Leading Through Transition - Jessica Whitney ’10

A simple but powerful leadership lesson: show up — whether in loss, transition or everyday life.

SUMMARY
Jessica Whitney ’10 reminds us that we often know what to do — the difference is actually doing it. Small acts of showing up can mean everything.

 

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JESSICA'S TOP 10 LEADERSHIP LESSONS

Here are 10 leadership lessons from this conversation:

1. Align your life with your values, not your plan

• Whitney thought she’d do 20 years in the U.S. Air Force, but family and faith became higher priorities than her original career plan.
• Leadership lesson: Be willing to pivot when reality and your values diverge, even if it means leaving a prestigious path.

2. Redefine success beyond titles and rank

• She struggled after leaving the Air Force because her identity was tied to “academy grad” and “officer.”
• Leadership lesson: Anchor your worth in who you are and how you impact people daily, not in your job title.

3. Use mentors to unlock “freedom to choose”

• A single honest conversation with her mentor gave Whitney “freedom” to imagine different possibilities.
• Leadership lesson: Seek out mentors who model alternative paths and will tell you the truth about tradeoffs.

4. Make decisions with the best information you have now

• Whitney references the Gen. George Patton quote about a good plan now vs. a perfect plan later, and emphasizes moving forward one step at a time.
• Leadership lesson: Don’t wait for total certainty. Clarify what you know, what you don’t control, then act.

5. Integrity = keeping and honoring your word

• From her transformational leadership class:
• Keep your word when you can.
• When you can’t, honor it: Notify early, reset expectations and clean up the impact.
• Leadership lesson: Integrity isn’t perfection; it’s proactive ownership. This builds trust and reduces stress for everyone.

6. Name the stories that secretly run you (“what’s undefined runs you”)

• Whitney recognized long-standing internal stories like “I don’t belong” from moving often as a Navy brat.
• Leadership lesson: Identify your limiting narratives (e.g., “I can’t disappoint people,” “I don’t belong”) so they stop unconsciously driving your behavior.

7. Create a compelling future and work backwards

• She describes standing in the future you want (for yourself or an organization) and asking, “If we were already there, how did we get here?”
• Leadership lesson: Lead by designing the future state (culture, behaviors, outcomes), then reverse-engineer today’s actions.

8. Show up for people — especially in their storms

• After her brother-in-law’s suicide, the support from church and Air Force community showed her the power of “just showing up.”
• Leadership lesson: You rarely know what others are carrying. Leadership is often simply being present, unasked, when it matters.

9. Align daily actions with stated values

• Whitney feels the most stress when her behavior and values (family, faith, health, service) are misaligned.
• Leadership lesson: Use misalignment (stress, guilt, burnout) as a signal to recalibrate how you spend time, energy and money.

10. Invest in small, consistent habits (1% better)

• Whitney references “atomic habits” — reading regularly, moving her body, cooking healthy meals and doing “one more rep.”
• Leadership lesson: Long-term leadership impact comes from small, repeatable behaviors, not dramatic one-time efforts

CHAPTERS

00:00:05 – Introduction & Transition Theme Whitney is welcomed to Long Blue Leadership. Host, Lt. Col. (Ret.) Naviere Walkewicz ’99, frames the episode around transitioning out of the military, and Whitney shares her background as part of a dual-military couple and early family life.

00:02:02 – Mentorship, Freedom & First Thoughts of Leaving Whitney describes reaching out to her mentor about transitioning to the reserves. That conversation gives her “freedom” to imagine a different life that prioritizes family and values over a 20-year active-duty career.

00:06:39 – Academy Lessons, Courage & Decision-Making Under Uncertainty Col. Walkwicz digs into Whitney’s use of the word “freedom.” Whitney connects her

decision-making and leap of faith to leadership lessons from the Academy — facing unknowns, focusing on what she can control, and acting without a perfect plan.

00:10:13 – Growing Up Military & Redefining Identity Beyond Rank Whitney shares her deep military heritage as a Navy brat and descendant of generations of service. She explains the identity shock of leaving active duty and having to redefine success beyond titles like “officer” and “academy grad.”

00:13:26 – Values, Overwhelm & Redefining Success in Daily Life Whitney talks about aligning actions with values: quiet time, family, health and rest. She contrasts the nonstop pace of active duty with her new season as a stay-at-home mom and reservist, and how she now defines success.

00:17:19 – Loss, Suicide, Grief & the Power of Community Whitney shares the story of losing her brother-in-law to suicide in January 2020. She reflects on hidden struggles, the “buying bananas in the grocery store” moment of invisible grief, and the profound impact of church and Air Force community support.

00:23:12 – Learning to “Show Up” for Others Col. Walkewicz asks where Whitney learned to show up so intentionally. Whitney recalls community support during her dad’s deployments, meals after her first child’s birth, and a commander welcoming her back from maternity leave — illustrating the difference between knowing you should show up and actually doing it.

00:26:11 – Serving Beyond the Uniform: Church, Family & Cadet Morale Whitney explains what service looks like now: leading a 120-woman Bible study and serving on the USAFA Class of 2010 Cadet Morale Endowment board, which funds morale events for top cadet squadrons. She highlights meaningful leadership without a visible rank.

00:29:20 – Transformational Leadership & Redefining Integrity Whitney shares lessons from a transformational leadership course she took (and later taught): integrity means both keeping and honoring your word. She gives practical examples (calling when you’ll be late, managing deadlines early) and uses a bicycle-wheel analogy to show how broken commitments make everything bumpier.

00:32:07 – “What’s Undefined Runs You”: Naming Limiting Stories Whitney introduces the idea that unexamined stories (e.g., “I don’t belong,” “I can’t disappoint people”) quietly drive behavior. She shares her own “I don’t belong” narrative from moving often as a Navy kid and how she consciously claims, “I belong here,” to lead more authentically.

00:36:50 – Creating a Future & Leading from It Whitney explains how leaders can “stand” in a desired future for their organization —

one of trust, transparency and camaraderie — and then work backward to identify the actions and changes needed today to get there.

00:38:33 – Advice to Young Jess: Vision, Risk & Trusting the Journey Asked what she’d tell her younger self, Whitney emphasizes clarifying what will matter at age 80, aligning life with that long-term view, being less risk-averse, and trusting God with unexpected pivots and new paths.

00:38:43 – Daily Habits, 1% Better & Long-Term Growth Whitney shares the small daily practices that make her “better”: reading and podcasts, surrounding herself with uplifting people, and health-oriented habits like walking and “one more rep.” She connects this to the concept of atomic habits and incremental growth.

00:40:52 – Closing: Character, Showing Up & Living Your Values Col. Walkewicz closes by summarizing Whitney’s key themes: leadership as character and presence, not having all the answers; simply showing up; and honoring integrity even amid uncertainty. She thanks Whitney for her ongoing service and impact.

00:42:05 – Production Note & Recording Date Ted Robertson notes that this Long Blue Leadership conversation was recorded on Wednesday, Nov. 19, 2025.

 

ABOUT JESSICA

BIO

Jessica Whitney ’10 is a U.S. Air Force veteran, leadership coach and conflict resolution facilitator who helps executives and emerging leaders design purposeful futures and take aligned action. Drawing on more than a decade of military leadership experience navigating communication, conflict and high-stress environments, she supports individuals and teams in overcoming limiting beliefs, clarifying priorities and building systems that foster confident decision-making. Whitney specializes in one-on-one leadership coaching and workplace mediation, guiding productive conversations that transform tension into trust and strengthen organizational culture. She is also a wife, mother of four and advocate for intentional living, dedicating her work to empowering leaders to align their identities and results with their vision for the future.

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FULL TRANSCRIPT

SPEAKERS:

Guest, Jessica Whitney ’10  |  Host, Lt. Col. (Ret.) Naviere Walkewicz ’99

 

Col. Naviere Walkewicz 0:04
Welcome to Long Blue Leadership. We're so glad you're here.

 

Jessica Whitney 0:08
Thanks so much for having me.

 

Col. Naviere Walkewicz 0:04
You know, one of the things we love to do, and we’re going to have some time really exploring a lot of the things that you've encountered in your journey, but we want to jump right into a place that is both relevant to our listeners, which is transitioning out of the military, but you did so in a way that was a little bit different, and maybe not on, like, the timeline of planning.

Jessica Whitney 0:28
I'm a 2010 grad, and so is my husband, Tom, and he was a nuclear missile operator, and I was a finance officer on active duty, and we started having kids in 2013 which was just amazing. But being a dual military couple, we had kind of been through a lot of separation and time apart, which is standard for military couples. And so in 2013, I kind of — I just had my first son, and I was back at work, and I was just feeling this torn feeling, because I always thought I would stay in the Air Force the full 20 years. I loved serving. I loved being in the military, and having gone to the Academy — just all the dreams and the hopes that came with that, and being able to lead and serve my airmen. But I was feeling this yearning and desire to kind of do something else, and that's kind of where the seed was planted at that time. And I reached out to one of my mentors, who was actually the coach of the lacrosse team at the Academy when I was there my freshman year. She's actually one of your classmates, I think. She's Anne Marie Hornby. She's from Class of ’99, and I just reached out on Facebook, and I was like, “I know, I haven't talked in a while, but I just wanted to check in and ask, you know, like, why did you transition to the Reserve?” Because she was always, you know, she was a teacher at the Academy. Like, she was always high performing. Like, I knew she was an amazing officer.

Col. Naviere Walkewicz 2:02
She was high performing as a cadet too, by the way.

Jessica Whitney 2:05
I'm sure she was. Just everything she did, I could tell she did it with excellence and love, and I just really respected her opinion. So I reached out and asked her just like, “Hey, can you just tell me, like, why did you decide to separate?” I'm just kind of feeling this tornness, and I'm feeling like maybe my calling might be something else than serving in the military, which, as an 18-year-old, you kind of go to the Academy thinking, “OK, I'm gonna have four years at the Academy, and then I'm gonna serve for five years, or 12 years, or whatever.” Like, you've got your whole life planned out, and then all of a sudden there's this, you know, pivot and decision that you have to make of like, “OK, wait, life is throwing some things at me that I didn't expect.” And I just wanted to know her opinion. And she just said such a sweet thing that resonated with me, that she kind of felt that same call of, “I wanted to spend more time with my kids. I wanted to be able to focus more on my husband and my family.” And while it was scary, she said, I know she knew that motherhood, or like becoming a stay-at-home mom and transitioning to the Reserve wouldn't necessarily feed all of her desires of competition and performing well and using her strengths to the utmost, maybe that she could — she also knew that it aligned with what was important to her and her family. And each family is different, and each career is different. So it really gave me freedom to say, “OK, I know successful women in the military who have families. I know successful women outside of the military who have families.” And you know, we choose to do the stay-at-home mom career, which was different for me, because my mom worked full time when I was growing up. So anyway, it gave me that freedom to kind of like pivot and think, “OK, what could the possibility be to like, create this life of being there for my family?” So fast forward, 2016 I was teaching ROTC at Colorado State University, which was a dream job, by the way, I absolutely love that job. And Tom, my husband, at that point, had already separated from the Air Force and was pursuing his career in professional golf. He was traveling to PGA Latin America in both the fall and spring of 2016, I had to go TDY to field training for seven weeks that summer. And I think we counted up being apart for over 40 weeks that year.

 

Col. Naviere Walkewicz 4:35

Majority of the year.

 

Jessica Whitney 4:36

The majority of the year. Yeah, and I did not really see staying in the Air Force, it getting any better, as far as, you know, having more time with my family and my husband. And I just felt disconnected, my heart wasn't in it anymore and serving, and I still had that little, you know, seed that had been planted when I talked to Wibs about, you know, like, “Why did you go into the Reserve?” And I talked to a couple other reservists who just loved the balance of being able to still serve in uniform while also being able to maybe have a civilian career, or just be able to have some more flexibility to spend more time and focus on their families during a season of life. And so in 2016 I'm sitting there my desk, like, “I just want to go home and take a nap. I'm so tired.” I had two kids at this time. I was like, “Oh my gosh, I'm just exhausted.” But I was like, “OK, I think —" you know, my husband and I prayed about it, we were just like, “OK, I think it's time to just take this leap of faith, kind of walk away from what we've known.” So now both of us would be out of the Air Force and pivot to something else, and like, step into that faith decision that for us, that the Lord's going to provide, and that we wanted to build and focus on the things that were really important to us. So showing that if family faith are the most important things, how was I using my time? How was I using my energy? How are we using our money? Did it reflect what was actually important? And so we made that decision, and then I got out in 2017 and separated. And honestly, it was the best decision ever. Now, I struggled a ton with my identity afterwards, because I just didn't realize that I really kind of was wrapped up in this idea, like, “Oh, I'm an Air Force officer, I'm an Academy grad,” and those things are, like, very focused on what you do. And so I had to kind of redefine what success was to me as far as just impacting the people around me.

Col. Naviere Walkewicz 6:41
I want to just interject here for a moment, because you said a couple of things that I really want to pull on before we get too far, because I think it really does impact some of our listeners and some of the experiences that they've had. So the first one, when you talked about that transition, and there was a key word you use, and you use the word “freedom,” — “It gave me a freedom to kind of things a little differently” after having a conversation with your mentor, and then, you know, praying about it with your husband. And so I want to just explore that a little bit, because did you feel like that freedom, or just the ability to kind of navigate that did touch on some of the things you really valued that you learned at the Academy, as far as decision making, and kind of, you know, taking this leap of faith and navigating what's not always known. And, you know, I don't want to say it's safe, but maybe it's not the safest path, right? So, like, can you just touch on that a little bit more? Because I think that is something that, you know, people question that, kind of, in that decision-making place.

Jessica Whitney 7:41
Yeah, I definitely think that in that decision, when I say, you know, we had this, I had this freedom to make a choice, we could, kind of, I could kind of lean back onto my time at the Academy of we were given so many challenges at the Academy and things that were unknown and things outside of our control, and you just learn to have an approach where you cannot problem-solve everything, but just like you can say, “OK, here's the variables I know that are true, here are the things that are outside of my control,” which just help you make clear decisions, and then just stepping into the fact that any decision, any action, is just taking one step at a time, and you don't have to have the whole future planned out. And in fact, in the military, you rarely do, right? I always kind of joke with my husband with, like, the quotes, but you know, like Gen. Patton, like “A good plan executed now is better than a perfect plan next week,” right?

Col. Naviere Walkewicz 8:40
Next week. Thankful I was able to contribute a little.

Jessica Whitney 8:43
Good job. Good job. Yes. And so just, but the fact that, like, just make — do what's best with the information you have now, and take action and don't just sit on it. And I think, but, yeah, that gave me that freedom. Because, yeah, it was a big step and leap of faith, because a lot of people think the military is, well, of course, it is a risky job, and especially risky in the sense of our physical harm and a lot of the challenges that we face. But in many ways, it's something we knew, know, and it's something that's very reliable, and it's something that we had, my husband and I had both lived for, you know, 11 years between the Academy and now. So it was a big leap of faith, as far as, you know, transitioning to the unknown, but we were able to kind of lean on just, “Hey, it's OK that we don't know everything. We can trust the skills that we gained at the Academy and trust the skills that we gain just in life to move forward.” And even with my husband, I'm like, “If this golf thing doesn't work out —" which, by the way, he's been a professional golfer for 10-plus years now, so it's worked out. I fully believe that we are capable of learning anything and doing anything if we choose to set our minds to it, and like we're gonna be OK, like, because of what we learned at the Academy and skills that we garnered. Like, we're gonna be OK moving forward.

Col. Naviere Walkewicz 10:13
I love that. And you started to talk about having to redefine yourself, and before we get into that, I think it's interesting, because you grew up as a dependent of — your dad served in the Navy, right? So we like to use the term, you know, lovingly, I was an Air Force brat. You're a Navy brat, so your identity going into the Academy was already one of a military dependent, right? So let's talk about this redefining your identity, because I'm sure that it was much more than, you know, just on the surface level, it seems really simple, right, going from this, but I'm still serving, so it's not really that different, but I'm sure it was.

Jessica Whitney 10:49
Yeah, it was a big transition. So as you mentioned, I was a Navy brat. My dad served for 30 years, and I come from a proud heritage of military service. My grandfather, before that, served in the Navy, he joined straight from the Philippines, and my great-grandfather actually served in the Philippine army and was in the Bataan Death March. So I've got a lot of history in the military and a lot of pride and service to my country. And my dad was always, you know, a hero to me and someone that I looked up to, as far as he was always, not the only serving in the military, but he would be a leader of, like my brother's Boy Scout troop, right, and volunteer with this, and he'd be active in the Rotary Club. And my mom worked full time and led my Girl Scout troop, and whenever he was gone to Bahrain for 16 months, you know, she held down the fort with three kids. Like, I just looked up to my parents and how hard working they were, and just how they were always serving something bigger than themselves and balancing family and all that. I still don't know how they do it. And we have four kids now. I'm like, how did you guys do all of that? But when I transitioned out of the Reserve, I just remember sitting one time, like, I was doing my quiet time in the morning, and I was reading my Bible. And at least for me, I had to remind myself my value is not in what I do. It's not in awards I get. My value is one, in Christ, and then two, in the actions that I take each and every day. And it's impacting and positively impacting the people that are around you right now. And honestly, it's a struggle every day, even today. I've been a stay-at-home mom for eight years now, and it's something I think we all struggle with — of like, what is our purpose in life? What is the reason — why we do the things we do? And each person really has to, like, struggle with that. So I had to, I think when I was really struggling with my identity, I had to redefine, like, OK, my worth and value is not in the title that I have or the rank that I have or anything like that. It is loving on the people around me really well and serving to the best of my ability with excellence in all we do right where I am, and that's the most important thing.

Col. Naviere Walkewicz 13:25
How did you get to that point of defining that? I mean, is it kind of in lockstep with your views of yourself as a leader? Or would you say it's just where you kind of settled into in your moments of quiet and through your prayer of, “This is how I define my impact and my —" you know, what that looks like?

Jessica Whitney 13:48
I think a big chunk of it was just continuous practice, in a way, each and every day, reminding myself, one, is what success looks like, because I think that as people who are highly motivated and being leader, you're like, you've got your to do list, you've got your things you want to do. I've got, like, a to do list, like, this long, you know? And yeah, and I would just tell myself, like, “I've got 25 things to do. I only did six of them.” Like, there was no way I was going to do 25 things in the first place, you know. So I think that as a leader in general, you need to be realistic about what you can actually accomplish each and every day, whether you're a stay-at-home mom or you're a leader in the workplace, and actually be able to, like, you know, time block and say, like, “These are the most important things. These are my priorities.” And probably just over, it's probably just over time of like, every morning, like, "OK, the most important things, like, got my quiet time in. I'm spending time with the kids. I went for a walk, I moved my body, and we're eating healthy meals. I remember when I was working full time, I would kind of be jealous of those people who, like, had time to cook a full meal, and, like, spend an hour maybe making dinner and, you know, have quiet time. I always felt when I was on active duty working full time, it was just like, get up early in the morning, go to daycare, drop off, work all day. You know, work out during lunch. Never have a break, and then run home, make dinner really fast, and, like, get the kids in bed, and there was no break, and there was no rest. And so I remember yearning for that when I was on active duty. And so when I first became a stay-at-home mom, and when I first transitioned out of the Air Force. I really had to remind myself, like, OK, what are my values? What is most important here, and are my actions aligned with that? And if they are, then that's success right there. And so I had to remind myself that every day, like I get time to make healthy meals for my family. I have time to go to the gym five days a week if I want to. I have time to put a, you know, like, say yes to things like this. I've got time to go speak at the Veterans Day ceremony at my kids school. Like, I don't have to feel bad about missing appointments for my missing meetings at work for appointments for my kids. I don't have to choose that all the time. Now, serving in the Reserve, you know, I still miss weekends where the kids have tournaments and games and stuff, but that's OK, like it there's, there's a balance in there. I hate the word balance, because I don't think you ever really achieve that. But I think that as leaders, you know, we have to — like, when you're feeling the most stressed, or when I felt the most stressed, it's when my actions and behaviors just haven't lined up with my values and what's most important to me. “So as leaders in your organization, if you know you guys are — your stated values, are, you know, XYZ, but you're over here doing ABC, then there's going to be disconnect in the organization.” So I think at any time, you know, when there's alignment there, then you're going to feel alignment for you as a person, as a leader.

Col. Naviere Walkewicz 17:19
I'd like to dig into those values a little bit, because we did talk about how you've experienced deep personal loss, right, in your family, and you know, how have the values, or maybe just your life experiences, helped you navigate that? Because, you know, I think people experience grief on all levels, and if you don't mind sharing your story a little bit, I think it just will allow others to understand how you were able to navigate through that and maybe continue to navigate through that today.

Jessica Whitney 17:51
Yeah, thanks for the opportunity to share this part of my story. So my husband's brother, Bob, was a 2008 grad, and unfortunately, we lost him to suicide in January of 2020. It was really just a complete shock when it did happen. It seemed like it came on so quickly. Bob was just always someone that when you walk into a room, he was always smiling. He was the light in the room. He was such a great husband and father. He was super active in his church and his family. And so a couple things that I took away from all of that was just one, we just never know what people are going through, what storms they are, like, they might seem perfect on the outside, and really, they're having struggles with maybe imposter syndrome or just doubt, or they're just having all sorts of issues, right? So you just never know. I remember standing in the grocery store after he passed away, and I'm like, staring at these bananas that I'm supposed to be buying for eight kids because we were like, up with them, you know, after the funeral. And I'm just thinking, like, no one around me knows that this just happened in my life, and I'm just standing here doing this mundane thing of buying bananas. And I think it, just, as a leader makes you realize that people are walking through storms all over around you, and if you're not currently in a storm, most likely you will be. After he passed away too, we were just blown away by the community support that he received, both from his church as well as from the Air Force family, but I know that it takes time to have good community. It takes — you have to invest time. And all of us, we're just so busy, but these relationships, these are the most important things that we can work on and develop the people around us. It kind of showed up for me in my unit, we had an airman who lost a spouse. He had three young kids at home, and his wife passed away. And I was like, we just need to show up for him, like, be at his doorstep. And we're in the Reserve. We don't live close together. We're not all stationed by the base. So, you know, it's like someone needs to go to his house, bring him a card, tell him we love and care for him as our Air Force family. And you know, he even commented afterwards, he was like, “You know what, you guys—” this Air Force family that he only saw one weekend a month. He's like, “You guys are my lifeline.” But I know that, for me, I really knew that we needed to show up, and that's because I knew what it felt like when people showed up at my door, when we needed it, you know?

Col. Naviere Walkewicz 20:51
Wow. I mean, I think that's really — I mean, to navigate that. And loss, I think you know, is as a journey, that it's still a life journey, right? And so, and I think the fact that you were able to lean in and you knew and expressed it in a way that you know, showing up for those and then seeing it happen actually in your unit, and being able to translate that. Have you always known, I guess, about showing up? Have you seen that in other leaders in your career or in your life, what showing up looks like? How that really defined you? Because I'm curious if you know that was all just developed in seeing that in that loss journey, or if it was something you've seen over time and then witnessed it?

Jessica Whitney 21:37
I guess I would say, if I'm really looking back, especially because I'm a Navy brat, right? We did live in places all over the country, and, yeah, we did have a good support system. Like my friends, my family, had people that would show up. Like when my dad was deployed, they would show up at the house when I was in high school. You know, we had such a tight knit community there, but I am thinking, like the first time I really felt that was with our church community. After our first son was born, people would show up at our house, and I didn't even know them, and they were bringing food to us. I was like, “Oh my gosh, this is so sweet.” But just, like, that power of community, and then even with leaders that I've had in the past, like my first squadron commander that I can remember, she, like, the first day I got back again from maternity leave, she had, like, just brought, like, a little vase of flowers and put it on my desk, and just like a welcome back, but like an acknowledgement too. Of you know, it's hard to come back after, right? You know, your first child, or any child, like after you have a baby, and then you come back to work, but just, you know, welcoming and showing up. And I think that this, I don't know exactly where it stems from, but, yeah, actually taking the time to do it, because a lot of us know we should do it, but do we actually pause long enough to do it?

Col. Naviere Walkewicz 23:11
That's a really great — I think that particular nugget, right? We know what we should be doing, but do we actually take the steps to do it? I think, is actually an important lesson right there. And, you know, would you say that throughout your experiences, and I'm really curious, because I think, you know, you talk about being a stay-at-home mom, but I'm sure your schedule is quite — you said you get six out of your 25 things done. Can you talk about how you're serving outside of the uniform? Because I think that that's really important as well. Service doesn't stop just because we take the uniform off. And I mean, it sounds like you're serving in your church and your community. You know, what does service look like to you now, through that leadership lens, maybe when you're not wearing a rank all the time?

Jessica Whitney 23:54
I have really looked at the areas of my life that I want to be active in, like, what's important to me? And in the church, I participate in the women's Bible study, and I'm one of the leaders there and kind of help lead. We have 120 women that come every Wednesday and I'm one of the leaders that, you know, kind of facilitates the overall Bible study. And I've just loved stepping into that role and using my leadership skills to encourage people and show up. And then the other board I kind of serve on is the Class of 2010 Endowment for Cadet Morale. And so our class, with our funds that we, you know, had raised throughout the years, decided to set up a morale fund. So the top squadron for each semester actually receives a $5,000 check from our endowment, and they can use it on whatever they want. And I just remember, like those cadets, those high schoolers that are transitioning to be future leaders of the Air Force, they are amazing. I am impressed every time I interact with them. And the Academy is hard, and I just want to offer that little bit of light, you know, to encourage them. Like, “Hey, you're on a good path. Like, just, just continue on. And here's a little bonus, bonus check.” You know, literally, we love that part. But yeah, so I just love to step into service where I can.

Col. Naviere Walkewicz 25:23
I'm glad that you shared that, because I do think it's easy for us to downplay our role and impact in the hats that we wear and the ways that we serve, and so I really appreciate you sharing that, because I think that's an important part of our stories you talked about with me before you know, redefining yourself. I want to go back to that because I think it has to do with being authentic and who you are. And so as you've navigated this new season in your life where you're still serving in these multiple hats and raising your family, supporting your husband, you know, where was that seed planted from, being an authentic leader, kind of, you know, being — leading with integrity, you know, maybe saying, “I can't do this, but I can do this.” Can you talk a little bit about that?

Jessica Whitney 26:07
Yeah, absolutely. I took an amazing class at the Academy, a leadership class that a friend of mine, again from the lacrosse team, recommended me, and she's like, “Jess, this class — it's called transformational leadership. It's way more than that. I really think you need to take this course.” And she was so right, because there are so many things that I carry over from that, from that course into my leadership, and then just my everyday life. And it was taught by Capt. Kari Granger, who's now Kari Zeller, and she's an Academy grad as well. And when I got to my ROTC detachment in 2016, so eight years later, this gentleman came into the office, and he's like, “Hey, my daughter teaches this leadership course called being a leader and the effective exercise of leadership. I really want to teach it at Colorado State, but I'm looking for someone to partner with, maybe through the detachment. Like, do you think anybody would want to co-lead this class with me?” And his name was Karl Zeller, and I was like, “I think I took this class when I was at the Academy, and it was amazing, and I would love to lead this class with you.” And so not only did I take the class at the Academy, I also taught it two semesters while at Colorado State, we kind of made it an elective class, and we had several cadets and cadre go through the class, which was just an amazing experience. Because I think most of us know that when we have to teach other people something, we learn it even better than when we go through it ourselves. So the kind of the main takeaways I had were one kind of heard the definition of integrity. We all know the Air Force's definition of doing what you know the right thing when no one's watching, when nobody's looking, but she kind of defined it more as both keeping your word and honoring your word. So we all know that keeping your word that's easy, but what is honoring your word mean? And her framework kind of laid out, honoring your word is, as soon as you realize you're not going to keep your word, notifying the person that involves saying when you are going to keep your word and then cleaning up any mess that you made by not doing it. So a quick example would be, you know, you're running late to a doctor's appointment. You get in the car, you realize, “Oh my gosh, I'm going to be seven minutes late to the appointment.” Instead of, like, white knuckling your steering wheel to make it in time, you feel guilty when you get there. You immediately call the office. You tell them, “Hey, I'm going to be late to the appointment. I'm going to get there seven minutes late. And, you know, I realized that this has an impact on you like, you know, let me know if I need to reschedule." Whatever it is, right? Most people are so shocked by this ownership that they are so much more gracious to you in whatever the circumstances are. And on top of that, you're not stressed. You're not, you know, white knuckling.

Col. Naviere Walkewicz 29:22
So when it really takes you nine minutes to get there? Yeah,.

 

Jessica Whitney 29:26
So hopefully overestimate.

 

Col. Naviere Walkewicz 29:28
Seven minutes and 40… Like, round down.

Jessica Whitney 29:29
My husband calls that, like, Jess math. I'm like, yeah, well, it's fine. It's fine. But, like, if you think about in the workplace, right, like, you have an assignment, you have something your boss gave you, it's due Friday. You realize Monday, OK, there's no way I'm going to do this. I can either stress about it, work super late hours and, you know, like cause all this extra stress, and then maybe still not accomplish and get the work done, and then show up to my boss on Friday and say, “OK, sorry, boss, I couldn't get it done.” Or on Monday, you bring up the conversation, you swallow your pride, and you say, “These are my challenges.” You manage expectations, and you're you guys together. Can you know, either reassign, get help or bump the deadline, whatever it is, but now you're no longer living in this like, fear of like, I'm going to be late or whatever, like you're able to perform better. And so they, in the class, they talked about how, with integrity, everything works. And they talk about the idea of like a bicycle wheel, right? There's spokes on a bicycle wheel, and if all the spokes are intact, it's going to run very smoothly, right? That's keeping your word and honoring your word, you're performing really well. Well, when you're not honoring and those folks and you're not keeping your word, or you're not honoring your word, some of those books are missing, so it's just going to be a little bit bumpier. And things are going to get done, but they're not going to get done as well as they would if you were honoring your word. So that's a big takeaway

Col. Naviere Walkewicz 30:56
That’s a great analogy. Wow. Yeah.

Jessica Whitney 30:58
So I apply that, I feel like in everything, because I think a lot of us will get in the way of ourselves, of just like, “Oh, I don't want to tell them and be late, or I don't want to, I don't know, disappoint someone, or I know there's expectations with my husband, but I'm just going to ask forgiveness instead of, you know, for permission,” or whatever it is with whoever. So anyway, with integrity, nothing works. And so I kind of take that away of, like, OK, what's expected of me? OK, I'm going to try to meet that. And that kind of lines up too with just this idea of what's your values, right? So if I say I'm a person that values fitness, do my actions line up with that. That's part of my word. OK, so I've said, I've said, “OK, I'm a fitness person and I want to be healthy.” Well, am I going to the gym? Am I eating healthy? Am I drinking too much? Am I — whatever? Do my actions align with that? No, OK, I'm not in integrity. It's not bad or good. It's just not working as well. Not going to accomplish my goals if I'm not in alignment with the other two things. And I'll just touch on them quickly, and then we can explore more if you want. But the other one is what's undefined runs you, which is basically means —

Col. Naviere Walkewicz 32:06
Wait, say that one more time.

Jessica Whitney 32:09
What's undefined runs you. So it's this idea of all of us have stories most likely from our childhood that we make up about ourselves. So like, I don't belong. I can't disappoint people. I have to get things done the right time. And we can probably all look back in our past and say, “I remember I got in trouble one time when my grandpa was at the house and I was late getting in, and he said, you know, you're disappointing your mom. You're not listening to her.” And then, all of a sudden, you make this life sentence for yourself of I can't disappoint my mom. I can't disappoint so now you have this filter, this mindset that all of your decisions and actions flow through that says I can't disappoint others. Well, of course, that's going to limit what you can and can't do, because it's filtering out half of, you know, a quarter of action, anything that could any —

Col. Naviere Walkewicz 33:03
Risk or grit.

Jessica Whitney 33:05
Exactly. And so what the undefined run you means you're never going to be able to completely get rid of these filters and things that you have, but you can name them and define them. So you say, OK, like for me, I was a Navy brat. I moved around a lot, and so I often felt like I didn't belong where I was. Like, I always felt like people already had relationships, all that stuff. So I do, I know that I will walk into a room like a Bible study, and in my mind, think, “Man, like, people just don't really connect with them. Like, maybe they just don't like me.” I'm like, “No, I've been here for five years. I belong here. I am a part of this group.” But it's this, you know, filter that I'm running things through, of I don't belong. I need to name that, remove it, and then be like, OK, I belong here. I am part of this group.

Naviere Walkewicz 33:54

So what have you named it? And have you removed it?

Jessica Whitney 33:59
I think it's more about just the awareness. So it's like that, we as leaders have to be aware of the things that are getting in our own way of being an effective leader. And so I — this is a big one for me, like the I don't belong. So even recently, I walked into a new group of women and I said, “I belong here. I am a part of this community.” It's like at my son's school, and I can contribute as me. I don't have to hold back, or, you know, be a certain way. I can be myself. I can be my authentic self and lean into this. And it was very freeing, because in the past, I have gone in and just kind of like sat kind of back, and I don't want to be intimidating, or I don't want to take over the conversation, or just whatever it is, I'm not being myself, and I have to tell myself, like, “I belong here. I can be myself if they don't accept me for me, that's OK,” you know. But I can't hold back just because I'm trying to fit in and just because I'm trying to be risk averse, or, you know, conflict averse, or something like that. So, yeah, just be yourself, right? But so what's undefined runs you. So as leaders, we need to identify what's holding us back, what's running our lives, right? And just name it. They have a phrase: “Name it to tame it.” So once you can put a name on it, then that often helps you change your actions, you know? And then the last one is just, I think leaders, you are a leader. If you are impacting something around you, the organization, the people around you, they wouldn't be who they are without your influence. So in that framework, we talked about creating a future as leaders. So you've got a current organization, and maybe there's, you know, like no one likes to hang out, there's gossip, there's toxic leadership, there's bad communication, no transparency. This is a very imaginary organization, of course. But you acknowledge, like, OK, this is what's going on. Let's create a future. What does the future look like that we actually want, with all the actions and things like, OK, we have transparency. We like to hang out. There's, you know, Squadron picnics. We go to PT and we all encourage and work hard. We handle conflict in a healthy way. OK, so if we're standing in that future and looking back, how did we get here? So the course is a lot about, like the whole ends, ways, means that the Air Force talks about, but just how can you stand in the future and look back and say, “How did I get to that spot?” And then that's how, you know, what's the next action you can take in this current spot?

Col. Naviere Walkewicz 36:49
Wow. Jess, it's almost like you read my mind, because there's two questions I actually want to ask you, and one of them is about looking back. So why don't we start with that one? First, you know, what is something you would tell yourself, young Jess back then that you could be doing then to help you be a better leader now? And is it actually what you just talked about, or would it be something else you would add?

Jessica Whitney 37:11
No, I think it would be just that. Like, no, where do you want to be even, like, let's say, in five years, or what's going to be most important to you in 80 years? Right when you're 80, when you look back on your life like, what's going to really matter? And start aligning your life with that. Now, some of that takes time, but standing in that future of how you want it to feel, how it looks, how you want your organization to feel. Like, start — write it down, put it on a vision board, talk about it with someone. And then I would say to myself, like, and then start working towards it. I think when I was younger, I was, you know, I was comfortable with where I was at. I was afraid to take risk. I was afraid to do things different than what I always thought I would do. And you know, for me, the Lord really worked in it, in my heart of just saying, Just trust me. Just trust me with that next step you have the direction you kind of want to go, and I'm going to take you on a journey that you know you're probably never going to be able to predict, kind of like, what I talked about at the beginning, like I pivoted, like it was completely different than what I want, and just be OK with that. That's the beauty of life is, you know, pivoting with what's in front of you, but just taking that next, that next step.

Col. Naviere Walkewicz 38:32
I love that. And then what is something that you do every day, just to be better and better is really you define better, but what is something you're doing every day.

Jessica Whitney 38:42
I love the books, like The Power of Habit and Atomic Habits and yeah, they're so good in just this idea of your daily actions are, what are, who you are, really like, how you show up in the world, because you can only control what you're doing today. Can't control what you're doing tomorrow or what you did in the past, and so for me, one, I do love to read. So I'm always reading books, listening to podcasts and all that kind of stuff. So I think, as a leader, just, like, surround yourself with lots of different opinions, read different things and just encourage my brain. Two, I love to surround myself with people that encourage me and a community that's going to help me challenge myself to improve. And then three, like those daily actions of self-improvement, of like, OK, how can I be just like, 1% better than I was yesterday, whether that be choosing to eat a little healthier today or going on a 30-minute walk, or, you know, when you're lifting weights like, Can I do five pounds more on this? Like, one or one more rep, right? Like, one more. But I do love that analogy, and weightlifting like, OK, I didn't realize that, you know, like, I can do one more rep this week than I could last but three months ago, you know, I've made huge improvement from three months ago. But you don't realize until after the fact. So I think, you know, being a high achiever all my life, it's like, you want to see these big, like, changes and, you know, immediately, but oftentimes it's in these, like, small moments of like, “How can I just be better today?” Healthwise, community-wise. Who can I love on today? How can I, you know, for me, like being in alignment with, you know, what I think God has for my life, being in prayer and focusing on the people around me. You know, that seems like a lot of things. That's why I've got 25 things on my list, ,

Col. Naviere Walkewicz 40:44
But you get a few of them done And that's OK, because you just gotta do one.

Jessica Whitney
Exactly, you just gotta do one.

Col. Naviere Walkewicz 40:51
Well, I can just share how much, you know, you really just like leaned in and shared your love and wisdom with all of us. And I think that's one of the things I really appreciated about this today: how you showed up for us and shared your authentic self, and so I just want to say thank you. You know, as we wrap up today's conversation, Jess, what's really stood out to me is that we talked about leadership is just about as much about character, but it's really also about, like, showing up and who you are. You know, you show us just that strong leaders don't just show up and need to have all the answers. They actually just need to show up, right? And just, you know, live their values, live with integrity. And I love how you said, you know, honor your integrity even when life is uncertain or changing. So, you know, I think your transition out of active duty could have been a moment of doubt and struggle, but you turned it into an opportunity to serve, and your family has continued to thrive. So thank you for all that you're doing in your community, and for all of you who need to hear this journey, for those that have also gone or going through a transition, this is a conversation you certainly don't want to miss. So again, thank you to Jess Whitney, Class of 2010. It's been a pleasure having you on Long Blue Leadership.

 

Jessica Whitney 42:05

Thanks again.

Outro 42:05
This Long Blue Leadership conversation was recorded Wednesday, Nov., 19, 2025.

KEYWORDS
Leadership, authentic leadership, transformational leadership, values-based leadership, character-driven leadership, servant leadership, integrity, honoring your word, keeping your word, accountability, responsibility, vulnerability in leadership, decision-making under uncertainty, courage, leading through change, creating a future, vision casting, aligning actions with values, purpose-driven leadership, redefining success, identity as a leader, mentoring, mentorship, developing others, showing up for your people, empathy, compassion, community building, resilience, leading through grief, supporting mental health, trust, transparency, culture change, organizational alignment, handling conflict, managing expectations, setting priorities, work-life integration for leaders, modeling behavior, investing in relationships, daily leadership habits, incremental improvement, 1% better mindset, self-awareness, naming limiting beliefs, “what’s undefined runs you”, authenticity, influence without rank, service beyond the uniform, leading in family and community, Long Blue Leadership.

The Long Blue Line Podcast Network is presented by the U.S. Air Force Academy Association & Foundation