The Happy Entrepreneur

Is a ‘happy entrepreneur’ a misnomer?

Being an entrepreneur is hard. Really hard. Or, in the words of Elon Musk, “Being an entrepreneur is like eating glass and staring into the abyss of death.” If that’s what it’s like when it’s working, given Elon is one of the most successful entrepreneurs alive, what hope do the rest of us have of enjoying it? Ouch.

I’ve spent a lot of my career recommending people become entrepreneurs, but sometimes I hesitate. At times I’ve coveted a 9-5, well-paid, corporate job. Admitting that, I feel a bit like a traitor to my vocation. Like David Attenborough suggesting he’d rather be an endangered species taxidermist. But the more I learn and talk to others, the more I learn that this is normal.

In this article, I want to address some of the things that I wish I’d known, or learned, sooner on the entrepreneurial journey. I believe there are ways to be happy as an entrepreneur, yet very few of us are and it requires even more work and focus to become one. 

Why Entrepreneurship?

Entrepreneurship is, in many ways, amazing. There’s something captivating about it; it’s empowering, creative, exciting and addictive. It’s a powerful, if not revolutionary, force in the modern world; with an intoxicating Schumpeterian ‘Creative Destruction’ occurring at rapid place in the music, media, hotel and taxi industries, to name just a few. As parodied in HBO’s fantastic Silicon Valley, entrepreneurs aim to “make the world a better place,” (and sometimes they even do)!

Despite how hard it is, it’s rare that people go back to a corporate job once they’ve tasted life in a startup. Yet for all of the media glamorisation, it’s often deeply unhealthy, stressful and – particularly in the tech sector – entrepreneurs have an extraordinarily low probability of success.

Probabilities and Hardship

By way of example, Google has 56,000 employees and more resources and freedom than perhaps any other company in terms of innovation. In 15 years it has come up with just one monetisation technique that contributes to ~95% of its revenues. Just one.

At the other end of the spectrum, 80-90% of startup founders that receive venture funding don’t exit with more than their (usually dramatically reduced) salaries. Just 0.1% of pre-funded tech startups ‘succeed’. That’s a terrible compensation for the stress and impact on their lives. The resulting psychological impact can be extreme, as these articles demonstrate:

Founder Depression by Sam Altman

Brad Feld, Depression 

Business Insider, Founder Suicides

The Journey

This photo, of the Wholi team on a retreat in Italy, fairly neatly sums up the journey...

This photo, of the Wholi team on a retreat in Italy, is a fairly good representation of the startup journey…

Given the difficulty and unlikely success, it’s important to try not to base all of one’s happiness on a result. One of our values at Wholi is enjoying ‘the journey’ – meaning that we want to enjoy the process and the day-to-day – regardless of the destination. Our values are aspirational as much as actual, a recognition of the things we want to be rather than necessarily the things we are. When things don’t go well – which they often don’t in a startup, it serves as an important reminder.

Mostly speaking, I have not been good at enjoying the journey, (Wholi’s journey is captured here on our Facebook page). I am beginning, slowly, to listen and act – to stress less and enjoy it more – with help from my team, peers and investors.

I am not transformed. The gulf between my ideal and actual self will always be there, but I am in the process of making some changes and I find writing one of the best ways to process, to understand and to set intention.

What follows is a (non-exhaustive) list of some things I’m working on and things I wish I’d done earlier, in an attempt to help others, or those starting out: 

Find out what you’re good at. Leave the rest.

I’ve only recently started coaching, so I can’t claim any Damascene moments just yet, but I am seeing glimmers. My coach tells me that his role is to find what people are naturally amazing at and help them find ways to focus those talents and leave the rest.

If there was a single piece of advice I could transmit to my teenage self it would, I believe, be this.

The issue is that what we’re good at often comes naturally, therefore we don’t identify it as a skill – we think it’s just ’normal’ – and as a result we don’t harness and enhance these skills into a super power.

One of my skills is empathy. I can often read a room, or a person, and am highly attuned to small cues, feelings, sensations and the emotions around me. Yet for many years – particularly throughout school – that empathy, or sensitivity was a weakness to be covered up, not a skill to be harnessed. I’ve spent far more energy trying to be tough than I have nurturing that skill and turning it into a superpower. Time to listen.

The ‘leave the rest’ bit is vital for entrepreneurs. The role often forces us to do a bit of everything. For me, I believe that has been destructive. Trying to be good at, or forcing the things that aren’t skills, has consumed a huge amount of energy in my life. Entrepreneurs often focusing attention on and believing that we must tackle every challenge. This is a mistake.

A initial closer analysis of my own ‘work’ has uncovered that many of the things that I’m best at, I don’t consider work and therefore I regularly feel guilty that I’m not working enough – even though by some measures I’m working a lot harder than I realise.

Certainly entrepreneurs will have to do things they’re not good at, but I believe that it is only by harnessing our natural strengths, focusing on them and recognising them – sometimes to the detriment of other ‘important’ things, or harnessing other people’s strengths to cover these – that we can truly be successful and happy; both in entrepreneurship and in life.  

Energy & Putting your own oxygen mask on first

Follow the advice about finding what you’re good at will transform (at least in my limited experience) one’s energy. If you harness a natural momentum, it’s easier to make progress.

If there was one measurement that would correlate with my being a happy entrepreneur (and therefore more likely to be successful), I believe it’s ‘energy’. Meaning how you feel on an energetic level — read this excellent HBR article for a better understand of what this means.

A friend (who’s also a coach) sent me this, claiming it’s one of the most important articles she has read when it comes to helping entrepreneurs. I agree. ‘Put your own oxygen mask on first’.

Entrepreneurs should be incredibly sensitive to their energy and foster it wherever possible. If you need to justify free weekends and evenings, just look at the HBR article in some more detail.

Founder Confidence

I’ve read a collection of articles recently about founder confidence and how often the brazen pitches and networking displays mask deeper, destructive insecurities that plague many founders.

Again, these tie into the previous two sections. If we find what we’re good at and leave rest, then focus on maximising our energy, we build confidence. Confidence is key. Entrepreneurs need to continually make decisions and hope they’re right. Often they won’t be. Yet we must have confidence. Study leading entrepreneurs – Elon Musk (despite how hard he claims it is), Steve Jobs and others and you’ll hear of a boundless confidence. I believe that confidence can be cultivated.

Get Support

Get help. Seriously.

Entrepreneurship is a lonely game, compounded by the need to present a positive, upbeat face to customers and your stakeholders. This exacerbates a failure to seek and ask for support.

Entrepreneurs need, desperately at times, to set up support mechanisms to help them. In my case a quarterly meeting with fellow CEOs where we ‘lift the kimono’ and describe what’s actually happening, provides some solace. Coaching, friends, team members, fellow entrepreneurs, networks, articles and other sources have too, but they need to be cultivated. Get over the issue of worrying that people will judge you because you have problems and ask for help. Lots.

I am still not very good at this, but trying to get better. Mark Suster wrote a great article about getting your mojo back here.

Finding Balance

Entrepreneurship is hard. So we put up with lots of hard things that don’t need to be so. A fellow entrepreneur I know gets up at the crack of dawn to catch early flights in order to ‘seize the day’. I believe it’s a huge drain on his energy and negatively affects his work. Another pulls an all-nighter once a fortnight, again, I believe, creating more of a deficit than a gain. As entrepreneurs, we should be looking for ways to make life easier, not harder.

I don’t schedule in early meetings, or fly late at night, or on weekends – even with an office in Romania. I spent a year carrying things to and from that office, before deciding to invest in two pairs of running shoes, two yoga mats, two sets of toiletries and so on. A small change, but my travel burden is a little easier. I try to ‘work like it’s the weekend. I worked from home for almost 2 years, before I realised it was much more costly to one’s emotional health than the expense of renting an office. My own battle with balance was the topic of my TEDx.

At Wholi, we have some role models who have found a semblance of balance. We love Richard Semler of Semco – his TED is here. Yvon Chouinard. 37 Signals, and Buffer. Whilst we at Wholi are in pre-product market fit phase, these companies have managed to grow into significant businesses whilst maintaining some balance and doing things differently. That’s truly inspirational.

If your life depended on it

There is a lot here, so much so that many of the topics could be an article – a book even – in their own right. Depression, stress, energy and so many solutions from meditation, sleep, diet exercise, therapy, coaching, holidays, avoiding things you’re not good at, mindfulness.

To sum up, if you were going on a polar expedition, you would be fastidious about your energy, your equipment and your health. While being an entrepreneur involves a lower risk of frostbite, it’s often a longer, harder journey.

If you’re an entrepreneur, treat getting this right as if your life depended on it. It does.

Sometimes we even go to cafes named after our values, just to remind us...

Sometimes we even go to cafes named after our values, just to remind us…

Recast

Here’s an article that appeared in the wonderful Waterlog magazine this summer and explains why I’ve not been writing so much recently…

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My hazy first memory is of trying to fish – a kaleidoscopic jumble retained by my three-year-old mind, reassembled 30 years later.

It all started with the discovery of a worm in our garden. I am unsure whether an instinct was ignited, or whether it triggered some earlier yet forgotten connection, but I was compelled to act. Bubbling with the youthful excitement unique to a small child, I clasped the poor creature between my little fingers and ran into our house, looking for something… anything that might help me sate my desperation to fish. Disgorging cupboards and pulling drawers to the floor, I turned the house upside-down single-handedly, the squirming worm in the other, before I unearthed a pink ribbon, deep in a drawer.

Rushing breathlessly back out to our meagre garden pond, I wrapped the worm in the end of the ribbon and made my first ever cast. My excitement became despair as I watched the worm unravel from the ribbon, plop into the pond and sink, writhing into hidden depths along with my dreams of fishing that day.

Whilst other anglers will understand this instinctual pull, most of society, my parents included, don’t relate at all. My first fish was eventually caught a few years, later with marginally better tackle and skill, in Hampstead Ponds, North London. Distracted, I was chatting to a friend when a passer-by mentioned my float was bobbing around. Reeling in I found a wriggling silvery-golden roach, as exciting to me as Charlie’s Golden Ticket, which served to end my dry spell and further intensify my passion.

I think, peering into the ripples of memories past, that I decided to become a Chorister at Winchester Cathedral solely because the River Itchen bubbled past my boarding house and that I’d seen someone catching trout in the sparklingly clear water when I went to visit.

There were many times I pulled my reluctant Mum or Dad out of bed at 6 in the morning to go and sit by some lakes in the rain. Very few fish were caught. I can only imagine how tedious it must have been for them. Without a mentor or more knowledgeable angler than myself, I relied on the programme ‘Go Fishing’ and the books I read to pick up my craft and, being someone who learns best through gathering up knowledge from doing something and being shown, I was bad. I bought and used the wrong gear in the wrong places. Like that first fishing experience in my pond, there was far more anticipation than action.

Only a few fishing memories – many unremarkable – remain. There were no Damascene monsters. I remember aged perhaps 9, hooking and landing a sacred Koi carp handlined from an large ornamental pond in Thailand, to the horror of the local staff at the hotel. There were trips to the local ponds where, armed with a  match-stick and a single maggot on a weeny hook I had some great hauls of teeny-tiny roach and perch. A hook straight through my finger (the largest thing I’ve ever hooked) resulting in a minor op at a local doctors surgery. A single trout, caught on my tackle when I’d gone to the loo by another angler in the Lake District. The odd crayfish and bigger perch and roach from London ponds. An eel from the Norfolk broads which slipped between the slats of my landing platform, wriggling away before I could claim to have properly ‘caught’ it, leaving me in floods of disappointed tears. I can only remember perhaps a dozen trips in a dozen years, most unsuccessful. There was little, it seems, to have sustained my dreams.

Later, in my mid-teens, I begged permission to fish in an old estate lake where everyone else was far more interested in the golf course. There, I started to come into my own. Fishing with three rods, I once had three carp on simultaneously – bringing two into the bank but losing a third on a rod that I’d clasped between my legs. My greatest day saw 14 fish brought to bank, including a few low doubles. Yet despite this increasing luck, aged about 16 I downed my rods and then didn’t touch them for close to 20 years. Fishing was no longer exciting, or interesting. Whatever magic that had cast its spell in my youth had slipped away, leaving me ambivalent.

In the subsequent two decades, I only fished a few times – catching wahoo and sailfish on a few trips in East Africa. I caught mackerel in the UK and went carp fishing on a couple of occasions with friends who had a plethora of the latest kit and I caught a few fish. My old tackle, which I’d brought along to demonstrate some kind of willing and past skill, served only to provoke laughter. Yet despite stirrings, the trips left me mostly uninterested. I’d felt an outsider, a disconnect between that old excitement and my knowledge, ability and desire.

As you get older you lose the childish wonder and excitement. Certainly, I no longer wake up at 5am, a gnawing bundle of anticipation before holidays, Christmas or buying something I’ve really wanted. A rod or a reel that previously would’ve had me salivating beneath the torchlit duvet covers of my youth are no longer a financial issue and yet there’s has been no draw… Fishing was, I thought, some adolescent fancy, a hobby relegated to immaturity…

…Until two summers ago.

A couple of trips fly fishing with a friend reignited a feint glimmer of memory. Now that I am a man – at least physically and financially – with my own car, sufficient income and free will, I no longer need to persuade anyone to take me fishing. Slowly the glimmer has brightened. A single fish in a few sessions was enough to rekindle something, drawing me in. It took a few trips, a few fish, a few copies of Waterlog – before I realised I’ve become hooked again. It’s crept up on me. I feel that youthful tingle stirring deep within me.

I am still unsure why I connect to fishing so deeply. Fortunately, now that I am older, perhaps wiser, I am also able to examine fishing and what it means to me more objectively. I am aware that the fish had little to do with it. In fact, I’ve realised, they’ve rarely had anything to do with it.

Reading ‘Waterlog’ for the first time, coupled with some of Chris Yates’s books and watching ‘A Passion for Angling’ have helped me understand this yearning. I don’t go fishing to catch fish. Fishing is my meditation. If anything, hooking a fish to me is the end of the anticipation and the beginning of the practical. Like a build up in a song or a kiss, it is often the moment before the break – in fishing the bite – the tension that occurs before the thing happens which is, for me, the purest, most magical moment. When I am actually connected with a fish, I feel a sense of anticlimax. I still enjoy playing and catching fish very much, but for me, it’s not the favourite part. Certainly I wouldn’t want to fish to deliberately not catch anything. If I was to cast an un-baited hook it would be almost the same thing yet it would be a hollow activity with little joy. I want to catch fish and will try my hardest to do so, but the catching part isn’t the climax that many believe it to be.

So what is it? I like to float fish far more than I do any other style of fishing. There’s something about it, the float providing a connection to a different world lying deep beneath the reflective surface. Watching a float is a meditation, everything else falls away and I am connected to it, which in turn is linked to the depths, almost plumbing a subconscious. Although fly-fishing never really appealed in my youth, that’s almost all I’ve done since this passion has been rekindled. A friend taught me the ‘New Zealand’ style, a way of float-fishing whilst fly fishing, where the fly sits deeper in the water, marked by a surface float. I’m told the purists frown on this type of fishing – some people believe trout should only be taken from the top of the water – but for me, this style of fishing is far superior. I am reconnected to the depths, and in turn myself, by that visual cue. It’s why I love it so much.

My passion has been rediscovered 25 minutes drive from my urban home, in a secret magical location that probably been the same way for hundreds of years. The routine itself holds some magic. I pick up a key, left for me behind a rock next an old estate building and then drive through a number of fields and locked gates. Then, passing through a canopy of oaks and beeches, I pull up next to the water. I’m received by a glistening, lily-fringed, four acre lake, protected in a valley by a ring of ancient woodland. Unlocking the beautiful gothic boat house, I look for the roosting bats above me that hang from two-hundred-year old rafters and load a punt in the cave-like basement, feeling a little like the Phantom of the Opera. Then, sliding out of the  musty dark, through ancient stone arches and into the light – I am reborn. The weight of whatever stress I hold drops away as I drift into this heaven. Usually the only fisherman on the lake, I watch herons and kingfishers as I manoeuvre into the places I’m slowly learning might hold fish, weigh anchor and try to take a little time to savour the moment and prepare my tackle.

Here, amongst the trees, water and nature, I am at peace. Sometimes I take friends but part of me is relieved if they cancel. When free from company, I’m treated with a few precious hours alone. I’d like to say ‘with my thoughts’ but instead it’s more like ‘without my thoughts’. A time of tranquility, of gentle anticipation and, of course, a few fish.

And so, fishing has crept back into my life. I don’t want to go on long fishing holidays or catch the biggest fish. I’m not interested in new tackle or toys. I’m not even that concerned with changing my rig, or trying new waters. The simplicity is far more rewarding. Getting to know the ins and outs of this location – where herons nest, where fish move, the different lights at different times of day. Diving off the side of the punt to enjoy a summer night’s swim. Where to position the boat so as to prolong the warmth of the evening sunshine through the trees as the day fades.

I simply love being able to take myself away and spend some evenings reconnecting with the natural, with myself. Whether I catch a dozen or a duo of fish, I am somewhat unconcerned. For now, it’s trout, the location and it’s familiarity that satiates that need. I feel a gentle pull to head back to course fishing slowly growing within me, but it will come when it comes. Perhaps most importantly I feel a solid reconnection with my younger self. I am making up for lost time. After years of abandonment, of growing up and out, I am back fishing two times a week despite my full diary. I never had a fishing mentor or guide to take me and teach me, but now I am that man.

I’ve come a long way, yet I am back where I started…

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Boarding Up the Soul

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To those unfamiliar with the concept, sending ones children to boarding school is a shockingly weird thing to do.

Imagine you had never heard of a boarding school before, and I explained to you that parents would not only choose, but spend huge amounts of money (the equivalent of the average UK wage after tax), to remove children from their families and instead hand them over to a large, loveless institution where these youngsters would be tended by adults in a ration of ~1:20, far from home, with far less comfort. You would assume I was preaching a kind of dystopian nightmare. A ‘Brave New World’ of education.

Yet because boarding school is so familiar to us in the UK – synonymous with cricket, stiff upper lips and the class system – we are immune to its freakishness.

Unfortunately, there is no control experiment for a child who went to boarding school. Which means determining its impact is a problem. Certainly there are patterns, but the combination of nature and nurture ensures that there are almost infinite permutations. As with other aspects of growing up, no-one knows its impact on the specific individual and with that views diverge wildly.

Plus education is so important that we must make considerable sacrifices, right?

To many, boarding is highly beneficial, resulting in a world-class education and ‘preparation’ for the world (hence a ‘prep’ school). Or at least it is benign – a sacrifice worth making. To others, it is mildly or deeply harmful – the source of immensely damaging and lasting trauma.

For many years, I’d not given a huge amount of thought to the process or impacts of boarding on me or others. It seemed to me in context, as it is to most of those who participated, normal.

Yet through therapy, reading and exploring, one looks at the ingredients that make up the recipe of ourselves and try to determine the effects of significant past events and circumstances. At dinner the other night, I was reminded that I’ve been banging on about boarding school for some time. It has become ‘a theme’ and in the spirit of only really understanding something when I have written about it, I want if I can, to shift from ‘banging on’, to a more thoughtful, considered perspective.

To be objective, it is first important to eradicate any guilt: let’s forget about the perceived ‘privilege’, for a while. Complaining about boarding school can be seen as deeply ungrateful or unfair, considering the opportunity and that privilege. I don’t give a monkeys. To sweep impactful experiences away because we ‘should’ feel something drives us toward too many emotional follies. To ignore these problems because of some perceived luck only serves to perpetuate and amplify these issues.

I don’t feel guilty about going to boarding school. I would also hope that I can eradicate any guilt if I conclude that boarding school is, as I fear it was/might be, extraordinarily harmful. I don’t want to shy away from it just because it might offend or upset people – especially my parents. I fear that much isn’t talked about because of guilt, avoidance and, of course, some of the perceived positives that come from the system, such as creating those that are stiff-upper lipped, tough and unemotional. Character traits that are in fact a source of pride to some British. Boarding schools teach survival, so those who’ve been through its process tend not to complain, or rock the boat because it was instilled in us that such behaviour was weak and disappointing. In addition, there is a danger that for those who feel the effects of the human condition more keenly, especially those who had an unhappy schooling, it becomes an easy scapegoat, something to blame or use as an excuse.

Plus, my experience is of course, only that.

I first went away to school at 8 or 9. Whilst I don’t want to write an extensive memoire, it is worth exploring some of the feelings it provoked… When I think back, I remember many things – although much I had/have forgotten (deliberately?).

There was a marked transition on arrival from my happy, tactile home life into a cold, austere high-ceilinged dormitory (that looked very like the below, although we were lucky enough to be allowed to see in colour) with squeaking beds, itchy nylon blankets, fierce matrons, and twelve other children. I remember rows of sinks, a perpetual clinical smell, shorts in winter, frozen mud-caked fields, fear and missing. The opposite of a home.

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In addition to becoming a boarder, I simultaneously started as a Chorister – singing seven services in a Cathedral a week and staying at school long into the holidays to ensure we were there for Easter, Christmas and Summer services. A Chorister’s life is extreme, cramming 2-3 hours of music into an already full day, most ending in a service dressed in a cassock, ruff(!) and surplice. Essentially embarking on a serious, adult and intensive job, alongside my schooling. Performing in an huge, ancient building each day with all of the strange ceremony that accompanies a religion. My childhood was murdered in that in that Cathedral.

Whilst the change was extreme, there was also a continual reminder of privilege, of excitement. It wasn’t all bad. As an eight-year old I felt grown up, I felt ready. There was the camaraderie of being part of something, of embarking in an adventure. I wasn’t ‘sent away’ – my parents are loving, kind, caring people – they just thought it was was the best thing for me. They thought the trade was worth it. They hadn’t boarded themselves, so they did not have first hand experience – although those that do often believe it was ‘the making of them’. I wonder if those people know themselves very well?

Yet there are some things that I have begun to see, with 25 years perspective, that are just plain abnormal. The unrelenting missing of those that you love. As hurtful as it might be for any parent to hear, there is a huge pain and misunderstanding associated with, essentially, becoming an orphan 6.5 days a week, even if it was a mutual decision to go away, a child isn’t capable of anticipating the pain.

A deeply intense hatred of the singing I had to do burned within me – so much so that I used to scream into a pillow to lose my voice. Strangely, the only respite that gave me was turning pages in an organ loft at the very same service that I was hoping to avoid – but it was enough of a rebellion and a change from the routine that it somehow helped and so I screamed and screamed. I longed to and loved to get sick, to stay in bed for a few days. I broke rules wherever I could, somewhat pathologically, my youthful spirit deemed harmful and dangerous.

When I look back, I simply didn’t know that the strength of the emotions I felt – the rage, anger, apathy, boredom, annoyance, missing, desperation – were caused by something external to me, or that they were abnormal. At that age, I had no tools to deal with or understand them, nor anyone save for remote, unemotional masters to model myself on or to seek solace from. There was no soft respite from school in the evenings or even when other normal children were on holiday. I thought the feelings I felt meant I was failing, a disappointment, that I was the problem, and because everyone else was hiding theirs, it was just me. So I just swallowed those emotions and learned to ignore them, to bury them away.

As a 9-year old you don’t have a clue what emotions are coming from where or how to stem those that are most painful. I didn’t know that the outside environment might be the problem. I thought I was alone in them. So much so that it took me many years to recognise that this wasn’t normal. The weakness associated with homesickness, in turn led to ignoring emotions because they were a noose that tightened as you struggled. Instead, I simply learned to survive, as best as I could… and the easiest way was to cauterise the pain.

As is mentioned in the documentary ‘The Making of Them’, there is simply no love in a boarding school, which means that for the majority of boarders lives, there is no love. Think about that. Go to a boarding school from aged 8 until 18 and you’ve essentially had a decade of surviving without love, with stunted emotions because you don’t want to feel the various pains associated with being in a non-loving environment, all whilst going through one of the most difficult times of life – puberty. 25-years later, I’m somewhat astonished that this is considered a good thing. Yet it’s so tied into the fabric of our society that even those who were subjected to it haven’t realised the impact or they have subsumed the feelings.

It’s unsurprising that a child shuts down. In my case, those years as a Chorister at prep school where followed by going on to a different school where for 3 years (out of 5), I was both unpopular and bullied. Bullying is unpleasant at any school, but at boarding school there is quite literally no escape. You sleep, eat, work and live with your aggressors and you cannot get away. You are trapped. That’s torture – to be reminded of your worthlessness every minute of every day without respite and, of course, without love or the sanctuary of home or just somewhere else to get away to. I think I’d rather go to prison than relive the 12-person dormitory situation aged 13, living amongst people that hate you and you hate. But I never really told anyone, I just lumped it because admitting you were struggling was a sign of weakness. My parents were no longer a support structure because they couldn’t help (save for extracting me from a school that they reminded me they were paying huge sums of money to keep me in). They would have, I guess, if they’d known, but I never told them. I kept quiet, as most are conditioned to do. So quiet that I haven’t even recognised it myself.

To this day, I think I have almost nightly dreams of rejection and of being cast out of a group. I say I think, because strangely, I’ve only recently become aware of these dreams, despite how regularly they occur. You might think that is an extraordinary oversight, to literally ignore something that happens every night. Yet remember, I have been schooled – for a decade – to carefully ignore these feelings.

I have spent much of my adult life feeling tired and never fully feeling rested, despite getting on average 8 hours sleep per night. I wonder whether this is because each morning my psyche has to painstakingly sweep an emotional basement of cobwebs under the carpet, and continues to do so subconsciously during the day? This might seem extreme, fanciful or just a neat scapegoat for the fact that I’m just not as sprightly as I used to be. Perhaps this is normal. Again, it’s hard to separate out the root causes or contributing factors to a infinitely complex emotional state. But I wonder. Are there scars that are still trying to heal all these years on?

Certainly, I believe there are scars that still significantly effect my love life. My relationships have been few and far between and have generally imploded because I haven’t been able to let go. I tend to have my excuses and my escape plan ready from the start – a self-fulfilling prophecy. There was a single big exception, when I fell in love very deeply, but I think subconsciously I thought that the relationship might make me ‘whole again’. That this feeling of love might cure my childhood wounds of separation. She never stood a chance. I plied so much pressure on that relationship, like a drowning man clinging to another, that I sunk it, the relationship ending with a mighty crack of my broken heart.

Through this prism of analysis, I notice classic symptoms of the effects of boarding in a previous post (Burned Man). Ironically (or perhaps poignantly), I am now in a relationship with the girl/lady who scooped me up after Burning Man, someone who saw me in my raw, unarmored state. Yet it has been a struggle for us both. I am not sure where I’ve put the keys to my heart that is hidden deep beneath my armour. Strangely, whilst I felt like I survived very badly at boarding school, the armour that I needed back then finally solidified many years later in my 20s and 30s, as if wheels had been put in motion for a Frankensinian (come on spell check, that’s gotta be a word) change that in fact took significant time to crystallise and was long past its sell-by date when it materialised.

I was and am sensitive person who has learned to keep my emotional nerve-endings protected. I’ve avoided authority (I’m an entrepreneur), I’ve avoided settling (living in multiple countries/cities as a single man) and I’ve avoided being trapped, or rejected (by being defensive and avoidant). This sounds very woe is me, but I had a fantastic time at University and have many wonderful friends and a deeply loved and loving family. I’ve pulled a huge amount back, but remnants remain. They say that boarding school kids do well in the world because of this emotionlessness, confidence and ability to survive in difficult situations. But I no longer think the armour does anything but weigh me down.

I started this post feeling like it might be a balanced exploration, but instead I find myself just astonished and more exercised than ever by the extremity of such a normalised practice in our society. I never suffered extremes like sexual abuse. Surely it wasn’t that bad? Reading other people’s articles (see below) brings painful memories. Those who didn’t go just simply don’t understand – in fact many who did don’t either. Those who went at 12/13 probably had a different experience from those who went at 8. In fact, everyone had a different experience.

Who knows, my control experiment might have had me suffering more going to a day school. I recognise that suffering is universal. I am not claiming this as my own, by any stretch of the imagination. At some point you have to take responsibility for oneself (like a good boarding school kid).

But today, I’d much rather feel well than do well, be open than be tough, have a heart than a stiff upper lip…

To grow I need to recognise what boarding was for what it was. Deeply traumatic and unhealthy. Now I simply want to coax that emotional me back out again from beneath the layers of armour – to value rather than to fear vulnerability… and, by writing, perhaps I can help others prevent, or at least recognise this problem earlier. I feel like I’m only just getting started with this topic – it is so deeply complex and masked – and yet I feel like I’ve said enough, perhaps way too much. That this is just self-absorption at fever pitch. There’s my boarding school ‘strategic survivor personality’ kicking in. Don’t make a fuss. Jolly good, carry on. Chin up.

But to be clear I’m not asking for sympathy. It’s not about excuses, but about recognition and working to enliven and exercise those deadened emotions, like a physiotherapist with a wounded body.

The accident has happened and it was exactly that, an accident. It was no-one’s fault – no one is to blame. It happened. Sorry Dad, you can’t have your money back. I am a survivor and now I must try to heal as best as I can.

Some further reading:
http://printheadz.blogspot.co.uk/2014/07/a-new-reflectionemotional-shutdown-and.html http://www.theguardian.com/commentisfree/2012/jan/16/boarding-school-bastion-cruelty
http://www.theguardian.com/commentisfree/video/2015/feb/11/boarding-school-early-age-child-abuse-video

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.

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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 (https://simpletom.co.uk/2015/11/05/wood-you/). 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…

Wood You?

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Let’s be honest, Autumn is not a great time of year to embark upon an experiment to live out in the open, in rural Somerset, for a month. On explaining my plan friends have chortled and parents have barely concealed their bemusement (perhaps because of their recent contribution toward the purchase of a new house).

Fortunately Bristol is a non-judgemental place. While Londoners peer at their feet to see if my marbles might cause them an untimely fall, my Bristol friends have tended towards intrigue – perhaps even a hint of envy, amongst a select few.

As I sit and write this, I am propped up in a makeshift bed beneath a bundle of blankets, wondering if my batteries will last me long enough to finish this post before I head somewhere to ‘plug back in’. A cup of tea steams by my side and I’m listening to the gentle pattering of rain against canvas, to leaves fluttering their way to earth, to the clicks, patterings and rustles of a wet autumnal wood.

I’d expected cold and wet, but mostly I’ve been toasty and dry. I’d expected sleepless nights, Blair Witch style, wondering whether that snapping twig was the last sound I’d ever hear… but instead I’ve mostly been lulled into the deepest sleeps by the gentle noises of the wood. It’s not the first time I’ve chosen an odd living arrangement, last year I spent some time living in Silicon Valley in a van, and that was fun… mostly.

On November the 11th, I will give my TEDx talk in Bristol, my adopted hometown – the city where I’ve felt most at home in my life after years of traveling. I wanted, as many do, to use the TEDx platform as a way to galvanise my thoughts. For many years, I’ve been sporadically blogging about simplicity, or at least what simplicity might look like if I was good at it. One of the reasons why I write is because it helps crystallise my views. It’s a mnemonic. It enables me to take a subject, force me to think on it and draw it to some kind of resolve, or at least help find chinks of clarity.

I wanted to do the same with the talk. Although it couldn’t have come at a worse time in terms of my professional life, I decided to accept as I knew it would focus the mind and enable me to get a deeper understanding of what I actually think about these topics that I’ve been blabbering about for some time.

Given how busy I already was – couldn’t I have mused on simplicity from the confines of Bristol’s many wonderful cafes? I could have. I should have, but I wanted to see what my ‘busy’ life would look like from the perspective of a tent in the woods each evening – what I would lose and what would gain from the experience. I wanted a mini-adventure, to explore the world here as part of my everyday, rather than donning a backpack and doing it a 14-hour flight away.

I will leave the learnings and experiences to a subsequent post. I have a talk to write and no matter how many words I add, or take away, it’s a long way from perfectly expressing what I want to say. David’s post captures that frustration perfectly. Yet that is, of course, the process I signed up for. At some point I will have to draw a line under the best collection of words that I can use to express how I feel – as I do on my blog – and push it out there into the world, wondering if I could have done better with an extra week, an extra month, an extra laptop battery.

But then the title of my talk is ‘Is Ambition Killing Us’, so perhaps I should give up trying, swallow my own medicine, and just do a very mediocre talk…

Here was my view during a quick check of the venue this morning… Gulp.

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#YearofAwesome

Much of my writing feels a bit bleak. A meandering through the reflective, therapeutic corridors of my life rather than the fun and frolics. Writing offers a chance to knead internal knots, a literary massage. Yet much of my life is filled with laughter, soulfullness, adulescence and fun, and as such these e-musings might give the impression that I’m a little more morose and negative than I am. Perhaps reflection reflects badly.

However, I’m not going to change that. It’s why I write here – to explore and to unravel, not to preach or even necessarily to be read. Selfish as it might be, I write for me. Strangely though, it is when I tune into that voice that my writing seems to connect most with others.

Last year I embarked on an experiment with one of my great friends – Jim Kroft – who I’ve written about on this blog previously. The previous year his brother had decreed a ‘Year of Awesome’ and had gone on to have exactly that. Probably on account of our uncharacteristic sobriety at a New Year’s party, we decided also to embark upon our own #yearofawesome and set about planning an awesome road trip in March of that year through California together.

Waking up the next morning with man flu, I didn’t get off to a go start. But 2014 did indeed end up being a truly awesome year.

In January, I returned to San Francisco to finish our time at 500 Startups. After a January of practice and planning I pitched our company to the world at demo day (video here, in case you’re interested). In the following weeks, my co-founder Raz and I quickly raised our round from some amazing investors as I bounded into meetings bullish on awesomeness.

Shortly thereafter Jim arrived and we embarked on a two-and-a-half week odessy, chasing bears, flying drones, taking photos, lighting bonfires and recording music videos that encompassed the Sequoia National Forest, Big Sur, Las Vegas, Joshua Tree, Mojave desert and Los Angeles. One of the best two weeks I’ve had in an age, spending rare time with someone who also has so little of it.
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It’s never good to be too self-reflective

Returning home, my business partner and I built a new team in Bucharest, hiring an extraordinary team of ex-Facebook, Twitter and Dropbox stars and mapping out a new technical architecture that would enable us to index two billion profiles in six months.

In the summer I returned to San Francisco for Burning Man, which was awesome in its own unique and precious way. That humbling experience and the continued road tripping through California with friends who are still very dear to me is something that has affected me deeply.

Later in the year I took my team to Sicily, won additional funding from an EU accelerator programme and bought my dream house in Bristol. Plus there were many more awesome moments… but my aim of this post is not to be a year of awesome diary, but instead to focus on the declaration and what it brought.

At University, I gave up ‘deep shit’ one Lent, which simply meant that rather than getting embroiled in thinking too much, I just lived. I didn’t let problems or issues get in my way. The #yearofawesome was similar – a simple recipe for living that enabled a lightness with focus. Whenever I found myself at a crossroads, I’d try to follow what was most ‘awesome’. It was a times trite, but mostly it fun to goad the bombastic. Anyone following mine or Jim’s Facebook feeds probably noticed the regular exclamations of #yoa. Certainly we annoyed the hell out of friends, lovers and even each other with regular exclamations to anyone who would listen with, “hashtag, year of awesome”, accompanied by our gesticulated fingers mimicking a hashtag. I know that one friend suffering from a bout of depression found the fact that we were having a #yearofawesome particularly hard. I’m sorry, it was never meant to hurt anyone. But all-in-all 2014 was indeed awesome. A reminder that willpower is indeed a power that can be switched on and off.

The point, I’m rather slowly making, is that armed with self-propulsion and an #awesome mental attitude, it’s possible to lift oneself up, to achieve great things, to enable great things to happen. No great surprise, other than perhaps the gentle reminder that we are indeed masters and mistresses of our own destiny. The extraordinarily annoying proclamations of ‘positive mental attitude’ if channelled effectively (and supported by friends) are indeed supremely powerful.

So… although I do reflect more than perhaps I should and have a penchant for being ‘in my own head’ and deep shit, particularly here… don’t be fooled (and please tell me to snap out of it if I delve too deep) much of what goes on between these ramblings is indeed #awesome. 2015 has been pretty good so far, albeit with a less bombastic flavour. Whilst writing this post, Jim called for the first time in a few months… Clearly the wonderful serendipity and power #yoa is still with us both. When I told him the post I was writing, he declared we must get back on it. Watch this space.

For now, it would seem that the #yearofawesome gets past on by brothers – in this case to my sisters’, one who got married and moved to Bristol, 10 minutes walk from me a few months ago. And to my other sister, who’s also diving into awesomeness as her music reaches more and more ears and exciting gigs fill her diary. Here’s to #awesomeness and below is a ‘one second every day’ clip of a couple of early months in the #yearofawesome. Enjoy.