Dear me: A letter to past and future self

Dear Chester,
Your birthday has recently passed, and a significant one some might say. A real milestone for many people! I think it’s a great time to reflect a bit on the past and look into the future a little. What are your fondest memories? What do you look forward to over the next few years? Well, let’s have a chat about that, shall we?

It’s pretty safe to say that 10 years ago, nowhere in your mind did you ever think you would be living in Australia. But here you are. It’s a little strange if you think back, isn’t it? Think back to when you were in your senior years of high school. You had absolutely no intention of leaving Vancouver to study. You were perfectly content to go to your local university without exploring other options. Remember how your first girlfriend always dreamed of studying out of town? But not you. You liked the safe and familiar haven that you knew. When your relationship ended with her, you reflected a lot on who you wanted to be in the future. You weren’t happy with how closed your life was. This became a very important juncture in your life.

A lot of people who know you today know you as someone who likes adventures, enjoys taking risks, trying new things and always having a case of FOMO. They would be a bit surprised to know how conservative you were 10 years ago.

On the good side of things, you’re definitely more open than you were in the past. You aren’t as rigid as you once were and you generally do a good job of embracing uncertainty and change. Some old ways do show up here and there, but you try not to let that stand in the way of the bigger picture.

I know that there are a few memories that are particularly important to you over the past 10 years. Most of them were life changing even if you didn’t realize them at the time. Among them include your first relationship, your experiences on exchange, your part-time business, and some of your travels in Asia. They all represent different turning points in your life. I think you know that it’s important to never forget where you came from, but at the same time, to not focus too much on the past. Though, I think you can still get better at this, since you can still let emotions get the better of you. At times that can make you honour past experiences a little too much. That being said, you’re conscious of it so I think you continually try to find the right balance.

In terms of relationships, well… if we’re looking for contrasting flips to match your shift from conservative to risk taker, it would be your change from “relationship king” to “don’t even know how to be in a relationship” status. Yep, I’m saying you suck in this area now.

In some ways, I think you have become too accustomed to being independent. It’s a tough thing to let someone into your life and it shows. You know yourself very well and have high emotional intelligence but you’re not the person who finds it naturally easy to be with someone else anymore. Do you remember when you were perfectly happy to be the follower while backpacking with Michelle in Australia? You’re not the same type of traveler or person anymore. You tend to dislike giving up control now. You relish being in charge much more than you think. It’s not a bad thing necessarily, since it can help you take control in other areas of your life, but when it comes to relationships, it definitely has a potential negative effect. I hope you stay aware of that and it doesn’t stop you from finding a long-term relationship. Nonetheless, I think you are at least a few years away from settling down. I think you’re simply having too much fun roaming the world while finding your place.

Growing a bit older, I know you appreciate your family a lot more now than past you. You’re not the best at expressing it but I hope you still make an effort, so they always know you’re thinking of them and how much you love them. Without their support, you would not have the opportunities you do now.

In terms of career stuff, I am proud of you for persisting in your journey. It’s definitely not easy and things don’t always come as naturally to you, but you didn’t give up and I think you learned a bit more about yourself and your motivations over the last two years. It will be interesting to see how the next few years develops for you. Pun intended. I think it’s pretty unlikely you will still be a pure developer in another 10 years time, but I could see you evolving into leadership type roles or spinning off ventures from side projects or collaborative work. I guess only time will tell.

For short-term goals, I would like to see you return to stronger goal setting habits for the rest of the year. I know the last 8 months have been a big roller coaster, but you reached where you said you wanted to go (from six months ago), so let’s get serious on those short and longer term goals now. I know you are looking forward to the new challenges of being in another city, a new company and also establishing your name in the dev community. It’s an exciting time!

You will likely find lots of interesting little adventures and stories over the next year, so soak in the experience, work hard, and stay humble. And if you ever have doubts, you have a wonderful family that loves and supports you.

So don’t worry, you’ll do alright.

Present day Chester


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