This year’s AfroTech Conference was an extra special one, filled with successful, inspiring leaders across a variety of industries, all eager to share a wealth of knowledge. One specific leader had a life story and advice that stood out: Sherida Y. Whindelton, a Lieutenant Colonel in the U.S. Army who dropped gems on carving out your career path, staying relevant and discovering where your side quests could lead.
When she joined the U.S. Army 24 years ago, Lt. Col. Whindleton was a college freshman whose main interest in joining was, admittedly, for funding to pay for her education. Today she is a Black woman leader who has parlayed her lifelong curiosity into a path in the technology space thanks to her Army career.
She has also, as she put it, “helped build the table” to offer others the opportunity to follow in her footsteps and grab a seat. “It makes me grateful for the foresight to recognize that it was a growing field and there was an opportunity to make the most impact. This is where the Army served as a launchpad to help me make a difference.”
We picked up more than a few pieces of wisdom from what she shared with us about her journey that could be keys to your own success in 2025:
1. Sometimes You Have To Build The Career Path You Need
Sometimes the path you envision for yourself requires you to pull together the pieces you need to travel along that route.
Over the past 25 years the world of technology has been rocked by evolutions in software, hardware, and the ways in which we use the devices and tools that power our lives. In order to navigate through those changes and maintain her role as a resource to her team, Lt. Col. Whindleton had to evolve as well. The U.S. Army has supported her growth with certifications such as CISSP, A+, Security+ and PMP. But in some instances, she had to ask for access to options that didn’t necessarily exist.
“If opportunities weren’t available, I advocated for myself to make them accessible,” she explained. “For example, while on active duty, I completed two master’s degrees, both fully funded. One was through the Tuition Assistance Program, and the other came through a program initially only available to civilians. I asked if the program could be opened up for military personnel, and after a conversation with the director, I became the first military person to join.”
2. Don’t Be Afraid To Test The Waters
If you only have an inkling of the direction in which you want to take your career, you may have to go on a few sidequests—like supporting a special project, seeking continuing education, or speaking to specialists in your fields of interest, for example—before you can map out your exact goals. And that’s perfectly fine.
Be open to testing the waters and exploring any interest you might have through taking classes, seeking mentorship and sometimes simply asking for what you want or need. That approach has allowed Lt. Col. Whindleton to propel herself into the many avenues and accomplishments she’s seen in her time in the Army.
“Remember, nothing beats a failure but a try,” she offers. “Step out on faith.” That sidequest, no matter how it presents, could lead to a connection or skillset that propels you into the next phase of your career.
3. Your Village Can Be The Key To Helping You Find Your Way
So what happens when you’ve explored a few things and you’re still not sure which direction to go in professionally? You may need to call in reinforcements: namely a mentor or trusted member of your personal and professional network.
“If you ever need to check the pulse on whether you’re headed in the right direction,” Lt. Col. Whindelton offers, “ask the people around you who want to see you win. I have had the support of mentors, colleagues, subordinates, and superiors as well as my family and friends which includes my sorority, Delta Sigma Theta, and the rest of my Divine Nine family.”
Professionally, Lt. Col Whindelton also benefited from the insights of leaders within the largest branch of the United States military, allowing her to get advice and direction that was based on the experiences of hundreds of thousands across a number of sectors and industries, while still operating by a very specific code.
4. As You Build Your Career Path, Remember That Others May Want To Follow
Following the path you are passionate about also illuminates a path for future generations. And regardless of what that path might look like, it puts you in position to effect change in the lives of others beyond your department, your company or even the vendors and colleagues you collaborate with. This, in turn, creates the opportunity for others to innovate even further on your goals and achievements.
In addition to paving the way for those who would follow directly in her footsteps and removing barriers that others had not even thought about prior to her, Lt. Col. Whindelton’s career has had a direct impact on countless others, even outside of the Army. Her leadership role has allowed her to award billion-dollar contracts, small business grants and more.
“My achievements are not just about me,” she said, “they’re a testament to what’s possible when you connect with the right people and seize opportunities.”
5. There Is An Answer To Every Question, And A Blessing In Every Lesson
“What I learned is, regardless of my experiences, there is an impact and there is a lesson to learn— good, bad, or indifferent. I can take something away from each one of them and add it to my toolkit whether it’s learning what to do or what not to do. And if it’s something I would not do as a leader, I think about what I would do differently to make the situation and decisions better.”
The end of the year and start of a new year are often periods of introspection for a lot of people. And unfortunately, many find themselves spending too much time and energy on what they deem to have been mistakes.
By adapting the mindset Lt. Col. Whindleton described to us, you open yourself to seeing every step you take as a step in the right direction… even when that means redirection.
6. Take Advantage Of The Resources Available To You
When trying to find your way or redefine your path, exposure can be one of the best tools at your disposal. For this reason, seeking a shift or a fresh path with a company that operates on a multitude of different levels can be the best cheat code imaginable.
The U.S. Army may be one of the best environments for professional self-discovery and growth. The number of potential career opportunities that exist across so many sectors makes it possible for anyone to learn skills that transfer to any imaginable career path in the public sector and to allow you to retire from the military with a number of professional accolades that rivals anyone else in your field. Additionally, the U.S. Army can lead you to a number of benefits and resources to support your education at any phase.
For those with tech aspirations, beginning your career as a Soldier in the Army can lead to exploring roles tied to everything from logistics to engineering to cyber security. And if you already have some experience on your hands, you can pursue a commission as an Army officer, leading to potential leadership opportunities.
If you’re interested in learning how the U.S. Army can help you craft the perfect career, visit GoArmy.com.
