Embracing Impactful Work and Driving Change: Insights from Anna Wheeler

• Anna Wheeler shares how her childhood influenced her to find her core values of confidence, tenacity, and self-awareness. 
• She talks about the importance of diversity and inclusion, and how mastering it has been the most difficult training in her life.
• Explaining her strategies to avoid burnout, Anna shares her father’s lesson that made her aware of the important things in life

1. Can you tell us about your childhood and the people who were most influential in your life? What are the values that shaped the person you are today?

I was born prematurely and was labeled failure to thrive until my teen years. I grew up in a small modest town and despite my early health struggles, I eventually grew to be  6 feet tall. 

I was raised in a very strict household, as was expected from my parents who were Depression-era Southerners. My father was a war veteran who served in World War II, Korea, and  Vietnam, is my hero and inspiration. He overcame an incredibly  racist and marginalized environment, and through reflection and personal growth, treated everyone with respect, regardless of where they came from or what they look like. He instilled  integrity and accountability as my foundation. My father taught me that no path is certain and the ability to make decisions is mine, and every choice I make may influence or change my end goal. His greatest lesson was that  it isn’t a mistake if  you are willing to learn from them.

I am  the youngest of four children, one of my sisters had addiction issues and her struggles made me realize the importance of making positive life choices. This awareness drove me to avoid self-destruction and instead focus on finding value in my capabilities. 

Instead of taking the traditional path and going straight to university, I joined the US military, and became one of the first female Black Hawk helicopter crew chiefs. Despite facing skepticism and bias, my upbringing taught me to find strength within myself rather than seeking external validation. The way I was raised required a sense of  self-awareness, a trait I worked hard to pass on to my daughter as well. She was once told that she would have to go to community college because she wasn’t a good enough athlete. I advised her to listen and accept criticism, but take time to consider where the criticism originates or if she would seek advice from that person. Often, those most critical are speaking from their own insecurity instead of a place of caring.

This mindset has helped me immensely in my career. Most of my career has been in male dominated fields where being a woman was considered threatening or invasive. Early in my career, the environment was even hostile. Relying on my core values and using doubts as motivation allowed me to find value in myself instead of being beaten down by a lack of support. Having such an outlook enabled me to work with amazing professionals who shaped my world.

2. Can you tell us a bit about your professional dynamic with Leidos?

At Leidos, I’ve found a place where I’m not put in a box. My eclectic cyber background, problem-solving skills,  and experience as a fixer / strategist and senior vice president have been valued. Unlike other places where insecure leadership sets boundaries, Leiods has phenomenal leaders who value long-term investments and vision. 

I started as a Solutions Architect and we had great success. For example, we built a workforce at the University of West Florida in Pensacola, with nine interns currently working. This led to a large contract, something that wouldn’t have been possible without the leadership willing to invest in me.

3. While researching about you, we came across Cakes4Kids, which bakes cakes for children in foster systems. What inspired you to join this initiative? And how has the experience baking for children from low-income families or foster homes been?

I’m involved with several charities, and Cakes4Kids is particularly special to me.  I love to cook, though I have to be gluten-free due to a digestive issue developed in Afghanistan. Cake4Kids bakes custom cakes for children in the orphanage system, with social workers requesting specific cakes for the kids. 

This weekend, I’m baking two dozen chocolate and vanilla cupcakes for a graduation. The children can request cakes themed after their favorite things, like Minecraft or Hello Kitty. 

Growing up feeling unwanted, I resonate with these kids. Many face slim chances of being adopted, so for them to know that they can request something special and have someone care enough to fulfill it is meaningful to me. 

4. We saw that you’re a certified Diversity and Belonging Facilitator. Workplaces are becoming more conscious about incorporating DEI Initiatives into their daily practices. How have you started seeing workspaces differently after learning about Diversity and Belonging?

The diversity and inclusion training was one of the most challenging yet impactful experiences of my life. The master facilitator taught me that facilitation is about standing beside others, not leading them to an answer. It’s about moving with them without letting your ego drive the path.

Understanding this role helped me truly listen for intent rather than seeking answers. It made me a more patient communicator, an improved leader, and a more effective negotiator by focusing on what the other side actually needs.

As the Chair of the Women’s Network at Leidos, which has 6000 members and 18 chapters, I’ve seen the power of partnerships with other employee resource groups (ERG). Our success comes from the support of both our female members and amazing male allies who actively participate as well.

5. What is one characteristic that you think is needed to be successful in any venture you wish to pursue?

Accountability, both for yourself and in holding others accountable. In one role, I was asked to act outside of my authority. The first time I agreed to it, but the second time, I insisted they officially give me that role and authority. When the deputy programs manager set me up for  HR action because he felt threatened, I asked HR to lay me off because I realized the work environment was becoming toxic. 

During a meeting with the HR and legal team, the deputy falsely accused me of various things. HR saw through it and reprimanded him, but I chose not to file a case. I held myself accountable, stood up for myself, and negotiated my seperation However, because I didn’t file, the deputy was never held accountable. This experience reinforced my belief in the need for constant accountability to ensure growth and integrity in any venture.

6. What is the one thing you enjoy the least about your career and what is the one thing that you enjoy the most?

Frankly, one of the things that I enjoy the least about my career are mundane tasks, like expense reports. While completely necessary, they take an immense amount of time that I feel would be more productive to strategic priorities. 

I’d rather do more impactful things, which is what I enjoy most about my career. I love to solve problems, empower people, build teams and technologies, and reach out to encourage professionals to try new technologies. For me, these responsibilities are incredibly enriching and feel more like playing a game than work. It always feels like a game when you’re passionate about your work.

7.  How do you prevent burnout, and what is your idea of taking a break to relax and rejuvenate?

This relates to the best advice I received from a one-star general and a mother to three teenagers. She said every person has a different capacity, and comparing our capacity to others could be a fast ticket to failure. She taught me I needed to be deliberate with how I prioritize my efforts.

I applied this advice by roughly calculating my capacity, and dividing my energy among the different parts of my life. For example, some days, I allocate 95% of my energy to work and 5% to minimal tasks like cleaning or running household errands.  Other days, I might give  85% to my family and only 15% to work. Such an approach helps me balance my priorities and forgive myself when I can’t give my 100% to everything.

This method has made me more compassionate and empathetic towards others. It allows me to be more supportive and forgiving towards myself first but towards others as well.

8. What are your most important life values and how did they contribute to the progression of your career?

My father taught me a visual lesson using a jar,  golf balls, pebbles and sand. The golf balls represent the most important things in life: health, integrity, family, etc. Pebbles represent the things we believe are important but are replaceable, such as jobs, houses, or cars. Sand represents less important things, like going to the club, wearing our favorite clothes, or going out for a fancy dinner. Lastly, he would add water, which represents everything else in life. As you add each layer, you lose focus on what’s beneath. By the time you add the water, you cannot see any of the things that matter most.

This visual representation keeps me focused on what I value most. My daughter and loved ones are my priority. Everything else can be changed and is replaceable. . 

I always remind myself at each turn to remain focused on those golf balls instead of looking sight amongst the pebbles.

9. What vision/goals have you set for yourself or are on your bucket list?

I have always dedicated my life to service. My unique opportunities, background, and skill set make me feel responsible for leaving the world better than I found it. 

Military service and the way I support the government give me national pride. I want to strengthen the United States from a safety perspective and support people in the countries that I’ve visited..

My belief in democracy, service and the opportunities I’ve had to travel the world and embrace a wide range of cultures have enhanced my desire to serve as an Ambassador one day in order to create a global impact, spread democracy, and ensure security for the countries that rely on the United States. That’s how I would like to conclude my service.

10. What is your favorite quote or mantra?

“Being kind costs us nothing.”

I am not a sympathetic person, but I’m very empathetic. I believe how we respond to a crisis defines its outcome. Nevertheless, we should still be empathetic towards others going through tough times and refrain from judgment.

Anna Wheeler shares her inspiring story as a US military chief and her work at Leidos. She explains how her childhood played a key role in her advancement in leadership, and shares her visions and dreams for the future. Anna’s journey highlights that strong will and dedication can turn our lives around while providing hope and encouragement to follow our dreams.