When Orin Pickering attended the graduation of his eldest son Jacob Beebe from Air Force basic military training in 2015, he had no idea that his own life was about to reach a turning point.

Beebe took advantage of the occasion to challenge his father to enlist in the Air Force, according to a news story from the 325th Fighter Wing at Tyndall Air Force Base, Florida.

Pickering was 37 years old and weighed 240 pounds at the time, so he thought he had no chance to join the Air Force – at least, at first. But then he started looking into what he would need to do to enlist.

“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, who is now an Air Force staff sergeant assigned to 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.”

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Pickering realized that in order to follow his son into the Air Force, he needed to lose weight – a lot of it. Time was also of the essence because he would eventually need a waiver for his age to enlist.

Orin Pickering
U.S. Air Force Staff Sgt. Orin Pickering, 325th Maintenance Squadron low observable structural maintenance craftsman, poses in front of an F-22 Raptor at Tyndall Air Force Base, Florida, Nov. 21, 2023. Pickering dropped 80 pounds to make weight and enlisted at the age of 39 years and five months, one month shy of requiring a waiver, after being challenged by his son. (Staff Sgt. Cheyenne Lewis-Roberts/U.S. Air Force)

Encouraged by his sons, Pickering started exercising and shed 40 pounds. Then he reached out to an Air Force recruiter, who told him he still had a ways to go. The recruiter told him that he could weigh no more than 170 pounds to join the Air Force and advised him to try to slim down to 160 pounds to be safe.

“Watching my dad get ready to enlist was crazy,” said Pickering’s youngest son, Dylan. “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.”

Pickering made it just under the wire. He reached his weight goal at 39 years and five months old – just one month before he would have needed a waiver to enlist in the Air Force at the time. Earlier this year, the Air Force increased the maximum age for new recruits to 42 after the service missed its Fiscal Year 2023 recruiting goal by nearly 2,700 airmen.

It turned out Pickering was not the only member of his family who was about to get a new set of dress blues. On the day that Pickering left for basic military training, his son Dylan swore into the Air Force Delayed Entry Program.

After becoming an airman, Pickering attended Dylan’s graduation along with Beebe.

“The experience was surreal,” Beebe said of his brother’s graduation from basic military training.  “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.”

All three men are currently Air Force staff sergeants, and they enjoy a friendly competition about which one of them can score higher on physical fitness tests, earn the most ribbons, and advance the fastest.

“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,” Pickering said. “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.”

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