I wanted to go skydiving since 2018. I had purchased a Groupon deal, but I had to cancel that plan due to a foot injury.
Recently, I signed up for a Launchpad with Careershifters to learn how to explore and identify alternate career paths. This is a workshop where we have different missions every week. The first week’s mission was to do a Roosevelt Action. A Roosevelt Action is a fun, exciting task that one has never done before.
While thinking about what to do, I suddenly remembered that I had never gone tandem skydiving. This would be the perfect Roosevelt Action for me. I checked with my wife, who agreed to let me do it!
I looked up skydiving options in the Bay Area. I also used ChatGPT for reviews and suggestions. Two showed up – Skydive Monterey Bay and Bay Area Skydiving. While I liked the idea of skydiving near the beach, I chose Bay Area Skydiving due to its proximity.

The day of, we drove to the location and had to wait over 2 hours for my turn. I met the instructor, Toshi. He helped me get into the jumpsuit and provided instructions on what to do at jump time and before landing.

The aircraft was small – there were a few solo jumpers, and two of us were doing our first tandem jumps. I had selected to jump from 15,000 feet (4.57 km).
While on the flight, Toshi strapped me to him. Once we reached our height, the solo jumpers went first. It was amazing to see them go out of the plane so easily.
Next was our turn – I realized I had no jitters and was looking forward to doing this. I don’t remember how we got off the plane.
The first thing that I experienced was the chill and the wind. It felt very cold against my face. I didn’t remember then, but we had jumped off the plane on our backs and flipped over!
Our photographer had jumped before us and started taking pictures and videos. Per Toshi’s instructions, I tried to scream during the free fall, spread my arms, and arch myself. At one point, our photographer reached out to me with his hand, and I tried to hold on to it for as long as possible.

The free fall speed is very fast, and the seconds go by quickly. It slowed down when Toshi opened the parachute, and we shot up. I could then enjoy the spectacular views from the sky. It still felt chilly, though. The recent deluge of rains made sure there was a lot of greenery. Having an unencumbered view of the ground from the heavens was breathtaking!
We made a perfect landing. The whole experience felt like a huge accomplishment. I had let go of my fears, embraced vulnerability, and enjoyed the moments.
I got a certificate at the end for doing this.
Would I want to do it again? Yes, definitely, and I would like to go higher – 18,000 feet (5.49 km) next time and over Monterey Bay!