I had 22 jobs I think by the time I was 23. Let’s go through them and what they taught me

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It used to piss me off a bunch when I was growing up – and I was the spoiled one in my family to begin with anyway!

But we grew up – 8 of us in a three-bedroom house. My parents were minimum wage employees and my grandmother (her husband had passed away many years ago) was also a dependent.

That meant fundamentally that my parents had 6 mouths to feed outside their own.

At any given time during the first 16 years of my life – money was tight outside of putting food on the table for us and putting us through school.

I am the youngest and so was experiment number 5 (my parents started on this journey of having children when my mum was 15!).

Being spoiled, naturally, I just wanted sh*t.

And my mum’s mantra was and always has been – ‘if you want that go and get a job!’.

I used to get £5 pocket money per week from my parents and that meant the world to me. With that, I could catch a bus to go to Uxbridge, my local town centre, as well as buy some penny sweets.

What I couldn’t afford however was to go to the cinema.

So I remember complaining about this very fact to my parents and my mum retorted – ‘if you want it – earn it.

Something about the pain of her response filled me with a determination then to go out and prove to her that in fact, I COULD earn more money by myself.

I was 13 years old at the time. And so my journey into paid work – whilst I was still, of course, in school and playing where I could for my school football team – began.

Trying to figure out how to make money when you’re in a low-income family at 13 years old does something to you. Keep in mind that ‘entrepreneurship’ did not even exist in my head really until about 22.

All I knew was the modelling I could see from what was in front of me. Hard f*cking work. And not something that was proudly spoken of or talked about.

It was just what you did. You work hard, take all the hours you can get from your employer – and survive – and by some stroke of luck…maybe even thrive!

So my first job then was a local paper round delivering the local gazette (the free local paper for our area) as well as whatever leaflets were bundled with the paper that week.

Even doing this by myself (I may have gone out with my brother once or twice) was a big responsibility for me. I’d be given a load of papers and flyers and be given the streets I needed to hit and then off I’d go.

I’ll need to ask my folks how I found this job…..

Deepak pauses for a moment and actually calls his mum:

Learnings From Jobs

Click here to listen to the actual recording.


At the age of 13 had asked the local newsagents if they had any work for me during the summer holidays (and others) I began working.

And this is how my first job delivering newspapers came about.

This need and desire to work were borne in me then, and it never ever left me from that moment. I mean the only way I could get the things I wanted was by earning money all by myself.

Without building this – it was clear there were limits to my existence.

Subsequently here are the jobs that followed:

1. Paperboy (1999)

My first ever job. This taught me that you get paid when you work. And I learned more about my local area. And that dumping newspapers was something that was commonplace. Thought about it. Never dared do it. This job lasted probably a few months and I maybe made £100-250 total

2. Mechanics Assistant at MOTEST (2000)

This was my 2nd job and my first experience in a mechanics garage where I got to be around ‘working men’. I got paid £2.50 per hour and remember getting let go because I stopped coming to work sometimes because it stopped seeming worth it. I did this for a summer

3. Washing Dishes Brunel Hospitality Suite (2001)

Brian of ‘Flying Brian’ got me this job. I don’t remember his last name – he was in the same year at Evelyn’s Secondary School as my sister. I would literally wash dishes for corporate events over the summer when I was 16 if memory serves correctly. I got fired once for calling in ill (and I was!) but they thought I didn’t come in because it was the same time as a World Cup match England was playing. And I didn’t even watch football then.

4. Uxbridge Market Stall – Labourer (2003-4)

Keith – my boss! I remember approaching him when he was setting up the market stalls in Uxbridge. He said yes and paid me cash in hand at the end of each week. I was 18 and pretty damn skinny, so I struggled a little but stuck around as many others had left. It was my first time working with someone one-to-one and it was a useful insight into working life and getting to know Keith better. We’re still friends!

5. Uxbridge College Admin Office (2005)

I remember pulling up in my VW Polo the first (and only actual) car I ever had. I’d work here during my summer off from university and work doing basic admin tasks – I’d end up doing admin jobs at various places

6. NHS Admin Assistant – Hillingdon Hospital (2006)

The same as above!

7. Factory Packing Chocolate Into Boxes – Lindt (2006)

I developed quite a good relationship with a local recruitment agency – Reed. We got on well, I’d call in regularly, and I was happy to do anything to earn cash – so off I went to packing factory boxes in Stockley Business Park for a couple of days. I remember my mum getting the Lindt token box of chocolates at the end of it. My family had never heard of Lindt before. We were used to Dairy Milk type of sh*t. So I dumped the chocolate in a cupboard and by the time I heard they were decent chocolates my mum had made light work of it. £70 worth of chocolate is gone LOL.

8. Factory Packing Mobile Phone Pieces – Samsung (2006)

I worked with a bunch of Chinese overseas students (I’m hazarding a guess – they spoke Mandarin the whole time) putting phones together. This was a surreal experience. I’d almost like to do it again. I did this for just two days. Still remember it well. Really felt like I was on a conveyor belt (there was one). A literal ‘cog in the machine type of experience.

9. Day Labourer – Construction Site (2004)

Another great experience. I had to assure Reed 2x that I’ll take ANY kind of job. This paid maybe £8/9 per hour and I said let’s roll! So off I went and wandered around a construction site moving rubble with boots, and a hard hat on alongside my trusty spade. Felt like a fish out of water.

10. Day Labour – Inside A Block Being Built (2004)

Same as above in a way except for this time I was inside a building wandering around lifts that were being built. I don’t remember much of the work because I didn’t do much work other than help some guys by passing them equipment. This lasted one day – but I still remember the lift being built

11. IT Support – Warwick University (2005)

The interview was quite amusing as my friend Zurab and I (hallmates in Cryfield at University in 2005) went for the same role. We both got it and I laugh because we compared interview notes. All the questions they asked Zurab were technical (I had no clue as to those answers). All the questions they asked me were about my travels (so stories) – turns out they had travelled also – my employer. We both got the job and the job entailed me putting people on hold and asking Zurab what the answer was to their IT problems. We worked together fabulously well

12. Learning Grid Night Supervisor – Warwick University (2006)

In my first ever night shift role I would start at around 7-8 pm and wander home at 3 am. I got this job in my first year at university and worked there during the exam period. Nothing much happened at night other than fixing people’s printer/photocopying issues and generally lounging about waiting for time to pass and then having an eerie walk back to my dorm at 3/3.30am

13. Learning Grid Advisor – Warwick University (2006 – 2008)

Probably my first significant job and whilst I was at Warwick University in my 2nd and 3rd year during term-time – I would work for the rest of my time at Warwick. I was proud because it was the highest paying job on campus at that time at around £10 per hour. I remember Dean and Rachel being my managers and being such amazing people to work for. We’d have regular team meetings, the sharing of ideas to benefit the learning grid as well as discuss the challenges and expectations of the position. This is where I discovered I had a real ability to speak well in a formal environment. And from here it’s where I first began helping other students write some banking applications (i.e friends I knew).

So this was part work, part social and part skiving on Saturday mornings. I basically figured out where the cameras could not see you (or someone told me – that seems more accurate – I can’t imagine myself figuring out sh*t). I’d start at 630am and realising 80% of the time no one came in before 8 am I’d just try and take a nap.

Well, I did this all of three times, got caught once and immediately then put a stop to it lol. Sorry, Rachel if you’re watching – I think it’s you who caught me. But all in all, was a really positive and enriching experience

14. Customer Service – Odeon Cinema (2004)

This was a great social job for me. I’d hang out with the other members of staff (mostly Brunel University students – and I was the youngest on the team. I’d enjoy watching movies, serving people on the till and yes – ‘cleaning up after movies’ but also watching as many movies as I could. I always remember Sujeeta my kitchen supervisor who suspected me of skiving/letting friends in for free but could never catch me.

Of course one time he did when I let in like 10 of my friends with a bunch of free food as well. Once I got caught I was given a 10-day paid suspension pending an investigation and then was given a final warning.

As soon as Gurdeep the overall supervisor for the team told me ‘Deepak they’re watching you like a hawk – make zero f*ckups now’. I quit lol.

I remember there being a girl called Harriet on that team that I quite fancied. She was a couple of years older than me (a pattern that would ultimately recur in all my future relationships). Not that we got into a relationship or she cared! I also met a guy I’m still friends with Aman Tensue

15. Customer Service – Natwest Bank (2004)

My first ‘corporate job’. Again I was the youngest person and I remember being the highest paid – more than some of the graduates. We had a proper training programme and hotel stay in Brighton. And all when I was 18 years old before university.

Our sales targets were to upsell customers (I was on the till) – and I did this really well – I was actually the top salesperson in the branch.

Our manager Nigel (or Neil) was impressed – but I couldn’t bloody balance the till at the end of the day.

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16. Audit & Tax Rotation Programme – Deloitte

This was my first real taste of the corporate world. Here I discovered another level. To even ‘be in the conversation’ you were a relatively high performer at a red-brick (i.e top) university and had passed all the interview hurdles Deloitte put in front of you. And then when you arrived – no one cared – because you were all equal again.

Being here was useful to get exposure to more of what the corporate world would be like. And I continued to discover my flair for presenting as I’d win pitching competition after pitching competition on the basis of my communication skills.

But mostly, I remember this for the boozy nights out and most everyone is very proud of themselves for even being there – and then ramping up towards the end to make sure you got a graduate job offer upon the end of the placement

17. Tax Graduate Consultant – Deloitte

The actual graduate programme was much more just about work. Again there’d been another cull as not all of the interns had made it to the actual programme and also – the credit crunch had hit and there was MUCH less fanfare.

Now the gloves were off and it was time to just get down to work. This meant deadlines, dog eats dog and learning at breakneck speed.

I hated tax (as you know) but loved the experience of this. I was around some incredibly smart people (as was required to work through complex tax legislation) and it was spoken around the office that law firms would farm their tax law work out to the people in this office.

Such were the rumours anyway – and I would have struggled. But I again discovered whole new levels of productivity and speed and an ability to just get things done.

This was a formative experience for me because whilst historically I’d always thought of myself as a productive individual – here I discovered how slow I was true.

And what an amazing opportunity it offered me to level up – just by discovering there were whole new levels to this all!

Learnings From Jobs

18. Graduate Rotation Programme – MEC

MEC (now Wavemaker) was an awesome insight into working for a media agency as part of yet another graduate programme. I learnt about rotating between departments and desks; being pitched to by various publishers eagerly trying to befriend us all as a means to find a way in.

That part was probably the most interesting piece for me. The schmoozing and social aspect of it gave me an insight into what it was like to be pitched to constantly.

And then also to party…potentially as much as I was pitched to.

Great environment to be in which in a different (but similar) way to Deloitte was driven by politics alongside an ability to manage the client accounts.

How this worked in effect was that (e.g) Tesla would give us a bunch of their advertising money and their targets and then we would decide how to spend that income across various publishers and more.

Learnt about an industry that I’d eventually become a full-time part of with Pearl Lemon

19. Digital Marketing Manager – Indoor Media

This time I moved from the advertiser side to the publisher side – i.e this time I’d be one of the companies vying for MEC’s business.

This was my Uncle’s company so it was my first opportunity to be part of a small but successful family business.

I have good memories of the team and the culture my uncle built here – and my cousin and cousin’s later wife would work here as well – alongside two of my aunties.

I didn’t do much really in hindsight – so it was more of interest to see how the company ran meetings, and sales calls and operated as a company. I saw people come and go over the years


20. Tax Consultant – Bourne Business Consulting

I had this job for a very short period. I think the company has since went bust – but I remember this role really for 3 things:

They were a tax consultancy and had a team of maybe 10-15 total people. It was a real insight into working on the same work as I’d be doing at Deloitte – but getting much more involved.

I could sense the buzz of tax-based entrepreneurship here.

The second was that I wished to keep my nose ring on and was told I couldn’t. It was only then when I said it was for religious reasons – I put together a research piece demonstrating how it was connected to my family.

I actually got commended for this and told it was definitely the way to become successful.

And the final thing I remembered was lasting there just one week and then handing in my resignation and getting paid £900+ for a week of what essentially had been training.

At the time I thought that was fantastic.

Looking back on it I felt bad as they were choosing to invest in me and I had taken advantage of that trust.

21. Receptionist – Barnhill Secondary School

My first time working in reception – and in a secondary school.

Comments such as ‘sir are you a teacher sir?’ amused me.

Being the only male as part of an elder white female contingent was also amusing.

I’d say I stuck out like a sore thumb – but only when you looked at the people upon reception rather than the students themselves in a very multicultural school.

I’d spend half my time sitting on the computer surfing the web and waiting for a student to walk past – and for those who were late in – making sure they’d register

22. English Language Tutor – Tutoring Agency (I forget the name)

This job was working for a tutoring agency right after I shut down Deep Impakt Recordings. I needed to make an income quickly so I signed up with a bunch of agencies. I was living at my mum’s place still and remember getting the tube to Kensington where this agency was based.

They had a roster of French clientele and ultimately there was one boy, in particular, I spent a lot of time teaching English.

This was the first time I ever got paid to teach – and as has always been my style – I didn’t do any planning and made it all up when I arrived – and still, it went well.

I enjoyed teaching this boy and thank this agency because this agency is what led me to start Gobsmackers (my tutoring agency) by copying their model effectively.


Before I started life as an ‘entrepreneur’ or otherwise…I’ve definitely worked in a whole range of jobs and got a fair sense of what working life was like.

All of the above excludes the many job interviews I had – as not every application I made was successful.

The whole process has been invaluable I think of the importance of just teaching me about hard work.

I had worked in some form or another from 13 all the way up to 22 in one form or.

So after a 9-year stint in employment – it was then I decided to do something different and move into the world of entrepreneurship – were an entirely different set of learning began.

And in the next email, I’ll talk to you about the emotional challenges I have faced along the way of making such sweeping changes in my life that have led to a lot of……

Find out in the next email.