support. So thank you for adding that. We talk a lot about on the show about sort of the loss of sense of purpose or the loss of community culture once you transition out of the military, but it sounds like you found a new sense of purpose with your nonprofit work, and you said in our pre-call, there's a certain amount of money you need for stability, but after that, it doesn't necessarily increase your happiness. So tell us a little bit about your entrepreneurial leave after the military, and your work with Level Up Aviation.

Jessica Ruttenber  13:07  

So whoever says money can't buy you happiness, you least have to pay your rent, because if you can't pay your rent, your child's daycare for your basic accommodations, you're going to be stressed, and that's going to outweigh whatever happiness. So if you happen to be in a position when you have a retirement check, or you have a partner that has another income, or you have some investments, I will say that more money isn't going to make you happier. You just need enough money. And I went and ultimately worked for Amazon, and I made a ridiculous amount of money working for Amazon, and it was a great experience, but I kept finding myself trying to work on a little nonprofit. I started to give scholarships to young people like myself who were struggling to work on their pilot's license and didn't have exactly the right mentorship or the right background to get into pilot training, because it is very expensive, civilian or military to get your foot in the door. In this community, we're talking like over $100,000. I found myself gravitating towards my purpose and wanting to do that more, and eventually, at the two-year mark, I transitioned from Amazon. They had an opportunity, because they were down. They were doing a lot of layoffs at the time. And I was like, this is meant to be because not only if I get laid off, do I get a severance check for two or three months instead of just quitting, I get more benefits. So it just made sense to me. I like to say they planned it that way. I didn't. It just happened to be that way, and I couldn't have been happier for making that decision. And now our nonprofit is thriving. So instead of working for Amazon, making them, make their quota of a million dollars a day, or whatever, I was doing as far as data processing. And I'm now making that for the nonprofit.

Kathleen Smith  15:03  

Awesome, awesome. So switching gears again, because we're all about making sure we touch on key topics here, something that's come up in previous episodes, and I think it's really important that we highlight it again, is the VA benefit in documenting injuries. I mean, we've heard from other people who have not had the experience of being able to get benefits because they didn't document their injuries. So why is it so critical for service members to document even the small issues for future stability?

Jessica Ruttenber  15:38  

Absolutely. Bottom line, let your ego go. You are trained to serve nonstop, and if you were like me, you had many injuries, one, because you didn't want to let your team down, or two, because I wanted to keep flying, and if I admitted A, B, or C, I might lose my flying status. But when you don't document this, you're not setting yourself up for success later in life. So maybe that knee injury doesn't bother you too much now, and maybe you hurt it playing football during fitness, after work, and you don't consider it an actual connected injury, but I promise you, the military has worn and torn your body. You've taken care of America. Let America take care of you. And if you don't document this, then you can't get benefits, and if you're nothing else, do it for your family. Do it for your kids, because when you get above a certain percent rating, you get more money in your retirement, more benefits, not just in dollars, but in hiring process if you want to work for a government job or certain states give certain like you don't have to pay taxes for property or for your license plate when you renew it. All these things are going to add up. I'm just gonna say, suck it up buttercup. You are owed this. Now is not the time to be like, oh, I'm fine. And if you're listening to this, and you've already done that, you can still go back and you can still claim it. You have up to a year after you separate, if you started the process that they will back pay you. After that year, you're just going to start getting the extra additional pay from that moment on. Does that make sense?

Kathleen Smith  17:27  

Oh, makes sense. Totally makes sense. How do you connect with other veterans? And did you have someone to help guide your own path?

Jessica Ruttenber  17:36  

Connecting with other veterans. I had a slow transition, because since my spouse was still serving, we didn't move right away. So the friends I had made, I didn't immediately get ripped away from, like some people when they separate. So my transition was a bit gray at first. And I would say one it's great to have an exit buddy. I had several battle buddies going through TAPs, trying to figure out a calculator of how much we're going to get paid in the civilian world versus our retirement. But what you really need is someone that's gone before you, because you can't describe this experience as much as you can try, as much as you can prepare. And I know we like to prepare in the military, but nothing is going to fully prepare you for the mental gymnastics that you're going to go through of losing your tribe and a little bit of identity of who you are, and whether you serve four years or you serve 25 years, you are tied up in your rank, your AFSC, your job, your MOS, your service, there's something, and if you don't have something to fill that void, it will consume you. And that's why I gravitated towards my nonprofit. I wanted to continue to serve, and it's okay if you don't want to do a nonprofit, but have something your kids, a hobby, an activity, and quite honestly, if you don't have an exit buddy that has gone before, just find one that you know from your unit. Go to social media, and I promise, even if you haven't talked to this person in five years, they're going to be very happy to share their experience with you, because they're going to want what is best for you.

Kathleen Smith  19:18  

That's why we call the show Exit Buddy, making sure that everyone knows that there are veterans who've done this before, and you can find your passion, you can find your tribe, you can find your mission. So you just shared a really good piece of advice. Is there one more piece of advice? If you could go back and give yourself a piece of advice?

Jessica Ruttenber  19:38  

There's a lot of stigmas. I think negative stigmas about mental health, and I waited, I think, too long into the process, because I didn't really consider it an issue. And I really wish that I would have searched for help sooner. I was going through a difficult time in the transition, and quite frankly, I got lost in the system because asking for help six months prior to retirement, I was already too far gone. So I would say you really need to account for not just your physical transition, as far as VA benefits and like, what are you going to do when you get out for income, but also mental health, that starts with an exit buddy, but also talks about for me, I had a warning trigger alert here, but my dad died just before that, my nephew had my sister had found him dead in his room from a drug overdose, and I was in it during a very difficult time, and I didn't. I was too prideful. I didn't ask for help. So find a way to address your mental health, whether you're in a good place and you just need some battle buddies. Maybe you can go to the VFW, where you're going look ahead, but start looking for that support, whether you need to go to mental health like I did, and I just straight up had to go to mental health and say, I am not okay. And even then, it still took months to get into the system. I guess I thought it would be like TV, when you walk in and you say, I'm not okay, and we got you from here, but it's actually a process or just connecting with other veterans in your community, even if they're not in the same service, like the VFW, just address that mental part, whether it's mental health or if it's just kinship with somebody else in your community.

Kathleen Smith  21:31  

Yes, definitely connect with people. And it's, I think sometimes you were talking about being prideful, and we don't think that we can ask for help, especially when we're part of really strong teams, and no one wants to be that weak link. But addressing something that is bothering you is a strength and a courage. It is not a weakness, and there are more people out there struggling than you know, and just connecting with another person and sharing your struggles is definitely okay, and it is a step to strength, not sharing your weakness. So Jessica, thank you so much for sharing your story. Really appreciate your time today, and thank you for all you do to advocate for women in the military.

Jessica Ruttenber  22:18  

Absolutely, thank you, Kathleen.

Kathleen Smith  22:21  

I am so glad that we got to talk to Jessica, because she is such a big advocate of women in the military. I love all of her posts on LinkedIn, celebrating so many thought leaders and barrier breakers on LinkedIn, and I didn't get a chance to thank her for that. So I'm going to thank her now for that, her passion for making sure that women have an equal opportunity to follow their passion within the military and continuing to do it all throughout her military career. I also appreciated that she shared, once again, that if you have any kind of injury in the military, please get help. Make sure that it's documented, so that you get what you are owed, as far as your VA benefit and your pay with that. That's a wrap. Exit buddies, be sure you share this episode with your fellow service members. Be sure you share it and other stories, and be sure to tune in next time where we share another really exciting story. Take care. Be well.