28 vs 33 vs 38

As I turned 33, I look forward and backward 5 years and try to find patterns.

I’ve been listening to a lot of The Last Five Years again lately. (My lifelong most-listened-to album of any sort by a wide margin.) And in combination with this project it got me thinking – what I am going to be like in 5 years?

38-year-old me

By 38, I’m betting I will have gone through another MASSIVE life shift. My last, of course, being the move to Montreal and flip of my career from run-of-the-mill-programmer to whatever you wanna call the awesome crazy shit I get to do now.

10 years without a major life shift is a few years too many. I still have a lot of things to accomplish where I am and I’m not dissatisfied with any particular aspect of my current situation, but I can feel the desire for a change starting to brew inside. That’s interesting.

28-year-old me

At 28, I had no idea I was one year away from completely changing everything about myself. I had finally found a job I felt good in but it crumbled that year as the company ran out of money. Take a look at that guy:

Me in the messiest office in the world, but also one of the most fun
Me in the messiest office in the world, but also one of the most fun

Messy office, but nicer hair. This was my “peak hair” phase when I still had enough to style and actually knew how to style it. It was a very brief window.

At that time I wasn’t dating much (even with the sweet hair), I switched from driving a Mini to a Volvo, and I was still living in the tiny 340 sq.ft. apartment that I loved. I was unhappy some of the time but not all the time. And that was a huge upgrade actually.

Most interestingly: I was practicing for the life I didn’t know was coming.

In my spare time, I was experimenting with building web apps. After having worked on different parts of many much larger applications, my thought was: “can I keep one live myself?” Can I do all the 100s of little things that are required to keep an app with thousands of users running? Design it, build it, deploy it, market it, support the users, maintain the code and make money doing it?

It was a fun experiment that started years prior but the results came when I was 28. And it was a resounding yes. It was a good feeling. It led to even more success in my day job and eventually let me start a company which in turn led to where I am today.

Looking at that connection, what am I practicing right now?

33-year-old me

Me a few days shy of 33, doing my best hipster-murderer pose
Me a few days shy of 33, doing my best hipster-murderer pose

I’m practising … having a life outside of work, first of all. My view on what I want and need from a romantic relationship has shifted a lot in the last few years. And I’ve gone back to full-time sobriety, a relic from my early 20s, which brings up its own set of challenges when trying to develop the social aspect of a personal life.

I’ve actually been revisiting a lot of my old hobbies. Writing and reading are getting a big chunk of time now and this blog is a small part of that. I have a long history writing a lot of stuff. I took part in Naowrimo and the 3-day Novel Writing Competition for years. I spent my early 20s in Starbucks on a PowerBook, and then a MacBook, writing story after story. But when Montreal came along, I stopped. Between dating and a startup, there was zero time for anything else.

This blog is a starting point. Just a way to get the words flowing again. By 38? I see myself back where I was and able to write as good as I could when I could write good.

Maybe. A lot can change by then.

The second thing is health. Ok, you can’t really “practice” health. Or can you? I’m in much better shape physically and mentally than I was at 28, but I’m still not perfect. And meanwhile my body continues to degrade. These days I work hard to stabilize my mental state and keep fit physically. So whereas at 28 I wasn’t even trying, now it’s a concerted effort. At 38? Maybe it’ll be sustainable with much less effort. Add in more engrained healthy habits, and more asking for help when it’s needed (probably my biggest current weakness) and I could be a very healthy 38-year-old.

That sounds really good to me.

But of course you cannot predict the future. So whatever the changes, I expect I’ll look back at 33 and think, “that guy had no idea what was coming.”

38-year-old me

You know that feeling you get like you’re still a kid pretending to be an adult? I think we all feel it from time to time. You see yourself in the mirror or in a nice shirt and think, “shit, I look way more grown-up than I feel.” It doesn’t matter what you accomplish or what situations you are in, that feeling is always lurking underneath.

I don’t expect that feeling to go away. But I would like to have made peace with it. I would like, at 38, to be able to own a nice suit and not feel weird wearing it. At the same time, I would like to be able to wear sweatpants without feeling like I’m a lazy turd.

Confidence, I guess you’d call that.

Not that I don’t feel confident now, it’s just more like a car that doesn’t always start. Some mornings, “here we go!” but the next I could be digging through my metaphorical garage for a bucket of wrenches. (That’s right, I keep my wrenches in a bucket just like my pops.)

At 38, the feelings of what I want and who I am will be more cemented. It sounds weird saying that. But the data and the trend is there to back it up. At 28, I was just starting to understand what life was going to be for me. At 33, I’ve made a lot of choices that I’m happy with, and there are many fewer areas of my life which are still giant question marks.

But beyond all that. Beyond being a healthy, confident person engaged in both his professional and personal life, there is one thing I think is central to my next self-improvement phrase. You’re going to hear a lot about it in this blog probably – and that’s gratitude.

10-year-old me

Lately whenever I get upset, for whatever reason, I like to look around at where I am and think about what 10-year-old me would say if he could see it.

For context, at 10, I lived on a farm in a small town (named Dildo, thank you very much) with a population around 500. I felt out of place but didn’t know why. Every day was either actively unpleasant or boring. School was too easy, farm work was unpleasant, and I was not equipped socially to deal with those around me. I had regular bouts of pretty intense anxiety. I don’t have a single fond memory of being 10 that I can recall. (Sorry mom, you probably didn’t like reading that.)

Talking to that 10-year-old kid is a good exercise to stay grateful for where I am now.

“Look, you live in beautiful city. You have a very nice, clean, comfortable place to live. (Just look at the size of that TV!) Your fridge is full of all the foods you like – you won’t find whole dead animals in plastic bags in the freezer. You don’t feel trapped. You’re happy. Your life is full of people who are interesting, and different, and challenge you but also respect you. You worked hard to get there – and continue to work hard – but it has paid off. And girls. Yes, there are girls.”

33-year-old me

It’s my 33rd birthday today, in case you were wondering why I wrote this. And reading back through it, I don’t think I captured the essence of the feeling that spurred it. The feeling of what the 38-year old me becomes is a good motivator for all this new habit building I’m doing, but my explanation didn’t quite capture it.

That’s okay though. One thing I’m getting better at is accepting that nothing is perfect. Not me, nor anything I’ve done or will ever do.

This is also the first time I’ve shared a link to this blog. It’s time to put it out there. I hope to publish something (probably not normally this long) every Monday. You can sign up to get emails and hold me accountable.

Your own +/- 5

Enough about me.

Do yourself a favor. Take 5 mins today and turn off all the noise around you. Think about what you’ll be like five years out. And what you were like five years ago. Find the trends and project them forward. What’s changed? What have you still not changed that you always wanted to? Is it time to let that desire go or push harder? What’s your next step?

Then ignore the words and focus on the feelings. There’s something there I promise. Let it sit. Then let’s compare notes in 5 years and see how we did.

MOAR!!!

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