Every week, thousands of family members and friends show up to watch their loved ones graduate U.S. Air Force Basic Military Training. In July 2015, a proud father, along with his wife and youngest son, went to Joint Base San Antonio-Lackland, Texas, to watch his eldest son graduate from BMT.
But this graduation was special to this family.
After reuniting with his son, Orin Pickering and his family toured their son’s dormitory. While there, newly minted Airman Basic Jacob Beebe, Orin Pickering’s eldest son, took the opportunity to challenge his dad to enlist in the Air Force himself. Orin Pickering was 37 years old at the time and 240 pounds, so his initial thought to the challenge was, ‘Yeah right.’
“The military was something he always felt like he wanted to do but was never up to the physical standards expected by the military, and [at the time] he thought he was too old as well,” said Beebe, now a staff sergeant and noncommissioned officer in charge of water and fuel systems maintenance with the 9th Civil Engineer Squadron at Beale Air Force Base, California. “I reminded him that as a young man, I was very unmotivated and if I can do it, he can do it.”
After returning home, Orin Pickering put a lot of thought into what his son asked him. He started researching enlistment requirements and thought to himself, ‘No way.’ After exercising and losing 40 pounds, his sons assured him he could make it. Hearing this, Orin Pickering decided to reach out to a recruiter. Weighing in at 200 pounds, his journey was far from over. The recruiter informed him the cut off weight was 170 but instructed him to aim for 160 pounds to be safe.
“Watching my dad get ready to enlist was crazy,” said Dylan Pickering, Orin’s Pickering’s youngest son. “He worked out every day basically sweating buckets just to lose the 80 pounds he needed to join, and not to mention keeping his sugar down. He did all of this while still working and trying to prepare me for life as an adult because I was going to graduate from high school soon.”
At 39 years and five months old, Orin Pickering succeeded in reaching his weight goal, a mere one month before requiring an age waiver. He knew it was time to go.
“The day I shipped out was the day my youngest swore into the Air Force Delayed Entry Program,” said Orin Pickering, now a staff sergeant and low observable structural maintenance craftsman with the 325th Maintenance Squadron. “We actually swore in together and that was a special moment for me.”
Six months later, Dylan Pickering continued the family legacy and shipped out for basic training.
“Both my father and I made it to my brother’s [graduation],” added Beebe. “The experience was surreal. Perhaps the proudest family moment we all share. All three of us stood together, in uniform, on the parade grounds. I still to this day have the picture of me and my dad ‘tapping out’ my brother from formation saved as my phone’s lock screen.”
Fast forward to 2023, now all three men are active duty staff sergeants and constantly use their Air Force careers as friendly competition between them. Who was an honor graduate? Who made rank first? Who will be the first to make technical sergeant?
“It's great to still be able to compete with my brother and dad, but instead of trying to beat them in sports and games, I try to do it with fitness scores, rank or even ribbons,” said Staff Sgt. Dylan Pickering, 441st Vehicle Support Chain Operations Squadron, Joint Base Langley-Eustis, action officer fuel and licensing. “But in the end its all love.”
The family as a whole is proud of the choice they made and can’t wait to see what future opportunities the Air Force provides.
“Having been afforded this opportunity to serve not only in the same branch as my two sons, but also to be able to serve at the same time with them has been extremely gratifying and the most rewarding experience,” concluded Orin Pickering. “I couldn’t be more proud of the boys we’ve raised. This journey has truly shown me that, when you have the right motivation and work ethic, you can achieve anything if you put in the effort.”