Tom and TEDx’s Excellent Adventure



TEDx – Behind the Schemes

My TEDx is done…

Perhaps short for ‘Tom’s Exhausting Diary’, or ‘Tom’s Extreme Dichotomy’, the latter encapsulating the hypocrisy felt giving a talk on simplicity whilst living an entirely complex life during the process.

Plus ca change.

Hopefully my outfit and, of course, the talk itself will help further explain how I feel and what I learned from the process…  this photo was taken a few buttock clenching seconds before going on stage. I look calm. I am not. That’s a pretty normal state of affairs for me. Many people have commented on how generally chilled out I appear to be…

Don’t be fooled. The last month or two have seen many sleepless nights. If I look younger than I am, my picture in the attic is heavily wrinkled.

A wise person I met a few weeks ago told me he never really understands something properly until he’s written about it. Too true. There’s a catharsis and comprehension that comes from taking the time to reflect on significant events, hence this post.

This talk couldn’t have come at a worse time for me – I was forced to write my ‘talk proposal’ during the only holiday I’d found time for this year. Spending precious moments on Vancouver Island holed up in cafes on my laptop rather than enjoying the place and time with my traveling companion.

I accepted the opportunity to do a TEDx for a few reasons. Firstly, I knew that like writing, it would force me to consolidate my thoughts. I’ve now been blogging for years and yet still am unsure as to where I’ve got to. I knew the TEDx would force me to crystallise some of these down to 12 minutes or 1500 words… to focus. Secondly, I’m terrified of public speaking, so this was a huge personal challenge, one that had sat on my bucket list for a few years. Why we put ridiculous, uncomfortable challenges on our bucket lists is also something I deal with in the talk – but I can summarise neatly in 4.5 words here – because we’re dumb.

Then, just in case I wasn’t cramming more shiny goals in to my magpie like mouth, I offered to live in a tent in rural Somerset for a month prior to the talk, as well as doing another talk at Bristol University in preparation. Double, triple dumb.

Which all would have been fine if I was a insomniac retiree, but I’ve also knew going into this that I was about to start fundraising for my business. Something that requires singleminded focus. Quadruple dumb, squared.

A TEDx talk takes A LOT of time. It was an intense few months grappling with ideas, cutting, editing, asking wonderful friends to look at the proposal and making further changes and so on.

Couple all of this with pitches to investors in boardrooms, negotiations, intense meetings and then finish the day with a trudge across a boggy field into a tent and you’ve got a highly chaotic, not-simple life.

So… What did I learn? What have I understood?

I don’t want this to be a spoiler, but there are a few thoughts I want to capture whilst they’re still fresh, as well as some of the 13,500 words and some that didn’t make it into the final cut… In no particular order:

– Nature, the outside and real life is only a put down screen and a front door away. My previous post, I hope, captures some of that wonder ( Adventures are easy to have, even if you’re at work in your normal life. At any time you could camp out for a night, or walk a different route home. Climb a wall, tree or hill. Sounds simple, I hardly ever do them.

– The more I immersed myself in the process of watching others’ behaviour, particularly with smart phones, the madder and madder the world seemed. 90% of a train platforms and whole cities filled with people staring into and relying on their devices, without even realising they’re doing it. Leave someone 10s alone and the majority will pick up a device. The damage this is doing to our psyches must be terrible. Almost everyone recognises this, but very few people do anything about it.

– We chase unrealistic, unreachable and unhealthy goals all the time, at the expense of our own happiness. People don’t know what makes them happy. We have no idea where we’re headed or why we do many of the things we do.

– Most people care more about the rewards of their work than the content.

What next… for me, a bit less. Some focus.

Perhaps a camper van to enable me to access the countryside more regularly. More of the same, I hope without quite so many of the rough edges and hypocrisy…

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…

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?


Congratulations, you’re very ordinary.

As I sit and write this, I overlook a tropical lagoon, mangroves and a few fishermen warming in the morning sun. A few energetic swifts wheel in a faint haze – evidence that despite the dry red earth and cloudless skies, the baked earth breathes life each day.

I am perched at a desk I made, 7m off the ground, sitting at this window in a house I built.  It is an extra-ordinary setting, and yet for the last few days I’ve been feeling rather ordinary.

Extraordinary Views

Extraordinary Views

I’ve been re-watching the TV adaptation of Any Human Heart by William Boyd, one of my favourite novels. Boyd sums the book up with the line, ‘Every life is both ordinary and extraordinary’. The book, and the series, is a reminder that life is a patchwork of experiences, good and bad, high and low, at times introspective whereas at others uncontrolled reaction to external events.

Even a life, with its fair modicum of ‘ordinary’, seems all the more extraordinary when condensed into 4 hours, or a few hundred pages.

What about all the uncomfortable visits to the toilet? What about the nights that seem never to end, spent half-awake worrying about things that in the morning seem inconsequential? What about the banal, useless and dull days where nothing really happens? Boyd goes some way to capture that in his book, but cannot encapsulate the true nature of time passing in a few short pages.

I’m here, in Kenya, because there is life around each corner, from swims in the lagoon, to colourful daily interactions. Yet perspective can shift these from the glorious to simply frustrating or what I call trouble in paradise.

As E. B. White said, ‘Every morning I awake, torn between a desire to save the world and an inclination to savour it. This makes it hard to plan the day’.

At the moment, I’m stuck there – somewhere between. In the ordinary. I’ve a weight of ordinary work at a desk to do, each day, in an attempt to create something extraordinary for myself and for others. Yet I’m wondering if extraordinary things do evolve from the ordinary, or if in fact I’ve got it all wrong and that if being extraordinary is the only way to produce the extraordinary.

It’s great to see Tenner, which I helped start get new life and I was reading Richard Branson’s comments on the site (surely extraordinary that a project I helped start now has the most famous entrepreneur in the world commenting upon it – give yourself that one SimpleTom). His comment, that you should do what you love is oft-repeated, clichéd even.

However, many modern businesses start with a huge amount of work, at a desk. The results can be extraordinary. Airbnb enables exploration of people, cultures and human interaction in a way that wasn’t nearly as easy 10 years ago. But the business has been created by a lot of people spending considerable time sitting at a lot of computers in a few offices (not taking into account the years spent at computers learning how to use the computers). Although developers love to problem-solve and some of the results are incredible, the thousands of nights spent coding cannot be described as extraordinary.

I’m lucky enough to know a lot of extraordinary people. But most of them do very ordinary things, most of the time. Not that that is a bad thing. However, where I find myself stuck today is wanting to kitesurf more than answer an inbox of emails, build a canoe more than re-design a user experience.

Don’t get me wrong. I’m utterly convinced in our vision and that this project is extraordinary. I know that this feeling is a passing phase after a year and a half of fun, effort and dedication. But sometimes the threads that weave together to form an incredible tapestry, or the notes that create a haunting melody are as a result of time spent in stitches (of the wrong kind) or learning and repeating endless scales.

The irony is not lost. Here’s a blog on simplicity and finding the extraordinary in the ordinary and here I am, writing a post on the desire for continual extraordinary-ness.

I recognize that every life – Darwin’s, Dahl’s, Newton’s etc have long stretches of ordinary. Today we’re fed with images from Facebook of people’s highlights (talking of Richard Branson, one recent facbook feed from a ‘friend’ was a picture of him playing chess with Branson on Necker). Those images don’t help me to remember the rewards, the extraordinariness, of ordinariness.

Perhaps it’s time to re-read Walden. Today I struggle with finding the beauty in the mundane. Moonlight can make the most colourful of landscapes appear colourless – some people might see it without the colour, others with accentuated beauty. They’re both there, in that moment.

I write this, not because I’m in a bad place, per se. A passing phase. But in recognition that simplicity is hard and because writing, exploring and sharing the feelings help.

I’ll leave you with a great post by Derek Sivers.