{ in·deed·a·bly }

adverb: to competently express interest, surprise, disbelief, or contempt

Message in a bottle

We often hear variants on the question “what lessons would you tell your younger self, if you could go back in time?

Responses vary, but typically include sage admonishments to apply hard won life lessons.

Invest early. Often. Patiently.”

Don’t worry so much about what other people think.

Slow down. Take the time to consciously enjoy the journey. Travel. Love. Laugh. Dance.

Sometimes there are some fortune cookie wisdom or flippant life tips thrown in.

Buy bitcoin in 2008.

Collect experiences not things.

That band you are a passionate member of? It never does get discovered.

You’ll never admit it publicly, but you end up regretting buying that fancy car. And the tattoo.

Taking the time to learn lessons from past mistakes is an important step towards not repeating them.

However, without access to a time machine, the premise of such a discussion is purely academic.

My younger son assures me he is working hard on building a time machine. He just needs some more AA batteries, cinnamon rolls, Lego, and the latest Tom Gates book. I must confess to not being entirely sure how those items will form a functioning time travel device, but I live in hope. Until then, we must remain patient, and focus on things that are within our control.

One such thing is looking towards the future, rather than backwards into the past. That poses a much more interesting question: what would you tell your future self, if you could go forward in time?

A real-life application of the old Pearl Jam lyric: “if he only knew now what he knew then”.

What insights and reminders would you write in a letter to your future self?

A blast from the past, like you might discover buried in a time capsule or a message in a bottle.

Letter to our future selves

This exercise is harder than it sounds.

Your future self will know more than you do.

They will remember much of what you know today.

Their perspective will have evolved with a decade or two more life experience. Different values and priorities competing for their scarce time, money, and attention.

What could you say that might have sufficient value to get your future self to pay attention? Rather than just humour your views from today, as we might indulge a precocious child?

The more I thought about it, the more interesting the challenge became. What would you say?

Some shallow platitudes about remembering how awesome or beautiful or talented you are?

Exhortations to be true to yourself? Live your dreams? To never give up, compromise, or surrender?

Such trite statements sound like t-shirt slogans or those self-help books that peddle easy answers.

Would your future self listen to such messages? Would they actually hear them? I doubted it, any more than we retain and apply those pithy quotes people endlessly recycle on social media.

How about a list of predictions?

These might provide an opportunity for a bit of “I told you so” for those that came true, and comedic entertainment for those that were spectacularly wrong. I recently illustrated my own poor track record of anticipating the future. I suspect I am not alone in this shortcoming.

Those might fall under the “interesting, yet irrelevant” category. Nothing actionable for your future self.

Rose-coloured reminiscence

I must confess that I was hard-pressed to think of anything my younger self might have written or said to me that would have changed my course or altered my decision making. Younger me had certainly been more naïve and idealistic. Traits that, like virginity, once lost you cannot get back.

I would like to believe that the younger me had been happier and more carefree, but I suspect neither would be true. Responsibilities had evolved over time, but their existence has been constant throughout. My mother used to say I had been born with an old soul, a nicer way of saying I have always been a grumpy old man!

The freest I have felt was while solo backpacking around Europe as a teenager. Yet even as I travelled, I deciphered the illusion for what it was: a temporary escape from the everyday.

You can’t run away from yourself for long.

A distant second has been my extended summers off, while following my preferred semi-retired seasonal working pattern. These provided a sufficient glimpse at life beyond FIRE to recognise that it wasn’t about the money. It never had been.

Contentment comes from taking control of time investment decisions. Having worthwhile things to do. Being surrounded by a caring community of loved ones to share them with. Spreadsheets may help in the planning, but play little part in the successful execution of life beyond Financial Independence.

Focussing too much on the numbers and neglecting those behavioural aspects is a recipe for failure.

An insight that was obvious in hindsight. Hiding in plain sight.

We spend our working weeks grinding away on a relentless cycle of commute/work/commute. Time poor. Wishing away our lives pining for the weekends and holidays. Fleeting moments of stolen time are allocated to chores and hobbies.

Yet those chores and hobbies become all that remains once paid full-time work is removed from the equation.

Attempting to fill the void created by the absence of identity, purpose, routine, socialisation, stimulation, and structure previously provided by that job.

A challenge that has confronted every pension age retiree.

Except in their case, various combinations of age discrimination, cognitive decline, and physical frailty often conspire to ensure their retirement is a one-way journey.

Unlike those highly driven and motivated early retirees, who voluntarily hit eject on the rat race.

More often than the popular narrative would have you believe, at some point a surprising number of FIREseekers opt to return to the fray in some capacity. Recognising the important role often played by externally imposed motivations in filling the void.

Maybe a different profession.

Possibly at a lower level. Reduced stress. Greater enjoyment. More satisfaction. Fewer meetings.

Perhaps played at slower pace. Part-time. Seasonal. Voluntary.

Availing themselves of the externally provided sense of purpose, identity, and community offered by a job nonetheless.

As MedFI sagely observed recently, this is the paradox of early retirement. The behavioural aspects.

But these are things I currently believe. Accept as probably being accurate. They might even be true.

If they hold up, my future self will already know them too. If not, then his beliefs would have evolved.

First principles

The conundrum resolved itself while I curated a batch of awesome content at Sovereign Quest.

Sonnie Bailey wrote about regret minimisation and looking toward the decisions we have yet to make. He republished a simple Tim Urban diagram which effectively demonstrated how decisions made (and avoided) led us to our current point, but the only thing we can control is what we decide next.

Meanwhile, Suraya Zainudin articulated a personal set of rules she applied to make good decisions. These were inspired by something Ramit Sethi had shared with his legion of followers.

Combining the two would create a decision-making framework guided by a set of first principles. An approach successfully applied by folks ranging from Charlie Munger to the US Olympic team.

Ray Dalio once published a book articulating the principles he had applied over his years as a successful hedge fund manager. It was worth a read, though dense and very long. For those with short attention spans, Nate Eliason summarised the key points.

Such a list would be timeless.

The principles benefiting my future self almost as much as their compilation would benefit me today.

So what might my principles be?


View the world as it is, not as you would like it to be. Ground decisions in reality, not wishful thinking.


Own your decisions. When things don’t work, own the failures too. It is never “their” fault.


Monitor and learn. What works? What doesn’t? Improvement lies in knowledge, not faith or hope.


Recognise the largest risk to achieving goals is your inner saboteur. Anger. Boredom. Desire. Envy. Fear. Hubris. Impatience. Pride. Good decisions are based on evidence, not emotion.


If X then Y is easy, but limited. What are the root causes? What happens next? What are the knock-on effects? Where does the money lead? Risk and opportunity abound, recognisable to those who have already done the thinking.


Our sphere of expertise is limited. If you don’t know, seek out the domain authority and ask.


Keep an open mind, but listen critically. Trust, but verify. Do your own research. Think for yourself. Make your own decisions. Do the right thing. It doesn’t matter what the cool kids are doing.


Goals won’t achieve themselves, so act. Break the big picture down into small steps. Plan, execute, and monitor. If an activity won’t take you closer to your goal, and won’t make you happy, don’t do it.


It is better to be good than lucky, but sometimes being lucky is enough. Life happens, get over it.


Time is the only truly scarce precious resource. Measure cost in terms of effort rather than money to focus on the important and screen out the noise.

Message in a bottle

The list of principles I ended up with was a motley assortment of conventional wisdom, hard-won life lessons, and innate cynicism. I backtested them against many of the major life decisions I have made, both those successful and those decidedly not so. They held up pretty well.

If objectively applied, the decision making framework would have screened out all my major failures.

Most (but not all) of my major successes would have passed through.

Those exceptions raise an interesting question about whether my framework is overly restrictive?

The simplest explanation is that I had gotten lucky with those other outcomes. They shouldn’t have worked, but they did. It happens. Unpredictability is what keeps life interesting!

I would be happy to use my son’s time machine to send those decision-making principles to my future self. My future self should be open-minded enough to listen to what they had to say, and take the time to validate once more the results that their application had produced.

Hoping for the best, but planning for the worst, I printed out a copy of the principles and placed them inside the “box of doom”, alongside a frightening assortment of old cables, chargers, and adapters. I only rummage through that box about once a decade, so it is as good a time capsule as any!

If you were to write a letter to your future self, what would it say?

If I only knew now what I knew then…


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  1. Mr. Fate 28 March 2021

    Excellent article and certainly provides some engaging content for further thought. A nice, albeit, challenging exercise. I’m sure, ultimately, I’ll end up somewhere near (if not on) the Pearl Jam lyric.

    I applaud your 10 principles and they definitely resonate with me as well. I like the notion of putting your past decision through the filter and the results.

    Thanks as well for the references as I’ll be diving more into those.

  2. soicowboy 29 March 2021

    I have noticed your wistful evocations of youthful travel experiences in recent blogs.

    You should know that there is an army of aging backpackers finding their way into all corners of the world (pre-covid obvs).

    You could turn your ‘rose-coloured reminiscences’ into future plans.

    Just avoid the party hostels.

    Meanwhile, I’m thinking about writing that letter to my future self.

    • {in·deed·a·bly} 29 March 2021 — Post author

      Thanks soicowboy, that made me smile.

      I fondly remember some of the older characters I met at hostels around the world.

      The 40 something who thought they were still a teenager.

      The corporate escapee or recent divorcée who was attempting to rediscover happier times.

      The ageing hippy who had been on the road since time began, seemingly knowing and known by everyone everywhere.

      The motivated pension aged couple with the sightseeing stamina that put people half their age to shame.

      The disaster medicine specialist or geological surveyor who bummed around in exotic locales inbetween tough jobs in very remote places.

      Hostels certainly cater for people from all walks of life. If I’m brutally honest, I suspect the problem would be me rather than backpacking. A form of the hedonic treadmill at work, I enjoy my creature comforts a little too much to be content for long living out of a backpack containing just a sleep sheet, two changes of clothes (one to wash, one to wear), and a passport!

  3. surayaror 30 March 2021

    Hi, Suraya from RinggitOhRinggit here. Thank you for the mention, I appreciate it. My first time being referenced in such academic way!

    Lovely article, adore the self-reflection. Your list of principles is very telling of your character and what you value. Wishing you the best in everything that you do <3

    • {in·deed·a·bly} 30 March 2021 — Post author

      Thanks for the kind words Suraya. I really enjoy your upbeat enthusiastic writing style, it makes personal finance seem fun.

      My university lecturers drummed into me long ago to give credit where it is due and “always cite your sources!“. Based on the feedback I’ve received, it seems (some of) my readers like the approach also as it gives them a little context about what they are likely to find at the end of a hyperlink, avoiding them blindly stumbling into an affiliate sales funnel or trusting a source that is comedically outdated.

  4. dearieme 1 April 2021

    Don’t forget to heed the wisdom of our ancestors.

    Mind you, the rotters mighty have spelled Beiderbecke correctly. (He’s the chap playing the cornet.)

  5. Aidan 3 April 2021

    I have used https://www.futureme.org/ to send myself messages into the future. It is always a surprise to see what I was thinking about in the past and how things turned out with hindsight. My past self seemed to be a bit of a risk taker if you ask me (now)….

    • {in·deed·a·bly} 3 April 2021 — Post author

      Thanks Aidan.

      It is funny how our impressions of former selves evolve with age.

      Edgy becomes daggy.

      Idealism becomes naïvety.

      Cool becomes a victim of peer pressure.

      Earnest belief becomes pretentious twaddle.

      Being loved up and in lust becomes familiarity and companionship (sometimes!).

      Things done for the adrenaline rush or dopamine high appear on a spectrum somewhere between foolish and downright suicidal.

      The toughness and camaraderie of playing rugby give way to the aches and pains of injuries past.

      All were (probably) worth it at the time, most are (probably) questionable in hindsight.

      How any of us are still alive, healthy, and solvent is one of the great mysteries?!

  6. Q-FI 12 April 2021

    Keep me in the loop on that time machine your son is building. I’ve always wanted one of those as well.

    Very good observation, “You can’t run away from yourself for long.” Usually takes people a very long time to realize this.

    “Time poor.” That’s another phrase that really resonated with me.

    Good virginity reference, and I particularly liked the “box of doom.”

    This is an exercise I’ve done before, more on the psychological/addict side, not as much on the career/life side. The older I get, the more I know, the greater the changes.

    However the most important question for me personally is not what would I put in a future letter to myself, but would my future self even listen? Hahaha. I’m becoming an “old soul” like you!

    • {in·deed·a·bly} 12 April 2021 — Post author

      Thanks Q-FI.

      It is always entertaining watching our perceptions evolve as our experience increases and (sometimes) our wisdom grows. Certainty, free will, and the “right” answer are all things I’m increasingly coming to suspect are the stuff of fairy tales. Except the bad guys aren’t the wicked witches or evil dragons from the bedtime stories, but our own unquestioning and easily influenced minds in the hands of distraction and discord purveyors.

What say you?

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