What a Digital Cleanse taught me about my Teenage Years

Having to review over twenty-thousand emails gave me a newfound understanding of past interactions that I had never fully understood. By the end, I gained a new perspective on who I was during my own teenage years

I’ve been using Gmail since 2006, and haven’t really deleted any emails since they started offering “unlimited storage”. Back in 2018, I went on a spree of deleting everything in my “Promotions” tab, which got rid of about three-thousand spam emails accumulated over12 years (felt great!).

Step 1. Now that Gmail is limiting storage capacity, I’m reorganizing my inbox to only keep what is relevant. I started deleting emails by searching obvious keywords, such as “receipt” . This way I managed to delete all the fitness class confirmations, city updates, Groupon emails, newsletters, and other clutter.

Step 2. I started scanning my inbox from “Oldest”, and felt a lump of nostalgia in my stomach as I read through the emails from my teenage years, including ones from my year abroad in Finland back in 2007. There were conversations about logistics from when I was sailing competitively, email exchanges with both my Finnish host families from when I studied abroad at the age of seventeen, and exchanges with my father back home who was checking-in with me, and sending me things I needed via mail.

Step 3. Left with twenty-thousand emails, I separated them into four categories: Receipts, Vouchers, Notes, and Memories. This last category is for emails reminding me of happy times and love, that I’d want to keep forever, and read through again one day. With this labelling method, I can bulk delete everything labelled “receipts” on a yearly basis, delete gift cards and vouchers as I use them, and delete notifications once no longer relevant.

Why am I sharing this? Because by reading your own emails decades apart, you learn a ton about yourself, and review your life from a very different perspective. After all, you are a very different person now than you were as a teenager, but most people don’t have a good sense of how they changed. Would you be able to explain how you were different as a teenager compared to now? Below are my key learnings from the process.

Category A: Understanding my life through the lens of people who helped me become who I am

1.Old emails can hold the key to understanding and re-living how much your parents loved you, even when you were constantly clashing. My father always communicated best in writing, and I never saw that until my late twenties. Re-reading those old emails as an adult made me realize that every time he asked me if I needed something or sent me a package, he was expressing love and care. As an engineer working long days for Silicon Valley companies through the 90s and 2000s, he didn’t have time to spare. Now, as a working adult, I realize how much extra energy he had to pull out of thin air to make sure he stayed on top of my school and sports activities. I also see that I wouldn’t have come as far as I did in life without that help.

2. Youth Sports take a ton out of the parents. I think of all the kids flaunting their college sports results, and taking way too much credit themselves. Good job, you won, and it was partly because of the adults who helped you get there. There is a reason many collegiate athletes come from privileged backgrounds, especially in water sports such as rowing, sailing, and surfing, since they require way more logistics than ball sports. Coordinating a youth sports team is a ton of work, and all parents need to help with coordination and logistics for things to go smoothly. I never realized this until I read these emails as a working adult.

3. Cheers to all the AFS Intercultural Programs volunteers that worked hard to make it possible for me to succeed during my study abroad year, mastering a very difficult foreign language and earning top-grades in a foreign high-school. I recently signed up to become an AFS volunteer myself, because there are so many 16-year old kids like me that need help developing the ability to understand the world as they study abroad, waiting for an adult to help and guide them. So if you feel fortunate and are looking for a good way to give back, look no further than to the people who have helped you in your past.

Category B: The world of Broken Communication

4. As I age, I tend to only communicate in English. I used to love speaking foreign languages, and always sought occasions to do so. When I lived abroad I loved writing in Finnish, and wrote a lot of emails to my friends and family. I also took advanced Spanish in Finnish school, and loved it. I would switch between conversations in 3–4 languages within the same day, and it felt satisfying.

Now I realize that I was trading breadth with depth. When I moved to the US and started focusing on one language, it helped me acquire a depth of communication that I never had before. In fact, when I speak any other language now I feel incapable of fully expressing complex thoughts, and it’s uncomfortable. This lesson is unique, because it only applies to kids with multi-cultural backgrounds.

5. We need to be more tolerant with teens as they experiment with communication. The way I wrote emails as a teenager was really embarrassing. Really embarrassing: shortening words in ways that didn’t make sense and warping grammar such as in: “OMG I miss yaaaaaa!” I made loud animal noises when messing around with my friends in school and thought it was funny.

Adults kept telling me I was ridiculous. And no, I didn’t see how ridiculous this was at the time. I could say the same about my Facebook posts by the way. Thinking back on how I felt, I recall a a feeling of never being fully able express the rollercoaster of emotions I was on. I remember feeling the need to say something extreme and different, scream, use words that didn’t exist, re-invent grammar, trying to be truly heard at all costs. So be kind to the teenagers in your life, they really don’t get it. When they will, many years from now, they’ll be embarrassed.

6. I sent out so many more emails than I thought when I was job-seeking and networking straight out of college. Had I tracked the work I was doing, I would have been proud, and that would have helped with morale while I was feeling lost and angry. I should start tracking more of the work I do at my current job, and any job in the future, as I think that would make me feel proud, and I’d have something at and feel better when things get tough.

7. I also received so many email inquiries from recruiters. People contacting me for jobs I had no interest or qualifications for, and it really made me realize how much these recruiting algorithms have gone nuts, and often make choices that make no business sense. Also, it seems to have gotten worse over the past decade. There has to be a better way to recruit candidates than that- no wonder we have over 10 million job openings in the US right now.

8. The most important learning of all: if I ever have a kid, I should find a way of communicating with them that they can review many years in the future- letters, emails, home videos. I like to think as time as circular, not linear, so even if they are not feeling my love and intentions in the moment, as long as they feel it at some point in their lives, even decades later, I will have communicated effectively.

Throughout this process, I thought about ways to automate it and save myself time, and then realized I would be doing the world a disservice. By the end of it, I became convinced that everyone should go this, at least once in their lifetime.

Thank you for reading. If you’d like to continue the conversation, you can find me on Twitter or LinkedIn.