Planning the Next 20 Years

I’ve been watching a lot of Andrew Kirby recently. This kid is less than half my age, but has twice the wisdom!

Recently, he talked about how you can look at your past behavior to plan a strategy for the future, and included a quote about a boat needing to know which port it’s heading to, or it’ll get lost.

Photo by Ivan Ragozin on Unsplash

I’m in my late-forties, which seems like a good time to reflect on the past and consider what I’ve done – and which of that has been most rewarding. Hopefully that can help me decide what to focus on for the next two decades.

Family & work

Wow. When I think about it, twenty years is a long time and so much has happened – getting married, having a kid, buying a house and starting my own English school. Interestingly, I did most of that in the first ten years, and there’s been nothing anywhere near as significant since then.

Is there anything in that period which I’d like to repeat in the next twenty years? Hahaha, I can’t say there is. I’ve no desire to expand my family nor English school! If anything, keeping the school going is a big enough challenge.

Health & Fitness

In the last ten years I got into weight training, running, cycling, swimming and hiking. I couldn’t do any of that at the same level again, but I did enjoy the trail running community I was a part of. I contributed a lot to it through the Kakamigahara Trail Run Project, but I feel that chapter is closed now.

I could volunteer myself at local sporting events. I might make some new friends and improve my Japanese. But I don’t really see how that would serve my life purpose, which is…. I don’t know yet! That’s what I’m trying to figure out.

Health-wise, yoga is something that I really enjoy, but at my age and flexibility there’s a limit on how far I can take that.

Hobbies & Projects

It’s only natural that our hobbies are the things that satisfy us the most, otherwise we wouldn’t do them! In my case, I’ve tried a few things over the last 20 years:

I had a good run making websites. I even led an open-source web development project. That was fun.

I had less success with learning Japanese and Chinese, and my attempts to learn the recorder and guitar were short-lived. More recently, I’ve been building an Eiken website for English language students, but my interest is waning.

Surprisingly, the one thing I’m most proud of – a video game that I made and published – turned out be the biggest waste of time ever from a financial standpoint. It sold over 2,500 copies and got rave reviews, but barely covered the cost of developing it.

In Pursuit of Happiness

It’s clear from the above that I’m too old, not interested, or not skilled enough to continue anything from my past into the future. But hang on a minute. Let’s think…

I suppose there are two parts to this.

  1. What is the end goal?
  2. How can I enjoy getting there?

Deciding a Destination

At my age, I have to sail my ship into a comfortable port. I dream about living even farther into the countryside, but being a short distance from food and healthcare has to be considered. Realistically, the sensible option is to stay where I am, though my house might need a complete rebuild if it’s to last another 30~40 years.

Okay, that’s decided, then. My end goal is to rebuild my current house so that it’s suitable for my elderly needs.

A Means of Transportation

Clearly I need to steer my English school so that it carries me to retirement. But this ship could well sink, so I’ll need to attach a lifeboat – a second stream of income that’s enjoyable to earn. Haha, enjoyable to earn. Is such a thing possible?

I could delve deeper into a hobby and pick one particular aspect that I both enjoy and would like to become an expert in. For example, creating educational material for a video game engine. That would combine my teaching experience with my interest in games and programming. It would also serve my desire to provide something of value. It’s satisfying to help people, you know?


Yes. The logic makes sense. Find a niche that you enjoy, become an expert in it, then monetize it. You might say, “Yeah, but there’s too much competition these days”, and you’d be right, so you need to market yourself so that you become the brand. You’ll be unique in your niche.

After all, I don’t follow Andrew Kirby just for his youthful wisdom. He doesn’t say anything that hasn’t been said, written and documented a thousand times over. It’s how he presents that information which I find appealing.

Right, so my plan for the next 20 years is to charm people into being my fans while providing useful content that I enjoy making.

If you like, you can find me on Twitter at @nick_ramsay. I'd love to hear from you!

2 thoughts on “Planning the Next 20 Years

  1. I think its really cool what you did with that video game. OK so maybe it just broke even, so what? It’s still a massive accomplishment and 2500 in sales is great! Maybe you could try making another game and maybe you’ll have even more success.

    Whatever you do, just do what gives you joy and I think the rest will come. All of the things you’ve tried so far have been worthwhile, even when you didn’t stay with them.. They were still experiences and brought you to something else. Keep going!

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