Reflecting on my thirties: The path ahead and looking to the future.

Having just turned 40 I have been spending considerable time reflecting on my thirties; what I managed to achieve, how lucky I am for the way things have worked out, as well as how my goal setting, planning and execution has helped.

You can read about what I’ve happened to achieve in during the last ten years in my post Reflecting on my thirties: Many great experiences!.

Following on from that post, I want to take the time setting some goals that I want to achieve over the next ten years.

The next ten years I’m going to continue to be highly focused on building my career and will be a lot more family oriented. While Tracy and I want to keep a good amount of travelling happening, with three kids, this might prove difficult.

For my personal goals, the following is what I’m looking to achieve.


I am already quite an organized person. I love Bankers Boxes and they help keep everything sorted. It is rare for me to misplace anything, and I am always within about 10 seconds of all of the family’s passports, birth certificates, social security cards, university manuscripts, as well as all other important, and not so important, documents.

I want to get even more organized in the coming year or two. One of the main things that I have almost completed is a system which allows me to automatically log into many sites (bank balances, investment, health records, flight prices, foreign exchange rates etc) and collect and store that information securely on my own servers. Automating this ‘digital leg work’ will definitely help improve visibility and provide a much better way for me to ‘keep on top’ of things.

The data that is collected is then accessible by an analytics platform and I’m currently implementing called Grafana which allows me to build dashboards and notification systems in cases where certain conditions are met such as a credit card approaching max for example.

This database also allows for me to consolidate information such as all of our expenses across many different accounts into a combined single ledger view. I feel this in itself is a valuable enough reason to do this work. For those who do software metrics, I’m basically building my own personal ‘Prometheus for life’ metrics server.

I feel by collecting this information and being able to better collate and view it over time, I’ll be able to stay on top of things so much easier.

The plan is to show these different dashboards on a TV in the kitchen so it will act as a morning ‘briefing’ in many ways.

I’m also starting to look at the prospect of hiring a virtual assistant to help both Tracy and I with the more time consuming tasks that don’t require our actual involvement. At the moment with COVID, we’re struggling having all three kids at home and creating a proper work environment, so an example tasks would be getting this VA to find out what is open and what is not around the area as far as child care, getting prices and availability and chasing a position down for Jack once COVID has passed.


I want to instil the idea into our kids that even though they are American born, they are also Irish and Australian citizens. The kids each have 3 passports and once I get my US citizenship in about 18 months, as a family we’ll have 14 passports.

It would be great to live in Australia or Ireland for a few years. There is a traditional wisdom that kids require the ability to set down roots while they grow up, but I’m unsure of the reasoning behind this. When I’ve asked people in the past who agree with this position, the answer is typically rooted in two separate areas, the social impacts of moving and the difficulties of moving.

Insofar as the social aspects, both my father and father-in-law are immigrants, every single one of my 4 uncles are immigrants, and I am an immigrant. My family has a very strong history for being able to make the difficult choice to totally replant their lives based on a vision of creating a better life. I feel giving kids a few opportunities to experience this early on in their life will hopefully give them the ability to make this an option in future and see the world as their home, not just where they grew up. There are also the huge benefits of learning how to make good friends in new places and gaining an understanding of people from other cultures too, which I think for kids is just invaluable.

The social argument is also becoming less and less prevalent as we continue to live more and more of our lives connected on the internet. Relationships are continuing to become more location agnostic and for older kids who are at an age of communicating digitally, this allows them to continue these relationships in some fashion even if they are not physically present.

Moving is often difficult, especially internationally, and this can obviously be amplified for kids. The main point here is that in most cases when a family is moving, they are often under some form of obligation for the move, such as work requirements or financial factors. Being pushed into a move is going to introduce a lot of unknowns and stress into the process compared to a move which is done without an obligation.

Another reason for this stress I feel is often not the new place, but the leaving of the existing place where the family has settled. Saying goodbye to friends knowing that you’re going to start living life somewhere else is quite different than knowing that you’ll be back within a year.

Moving to Australia or Ireland may or may not happen, this is one of those goals which we need to wait and see if it would be beneficial on balance or not. The kids personalities and the little people that they start growing into will dictate if this would be a good option.

As far as more local travel, I’m still very much looking at the prospect of getting a caravan so that we can make spur-of-the-moment decisions to just go away and explore on the weekends. With three little kids, this is definitely, by far, the easiest form of travel and is arguably the cheapest. Both Tracy and I were fully remote workers for a number of years combined before COVID, and while I’m moving back to co-located work, if I ever do go back to fully remote, it means that we could literally take a few years travelling around the the entirety of the Americas before Jack starts school.

And there is the question of travelling to Australia so that my family can meet the kids. With three very young kids, getting on a plane at this point seems impossible. We’re working on getting an Au Pair who would be able to also travel to Australia and help us out on the flight, but currently Au Pairs have been banned from entering the country as a way of stimulating the economy. Another entry in the encyclopedia of ‘Acts that defy logic and reasoning from President Ineptitude to make American lives harder’. I’ll save my rhetoric on the simplemindedness of those single issue voters stanning the current president for another post… November can’t get here soon enough, anyhow…

Generally, travelling is going to be one of those things where we’ll need to experiment and see how things work. It will definitely be something that I’ll be seeking out and trying to continue over the next ten years though.

Pilot License

For the first 40 years of my life, I have always suffered with an almost physiological aversion to heights. This has been something that I’ve tried addressing in a number of different ways, but nothing has really stuck.

I can almost collapse in a heap in many situations involving heights, even when it is not me near the edge. Someone making jerking motions near the edge of a balcony or cliff, even when I’m many metres away from said precipice, often sets off some type of physical fight or flight response in my body that I have very little control over. It’s a weird type of sensation which you could perhaps describe as ‘physical anxiety’.

My plan for my forties is to start taking flying lessons as a way to address this. I previously had issues with flying during my twenties, especially with takeoffs, but this has subsided in recent years to the point where I look forward to all parts of a flights. I no longer have any problems with air travel and I feel that by ‘taking control’ in such a situation may further numb me to heights in other contexts.

Apart from this, obtaining a Private Pilot License will obviously open up an amazing number of future opportunities and experiences for my family and friends. The geography in the Western USA is just amazing and being able to explore it from the sky would be just unbelievable and breathtaking.

Having looked into it, I’ve found that the costs for flying lessons and hiring aircraft is actually lower than I’d expected which is great. It is still a very significant financial investment but one I feel is definitely worth it.


I absolutely admit I have always had a bad approach to eating and exercise, and I feel that in most cases for people like myself, this comes very much from the how you are bought up. By no means am I making excuses in any way, I just haven’t found the method in life that works for me.

Those who know me personally know that I’m not a lazy person when it comes to physical exercise and getting in and rolling up my sleeves when there is something to be done. Tracy has previously mentioned that the first time we moved she was quite shocked that I would be fine moving a 3 seater couch, large fridge or other large appliances, including everything else in the back of a van all by myself. I actually really enjoy making a go of a task, getting in and trying to get things done as quickly and efficiently as possible, I’m not the type to ‘finish things up tomorrow’.

I also like getting into a rhythm with exercise, and only in the last 18 months have run a number of half marathons on the weekends. The difficult thing with this is my love for what I do is stronger, and I find it difficult to pull myself away from my work. It’s not a case of avoiding exercise, it’s a case of being distracted most of the time.

At this point in my life I’ve realized that I need to add a social aspect to my exercise in order to keep me on track. It is a lot harder to break a commitment to other people because you’re caught up in your work compared to just making the excuse that you’ll go for your run in another hours time, eventually working past dinner time. The social aspect requires you to keep your word in a stronger way.

We’ve only recently moved to San Jose and the running opportunities around our local area aren’t great. Tracy and I previously use to do a lot of big hikes on our weekends but with three little kids now, this has become much more difficult.

So at the moment I’m looking at what group orientated opportunities might be available in our area once COVID has subsided. I actually enjoyed PT when I was in the Army so I’m even looking at the possibility of cross-fit or similar.

And this is not so much about my own health anymore but also the health of the kids and bringing them up in an environment where looking after your health is a very important thing.


During my forties I’m looking to become as skilled in investing as I became with software engineering in my thirties.

I already have decent experience with trend trading FOREX using tools such as MACD and Bollinger Bands and I have spent a lot of time building MT4 trading bots quite a number of years ago. I want to start getting back into the quantitative approach of investing but in a much more professional manner.

While I’m looking to continue to build my skills in software engineering which I believe I will have ample opportunity to do through work, I want to start getting to understand the path that leads to becoming a Quant. I’m looking to do this through also learning Python to a much higher standard and from what I’ve read so far, I also have a good starting knowledge in business financial accountancy and theory, data science and statistics and in general investing knowledge to build on top of.

Getting a Caravan (Or in US English ‘Travel Trailer’)

I miss owning a caravan, I miss it a lot. Even though it can be a hassle storing it when it is not in use, the benefits of being able to just leave for a multiple day holiday given only a few minutes notice is just amazing. We have a large driveway at our house in San Jose which would easily allow for a large caravan to be parked without getting in the way as well, so the storage issue is more about what the neighbors might think, not so much the logistics and costs.

Second hand caravans in the US are WAY cheaper than in Australia. You can pick up a good quality trailer complete with shower and toilet sometimes for under $10k, where the equivalent would be about $35k in Australia.

I believe this is due to a total cultural difference between the countries. Caravans in Australia are seen almost as a status symbol; you’ve made it if you can afford to keep one. In the US they are more often associated with a lower financial position; think the term ‘trailer trash’. I’m slowly influencing Tracy toward the more Australian view point…

In my opinion, the West Coast of the US offers some of the best road trip geography possible. With a caravan, we’d be able to take the entire family away for trips at a very short notice and could just explore around California. We definitely have the vehicle for it already as well, owning a 5.4L V8 Ford Explorer, so it wouldn’t be too much of a project getting everything set up. Just got to keep checking Craigslist…

Build a library

Buying books in the states 2nd hand via Amazon is fantastic. Books are quite expensive in Australia, and the online ‘after-market’ choices are pretty slim.

Amazon was built on books, and their service today is still fantastic for this. I’m continually picking up many books of very high interest for less than $10, and the quality is often great.

For me personally, there is still something about having a hard copy of a book. Digital copies are great, but absorbing information from a PDF I find much more difficult.

I do have an 80Gb+ library of thousands of IT books which I have indexed for searching. This allows me to search for topics much better than can be done online, and serves pretty much as a ‘first-stop’ in the process, as I will often buy a hard copy of a text when I find something that is useful.

Complete a Marathon

As mentioned earlier, I managed to run a few half-marathons for the first time just prior to hitting 40 but the opportunities for running where we’re living now are not great.

I do however want to run at least one marathon in the next few years. The most difficult part of achieving this goal is not so much gaining the motivation, but finding the time with three young kids.

When I started doing the half marathons, we only had our eldest son at the time. This was plausible even if it meant that Tracy would need to take the entire morning off to focus 100% on him. Now with three kids, this isn’t possible, so achieving this goal is going to take finding some solutions to be able to get the time.

Scuba diving

I did my Open Water Certification in Thailand off the Eastern Coast of Phuket around my mid thirties and loved every second of it, but I haven’t chased it as much as I should have since. This has mostly been on the account of being too busy doing other things.

Diving around the SF bay area supposedly isn’t that great from what I’ve read online. The best option appears to be getting down to Monterey Bay.

At the current time, it is a little over an hour drive from where we live to get to Monterey which means that, like doing a marathon, achieving this goal is more about getting a suitable situation set up so that I have the time.

Further education

I took a Graduate Certificate exit award from my Master of Data Science degree at the end of last year as studying was proving too much of a time expense.

If I can obtain RPL for certain remaining parts of the course, I should be able to complete the Masters degree within one year. The value of doing this, I’m not so sure of though.

Google does provide amazing support for further education and I still need to investigate the full breadth of what they have available as well.

In all honesty, the next ten years will likely be too busy with family for doing formal education, but I still have my eye on doing a PhD once I get to retirement age, if that’s still a thing in the next few decades…

Start a non-profit around enabling education

One thing that I’ve wanted to do for a while now is to set up a non-profit around enabling education and I need to investigate the process for this more for the US context. The idea is to follow the concept of giving 10% of your income to causes as described in the book great book ‘Richest Man in Babylon’.

The general idea I have is to create a non-profit who operates as a fund that invests only in certified B corps or those with a core commitment to socially responsibility.

The long term plan would be to build the fund over a decade or two, continually reinvesting gains and aim to have this company to a point where it has significant funds under management by my fifties. This fund can then be used for scholarships to help disadvantaged people gain better education.

I’m a firm believer that all of the world’s problems can be solved with education at some level and the core of my Digitally Enabled consultancy was an example of this.


I spent most of my twenties playing in bands, and while music is a very gratifying activity, it has a very small return otherwise for the time that you put into it. In saying this, the social aspects of playing in a band are great.

I’ve found that as I’ve become older, it appears to become harder to find people that you would like to spend time with. There are a number of reasons for why this is so, but in most cases I feel that it is due to your personal time becoming more scarce and of higher value, meaning that you become more risk adverse to unknown social situations.

If I’m going to spend the time doing the practice and gigs, I want to make music that anyone can get into. About ten years ago I came up with the idea of creating a band where you could play music in the lobby of a block of flats, and you’d get people come out to dance, groove or just ‘be a part of the music’ without getting noise complaints (although, things have changed a lot in the last ten years as far as people being happy that others are enjoying themselves).

If I am going to start playing in a band again, it’s definitely going to have to be a soul band.

I’ve realized that the type of music which is going to get the most people interested during a live set is definitely part of the soul genre. Apart from that, it’s definitely a lot of fun to perform as well.

Otherwise, I’m definitely open to the idea of going more classical and joining a brass band again (I have about 5 years of experience playing Tuba) or if possible, an orchestra.

Found a number of smaller niche businesses / products

In the 5 years preceding joining Google, I was working on Deckee which I co-founded five years ago. While I am no longer involved as a full time participant and only as an investor, Deckee is an ongoing concern and is continuing to grow strongly. I’ve previously written about Deckee in other posts, but suffice to say that I learnt a lot in this time and got the opportunity to learn so much more than I would have working a standard 9-5 job.

One of the really big lessons that I’ve learnt over the last 5 years meeting investors is that most of the people who are successful when starting companies often start off with smaller aspirations than you would expect. The fascination and fandom of the ‘startup industry’ has led to a lot of people to chase some pretty wild ideas and living in San Francisco, I’ve met a lot of people chasing these ideas hard.

Some times these ideas work out and are extremely financially rewarding, but in nearly every case, it ends up being a learning experience for those involved. Setting out to build a unicorn style business is a huge amount of work and in most cases, comes down to absolute dumb luck more than good decision making.

I truly believe that Deckee is chasing something that is possible and I feel it is on the right track to achieve that vision. Other ideas that I’ve had over the last 5 years don’t fit into that category at all though.

After building, I realized that only a small amount of work leveraging your skills to build something that is valuable to other businesses is a great strategy. Aiming for a 6 or 7 figure mark for an ‘exit’ is a much quicker build and way easier sell than trying to create something that eventually rings the NASDAQ opening bell.

While I likely won’t have the time, any side-projects that I look to take on in the next ten years will be focused on this concept of ‘stretch goals’. Achieving the desired outcome will be a stretch, but not impossible, and the path to success is based on long horizon planning and good decisions, not finding the luck you need.

Motor Bike License

I’ve been saying it for more than half my life now, but I’m still planning on getting my motorbike license. Now living in the Silicon Valley, this will cut down on commute times by a significant amount and make it much easier to park once we’re past COVID-19.

I’ve also talked about doing a cross country bike tour of the states for about 15 years now as well. At least this will be one step closer to this goal, even if it is something that I can’t do until the kids are older and self-sufficient!

Aquaponics and Vertical farming

I’ve been wanting to get into aquaponics for a long time now and with the recent rise in popularity and success of vertical framing, starting a bit of a hobby horse with these concepts at home is something I’m really interested in doing. Startup has been doing some amazing things in this space if you’re interested.

I still think that in the future people will not understand why most of us had large patches of dirt around our houses which could be used to grow food, but we all decided to grow cow food when none of us even owned any cows… Grass really is probably the least useful things you can grow on dirt.

I’ve seen it often stated that the absolute minimum area needed to sustain a single person growing a vegetarian diet is around the 20m by 20m size. With the introduction of vertical farming techniques, I’m interested in what sort of benefits and orders of efficiencies this would this introduce? Could we get to a point where we could grow close to all the food for our entire family within a large yard??

A future where we all grow most of what we need is an interesting thought. If everyone is close to self-sufficient in what they consume (not just food, energy, water what they smoke too), what does this mean for all of our current environmental concerns? It’s an interesting concept to play around with.

Wine making

I did quite a bit of home brewing in my teenage years and through my twenties. It was always an enjoyable activity making beer and a great social activity trying out the different batches. While the social experience of things was always fun, the taste experience could sometimes leave a lot to be desired. The calorie intake from home-brewed beer is often exceptionally high compared to factory beer as well which is not good, especially when you you are surrounded by huge amounts of it just waiting to be consumed! For this reason alone, my days of brewing are definitely over.

While beer brewing is out, the idea of getting into wine making is something that I’ve recently been thinking about trying out.

The Bay Area is surrounded by a number of great winery areas meaning that gaining access to wine making resources shouldn’t be too difficult. My father-in-law has previously won a number of awards for his home made wines as well so I have access to some great knowledge and skills to get started. It would actually be an oversight on my part to not keep the family tradition going, right? I’m pretty much obliged to work towards building my vintner skill set!


I’ve recently been looking at the possibility of building an extra shed in the backyard of where we’re renting and I’ve become engrossed in the idea of building structures such as sheds, barns, even small houses.

We obviously don’t have the space for it now, but a long term aspiration for me is to get a property which we could use for camping and just getting away. We have a few friends that have properties like this and the idea of being able to have a semi-permanent camp somewhere would be great for the kids as they grow up.

Being able to build a small house, multi-use barn or a bungalow style structure on such a property would be something that I would absolutely love to do.

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