Ann’s first flight lesson was Aug. 29, 1960, in an Aeronca Champ from Young Field, west of Ann Arbor, Michigan.
Not seven years later, on June 9, 1967, Ann and crew took off from Oakland, California, in a Lockheed Electra 10A to honor Amelia Earhart’s round-the-world attempt 30 years prior. A flight that concluded successfully on July 7.
But I’m getting ahead of myself.
The Ann in question is Ann Holtgren Pellegreno.
All pilots, regardless of accolades achieved, all start at lesson #1. And the path to becoming a pilot is often deeply personal and sprinkled with moments of happiness and success, as well as failure and fear.
As Ann learned to fly, she journaled about her lessons and experiences far beyond the small space in a logbook. In 1963 she typed those memories into a manuscript. For most of the next 50-plus years, she thought those pages had been lost forever.

On a fateful day in May 2020, the long-lost manuscript resurfaced. Today, it is a book titled, “The Sky and I. How I learned to fly… before I flew around the world six years later.”
Flying along with Ann as she struggles with learning to control the Champ was a walk down memory lane for me. It brought back many memories from my time learning to fly. And I suspect it will for you as well.
On Ann’s 10th lesson she finally felt in control of the plane.
“Suddenly, I realized that the plane was no longer leading me around the sky. Instead it was bending to my will. Left turn. Right turn. Watch that altimeter. Maintain the altitude.”
On Nov. 18, 1960, Ann soloed for the first time. As I consumed her description of those moments, flying alone for the first time, I could feel my heart beating faster.
Is it possible to forget your first time? I think not.
Flight instruction, thankfully, has progressed a great deal since 1960.
During a Jan. 20, 1961, lesson Ann’s instructor takes over during a landing and says, “You can’t let that seesawing start. Did I mention you should move the stick forward a bit when the wheels touch? That will keep the plane on the runway.”
Ann’s reply, “No. You never mentioned that.”
An idea followed.
“This may sound silly, but I think I’m afraid of the propeller hitting the ground,” says Ann to her instructor. “I’ll turn the engine off. Would you raise the tail until the prop touches the ground. Then I’ll know how far the plane can be nosed down before the prop touches.”
I recall a similar lesson from my primary instructor using our J-3 Cub more than three decades ago.
On March 25, 1961, Ann learned a lesson applicable to today. As Ann flew a solo cross-country she became caught up in the “business” of flying.
“One of these times I was startled to see another small plane about a mile away and slightly below me. Perhaps more time should be spent looking out the window instead of at charts and instruments.”
That should sound familiar.
Ann and her husband, Don, learned to fly at the same time. Many years later, after decades of flying many miles together, meeting all sorts of wonderful people, and restoring airplanes, Don asked Ann, “What would our lives have been like without aviation?” They both answered, “BORING.”
Whether you are a many decades pilot or just cracking the FAR/AIM for the first time, The Sky and I has something for you. For the former, you will enjoy a chat with Ann as you share with each other your stories from learning to fly. For the latter, this book should offer hope and inspiration. Oftentimes flying doesn’t come naturally, until it does. Keep at it, you can do it.
The Sky and I is 198 pages, includes 40 illustrations, and is priced at $25 at SpecialBooks.com.
Yes, Ben, it is possible to forget your initial solo when a more significant emotional solo event kicks out of your memory.
While learning to fly my senior year at Norwich Univ, I was scheduled to fly one day solo. The snow was falling lightly, but at a steady rate. I called over to my instructor at Edward Knapp Airport to cancel my flight. He stated that is really wasn’t snowing on the other side of the mountain from school. So, I grabbed my flying gear and drove to the airport. It was snowing there pretty much like on campus. Here’s where ignorance is bliss kicks in. I asked if I could really fly in this snow fall and he stated sure. I then asked what I should do if I lose sight of the airport. His response, “Just circle around, it will reappear.” Out the door I went, pre-flighted the C150 and I took off. First pattern was fine and rolling out on downwind for my second pattern, sure enough the airport was gone. The snowfall was thicker. I must have done a decent job circling around since a few minutes later it reappeared. Now my evolving ADM sprouted and I made the next landing a full stop. My instructor wanted me to go back out, but I knew I was lucky to be able to tell him, NO.
So yes, it is possible to not remember your initial solo and as hard as I try, it is gone from the old memory from a long time ago.
Thank you, Ben, for publishing this and for publishing the link to Special Books. My love affair from afar with the Ann Pellegreno story began in the 1980s when I discovered her account of the ‘round the world trip (World Flight).
There have been many articles written about Ann and her remarkable career and an internet search reveals films and articles galore. Her story is just the kind of reminder that many aspiring pilots need to go forward with their training.
I’ve bought my copy of “The Sky and I” to give to a former Young Eagle who is just beginning her journey into the air.
THANK YOU! Ann deserves so much gratitude for writing this book! Know what else it is great for? It’s great for getting back in the air in one’s Luscombe after a hiatus. Why, especially? Because Ann writes in the language of old school tailwheel basics that we can all recall learning. Me AND my old Luscombe can read, hear and interpret the language – we both can feel it and it is refreshing. What a gift!
..and Thank you, Ben, for sharing that wonderful book!