Interview with Sheri Swokowski

There are women whose courage reshapes institutions. There are women whose truth reshapes hearts. Colonel Sheri A. Swokowski has done both, with quiet grace, unwavering integrity, and a patriot’s heart that never stopped beating for justice, even when her country struggled to understand her. Sheri is the highest-ranking openly transgender veteran in the United States Army. Over nearly 35 years of distinguished service, she rose from the enlisted ranks to the rank of Colonel in the Infantry, a place where few women, and no openly transgender women before her, had stood. Her journey was marked by leadership, resilience, and sacrifice. After retiring from the military, she continued her service to the nation in civilian roles at the Pentagon and the U.S. Forest Service, and later became a powerful voice for transgender rights and inclusive policy, working alongside allies such as Congresswoman Tammy Baldwin.

 

But behind the impressive résumé is a woman who made the hardest decision of her life in her fifties: to finally live authentically. The cost was steep, relationships, career opportunities, and the comfort of familiarity. Yet in embracing her truth, Sheri found joy, strength, and a new mission: to ensure that others like her could serve and live with dignity. Whether wearing her female Infantry officer uniform at the White House Pride reception, mentoring younger trans women, or volunteering tirelessly with organizations like the ACLU and Fair Wisconsin, Sheri has never stopped marching forward. In every room she enters, she carries not just her story, but the hopes of countless others still finding the courage to live theirs. It is my honor to share this conversation with a woman whose journey exemplifies grace under fire, authenticity against the odds, and the enduring power of truth. Ladies and gentlemen, meet Colonel Sheri Swokowski.

 

Monika: Today, I have the great pleasure and honor of speaking with Sheri Swokowski, a trailblazing advocate for transgender rights and a former U.S. Army colonel. As the highest-ranking openly transgender veteran in the United States, Sheri has broken barriers and inspired countless others with her courage and leadership. Welcome, Sheri. Thank you for joining me today! 

Sheri: Hello, Monika! Thank you for having me, it's a pleasure to be here and to share this conversation with you. I'm always grateful for opportunities to raise awareness and help others understand the experiences of transgender veterans.

Monika: Let’s begin with your remarkable professional background. You’ve built a distinguished military career that spans decades, and you’ve broken barriers along the way. Could you walk us through how your journey in the military began?

Sheri: I enlisted in the Wisconsin Army National Guard after high school and shortly thereafter started working full-time as a federal employee. A dozen years later, I had the best of both worlds, as I was offered an opportunity to go on active duty in support of the Wisconsin National Guard. 

 

Interview with CNN (YouTube).

 

Monika: And once you transitioned to active duty, how did your career progress over time?

Sheri: I was a career infantry soldier who spent almost 35 years in uniform. I advanced through the enlisted ranks, attended the Wisconsin Military Academy, and earned a commission as a Second Lieutenant. I made the most of many opportunities and served as a Company Commander with two deployments, although in my day, they were to Europe. I served on a two-star staff and was the Force Integrator, Strategic Planner, and finally the J1, Director of Manpower and Personnel.

Monika: After retiring from the military, you continued to take on impressive leadership roles. What did that phase of your career look like?

Sheri: I retired for a short period and then went back to work in the Washington, D.C. area as a lead course instructor at the U.S. Army Force Management School, Fort Belvoir, Virginia. I then served two and a half years as a senior analyst at the Pentagon in Washington, D.C., followed by three years as Director of Human Resources for the Rocky Mountain Region of the U.S. Forest Service in Denver, Colorado. I returned to Wisconsin in 2013 to spend time with my children and grandchildren.
Monika: In The New York Times series Transgender Today, you shared a powerful personal story. What struck me most was how candidly you expressed your disappointment with the way the Army treated you during your transition. Could you take us back to that time and describe what happened?

Sheri: I was a government contractor in 2007 when I decided I needed to live authentically. I advised the HR Director that I was taking a six-week leave of absence and would return as Sheri. They had no experience with transgender employees, and it showed. When I returned, I was greeted by the Director, a former three-star general, who thanked me for returning and then announced they had already hired my replacement. While they had hired an instructor, my replacement was not hired for six months after I returned.

Monika: That experience must have been deeply hurtful, and it clearly motivated you to speak out. How did that moment shape your path toward becoming an advocate for transgender rights, particularly within the military and in employment law?

Sheri: Being from Wisconsin, I was proud that Representative Baldwin was the first openly gay individual elected to Congress. She was from my home district in Madison and was sympathetic to the transgender rights movement. She shared my story with the House of Representatives in 2008–2009.

Monika: You’ve witnessed firsthand how representation and advocacy can evolve. What kind of progress did you see in those early years of transgender visibility in politics? 

Sheri: Several years later, Baldiwn shared with me that in 2008 only a handful of the 435 Representatives in Congress had been visited by a transgender constituent. By 2011, all members of the House of Representatives had been visited by a transgender individual.

Monika: You’ve become a symbol not only for openly transgender soldiers but also for the estimated 15,500 transgender service members who remain closeted. In your view, what were the key milestones that helped pave the way for trans people to serve openly in the U.S. military?

Sheri: After a coordinated effort that began in 2013 by Servicemembers, Partners, Allies for Respect and Tolerance for All (SPARTA), the Department of Defense announced on June 30, 2016, that transgender service members would be able to serve openly, effective immediately. The U.S. finally joined 18 of our allies who already permitted trans service members to serve openly. This was a historic moment that validated years of advocacy and tireless effort across many fronts.

 

At home in Windsor, WI. From "Our Lives -
Madison" Magazine. Mar/Apr, 2015.

 

Monika: What made this breakthrough possible, and who were the people behind it?

Sheri: Although this was a collaborative effort between the Department of Defense, medical experts, and advocacy groups like SPARTA and The Palm Center, our success was largely due to the dozens of transgender U.S. service members who came out to their commands before the ban was lifted. They are the real heroes of the issue. I am happy to have played a small part in lifting the ban. Their courage helped shift perspectives at the highest levels of military leadership.

Monika: You were also a pioneer in having your service record updated to reflect your true identity. What did that moment mean to you personally?

Sheri: In April 2015, I successfully had the Army Board for Correction of Military Records update my record of military service and provide me with a DD 214 that reads: Sheri A. Swokowski, COL, Army, Infantry. As a result, I was the first female infantry officer recognized by the Department of Defense. I used the opportunity to wear a female infantry officer uniform to Pentagon Pride and the White House Pride Month Reception in June 2015. That recognition was both deeply personal and profoundly symbolic of the progress we were making.
Monika: You transitioned later in life, in your 50s. Do you ever wish you had come out earlier, or do you feel the timing was right for you?

Sheri: I have often thought about this. Although I hid my identity for five decades out of love and respect for my family and the job that I loved, I don’t believe I would have done anything differently. My experiences, while impersonating a male for 50+ years, provided me with many opportunities to acquire skills that would serve me well during my transition and later in life. 

Monika: During that time of transition, did you have a support system or role models who helped guide you?

Sheri: In Washington, DC, I was fortunate to find a support group of a dozen or so individuals; we were all transitioning at the same time. I gained a lot of strength and insight from sharing experiences with those individuals. I am still in touch with many of them today.

Monika: Today, are there any transgender women you particularly admire or look up to?

Sheri: I admire, and count as my friends, several individuals around the country. I admire Dr. Becky Allison, an MD from Phoenix who transitioned a decade before I did. I also admire Amanda Simpson, who most recently served as Deputy Assistant Secretary of Defense for Energy. She was the highest-ranking transgender Presidential appointee serving in the Obama administration. Another individual I admire is an anonymous Justice Department official who has played a role in my life and the lives of transgender Americans by advancing transgender rights at a national level.
Monika: For many transgender women, the journey toward authenticity often comes at a steep personal cost, estrangement from loved ones, loss of careers, and diminished social standing. Did your decision to come out come with sacrifices of your own? What was the most painful part of your experience? 

Sheri: The most difficult thing for me was causing pain to those I loved, particularly my spouse. As a result of transitioning, I have lost contact with siblings, my ex-spouse, some friends, and co-workers. I have found that losing friends and colleagues has been mainly generational. It appears older individuals find it more difficult to accept advances in the medical arena. Still, I believe that time and education can soften even the most rigid perspectives. 

 

CNN Studio, Washington, DC. 8 Jun 2015. One day
prior to Pentagon Pride where she would be first
female Soldier to wear an Infantry uniform.

 

Monika: Was there any difference in how people from different generations responded to your transition?

Sheri: Yes, younger individuals have been exposed to diversity from an earlier age and tend to have fewer issues with transgender people. I am very grateful my two children are fully supportive and love me for who I am; my three grandchildren are the same. While all losses have been difficult, the last dozen years of my life, since transitioning, have been the happiest by far. Living authentically has brought me peace I never thought possible.
Monika: In recent years, we’ve seen a growing number of transgender women stepping into the spotlight, as models, artists, writers, entertainers, and leaders in politics, science, and business. Laverne Cox famously declared, “Trans is beautiful,” and her words have resonated with many. Do you believe this visibility signals a real cultural shift, or are we still in the early stages of broader acceptance?

Sheri: Change is happening, more so in some places than others. This is due to transgender individuals being more willing to be visible and tell their stories. Face-to-face communication is critical; you cannot hate someone whose story you know.

Monika: Despite some progress, violence against transgender individuals, particularly women of color, remains a heartbreaking reality. Why do you think this kind of hatred persists?

Sheri: Here in the U.S. we just experienced the 13th murder of a transgender individual this year, almost all women of color. Society’s refusal to accept the evidence that being transgender is a medical condition hampers our efforts. Cultural acceptance always lags formal recognition, and the transgender issue is no different.

Monika: Within the LGBTQ community, do you feel the “T” receives the attention and advocacy it deserves, or is it still overshadowed by the broader movement?

Sheri: There is much more cooperation in the U.S. between national groups and the trans community. As an example, the Human Rights Campaign has now taken up the cause of transgender rights. Their national press secretary is a young trans woman, Sarah McBride.

Monika: How do you feel about the way transgender people are portrayed in mainstream media, whether in film, literature, or journalism?

Sheri: While I am grateful for the many film portrayals of transgender individuals because they help us get the public’s eye, I am more grateful for authentic individuals who have the fortitude to tell their stories on smaller stages. I also appreciate talented writers like Jennifer Boylan, who tell their stories via print media, and researchers like Brynn Tannehill, who publish some fantastic, realistic data to support transgender individuals.

Monika: Do you believe transgender women can one day rise to the highest levels of political leadership? Could we even see a transgender president or first lady?

Sheri: Yes, certainly. Our gender is not an inhibiting factor, but a force multiplier. The aforementioned Sarah McBride will be an elected official at the national level before long. She is 26 and was the first trans individual to speak at a national party convention in August 2016. A transgender candidate for Virginia representative just won her primary by an overwhelming margin and now faces a Republican incumbent this fall. 

Monika: Some say that just as birth control gave cisgender women greater freedom, cosmetic surgery has helped liberate transgender women from the anxiety of “passing.” Do you think this is true?

Sheri: Most people in the U.S. remain prisoners of passing because cosmetic surgery is not covered by insurance. Although reassignment surgeries are covered by most of the Fortune 500 companies, few states mandate gender-related health coverage. I was fortunate to be able to afford all surgeries as out-of-pocket expenses; I am one of the privileged. Most are not.

 

Keynote speaker at Fair Wisconsin's inaugural
Veteran's Day Luncheon. Madison, WI; 10 Nov 2016.

 

Monika: Many transgender women write memoirs to share their stories and inspire others. Have you ever considered doing the same?

Sheri: I have been asked many times, but there are books already out there. Don’t know what I need to add to existing references. We’ll see.

Monika: And finally, what role has love played in your journey? Has it been a source of comfort, or a challenge?

Sheri: I was married multiple times, but my marriages were doomed from the start. It is extremely difficult to be in a relationship when you are not authentic. Now that I am authentic, I find very limited opportunities. I am lesbian, and the two dating conversations I’ve had in the past four years have both ended when I inform the interested party of my past. I believe it’s important to be honest from the start.

Monika: Are there any new passions or projects you're currently dedicating your time to?

Sheri: I spend most of my time volunteering for non-profits. I am the Vice-Chair of the Fair Wisconsin Education Fund and serve on the Board of Directors of the American Civil Liberties Union–Wisconsin. I have spoken coast to coast and will continue to help inform others. Fun activities include biking and golfing (5 handicap).

Monika: What advice would you give to transgender girls who are currently struggling with gender dysphoria?

Sheri: Transitioning is the most difficult thing I did in my life. It is very complex; I had to weigh benefits against consequences and choose the most appropriate time to be authentic. I know once I got started, I wanted to be at the endpoint the day after I started. That’s not realistic. Have a strategic plan that addresses short-, medium-, and long-term objectives. You must be willing to lose everything you have and be strong enough to survive.

Monika: A friend of mine, Gina Grahame, once said we shouldn't limit our potential based on how we were born or by comparing ourselves to what other transgender people are doing. She said our dreams shouldn’t end on an operating table, that’s actually where they begin. Do you share that perspective?

Sheri: Surgery is not necessary to be authentic. I know many individuals who have been unable to physically transition and do so only socially. Our dreams begin when we start living authentically.

Monika: Sheri, thank you so much for sharing your story and wisdom with me!

All the photos: courtesy of Sheri Swokowski unless specified otherwise.

© 2017 - Monika Kowalska

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