I’m staring at an oak shelf filled with cannon-fodder rank whiskeys, my sober body lazily propped up by an indifferent bar. The faint echo of the barmaid’s question shimmers through the wormhole from where a heartbeat before I’d existed in the pub, “what do you want?”.

I no longer feel tethered to this earth.

Let’s backtrack 60 minutes. It’s 18:30 on a Wednesday, 22 October 2014. I’ve just received an email from a customer in India, jovially enquiring if I’d seen Google’s new tasky email product, Inbox. And how will it affect my own product – the one that had trail-blazed “emails as tasks”? “Oh yes”, I tell him, commencing my sprint from the starting blocks of the Seven Stages of Grief, “it looks good doesn’t it? I sure do wish them well”. I genuinely think my well wishing to a $200 billion dollar company is an act of charity.

By the time I’ve ambled, wild-eyed, down the pavement to the pub, internally I’ve raced through the Stages to Depression. And then I trip. The simplicity of the barmaid’s question has floored me, what do I want? Which to answer, we’re both rather alarmed to discover, is requiring me to urgently re-evaluate the last few years to find out who I’ve become.

Much later, in writing this piece, I’ll discover that this feeling of disassociation from the world is called Cognitive Dissonance. It’s very much like a panic attack. A psychological stress triggered by becoming aware of the contradiction between your personal beliefs and the actions you’ve taken (or not).

Have you ever promised yourself that some undesirable situation will change? “I’ll stop working so hard”, “I’ll catch up with Bob”, “I’ll learn that new skill”? Deep down, you know you’re the kind of person who ultimately lives the way of the change. Then you suddenly realise it’s the 3rd year you’ve said that, and you’re winded like a dizzying punch to the gut. You’re not alone. I call it a slap from life, and that’s Cognitive Dissonance. But it isn’t really what this article is about.

This is about re-imagining opportunities as a basket with many poisoned apples, an ingenious secret to a life well lived, so that your death bed isn’t spent weeping to the nurse about going into eternity with regrets. Those stings from life’s slaps are a great teacher, if you want to become a connoisseur of apples.

But first, back to the story of my awakening…

How complacency had sneakily ensnared me in a gilded cage

Let’s go back to the earliest point of this journey. As I prepare to leave university, a dear friend of mine is resolved to having a glittering corporate business career. My distaste towards sacrificing time, rooted in my adored grandfather’s life spent building for retirement only to promptly die, means I’m pretty sure my friend is going to turn 30, look back at his lost 20s, and regret it.

With all the simplistic arrogance a 21 year old could muster, I’d tried to dissuade him of this, and now had nothing left to do but build up my own guilt-free body of evidence for a joyous “I told you so” a decade hence. I travel, I love, I satisfy my mind working on little hobby products of even littler consequence, and I keep my nose in the air for the scent of a purpose.

By 2006 I’m 23, and in sharing ActiveInbox publicly – a tool I originally built to help myself – I’ve just learnt the one rule in business that truly matters: build something people want. But that trickster Fate whispers it so quietly that I instead hear another lesson: building something people want is easy.

Thus I tell myself, “What a life of freedom!”, because things seem so relaxed and are changing so slowly I barely notice this little acorn of creation is growing into my personal black hole.

Let me briefly pause for bonus lesson for fellow entrepreneurs: the exact reason for my downfall is my unquestioned insecure impulse to please an ever-growing number of customers, and my inexperienced, somewhat bonkers dream so typical of geeks, that I can retain more freedom by avoiding the noisy shackles of a team. I’m slowly getting crushed.

Looking back, I’m letting all of this happen for a reason that would have blown my university self’s mind the most… I’m loving this cage I created and the addictive gameplay within. Not even the increasingly frequent 6am adventures walking home with an urban fox – somewhat unwillingly flung into the role of my chief confidant – woke me up to realising there was a problem.

Those six years of complacency had gently reduced my sense of identity to just “the guy bootstrapping a product”, which was my unseen reality so at odds with my mental belief I lived fully.

It took Google Inbox threatening to destroy that remaining piece of my identity to wake me up to the questions… What would actually be left to proudly remember of that era? And which of my other life muscles might still work for the future?

The key that unlocked the cage is… gaining momentum

Those two questions, spinning nauseatingly in my mind, opened my eyes to the secret of harnessing the remaining moments of our pathetically finite time.

The common advice is obvious enough, although as I found, not easy to remember day to day: observe time is slipping away, ruthlessly prioritise only the things we’ve chosen to value, and course-correct those values often.

But I also realised there’s a less spoken about solution: our ability to seize the remaining time is dependent upon the momentum of our life narrative. Plainly, if we believe we’re doers we’ll continue to be doers, but if we believe life has kicked us down, we slowly withdraw. (It’s not just psychological, it’s also a physiological feedback loop: perceiving yourself to have won or lost your chosen battles – themselves just a personal narrative of your choosing – affects your testosterone hormone levels, compounding your likelihood of winning in the future).

So what slams the brakes on our personal narrative the most? It’s actually the hardest aspect of our mind to control: our sensitivity to what we didn’t do while we had the chance (you’ve no doubt already twigged this is the recurring theme of death bed regrets).

Psychologists call this ‘loss aversion’: we’re wired to prefer to avoid losses rather than enjoy equivalent gains. That’s why awareness of these lost opportunities causes us to dwell excessively upon them as regret and evidence of our weakness, slowly killing our momentum…

…. It’s why minimising lost opportunities from now on is the ultimate KPI to grow a positive identity and fuller life.

Back to the pub… it had finally come into startling clarity: the barmaid’s question had so terribly tripped me up because, with the immediate probable loss of my whole identity, who was I to be making choices? “Choose me something, anything”, I pleaded from my far away galaxy. (In fairness to her, she did so with glee – delighted that the man who gave all the external indication of a major ketamine problem was an issue about to be resolved).

The lifestyle change: learning which opportunities you want (the rest are not opportunities)

If you take only one useful thing from my experience, let it be that missed opportunities harm the rest of your life, compounding like a financial debt that glacially shrinks your confidence in what’s possible.

But a lifetime has infinite possibilities, we’re always going to have to turn some of them down… Do they mean we’re doomed to slowly shrivel into a meek cog? The stereotypical neutered old person? Not if we define what truly represents an opportunity for us, so you can peacefully discard the rest. To do that, we need to figure out our values.

A formula for a life well lived

A very simple mental framework to live by is called Opportunity Cost: the price of not taking an alternative path. To fit the economic mould from which it originates, time should become our true currency instead of dollars or pounds, and my preferred benefit is happiness. What investment of time, which is finite, will yield the greatest happiness?

The way to calculate that predicted happiness depends entirely upon your values…

Encourage little value-correcting slaps often, rather than large slaps late

Few of us are lucky enough to have such powerful events early in our lives to definitively shape our values. At least the ones we’re conscious of.

Unfortunately, that’s why my story about Google Inbox is unavoidable. It takes hard shocks to awaken us to our values. The best we can hope for us to get them quickly.

This is why I try to flush them out little & often, by putting my ear to the ground whenever I feel low:

  • Steve Jobs simply said, ‘for the past 33 years, I have looked in the mirror every morning and asked myself: “If today were the last day of my life, would I want to do what I am about to do today?” And whenever the answer has been “No” for too many days in a row, I know I need to change something.’
  • I’m very cognisant of my grumpiness towards others. If I’m not feeling charitable, it’s generally a sign I’m defensive – and I just probably haven’t thought about why yet.
  • And I’m more vigilant, now, for that most dangerous rationalisation of all: “it’ll make things better for the future”. It’s not that we’re wrong, but we need to time-box how long we’ll give it to bring us that better future, otherwise a decade will have shot passed, opportunities gone forever, and statistically, the anticipated future probably won’t have arrived.

Staying bold as you receive the slaps

No one has a perfect story. But it’s those who choose to interpret past events optimistically who become robust.

The two most effective things I’ve found to achieve this are:

  1. Introspect on the impact of negative events, so you can remember them as opportunities to grow.
  2. Acknowledge and thoroughly research insecurities, and add their cause into your story of how you came to be your special self. The curious thing about insecurities is many come simply from not being sure in who we are, so by simply having them explained, we increase our confidence in who we are, reducing the insecurity.

Ducking unnecessary hits #1: consider how you’ll react to predictable events

We’re notoriously poor at imagining our future selves. Many people don’t have sufficient savings, or insurance, for example. Tellingly, research found that when people were shown a photograph of themselves artificially aged, they went and bought insurance. Imagination 0, Punishing Reality 1.

So you’re probably not going to do well at this. That’s ok, neither is anyone else.

But ideally, you’ll test how your values hold up against things you can be reasonably sure could happen. How will you feel when… Your knees fail and you can no long do physical activities? Your parents pass away and can never hug them again? You reach old age without a companion? AI makes your skills irrelevant? You have to move countries and need a hobby that will help you make new friends? Or the biggie, if kids become your life and you need an income and skills to pass on, and have simultaneously lost the chance to do your bucket list. (The best thing I ever heard regarding prioritising income to support them, rather than fun times playing with them, is Alan Watts’ beautiful phrase that you’ll only teach them life is “all retch and no vomit”).

Ducking unnecessary hits #2: Reasoning from First Principles

Inconsistently learning only when life sporadically teaches you, often leads to you over compensating into more mistakes.

After 2014, I reacted by welcoming risks again: I took up a new and terrifying hobby, I experimented with different lifestyles, borrowed money to grow the team, and began inventing new products. But in doing so, I also took my eye off the boring bits of work. Which meant last month, we got floored by Google again when they merged Inbox into Gmail. This time it wasn’t as existential, but nonetheless could have been far less painful with some mundane preparation last year. My value lesson was that I really love making products for our users, and the fear that it could be taken away means I have to keep on top of the little things.

Luckily, there is a scientific method for filling in your missing values before you make a mistake: reasoning from first principles. This is what I should have sat down and done after Google Inbox. When faced with a decision, rather than taking the shortcut of ‘because others do it’, or a pendulum swing away from where you were, boil the choices down to their fundamental truths, and then reason up from there to which one matters more. (Handily, doing this a few times typically awakens you to values you didn’t realise you had, making your choices faster in the future).

Becoming aware of how time slips away…

This is less about making the right decisions, and more about realising the unguarded way we lose a little life each day. Because life is short, but it feels much longer.

There’s a foible in our ancient brains that means we’re terrible at understanding how little things add up over time. Typically it’s relayed as financial advice, but as time is the ultimate currency, that means minutes, hours and days too. Spotting where time slips away over a month means you can make big changes to release more of it – personalised to you. (I’m often guilty of losing up to an hour of my work day to YouTube. Over a year, that’s 30 whole days that could have been invested into something lasting.)

The other advantage of tracking time, perhaps with a journal, is to protect the positive sense of who you are from the greedy mitts of your own memory. Now in my mid 30s, I’m slowly forgetting a lot of the joyous moments in my 20s, which is contributing to my sense of a smaller possibilities in life.

… and then blocking up the rabbit holes

A curious thing happened when I took up a hobby that required me to be somewhere on time or I’d miss it – I no longer worked late. My brain tends to get myopic as the day progresses, diving ever deeper into the work, which means stopping is unlikely and worse, sleep is hard to achieve. Having the hobby in the calendar solved both of these, forcing me to close the lid and switch off my brain from the addictive drug of work.

More generally, I’ve found planning – although still a weakness – wonderful for handling that awful situation that arises when you have a heightened sense of mortality, but no immediate plans, and an insufficient set of values to protect you. It’s an extreme story to tell… but I once seriously considered trying Morris Dancing in a blind panic, because I thought anything would be better than rueing an empty Sunday afternoon on my death bed.

Because we’ve only a few heartbeats left

This is the longest piece I’ve ever written, which is dangerously close to making all this a chore, when in fact the whole topic should be a delightful generator of exuberant little moments.

So, if you’re ever in need of a little pep, don’t read this, go see Tim Urban’s visuals on how many books you have left to read (or more sharply, how many endings will have to go unknown for eternity), and how few times you’ll see your parents again. Or, sit back and listen to my all time favourite rallying cries, Frank Turner’s Photosynthesis and Long Live The Queen.

How can we clear our heads of nagging noise, to seize those opportunities?

Can I show you a product I’ve been working on?

I briefly mentioned that one of the things I changed in my life was to start working on new products after ActiveInbox. They’re all driven by a desire to free up our headspace to achieve more.

The first one, Mailtrics, will automatically tell you where your time goes in email, and especially where it’s tediously wasted, so you can rescue it and invest the time into something meaningful instead. Oh, and it’ll be wicked smart at protecting your privacy too, as we’re going to the cutting edge of tech to provide Provable Privacy.

By signing up for Mailtrics, you’ll get a sneak peek before anyone else, and more emails on the subject of how people live life well will come – although the next one will a mercifully short at under 200 words!

Categorised in:

This post was written by AndyM

  • b00ky

    Wow! Thank for sharing such introspective thoughts about what you have been through and learned. A combination of sad and enlightening!

    • Thanks 🙂 The good news is it doesn’t *feel* sad, as the lesson came early enough in life… but one’s brain does love rationalising itself as form of defence… (Maybe that’s another post, and another test… “Would your 21 year old self agree with whatever nonsense you just said?”!).

      • Richard Keyser

        Unless you want to get into the actual percentages of those who do and those who do not, the correct answer is more likely than not. If you make it to 40 and still haven’t considered the possibility that you have been lying to yourself all along, you are either woefully inadequate, suffering from a total lack of insight, terminally altruistic, or all of the above, you will “more likely than not” live out your life in blissful ignorance. It sounds like you didn’t make it past your early 20’s when you ran into the rigid and inflexible wall of reality. The miracle is not that you survived, although that truly is a wonderful thing. The miracle is that you gained almost a lifetime worth of insight. Now that is priceless. If you want some advice (but it’s free so keep that in mind), I think you should find out how many 21 year old selves believe what you wrote about and how many don’t understand it. The results are likely predictable, but it would give you something to think about in the event you start having anxiety attacks while trying to outguess Google. Your article was enlightening, painfully honest, and painfully true. I enjoy reading your posts. Very much. Keep writing.

  • Peyton Welch Stafford

    Andy, good to hear from you. I’ve been through some changes related to startups and questions about life, too, since last we talked. I hope Mailtrics takes off.

    • Hey Peyton! If you feel like sharing them, I’d love to know what helped you along the way?

      • Peyton Welch Stafford

        For me, it’s been about wakeup calls. For instance, I was working with a startup that could convert any book into a number of large print formats for visually impaired readers. We actually gave away a Kindle as a drawing prize at a trade show without realizing that the Kindle technology (soon followed by iPad) would make our product obsolete for most people. I don’t think the problem is complacency so much as being unrealistically optimistic about mass adoption of one’s product. When battling these giant companies that dominate the market, and battling other startups that have unicorn funding, it is easy to be overly confident. Then, wham! The wakeup call hits.

        • I think the most cathartic thing I managed was to simply understand why the dice was loaded…

          Corporations have been able to shrink their R&D budget, because lots of people now want to be entrepreneurs. So lots and lots of people take funding on their dreams, and most will fail, but that loss isn’t incurred by the corps. Instead, from their POV in the garden of Silicon Valley, many seedlings get planted. Google/FB/Amazon/etc. then get to stand as the farmer, ready to pluck any promising flowers (ideas) that grow. The flower can’t represent itself at market, only the farmer has that power.

          Amazon has been accused of this practice for years by watching what is successful in their market place and selling it themselves. Facebook bought Onavo, which reportedly is what gave them the evidence that tbh was an app to buy while it was still only a few weeks old ( https://twitter.com/dhh/status/900893798821134336 ).

          But I think it depends where your ambition comes from. For me it’s the pleasure of creating new products that haven’t been tried before, and having the autonomy to work on those ideas (Daniel Pink’s research on this as true motivation really resonates: https://www.youtube.com/watch?v=u6XAPnuFjJc ). If they don’t get to live long enough to become huge, that’s personally frustrating, but I still take pleasure in seeing the concept take hold.

  • Angus

    Thanks Andy! As I was reading I was thinking ‘I must send some “Wait But Why” stuff. This is so similar’ and then you had links to it.

    Mailtrics sounds intriguing. Can’t wait to see it/use it.

    Have a good weekend!

  • Just a couple of things (and a massive collective high five if you made it through my giant wall of text!)…

    1. If you’re got a similar story about wake up calls, I’d welcome you sharing them in the comments – if you feel comfortable. The by product of having a visceral sense of mortality is I do love talking about this stuff 🙂

    2. My apologies for anyone who got the dreaded “502” error at first. It turns out sending an email to everyone at once sends your server crying into the corner…

  • Brian Maloney

    I discovered that I like to make families happy making the BIGGEST bubbles of their lives… so now I do that around the country as “Grandpop Bubbles.” See the most beautiful photos of giant bubbles beingmade by me and the happiest families you will ever see at http://www.facebook.com/GrandpopBubbles/photos, or just search Google Images for #gpopb or “Grandpop Bubbles”.

    • I never once imagined I might see something like this when I when I was scribbling down my thoughts… thank you for a truly uplifting Friday surprise Brian, this is fab 🙂

  • Dave Armstrong

    Thanks for this Andy. I have a “few” years on you and have a reasonably well-formed “rule of life” which guides me. Nevertheless, one is always challenged when major life decisions are set before us (or life course corrections are thrust upon us!). I’m actually in the process for working through such a major life decision right now. Be encouraged: even with the grey in my beard, your wisdom was a reminder to keep the most important principles in view. Thanks for baring your soul…

    • Thank you Dave, truly, I didn’t necessarily expect it to help anyone but I’m thrilled it has. I hope the decision goes well (and if you want to share your rule of life, I’d really like to hear it).

      • Dave Armstrong

        Happy to share it with you. I’ll drop it into your email

  • Marco Bertalot-Bay

    Dear Andy,
    The experience you describe is not so rare! It is known and called by the story os Parsifal!
    Congratulations! An important step for every 1s life!

    • I confess Marco, I just had to google ‘Parsifal’ (I’m a cultural heathen). It strikes me as simultaneously romantic to have a life of wondering discovery (or as Buddhist’s might put it, the joy of the Beginner’s Mind), and a major failure of our mind’s in their habit of having to repeat the mistakes of those who went before 😉

  • Thanks Andy. It’s reassuring these days to learn of the person behind the code. In a way, that’s the critical difference between ActiveInbox and whatever Google will come up with. The Google path is towards “smart” thanks to the algorithm: deciding for you when to remind you to answer that email. Todoist has gone down a similar path. But your platform is resolutely manual, which takes more of our time but ensures that we remain mindful of what’s happening. Your scene at the bar underpins that ethic very nicely.

    • Thanks Kevin! I think ‘smart’ is really interesting, and to be honest, the day (the year) they truly crack it it’ll be hard for the little guys like us to find our niche.

      But the kind of smart that says “trust us, you can switch off”… well, of course a lot of us don’t have brains that work that way. We still need to see the puppet’s strings to appreciate how everything fits together. To trust our systems.

      I hope to always pursue a blend where we (the users) have full control, but the benefit of us much magic as possible 🙂