The Drawbacks & Loneliness of Entrepreneurship

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It’s day 12.

Here we go again –


Kick off!

Let’s see what ground I break over the next hour!

Right now I’m sat in the Hotel Ibis – and minus the overnight Spanish member of staff who works in two jobs and looks like a ghost each time I see him – 

It’s me 

deepak shukla

With my cup of Earl Grey tea

Bashing away quietly at my keyboard.

And now I’d like to begin –

The music blared as we all stood around the small booked table and two-stepped the night away. 

It was 10pm, and I was stood in a bar/club in Shoreditch whilst Dalvir, Tom, and James Biggs would weave effortlessly in and out of conversations

I was struggling with knowing what to say.

With how to say it.

And what the point of it was for.

There was a time long ago when I’d travelled the world and spent days with people that I met along my journey just chit-chatting. Especially during the periods out of college, then university when I’d travelled the world.

I remembered them for being really happy times in my life.

And the laughter and fun that came with the journey.

The guys at Toms’ birthday party at Old Street Records I’d known since even before those days – I’d known since I was 15 years old.

I remember at that time – one of my ‘tells’ was I’d always lead with questions.

Questions was my style, learning more about those around me.

Growing up my family weren’t storytellers much.

We were people of function, and discussions were kept to a few subjects about school, education, work or otherwise.


An awkwardness cascaded over me as I stood there wondering what in the hell I should say.

Talking about work was pretty much all I talked about.

My work is my life.

So what then to discuss with my school friends, and it made me reflect upon my conversations with some of my team.


Ion, Joe and some others would often make reference to their personal lives and what they were up to.

I listened and gave it a passing thought, but my focus was always on work-orientated discussions and little else.

Over time my entire team has become cognisant to that and there is barely any discussion about anything else.



An old photoshoot I did for a solo mixcd when I was 21 

This has come from spending closing in on half of my life alone.

After I finished university and left all my corporate jobs behind – I remember the transition from being in continually in social environments – to running a recording studio from home.

I struggled immensely with the loneliness it bought. 

With spending my days by myself whilst everyone was busy with their day jobs and the social networks that came with it.

It would ultimately take me a few years to adjust.

My parents’ home was empty for hours throughout the day, and as I got used to this new world I was living in…

I became more and more like my father.

My external words became internal discussions, and discussions became intuition and the world of my words moved inside my head.


It’s strange to think that for someone who can write so consistently, that small talk was something I really struggle with.

But it has become more and more apparent that from working alone – there are some skills that you enhance – 

Productivity, output of work – that I’ve honed over the years of working and got used to getting thing after thing actioned.

And there are some things I’ve lost – 

With my partner, I talk far too much about work – and outside this, my stories are uninteresting and still in some way work-related often.


“How’ve you been mate?!”

James Biggs was asking me – 

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James was interested in the entrepreneurial side of my life – so had given me room to discuss what was happening. And even then I struggled.

Within 2-4 minutes it was all over.

And then we moved to a space I was much more comfortable with – asking him questions about the challenges of his workplace and what his work entailed.

He was happy to oblige and talk me through the mechanics of his work.


It’s funny how things have changed over the years.

When I meet prospective new hires that are looking for work I actively avoid working alongside others.

When clients wish to meet – I tend to avoid it.

My call slots in my calendar are ten minutes long – I’m sure this has lost me a sale or two.

Now, if calls I’m on last longer than thirty minutes – something in my head tends to violently resist the continuation of that call.


My desire for small talk has diminished further still since I start Pearl Lemon.

Between Strawberry, my cat and the world of WhatsApp with my team, it seems there is not much else I need.

There’s still a couple ‘lads’ groups that I’m part of on Whatsapp where it’s a bunch of friends:


Lads lads lads!

My involvement over the years has continued to reduce and my cousin (Ajay in the image) – my relationship with him has probably changed the most.

There was – for several years – me undertaking a chase of him to meet up and hang out – and that was a happy pattern we engaged in for several years.

It has – over the last 3 years – now changed more so that he will message me.


What people don’t tell you about entrepreneurship is this – especially if you run it in a remote fashion as I do:

  1. It is a lonely road. The nature of being the person in front is that at some level everyone reports to you – so the work friendships you keep are dependent upon your business success
  2. You will if you run your company anything like me – spend most of your time alone. I’m alone pretty much from 430am until Strawberry and I spend the evening together after work
  3. The ability for you to engage in small talk will fade over time
  4. When you’re in social environments with old friends – you will see your differences more and more
  5. You’re trying to make your way to ‘the top’ – it is meant to be lonely. You’re trying to do things that most people are simply not prepared to do


We jumped into Adrian’s car to head back home to Fulham and spending a couple of hours at Tom’s birthday party.

I felt some sense of relief.

I couldn’t remember the last time I’d spoken for more than 5-10 minutes in a row about a non-work/business related event.

The evening had tested me – and as we drove off into the night…

I wondered in 10 years if it would still be the same.


It’s a wrap – catch you tomorrow 😛