Do I Retire?

I’m in my early 40s and I just resigned from the last place I was working.

A guaranteed income.

Stopped.

Why

Why did I do this?

Happiness - The first point of reference was my happiness. Around the workplace I was insular, not happy and focused on just getting the task done. I had no mental space for being present and enjoying the moment. Grumpy and dissatisfied really sums it up.

Remote Work - once I had experienced remote work, the freedom that it affords you - it was close to impossible to go back to driving down town to work again. It enraged me driving 40 minutes, one way. Looking at the lines of people doing the same thing, all at a standstill. Pointed in the same direction - down town. It enraged me that I was part of this system, this enslavement. Forced to be a sheep - no power to overstep it. I would drive 40 minutes one way to get out my laptop, open it and jump on a Teams call with the people sitting right next to me. This really pissed me off. An hour of my day burned commuting felt maddening.

Change - I’m also a creature that loves change. I get bored of the same routine.

Type of work - I believe that being in Software has become more and more competitive given all the YouTubers coaxing newcomers in, Immigrants and now AI. See this post on my thoughts. I don’t think it to be far-stretched to imagine that in a few years AI could replace Software Engineers in many areas.

Control - As I’m getting older in life, I find it really hard being told what to do. It could be partly down to being a contractor for so long. I’ve had a long stretch of having no one directly telling me what to do, so when it starts to happen - it angers me.

Life is too short to be miserable. I’d like to use this point in time to reflect and try to identify the direction I should be heading.

What

Now when I think of what I would like to be doing going forward, it gets a bit fuzzy.

I’m at a point where I could choose to retire, be semi-retired or carry on with full time work.

We need about 50k per year after tax to cover the delta on living costs.

• Retire - I could retire while my wife continues to work. This sounds shitty, but would afford me the ability to radically pivot into something that I would enjoy. I ran the numbers yesterday and yes this is a possibility. I could sell ~50k of assets per year and be retired. This would be selling assets as capital gains, so would be taxed favorably.

• Semi Retire - Do occasional contract work here and there for about $65k of employment income.

• Continue Working - Do something that fixes my previous pain points and keep on working full time.

Honestly, it is both reassuring and daunting having these two new options of Retirement and Semi Retirement. I’ve come to realize that I don’t like too many options and like constraints. For the last 10 years - I’ve asked my wife order my sushi for me as I hate too many choices 😆

If I was to retire I would look at doing something that I enjoyed and could grow, that was of my own choosing.

I think the main problem is there are things that you would like to do, however there may be no demand.

Ikigai

I saw this diagram years ago and remember thinking how useful and logical it was. I’m going to use the Ikigai diagram to compose What I love, What I am good at, What I can be paid for and What the World needs.

My loves have changed over the last 10 years so it is important to reflect upon that. Also what the world needs has changed in the last decade.

What jumps out at me is that I am currently roughly around that bottom area - Comfortable, but feeling of emptiness.

The missing segment is doing what you love.

I started off my career doing what I loved. At that point in time - 20 years ago it was full mid-zone of Ikigai. It was something that I loved, something the world needed, something you can be paid for (no one was doing it) and something I was good at.

Since then, it has fallen out of love with me, the world needs it less and the pay has dropped. So logically it is moving more to the left hand side.

I need to shift my diagram back to include that love aspect.

My Homework is now to fill out my own diagram using Figma. Being true with myself on What my loves are, What I am good at, What I can be paid for and What the world needs.

I’ll likely keep that result private, but it should be helpful in setting a North Star to guide me. If you don’t set this north star - you will focus too much on all the steps rather than the end goal. This can be overwhelming for your attention.

For example - all the people promoting Drop Shipping, Alt Coins, AI Startups - they are all competing for your attention. A true destination in mind will help you immediately cut out anything that isn’t a steppingstone in the path to YOUR ideal destination.

I’m not sure of the path, but will be doing some deep soul searching to find what makes me happiest and whatever will help my family.

Finding Comfort in Uncertainty

In the mean time, I find comfort in listening to Napoleon Hill’s guidance and getting out into Nature.

Of all places - the nature near me is my happiest place (I just need to get myself an adult sized dirt bike next).