What Teaching Seniors to Use iPads Taught Me About Life
It became more than a side-hustle to get me through college

Last week my mom dug up one of my old business cards from a business I started in high school and got me through college. It was called “Smart Fingertips” and I taught the elderly how to use iPads and iPhones. Be sure to read to the end for some last words of wisdom from one of my students.
When I was studying at the University of Florida in 2014, I had a side hustle. I taught the elderly how to use their iPads, iPhones, and computers. It started because since high school I’d been volunteering once a week at the local senior recreation center teaching technology classes to groups of 10-40 people in a classroom. It’s no easy task explaining to someone what “cloud storage” is or that their photos live in the cloud or that all their music they ever want to listen to is on their phone. Remember all of this was relatively new back then.
Often after class, people would ask if they could hire me to come to their house and help them learn to FaceTime their grandkids, type the book they’ve always dreamed about writing, or how to email their friends. They paid me well and it was something I enjoyed.
Over time, I realized they didn’t just want to learn technology to stay connected with their families; they wanted the company and friendship that I could provide them at home. Often, after our lesson, they’d offer me cookies and lemonade, and we would just have conversations.
At one point, I had about six clients at once. I’d go to their house and teach them how to check email, then rush off to my university class. After class, I’d go to another client's visit and show them how to text and send photos to their families.
I always felt strange charging them because I knew they were really just lonely. For me it was like having adopted grandparents because my own lived in a different country far away. In fact, I’d been teaching my own grandparents how to use their iPad for years just so we could talk more often since we only saw each other once every few years.
For my clients I was the once-a-week visitor they could count on. I was their friend. I would do it for free, but they still paid me $25 an hour plus tips sometimes. As a broke college kid, that felt huge (consider this is also in mid 2000’s prices). Especially because I knew my friends working at bars and coffee shops made less than half of that per hour. It felt like I had discovered some secret.
For me it was combining my interest in technology with ability to connect with people. Not only was it something I enjoyed, it was something I could see that was rewarding for people. It was a service that was more about patience, listening, and conversation, than actual technological knowledge of the newest devices. A lot of them had newer iPhones than me which required me to stay on top of the latest innovations.
Beyond that, not only were they able to connect with relatives who lived far away, but they gained access to the world. Showing them the magic of GoogleEarth to walk the streets of countries they never got to visit in their lifetime. Introducing them to documentaries on Youtube of topics they were interested in. Games to keep their brains active. They felt more empowered and independent.
In all, I volunteered at the senior recreation center every week for about 6 years. The one-on-one lessons business lasted for about 4 years. I wish I had kept a list of all the people I taught. Because each person taught me something different.
Like the woman Rosemarie who was determined to write a children's book at the age of 85. Or the German lady who was independent at 92 years old and still sharp and wanted me to help her with her New York Times app. My friend Sam who also volunteered to teach at the senior center, and we tag-teamed the classes. He was always generous, dedicating his time to his peers and to me. He and I bonded over our admiration of Apple and became good friends. To this day we still exchange emails.
As I got busier with school and life, I went off to work in New York and then to spend my summers in Austin. I’d go visit Colombia and take trips to California. But once the semester started again, I’d always come back to them with stories of my travels. They loved it.
In fact, while I was living in New York City in 2017, one of my iPad clients came all the way from Florida to visit me. Rosemarie was around 82 years old at the time and had lived in New York in her youth. So upon hearing of my adventure working in the Big Apple, she didn’t hesitate to get on a flight in December. We met up at the Metropolitan Opera House on the corner of Broadway and Columbus. She had hailed a taxi by herself and when we both arrived it was snowing heavily. We saw Mozart and the Magic Flute at the MET then got dinner at a fancy restaurant of her choosing. She expressed how grateful she was for me not just helping her with her iPad, but her children’s book, and that because of me she found an excuse to visit New York again for the first time in 40 years and that it was probably her last time in the city.
It all ended in 2018. I graduated University and had a life waiting for me in Austin, Texas. I left Gainesville for good and haven’t returned since. The saddest part for me was leaving all of those elderly wise client friends. It was a painful goodbye because I knew it was likely I’d never see them again. It was goodbye.
During my time in college I think I had more friends over the age of 70 than people my own age. I was usually surrounded by wise people who talked to me about their past and helped me gain perspective on my life. I wish I would have written down more of those things they taught me. Because I think they taught me a lot more about life than what I taught them.
Among the things we can learn from them are:
It’s NEVER EVER too late in life to learn something new. Stay curious.
Never too late to chase a dream, no matter if it sounds ridiculous.
That it’s always worth keeping in touch with the people you love.
The importance of friendships especially as we grow older.
How crucial it is to keep our brains active and keep as many hobbies alive.
Have fun and be light hearted. Not everything has to be so serious.
Do as many things in life we care about as we can (take the trip, write the book, get the scuba license, sky dive, spend time with loved ones, explore, do what makes your heart sing). Because even retirement doesn’t guarantee we will have the circumstances or health to do them.
Be generous not just with our time but with our stories, knowledge, and wisdom.
The best gift we can give someone, is our time.
The other day I was looking through some documents and found a paper note that one of my clients, Jean, had written me back in 2018. I don’t recall the details but it was likely a goodbye note from my last visit with her before leaving Gainesville:
“Go out and have an adventure. Live your story. You are young and free. You aren’t strapped down by a mortgage, house, kids, or spouse. Just take a leap and go out and have an adventure. This is the best time in your life. Just go out and do it.” —Jean L.
Jean was probably in her late 80’s back then and I was 22. Which means she’d be close to 100 now while I’m 29. I wonder if she’s still alive. But her words certainly are. I’d like to think I’m trying my hardest to make her proud and follow her advice. It doesn’t mean we can’t pursue adventures if we own a house or are married. I think she means if we have the opportunity to take a chance on ourselves, that we take it. Just go out and try. Live your story.
Such a heartwarming story! Reminds me of Staffan and Ammar befriending Dorothy actually 😁And always amazing how creativity and entrepreneurial thinking can open up unexpected perspectives. Kudos - as always a great read 👌
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