Season 1 Episode 3


I’ll start this episode with a journal entry I wrote just after I quit my job. I was sitting in an airport in Ethiopia, getting ready for a crazy trip round East Africa. Here goes..

“A few days ago I walked out of a comfortable and secure job to try and make it on my own.

I have come to realise that we are the architects and builders of our own prison walls. Only the walls are not menacing, towering, barbed wire fortifications. They are the intangible constraints of the familiar. It’s not so much a comfort zone, as it is a comfort cell. And whilst appeasement lies within the cell, happiness lies outside it.

Through spending a year in the 9-5 routine, I have come to the conclusion that it is quite simply something I refuse to maintain. Luckily, the skills I have learnt over the past year are already proving to be of exceptional use and have, to a large degree given, me the opportunity to pursue consultancy, international development and enterprise full time.

I’ve been saying for the last few years that a dream of mine is to travel the world having a good time: eating food, shaking hands and helping people out. Without realising it, I have taken perhaps the hardest step towards that dream.”

This is episode 3 of Tim Quit His Job. The show that follows me on my adventures into the wilderness as I quit my job, start a business and try and make it on my own. It’s a show for people who like to do things differently. For people who want to break away. For people who believe there is more to life than the 9-5. I’m not a guru, not an expert, not a preacher – and I don’t try to be. I’m Just a regular guy with a microphone trying to document my journey, share what I’m learning and be honest about my experiences.  The podcast is produced, edited and instrumentalised by the mighty Henri Victorious. That’s Henry with an I instead of a Y – he’s a bit French.  Check him out on Spotify. And For extra content and transcripts of these episodes, head over to my fledgling website Enjoy the episode…

In the last episode I spoke about the feeling of being stuck, of feeling like you thought life would be more interesting at this point, of feeling like you’re not being challenged enough, not reaching your full potential. Many people feel like this, most people I speak to in their 20s feel this way to some degree. As I said in the last episode, I think part of the story is that we grew up being promised too much, told we were special too many times. And that also this generation, my generation, has a particular habit for lacking a degree of gratitude and appreciation – I know I do. But there’s another side to this story, and it’s that I feel like my generation has been let down a bit.

We were sold this myth that you experience endless and uninterrupted progress throughout life: starting from nursery, working your way up to secondary school, college, university and then moving seamlessly onto the career of your dreams. It was a myth we were told to get us to suck it up and keep going to school, because if we didn’t, we would be jeopardising this future. But as soon as you graduate from university or leave school for work, you realise it was just that – a myth. Life is not a steady road, and it certainly doesn’t always go in the right direction. Instead most of us ended up in jobs we don’t really like, with mountains of university debt we don’t really understand, and with degrees we have yet to put good use. I’m generalising, but you see my point.

We’ve also been sold a lifestyle. A lifestyle that is not only peddled and exaggerated by influencers and celebrities, but also by you and me. A lifestyle of fitness videos, holiday selfies, photos before nights out and close-up shots of amazing meals. I’m definitely guilty of most, if not all of these, I can’t seem to cook a single bloody meal without sharing it on Instagram these days…The imagery of this lifestyle reminds me a bit of the TV show Friends, where you see them hanging out all the time, but you hardly ever see them working – surely the thing that hey (apart from Joey) spend most of their lives doing. Looking through social media, you rarely see posts of us at work: Enjoying our jobs, making the most of the 9-5, being proud of what we do to make an honest living. It’s as though we feel the need to ignore that aspect of our lives, hide it, because we’ve come to this collective conclusion that working isn’t living. And yet, it’s what we spend most of our lives doing.  

We have heavily burdened with the weight on unrealistic expectation. We are now led to believe that you hit your peak at 25. And if you haven’t got life – whatever that is – figured out by then, that you’re a failure. If you’re not in the perfect career, on the right path, living your best life by that time then you’ve lost the race. This is crazy! When our parents were growing up, you weren’t expected to find career success until deep into your 40s or 50s – when you were a grown man or woman, wise about the world. Your 20s were not for showing off to everyone that you had already won at life, or crippling yourself with anxiety as you compared yourself to others. It was about peace and love, about figuring it out as you go along, about growing up, making mistakes, learning. It was about stickin’ it to the man, not trying to BE the man. Our expectations are now so ridiculously high that it’s almost impossible to feel content. Impossible to just enjoy being a young adult, without also worrying that you are wasting your time.

I’m generalising and exaggerating of course, but to at least some extent that story resonates with all of us. But what are we going to do about it? What are you going to do about it? How are you gonna get yourself out of this situation? I have absolutely no idea, sorry, but I can start by telling you how I started to get out of the rut I found myself in.

The next section, where I talk about myself, goes over these bullet points. From 9:09 – 12:55

  • Wearer of many hats
  • Talk about what your title might be: Freelance consultant for non-profit startups
  • Always been good at convincing people
  • Pretty good at writing
  • Then I worked for a charity: differentiate from AI
  • Talent turned to bid writing, which I got better at as I learned about community projects from my job
  • Got lucky with the first bid
  • Then we had the security company – then the cleaning company
  • OMG we’re gonna be so rich
  • Left my job
  • Spent a lot of the remainder of my money in East Africa. We were working to get our own charity registered in Kenya, a dream of ours
  • Then I headed out to Uganda, as I worked there on a project between my second and third years whilst I was studying. I ended up buying a small plot of land there with a friend of mine. That’s also a story for another time. Went there to build a fence to protect the land
  • Then I went to Tanzania, as I had just landed a client there who wanted me to write a bid for them.
  • Then the problems…
  • Failed companies
  • Bid writing sucks, don’t get paid unless you win
  • But… Every cloud has a silver lining. You must be grateful of your circumstances
  • Living the dream and the nightmare. It’s like travelling
  • What’s next: new business models for the bid writing that enable a more reliable stram of income, getting into the movie business (helping people get funding for their films and write and present their stories), progressing my foray into property development in East Africa, helping to save the 3,000 year old frankincense industry in the highlands of Somaliland,
  • I’m more of a hunter than a grazer
  • Adopting this lifestyle has been stressful, but im pretty good under pressure. Better even. That without it
  • Being able to manage my time more flexibly has also had a few other benefits. It’s enabled me to be able to start this podcast (a dream of mine), compete in fihgint sports again, currently im boxing for a club in East Leeds, and spend more time with my girlfriend – unfortunately for her…
  • I’ll go into the ups and downs, trials and tribulations in more detail at a later date.

Now, I don’t expect that the story of how I ended up doing such a bizarre range of niche money making activities will resonate with many people, or even be of that much use. But I do think it’s important that I get it out there at this stage of the podcast series, just so you know that I’m not faking it, and that I am finding ways to survive outside of the regular 9-5. At some point I’ll go into more detail about things I’ve read and listened to over the past couple of years that have helped me move along this journey.

Instead, I’ll finish here  by talking about ‘risk’ and what economists call ‘opportunity cost’. When you tell people that you are about to quit your job and pursue some kind of hair-brained, ill-conceived money making plan like I did – the first thought that probably flashes through their mind is  – ‘gee, that sounds a bit risky’. However, we humans are incredibly loss averse, we have a far stronger emotional reaction to losing £100 than we do to gaining even £150! This hatred of losing, this tendency towards caution, has been evolutionarily hardwired into us, and it has its merits. But in the modern world, this embedded hatred of losing leads us to exaggerate the size of the risks we face in life. The more time you have to analyse something, inevitably the more risky it becomes in your own head – that’s why they tell you not to hang around too long at the top of the diving board or the half pipe, just jump.

In my situation, and perhaps you’re in the same boat, I wanted to make a change in life, but felt crippled by the risk of doing so. Visions flashed through my mind of ending up broke, penniless, alone, embarrassed, having thrown away life and dying filled with regret. It’s very dramatic. But also very unlikely. In ancient times, sure, confronting risk meant potential death at the hands of a predator or rival group. In today’s society, particularly in the first-world, failure to make things work outside of the 9-5 means, at worst, that you’ll have to borrow a bit of money from family or friends, claim some form of benefits to keep you on your feet and find another job in the short term until you try again. That’s not that bad, is it?

And this is where opportunity cost comes in. Opportunity cost is the value of the option that you don’t choose. It tells you the cost of not taking an opportunity. It’s a way of weighing up the cost of choosing one option over another, but when applied to taking risks in the modern world, it can make us realise that the real risk sometimes lies in not taking risks. Personally, I wanted to travel more, solve a broader range of complex problems, and be in charge of my own income. That was what I really wanted. And by not taking the ‘risks’ associated with quitting my job to do so, I was actually risking throwing away that dream, and living a life of regret. People always talk about ‘making the decision’ to start your own business, or go your own way, but what they don’t talk about is the fact that everyday that you wake up and don’t make actively make a change, you are making a decision.  A very important one. You are making the decision to keep things the way they are. Making the decision to not live life on your own terms. Making the decision to let your dreams and ambitions slip away.

When I was confronted with the grim reality that the path I was on was going to give me neither happiness nor fulfilment, thinking of risk and opportunity cost in these ways made me understand that the decision was easy. Decide to chase my dreams, or decide to be bored and unfulfilled – which one do you think I chose? Which option would you have taken? And what’s the worse that can happen if it all goes tits up anyway?

More than any Instagram quote, podcast or book – it was this realisation that ultimately gave me the courage to do what needed to be done….

Thank you for listening to episode 3 of Tim Quit His Job, I hope you’re enjoying the episodes so far. If you want to read transcripts of the epsiodes, or look at any extra notes and links I feel are relevant to the episodes, head over to, I started it a few days ago and I’m going to keep developing the website, adding more cool stuff to it, and making it look nicer as we go along. I’ve had a lot of feedback from people saying I should do some interview-style episodes, where I talk to other people who are in a similar position to me – finding out what made them take the leap and how they are finding things now. This is a relief to me, as I’m going to start running out of things to say real soon, so the next episode, or the one after, will have a cool, long-form discussion that you can listen to as you go about your day.

See you in a couple of weeks…


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