How I Ran My First Marathon Aged 23 (In Chicago) After Only Running 3 miles

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Hey Guys,

I still remember when I went to a conference that ultimately changed my life – back in 2008

I had graduated from Warwick University and was standing (somewhat) smug with my job offers from:

  • Deloitte (Graduate tax consulting scheme)
  • Mediaedge CIA (now Wavemaker) (Graduate rotation programme)
  • An IT recruitment sales role (with 65k OTE – I don’t remember the company name)

But something still didn’t quite feel right.

I had deferred my entry for Deloitte upon getting the role as an intern on their summer scheme in the summer of 2007.

So I had a year off, and the plan was to do some travelling (maybe), and…figure out what the hell I was doing with my life.

(Jobs, as it turned out, were not on that list)

That’s when I signed up for this interesting conference (run by an Aussie whose name I forget – but let’s call him Richie) in London.

A weekend ‘we’ll change your life type thing on Eventbrite.

The fact I was even looking for such an event (and indeed signed up) will tell you a little about my character.

In truth – I don’t remember much about that event, but I remember the most important aspects of it.

I remember that the main premise of the weekend was don’t work to live; live to work by making the work you do work that you love.

And reframe your situation. Instead of saying:

“Right Deepak you’re going to take your £27k job offer at X and not pursue your music career,” Richie said – you need to think…

‘How can I music generate a full-time income for me?’

Even asking that question TOTALLY blew my mind as a 21-year-old.

I had been an English Literature major who thought I was ahead of the game – as my peers were looking at further education programmes, moving into theatre, paid writing work of various kinds or just struggling to find ‘well paid’ work altogether.

And here I was being a badass with a Deloitte job.

Only later would I realise that I was building a ‘honey trap’ for myself – and that I’d been thinking about things totally wrong (more on my Deloitte story to come in later emails)

But there was a 2nd thing that Richie said that also stuck with me that has also changed my life forever.

Leave nothing on the table.

If you’re going to do something, and spend time doing it – give it your absolute best shot.

And so it made me wonder – what kind of results could I achieve if I added some seriousness to a hobby?

My hobby at that time had been weight training throughout the university.

But outside of keeping in shape – which I took somewhat seriously as you can see – I totally half-arsed everything else

If you look at my original shape (which I’m closer to now) at 19 – you’ll see how God made me – and that I was clearly born to run!

Although to be honest if you dig into human evolution you might argue that many of us were.

I am skinny with little natural muscular mass on my legs so I don’t cramp or suffer issues more muscular folk have.

Also – I have size 11 feet that are like flippers.

Talking of my feet – I’m almost totally flat-footed which provides great shock absorption for my knees and allows me to run great distances without injury and through arduous terrain.

Cardiovascularly – my red blood cells (as I would find out in my teens) have a slight distortion which makes them more adaptive to oxygen.

With all of this in mind – I’d discover that yes…I was born to run.

So naturally before uni (from 14 onwards) until after university (right now at 33) – running has always been what I felt I was meant to do.

However – the furthest I’d run at that point was my Black park runs with my secondary school friend Tom on a 3.5-mile loop which Tom would beat me on every time.

That was the extent of my running.

My insecurities upon starting university in 2005 and hitting the gym as a means of looking good to put to bed any opening there may have been for running.

So the furthest I’d even run was <4 miles up until I was sat there…

Hearing what Richie had to say.

And I completely heard it.


That weekend totally changed my life.

Before the event was finished…

I booked a 3-month trip through South America (starting in Caracas, Venezuela and flying out from Buenos Aires, Argentina)…


Booked a flight to Chicago…where I would run my first-ever marathon (in 2009).


Booked a trip to Germany

(side note I blogged about ALL of these experiences :P)

South America (link here)

Germany (link here)

Chicago (link here)

And all of the above – in the space of just ONE weekend.

I’d never acted so powerfully in my life it felt like at that moment.

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The conference left such a mark on me that I actually booked all of the above trips on a credit card.

I simply didn’t have the money to actually do all of those things that weekend.

There was an opportunity to buy a bigger programme with Richie and I’m sure it would have been amazing – but I got the insight I didn’t know I was looking for when I walked out of that conference.

And so I chose to spend the credit card money I had – on booking those trips.

So I guess the underlying theme here is about of taking control of your life and seeking out experience and adventure – as opposed to actual marathon running 😛

And this, in turn, generated many more actions (i.e needing to pay off my credit card)


So (over the following months) the funds for travels ultimately came from:

  • Deloitte: (and their ‘golden handshake’ programme where they give you 7k interest-free to spend on your gap year)
  • Barnhill Secondary School reception and Uxbridge College Admin (two places I had to work part/full time to earn some extra pennies for my trip)
  • Borrowing money (My sister lent me some money for this trip – which I would pay back some years later)

So that notion…that “if you’re going to do something – then give that something your absolute best shot” was such a mind-blowing notion to me.

It stuck with me and ultimately led me to –

  • Going away to the USA for the first time.
  • Going with my French girlfriend (at that time) together to Chicago.
  • Discovering couch surfing
  • Staying with Darryl (whom I’m still connected with on Facebook)
  • Running my first-ever marathon

And much more >>>>

Training for a marathon whilst I was backpacking through South America (nosebleeds running in La Paz; getting chased by dogs in a construction site in Potosí, running down train tracks in Buenos Aires)

Featuring in local newspapers and national radio when I came back (as for part of my training I ran from my mum’s place to Buckingham Palace).

And raising money for an Indian charity through the Prince’s Trust (I think I raised less than <£200 lol).

And all of this cascade of events ultimately came from that world-shattering notion that Richie shared with me.

Since I WAS running – why not try and give my best to it?

And do this by setting a real tangible goal.

Humans are driven by creation; hard work; and having something to strive towards.

I didn’t know it then – but I was tapping into a fundamental part of the human psyche about goal setting, and having ambitious goals and all that it could bring (like Chicago town pizza – a pleasant upshot of the trip).

My ‘impulsiveness’ that I’ve had all my life – has its roots in moments like this.

I heard something mind-blowing – and immediately did my best to align it to my life – and I would certainly suggest you consider doing the same thing.

It’s weird looking back and realising that it was that moment over a decade ago that ultimately led me to compete in 40+ endurance events I’ve done around the world today.

Going back to the Chicago 2009 marathon – my first ever marathon…

My time was pretty horrendous – 4 hours. and 47 minutes (check out my blog I kept on the whole trip for more).

I would not want to be waiting for me at that finish line.

But Daryll did.

And Charlene did.

So I share that time with you and share it with pride.

That time led to dozens of more times 😛

And that crappy run that led a nurse to ask me if ‘I need medical assistance’ at the end of the race when I was doubled over – has bought me so many more things in my life.

And so this email (I guess) was never about what I gave in the race, but by deciding to race – what the race gave me.

What race can you start running?

Changing tact as we finish up – the other race I have been attempting to run is building a path to my financial freedom – and it is in this that I’ll return to for the next newsletter

And talk to you about how I’m continuing to build passive forms of income.