Not Me

It is... most of the time

It is… most of the time

[Sorry, a little behind posting this...]

It’s New Year’s Day and I have a splitting headache. It’s a year to the day that I split up with my girlfriend. That wasn’t a good day. I had a headache then too.

Despite the similarities, a lot has changed this last year.

Indulge me for a moment, I’d like to do a swift year ‘in review’, if only to focus on something I’d like to bring into frame – something that’s not about me.

Last year my revelry induced my pain. This year, I remained stone cold sober on New Year’s Eve. Clearly my body, so unused to clarity on the dawn of a new year, decided to take matters into it’s own hands, and today I woke up with man flu.

A poor start to the year, but despite the surface snuffles and tiredness, I feel good within. I’m fresh back from San Francisco, where I’ve just spent two months on 500 Startups, a leading accelerator programme.

I’ve been living in a van and wrote this article about my experiences early on. I was asked to write another, which followed here.  The van is emblematic, a reminder to myself that I am alive, and adventure sits everywhere if we chose it.

The experience has been a rollercoaster ride of highs and lows, something I tried to capture in this, my most recent article. One of my new friends Nicholas Holland, also explores the pressures in a great article here.

It’s been a tough year. I’m home, halfway through the accelerator feeling that ‘the score’ is 0-0. Perhaps 0-1 against us. I’m flying back in under a week for the second half, with all to play for.

Yet I feel good, despite the score. Why – because I can honestly say I’ve been giving life everything I’ve got. Whether for the first time, or at least for the first extended period, I feel ‘in flow’, dedicated to a single focus. I’ve not worked like this before, with a sole direction, and I’m loving it.

Two weeks ago I did a skydive with some of my accelerator batch. My dive wasn’t without drama. After an extraordinary few seconds in free fall, my instructor pulled our ripcord, only to shout ‘shit’ repetitively. Not the words you want to hear in that situation, I can assure you.

I looked up to see our parachute tangled and we continued to descent at considerable speed. After a nervous 10 or so seconds (a long time in that situation) he managed to pump some air into the canopy and we were out of trouble.

It somewhat embodies how I’ve felt these last few months. Exposing myself to life and its risks, with some hairy situations, but feeling exhilarated. I’m not sure if the parachute will open, but I’ve flung myself out there, all the same.

Something has changed within me, whether permanently or not I don’t know. For now, I’m embracing this change and the sense of power I feel at present.

Which leads me to the crux of this post – a resolution.

Toward the end of my stay in San Francisco, I read an article that incensed me and forced me to write back. As I’ve lived in the city, I’ve always been painfully aware of the number of homeless people that live there. It’s something that has made me want to take action, somehow.

The letter I wrote received thousands of views and I’ve had many people write to me to offer their support. My resolution is not just to try to organize this event, to try to raise awareness and money for the homeless of San Francisco, but speaks to a deeper mission this year.

I want to make this year about other people. I am painfully aware, as has been the case with this paragraph, that I start too many sentences with ‘I’. I (there I go again) feel that my life over the years has been very I-oriented. Whether with this blog, my business, social life, skills or time – I’d like to try making more things not about me.

I sense that 2014 is going to be an awesome year, in one way or other. There will be a lot of hard work and a lot of isolating moments, with myself and my partner pitted against the rest of the world as we try to grow our business.

This year, I’d like to make an effort to orientate my days, my work and my time around other people. Whether putting time into organizing this sleepathon, or to speaking to the customers of my business and focusing on solving their issues.

It could go horribly wrong at a time when perhaps a little self-centeredness is needed, but I sense the opposite. There’s a selfishness at the heart of this – I do hope that my business, my work and my relationships improve – but I want to practice abundance by giving back and giving away.

So 2014 for me is not about me. I’m not sure how that will manifest itself – I’ve the fragment of an idea, a sense that its something I want to explore and that it will lead to wonderful things.

For now, I hope you are superb.


Work Like it’s the Weekend

I've no idea who this is, but I like his attitude... and his painting

I’ve no idea who this is, but I like his setup… and his painting

Over the last month I’ve been living in a van in Silicon Valley, more on that here and here. I’ll post some adventures soon on Simpletom… but today I want to explore working like it’s the weekend.

I get my best work done at the weekends. Not that I want to be working at the weekends, mind. But weekend works comes with a calm that is enviable to my midweek self.

In Leonard Cheshire’s, (a hero of mine) biography, he mentioned that whenever he wrote a letter, even if he had a pile of them, he’d write each one as if it was the only one he needed to write. Although it meant the pile took longer, he was able to give himself to each letter, without the shackles of time constraining his focus and commitment to each. It meant he wrote fabulous letters.

At the weekends, I’m not subjected to the deafening tick-tock of the progress clock, which leaves me rushing from moment to moment, task to task and meeting to meeting. I’m not sure I finish anything, or am ever ‘in the moment’, during the week.

We should work like it’s the weekend everyday. At the weekend, there’s time make a cup of tea, stare out of the window, take 15 minutes off to play the guitar, write a Simpletom blog (the infrequent nature of my posting is perhaps indicative of the healthy lack of weekend work) and do meaningful stuff that ‘I don’t have time for’ in the week. We’d have time to think and put that thought, carefully and considerately into our work.

We would do more substantial, more committed, more thoughtful work, if we always worked like it was the weekend. Today, we’re so subjected to the immediacy of things that work has become frantic. The bygone days of long boozy lunches, trips by steamer, disconnectedness seem far, far away – yet some pretty epic work (and thought) was achieved. Most modern thought-leaders and doers seem to want more time to think and breathe. Why don’t we just give it to ourselves. Why does midweek work have such a different texture from weekend work, even though it’s the same thing. Why do we prescribe one pace for one and another for another?

If we worked like it was the weekends, perhaps we’d not get quite as much done, but I’m pretty confident we’d get what we needed to do done, with more meaning and quality – of life and work. And so for another cuppa…

It’s OK


I am currently here, but I’m about to move back to San Francisco whilst wanting to settle here, where I’m trying to to buy a house.

Well done Simpletom… you’re managing, quite dedicatedly, to ignore all of your own advice.

Over the next few months I will immerse myself and my business in 500 Startups, a prestigious ‘accelerator’ programme for tech startups. So, I’m about to embark upon an extremely intense few months whilst also trying to remember this and this. It’s going to be a whirlwind where a certain amount of schizophrenia will inevitably occur. But as my wise sister often says, with perhaps one the simplest adages for repelling self-doubt:

“It’s OK”.

Edward De Bono in his book Simplicity suggests 10 rules for simplicity. The first is ‘you need to put a very high value on simplicity’. The second, ‘you must be determined to seek simplicity’. This is valuable advice for the simplicity-seeker. Simplicity is not easy, nor does life unfurl the way you want it to.

I could chastise myself for putting myself in this, another situation where the simplicity I seek will be harder to maintain. I could wind myself up with concern, or frustration. But, actually, it’s OK.

Last time I was in San Francisco, I had dinner with an old friend who’s now raised close to $20m for his tech venture. He was philosophical (unsurprisingly, given he has an All Souls Fellowship in Philosophy – the ‘hardest exam in the world’) about running a tech venture and whether it will succeed or fail, reminding me what a privilege it is to be in this position. In fact, a couple of the most dogged, determined entrepreneurs I know seemed to have softened slightly and become more at one with the idea that, whatever the outcome, it’s OK. I don’t want to get too ‘Cynical Valley’, before I’ve even started.

So, here I come. It’ll be OK.

Though regular readers will be pleased to know that I’m not going completely native. There’s still a bit of a tree hugger/determined-simple-seeker/adventurer at heart, given I’ve just rented one of these, which will be my home until Christmas. Car parks of Silicon Valley watch out.

I’ll try to keep you updated on my progress as a technological entrepreneur vagabond.

Let’s hope, for the sake of my new colleagues, I can find somewhere to shower each morning… or I’ll have to rebrand myself SimplePong.  But I scents that it’s going to be OK too (sorry).


(or the art of Growing Down)

A previous, very silly, birthday

A previous, very silly, birthday

Yesterday was my birthday. I was dressed as a ninja cow at a festival, squeezed into a west-country barn full of ‘Almost Farmous’ revellers. We were ‘The Moo Fighters’, naturally. Seconded only by ‘Daft Skunk’.

The weekend consisted of dancing, laughing, drinking, firing water pistols at unsuspecting crowd members and generally indulging in large dollops of mischievous fun.

All perfectly acceptable fun for us youngsters, right? The issue being that I turned a wizened 34. My birthdays haven’t much changed since I was 18 and today my bones ache.  Peter Pan is alive and well and, as a casual glance around the festival would suggest, he’s not alone. You can spot him easily – he’s the one with the bags beneath his eyes.

Are we eternally young, or merely adulesents?  I wonder at what point we’ll become too old to find squirting people with water on a dance floor and then hiding most entertaining, and whether or not that constitutes a good or a bad thing?

I hope never. I’d like to nurture many of the wonders of youth – the lack of responsibility, humour, mischief, laughter, untidiness, carelessness, late nights, giggling, dancing that immaturity brings. I’d much rather live in a Roald Dahl novel than one by Austin, or Tolstoy, with their endless stream of grown ups, or children masquerading as adults.

We have many interwoven, sometimes contradictory, relationships with youth and growing up.

I was a late developer. As a summer baby, I was always playing catch up with hairier and taller friends in my year, some of whom had 11 months ‘extra time’. Not inconsequential when you’re a wee nipper on a frozen ruby pitch. Amongst those peers, I’ve now friends who’ve had three children, are captains of industry, divorcees, widows, drug addicts, alcoholics and celebrities. Some seem exceptionally grown up, with houses in expensive parts of London, pristine wardrobes, pensions and all the dinner party chat that complements their choices.

Others… well… haven’t. Yet some of the latter are more emotionally mature than the former and have had ‘richer’, more interesting lives. One friend could be described as the ‘furthest behind’, in terms of their careers… is one of the wisest, most worldly, experience-rich person I know. Another, a great friend who writes wonderfully here has just set off backpacking around the world, one-way, in his mid-thirties.

I’ve never understood the rush to grow up. Being one seems to mean attending parties where conversation never steers beyond pleasantries or politics. It means subverting ones true beliefs or self-expression. It results in wearing a uniform of chinos, collared shirts and boat shoes. It can mean rounding out all the passionate edges of youth and becoming ‘just another’ conformist. Add a bunch of reality, a sprinkle of boredom, a dash of failed ambition and a liberal sprinkle of responsibilities, loneliness and hard work to the mix and slow bake… and before we know it we’ve become a grown up. Past tense.

And yet, on the flip side, I’m envious of those adults who seem settled, self-confident and aware.

At a wedding a week ago the electronic music selection resulted in every person over forty retreating to the bar, save for one sixty-something who wasn’t scared to get involved. I’d rather be that person. Yet I want to do it because it feels authentic, not because of psychological stunting, or because I refuse to accept I’m the age I am. I’d like to be the godfather than a child goes to for both fun and sage advice, not one or the other.

Being ‘trapped in escapism’ is often an attempt to maintain the freedom of youth and avoid responsibility. Responsibility and maturity, particularly emotional maturity is, in my mind, always a good thing and yet so is a youthful energy and disposition to trying new things. Youth evokes passion, dreams, a healthy recklessness and hope that a weary elder can swat aside in the desire for routine, conformity and comfort.

So what to do? Can we bounce around like a child at a festival one weekend whilst holding down a job that requires huge responsibility, without giving one or the other short shrift? Can we extract the best from both maturity and immaturity?

There are good examples of a balance – The Dalai Lama, despite the weight that comes with being a religious leader, has a lightness, a giggle and a curiosity to match any child. David Attenborough, when asked about his passion said, “Many people ask me when I became interested in natural history. I’ve never met a child who isn’t, so I ask in reply at what age other people lost interest in the wonders of the natural world. I just never did”.

It’s a great shame when someone becomes too sensible to swim in the sea, dance, laugh, play practical jokes or takes things too seriously because they might look silly or get dirty. Both this beautiful poem as well as our deathbed regrets suggest that retaining the better parts of our youthfulness is important, and hard.

Let us nurture the wonders of youth. Let us be sillier, swim more rivers, make more mistakes, keep in touch with friends, work less hard, walk barefooted earlier, pick more daises and allow ourselves to be happy. I’ve started already this summer and it’s working. Come join.

(And I must leave you with this, which is the view from my window as I write this…)

Bristol evenings...

Bristol evenings…

Trapped in Escapism

In flight...

SimpleTom in flight…

One of the wonders of the modern world is opportunity.

As an entrepreneur, I’m continually excited by what is possible. Aided by lightning fast connectivity, jet engines, computing technology and a plethora of beautifully indexed information available at our fingertips… the world is our oyster, lobster and winkles too.

In a single week, an indefatigable person could dine in a San Franciscan Michelin-starred restaurant, walk through an African slum and give a talk at Davos. Another might kitesurf, skydive, go to a sex party, take mind-altering substances, play a gig at Glastonbury. Why stop there… why not combine the two?

It’s all possible if you read enough Tim Robbins, Tim Ferriss, Hello magazines or believe the latest Hollywood blockbuster. It’s just so disappointing we can’t clone ourselves because life is too short, you’ll get all the sleep you need when you’re dead and time is money.


I wonder where the being there for your friends, reading Bill Bryson on the toilet, doing some community work, empathy, writing, having an evening to think, meditation, going for a walk, sleeping well, responsibilities, calmness and, of course, simplicity fit into all this?

Have we made opportunity and escapism a fetish that undermines our ability to live healthy, happy lives?

This evening, back in London town, I have a couple of hundred restaurants and bars to choose from within a couple of mile radius. I’ve a few dozen applications, websites and guidebooks to help me choose them from and 7 devices in this house I could use to do so. I can tickle almost any gastronomic whim. With the means, I can go anywhere and do almost anything. Boy, isn’t it great to have all these options. I need to have options, otherwise my life is stale and we’ve wasted all this development and human endeavor.

I think not.

Do we even notice the joy of drinking a cup of tea, with leaves that have slowly grown and been picked by a 5th generation farmer on an Assam mountain-side? How many gastronomic delights are wolfed down, or sensations are given almost no attention, despite their wonder?

On a personal level, whether affected by these external forces, or driven by my own upbringing (being a professional musician aged 8-12, with all the discipline, restrictions and constraints that accompanied, was not at all healthy) – I’ve started to recognize that I’m trapped in what seems like a global pattern of escapism.

In fact, I’m really rather brilliant at it.

For me, the manifestation has meant that over the last 10 years, I’ve lived in lots of places, met loads of people, holidayed and partied across the globe. I’ve started a number of projects and finished very few. I’ve dated some wonderful people who I usually abandon because like all good entrepreneurs, I need an exit strategy, or just because if I’m not about to escape or if I don’t have an obvious alternative or escape plan then [alarm bells] my options are limited.

How sad. The kaleidoscope of opportunity has cauterized continuity and community.

Don’t get me wrong, it’s often been fun. But, I’ve noticed loneliness in myself and others who pursue these tantalizing escapes, scrapes and adventures. In the midst of being Peter Pan and chasing freedom, I’ve too often found myself alone, somewhere between one place and another, one relationship and another, and one piece of work and another. When the music stops, the escapee can find themselves without a place to sit. When I read stories of billionaires and their multiple homes, wives, yachts, interests and hyper-dysfunctional families, I am reminded that choice is a burden. When I look closely the eyes of those chasing ‘the capitalist dream’ at ‘exclusive’ events, I’ve started to notice the fear, loneliness and desperation behind the tanned, moneyed pearly-white smiles – which seems to get worse the closer these dreams get to fulfillment.

Recently, I’ve noticed a shift in myself to want to settle and to take on responsibility and commitment, even if it means I’m not as free. I’ve noticed that freedom comes from these commitments rather than from opportunity. With a solid and stable home, meaningful consistent work, regular friends and monogamous relationship, I sense we have the foundations upon which to be even freer, rather than chasing the elusive idea that freedom comes through keeping our options open.

Harder, Faster, Dumber

A trip I took down the Mangoky river in Madagascar. Harder for this guy than it was for me...

A trip I took down the Mangoky river in Madagascar. Harder for this guy than it was for me…

A friend just asked me if I wanted to do an ironman or an ultra marathon with him.

Erm. No thanks.

I remember doing just the ‘normal’ (i.e. little) marathon a few years back. It was hard and not much fun and I don’t think my knees have ever been the same since.

Yet, I’ve described doing a vipassana as the hardest but most rewarding thing I’ve ever done and something I’d like to do again.

So I’m a little confused. Are the hardest things worth doing? Where should one draw the line? Does hard = good/rewarding?

There’s a prevailing mentality today that in order to succeed we must overcome really tough obstacles. We should work harder, get up earlier, run a bit faster.

I’m all for pushing the limits, but I’m not convinced that things being really hard necessarily makes them worth doing.

I’m still astounded by the number of people who want to climb Everest. Really? Why? Lots of people have done it. An 80-year-old man has done it. The mountain is covered with bodies and trash. They’re thinking about putting a staircase at the top. Seriously. A staircase.

So why bother? What does it achieve? Is it ego? Do people want to climb the biggest thing out there because, well, otherwise their lives are small and insignificant? I’d posit they’ll remain so, even if they do a half-hour headstand on the top, or climb the whole thing backwards.

If you’re a taxidermist, is the Holy Grail a blue whale? Or the flea?

At university, the course I found the easiest was the one I came top of the year in. It felt easy, yet if it wasn’t for external validation the fact that it wasn’t difficult may have left me to assume that it was the subject that was least valuable or I wasn’t good at it.

Over the last year I’ve worked really, really hard. Probably the hardest I’ve ever worked. I felt that the harder I worked, the more likely it was I’d overcome the obstacles we faced. As a tech business, the odds are bad, even for the bestest of teams. To beat those odds, many commentators suggest working ungodly hours… after all, god rested on the seventh day, or seemingly ever since.

Yet looking back over the last year, I’m not sure the 70-hour weeks have been much productive than the 40-hour weeks. In fact, surfacing the far side of this year of work, I wonder if in fact they have been less productive. A scary thought.

In the last month or so, we’ve hit upon something new and suddenly our business feels like the market is pulling it, rather than we’re pushing it. I have no idea whether or not we would have made this discovery if we hadn’t worked so hard. It’s early days – I don’t want to jinx what I think is a good momentum before it’s proven, but the early indicators are good. The important thing to note is that it doesn’t feel so tough. Is that a sign that it’s not worth doing, or in fact, as I think it might be, that we’re just on to something better?

At what point does pushing something difficult move from productivity to insanity?

It’s wonderful to fully throw yourself into something. To give it 100%. But it’s really important to recognize, that working at 100% capacity means you have to take breaks. I think I lost sight of that last year. In order for me to work at my optimum capacity, I need to only work some of the time, or the additional time spent working can be counter-productive.

As a business, we kept pushing and pushing what we wanted to achieve, and worked harder and harder to achieve it. I wonder if we should’ve stepped back and asked whether or not the fact that it was really hard meant that maybe we weren’t quite doing the right thing. All the blogs and books I’ve read about tech businesses dictate that the founding team must work round-the-clock to make something work. So I felt that by pushing as hard as I could that we’d overcome the biggest issues through sheer tenacity. Yet I wonder whether the ‘work hard’ mentality blinds us to the reality, that if there’s too much resistance, we’re probably doing something wrong. Where’s the balance?

An ultra marathon will never be easy… and I imagine that it’s very rewarding, in some ways. Yet like water in a river, do we achieve more if we follow the path of least resistance, or should we create obstacles in our path to show our strength?

Why Standing Still is Better Than Movement

My friend Pete, taking some time out from a group holiday to sit and write...

My friend Pete, taking some time out from a group holiday to just sit and write…

We are who we are.

No matter how hard we try, we’re unlikely a Damascene moment will transform us into the person we’d always hoped we’d be.

You might if you try over a number of years, change a bit. But it’s unlikely. Plus, we forget that we can get worse as well as better. Years sitting at a desk, or in an unloving relationship, can mean we become worse, not better.

I know now, despite many years railing against it, that I’m better off sleeping regular hours. I’m not very disciplined, but I have a strong will that can combat that lack of discipline. I’m lucky enough to have been blessed with a good mind, body and ear – I find work, sport and music comes easily. But that means I’ve not had to fight to be OK at them, so I’ve been lazy with those talents.

I’m good with people, but I’m also impatient and judgemental. I need people around me, to help me be a better person and yet I can lose and isolate myself in my own world. I love being active, yet I find it hard to get started and so laziness can easily prevail without a catalyst.

It’s good to try to know oneself and to work with, not against oneself.

When I did the vipassana, it gave me a chance to sit and just be and start to come to know who I am. For a while, my ego, or just sheer boredom, fought against the practice. Eventually, without anything to distract, I was forced to listen to myself.

I noticed, deep within me, somewhere at the very core of my being, that there was something constantly moving, a restlessness.

It’s hard to explain, but it was almost like there was a motor whirring deep in my abdomen. Something tense, aggravated and angry. A psychological hornet.

Vipassana enabled me to listen to it… to feel it. I realised that it had been there all my life, without ever stopping.

Throughout the 10 days, I not only noticed this phenomenon, but occasionally the motion would stop, just for a second, and I felt at peace. I remember there was a deep sense of release when this perpetual movement took a moments breather.

That’s why I often felt exhausted, I thought – because when asleep, awake, resting, drunk, happy or sad, I have been using energy to fuel this motor. A motor that does nothing. A motor that is powered by fear, stress, ambition ego and expectation.

The motor only stopped completely during vipassana, but my sense is that it moves at different speeds depending on how I feel – the faster it moves, the less balanced I am.

The motor exists to ‘drive’ me and ‘propel’ me. It is a force of ego that attempts to make me a better person and push me on, and yet it is destructive. It consumes energy without contributing. Its wheels spin in its desire to propel me to places that, paradoxically, can only truly be reached naturally.

This is a strange concept, but I’m now aware of its presence within me, almost as if my ear is now attuned to the noise it makes.

I’ve also noticed that lots of people seem to be powered by a similar energy. When we talk of stress, anger, frustration, ambition, anxiety, insecurity, desire… the elements that combine to create attachment – I notice this motor in others. I imagine the motor and the energy is used and dispelled in many different ways. We all process and cope differently. But boy, what a waste of energy.

My battle… In fact that’s the wrong word, because it wants a battle.

My challenge, I should say, is to slow it down and let it stop. To starve it of its fuel. To give up, let go and let be. To recognize that change comes through acceptance and can only be reached without this motor running.

Mental note to self (although so difficult to remember) – I am what I am and the more I nurture my individual self, the less fuel this motor has and the more likely I’ll get where I want to be.

Which, is right here, at peace… rather than over there, at pace.