jasraj's journal


a longer version of my story so far (in ~8,000 words)

Gosh, I’ve been tinkering my short bio’s online (e.g. twitter) for what seems like forever now, but it’s been a good while since I penned a lengthier ‘about me’ section.

Come to think of it, I have written a handful of long(er) introductions on the various blogs I’ve run. But it’s been a while since gone all-out with an introduction and given myself permission to share my story at length. And to be honest, lots has changed in the last few years, and even in the last couple of years, so this is probably as good a time as ever.

I was also inspired by other about me stories in the About Me Stories publication, which I’ve recently discovered since recently returning here to the Medium platform.

When I first joined Medium, I shared the below, my first ever blog post:

📝 My story so far (written: July 14th, 2015)

Here’s me checking back in for a more thorough and renewed ‘life update’.

Okay, so here goes…

Little Jas

The very first personal blog I had was my Medium one. That was the first time I introduced myself online, and it was nearly seven years ago now.

I opened that one using my full name, Jasraj. It’s always been shortened to Jas, to make it easier for others to address me, but I’ve recently been trying to try my full name on for size again. Jasraj [“jus-raaj”].

So, hi, I’m Jasraj. And now let me think of little Jas, the guy who lives on in me even if I am thirty-two now. Here he is.

We look kinda similar, don’t we?

So that was me as a kid. Sweet, wide-eyed, playful and naïve. I like to sit under my desk and pretend I was in a rocket-ship, play with my toys, and watch cartoons. I used to wake up especially for the likes of The Smurfs, The Snorks, Tom & Jerry Kids, The Moomins, The Lampies, Aquila, or whatever happened to be showing on BBC2 in that 7–7.30am slot over breakfast before it was time to leave for school.

I also loved to dream up stories for my little brother; one moment I would prepare him for a make-belief battle, and the next I would let him know that his brave efforts had afforded a meeting with the king to praise him. I played the different parts, including the king. I’m not sure he knew exactly what was going on at the time, but I sensed he appreciated that brotherly bonding time as much as I did. I recall we also used to put on little comedy shows to make the other laugh… I still remember the theme music slash intro I made up (“Welcomeeee to the shooow… the show of laughter, the show of joy…”). I’ve always had a rich and vivid imagination.

At school I remember being the same sweet and innocent kid. I loved to learn about things and so I liked my lessons at school. I did struggle a bit when I first started school, though, aged 4. I remember being bulled a little in the playground, and I would dread every PE class; I was terrified by all the gym apparatus — whether it was balancing on the beam a couple of feet above the ground, climbing over things… just generally being away from the ground wasn’t my thing. I generally wasn’t a happy bunny there, and I remember bursting into tears over my homework one evening. Thankfully mum noticed what was going on pretty quickly, and I was fortunate that my parents had the resources to send me to a lovely little school that would become my little home away from home for the next six-and-a-half years.

Oh how I loved that school. The kids there were much gentler, and the school itself was this old Grade-II listed building that felt like a big house. I remember entering through the front door and going up the big, wide spiral staircase to go “upstairs” to my classroom. It was kind of Hogwartsy come to think of it.

It was like we were all one big family there. In fact I remember sweetly-but-embarrassingly calling one of my teachers “Daddy” one time. I wanted to die a little, but Mr. Malam was lovely and he did feel fatherly. I played Chess at school (I played on board #1 eventually, and went on to compete at national inter-school tournaments), and Mr. Malam was the head of chess club so I got to spend time with him and the other chess kids pretty often, both at school and on the weekends for competitions.

So I have very happy memories of that school. Little Jas loved to learn about everything, he thrived in spelling tests (Dad had taught me how to read, something I’d failed to learn at my first, not-so-delightful school that my mum had pulled me out of, and I’d fallen in love with books), and he took great pride in all his homework, taking every piece very seriously, writing very neatly with his fountain pen, and generally getting good grades with smiley faces and gold stars. The teachers and my classmates were lovely, and even my less-favourite lessons like PE/Games were bearable in that warm environment. I have such fluffy memories when it comes to that little school.

“Big school”

I left aged 11 to go to “big school”, otherwise known as ‘secondary school’ here in England (you might know it as ‘high school’), and though it was an adjustment going to a much bigger class size/year group, bigger assemblies and bigger buildings, I slotted in there pretty nicely. I lucked out somewhat when it came to the year group I was assigned to, we were probably the most-well-behaved and nerdy class by overall standards, but it felt like that was exactly where I was supposed to be.

My love of learning continued… like I had at primary school, I pretty much enjoyed alllll the subjects. I had a pretty great time there until the age of sixteen, even with that year being the first “important year” when it came to exams (I’d gone through two rounds of SAT exams by that age, but those felt pretty chilled).

My Gallup Strengths the last time I completed the assessment (as an adult), in no particular order: Input, Intellection, Learner, Empathy, Futuristic

At that point a couple of things happened. Firstly, I had to whittle down my subjects and choose just 4 subjects to take for my first year of A-levels, which would in turn impact and inform what I was intending to study at university. Coming from an immigrant family, and going to a grammar school, and also being perceived as pretty able and “academic” (whatever that means), there really was no other option for me but university.

Up until that point, I had loved to learn for the sake of learning and enjoyed the variety that came from my schooling experience. I’d enjoy creative writing and studying Macbeth in English, or learning about the old language of Latin and accompanying Roman history of that time, about the World Wars in history, about animals and plans in Biology, or electricity and space in Physics, and so on. And so when it came to choose, I honestly didn’t want to choose. But seeing as I had to, I felt I had to choose the “proper” subjects in order to do something prestigious at university. So I picked Maths, Biology, Chemistry and German (dropping German for my second year of A-levels).

The second thing that happened was that we had a bunch of students join from other schools, I became part of a new ‘form group’ and classes were all mixed up according to the subject options you had picked. All of a sudden I had early morning tutorials with a different bunch of people, and I was sharing classes with different folks away from the same group of 30 people I’d spent mornings and all day with in my class. (I literally still remember the order of the register from those 5 years I spent with that class, and I’m also thinking about organising a re-union for us all using the email addresses we all left in our yearbook… this year marks fifteen — FIFTEEN! — years since I left secondary school. Wild.

Those last two years of school were tough for me. Up until that point I had enjoyed just ambling along and learning things for the sheer enjoyment.

I was not prepared to whittle all the subjects down to merely four options, nor was I prepared to decide what I wanted to do with the rest of my life… which is what I felt I was doing in making those choices.

I feel like I’m a part of somebody’s master plan. Go to school, get a job, get a mortgage. All I’m really doing is dying… (Avicii vs Nicky Romero: I Could Be the One)

When asked “What do you want to do… (at university, as a career, with your life)?” everyone seemed to have an answer. It was like you needed to have an answer. Looking back, I feel like most of us were just making it up and low-key freaking out beneath the surface, and the blasé-delivery of the answer we offered was actually one we were just sort of making up and trying on for size.

I struggled through those two years at school. Those “proper” maths and science subjects I’d chosen and had quite enjoyed up until that point suddenly became not so interesting. They took over my school-life, learning became more rote, to get top grades for university for a course… i.e. a course I wasn’t sure I wanted to do, at a place I didn’t know I wanted to go.

It all felt very overwhelming and disorientating.

My yearbook photo, taken in my last year of secondary (high) school.

University and my first office job

I ended up applying for one course, studying another, and dropping out after a year. I then had a year of working in my first “proper job” in an office for the first time, which was actually pretty novel and fun for me. It was a corporate with a friendly and laid-back culture, and I had my first taste of working in a professional environment in a team, and I had my own group of customers in Northern Ireland who I was process orders for, and deal with any stock-related enquiries as they arose, through a little bit of internal research and gentle haggling with company colleagues in other departments. It was a long journey each way, we’re talking two hours on a couple of trains, which made for long days but I quite liked the train ride. I re-applied for university during that year of working, securing an offer to study a difference course at a different university. So I went back and, again, dropped out after a year.

Especially that first time at university, I’d felt like a fish out of water. It was something to do with being in a new environment, away from home, and having all the freedom in the world (I could… skip lectures with like no questions aske?), but not quite rooted in who I was and what I was doing there.

Up until that point, innocent little Jas had been carried along by the currents, with a structure telling him what he was supposed to be doing (go to school… do these exams… make these choices… and so forth). All of a sudden, I was at university but I was away from home and I felt like I had these choices and decisions I could make for myself but I wasn’t used to having this level of responsibility and I really didn’t know who I was or what I wanted.

Deep down I was scared. I had no idea what I wanted to do with my life, and committing to something felt scary. Not least because, whether it was my A-level classes during those last couple of years at school, or university lectures, the way things were taught just felt so… mechanical and boring, without any real variety. Like I was being spoon-fed all of this stuff for some apparent meaningful purpose beyond passing these rote exams. And then maybe end up doing something vaguely related to those exams. When, in actuality, I didn’t know what I wanted to do and I couldn’t help but feel that what I’d end up doing would take some sort of discovery process. Hmm. You know, looking back, everything I studied in a formal education environment (school and two stints at university) just felt really dull and meaningless.

I feel like being all alone at university represented one of the unhappiest chapters of my life. I didn’t know who I was, what I was doing there, what my interests and passions were, and who “my people” were. And I was yet to really become aware of my personality and temperament, insofar as being an introverted and sensitive guy. I would just hang out with anyone and everyone, living for these temporary bursts of excitement when I’d go out and party with people I felt no connection with, and then end up hungover and miserable. This would happen both times at university, slowly I became more disconnected and miserable, skipping lectures and literally holing myself up in my room for days, emerging in the middle of the night to get something to eat when no one else was around. During this time a pornography addiction took hold, too, as I looked to numb out from the deep unhappiness I was feeling about everything.

And so after dropping out from university for the second time, something I felt really uncomfortable about when it came to my parents as I figured I would be made to stay and finish my course, despite being so unhappy and having zero clue about what do with my life. And I also felt guilty for letting them down and being a failure and all those things too. I felt pretty isolated and alone and unsettled during this whole period.

Joining — and leaving — “the City”

By this point it was shortly after the economic crisis and I was degree-less in a country — and a world — still trying to recover from the deep recession. At that time, I remember feeling like my life was f*cked and over. It feels ridiculous now, but my reality at that time had been so primed and set for “school — university — prestigious job” that I felt I’d f*cked my life up and I didn’t know what my future would now look like. Moving away from this deeply-held story would be a process.

Looking at the options I felt were available to me, I knew I enjoyed working with and helping people, and at that time I still felt I needed to make lots of money.

Why lots of money? I felt like that’s what I, able and “academic” grammar-school Jas was supposed to do, and I felt like I owed it to my parents for everything they had done for me and how hard they had worked to put me and my brother through great schools. And I quite liked the quality of life I had been given (a nice home, annual holidays, and such) too.

So I ended up in a recruitment job. I’d had some office job experience from my ‘year in between stints at university’, but I wasn’t quite prepared for picking up the phone to random people to headhunt them, or to try and take on clients to help them fill the vacancies they were hiring for. Going through a ‘training programme’ with a cohort of fellow (mostly) twenty-somethings helped, but even so it was a case of trial-by-fire.

The first recruitment company I joined was a big firm, and after the training I ended up in a team with a boss I found tricky. He was a micro-manager and always asking what I was up to or looking over my shoulder. What made it worse was that he sat next to me and so after about a year of being micro-managed, plus the long and exhausting days as an introvert doing sales (I’d often leave my house at 6.30am to commute in, and sometimes not get back until 8 or 9pm, or sometimes even later) I was eventually worn down until I could take it no more. I ended up getting off the train one day, diving into an internet café, and putting together an email to say I’d had enough and wouldn’t be coming back in. The Director who had been in charge of my training programme found out what had happened, invited me for a coffee to find out what had happened, and invited me for a position in a new team that she was taking over. I was kind of grateful and also surprised… she was someone I looked up to and clearly liked me and saw enough potential in me to offer me something in her team, after I’d done this whole maverick thing of firing my old boss via email. So I ended up joining this friendlier team with a way more chilled vibe, but I found myself in a position where I was sharing a speciality with someone else (a guy called Andy), and because I was the new kid on the block Andy was given like 80% of the existing client-base, whilst I was given very few existing clients and tasked with finding new business. I spread myself far too thin and so never really got off the ground. And so long story short it felt my time at this place had come to an end, so I looked for a recruitment gig in financial services somewhere else, and I knew I wanted a smaller firm with friendly folks and a healthier culture.

After interviewing at a few places there was one in particular that I really liked, I interviewed with the CEO and after finding out I had been turned down shortly before a summer vacation with my family came to an end, I remember sending an email to him to ask him to give me a chance and that he wouldn’t regret it. It worked, it turns out CEO Rob liked my pushing back, and it turned out to be a good move for both sides because I enjoyed my time there, as much as I could enjoy recruitment, I really liked the people and I ended up becoming one of the top-performers there. The days weren’t quite as long either, but this was still me doing a sales job in an open plan office which, with my introverted temperament, was tough on my energy levels.

And even during that last full year at that company where it felt like the previous three-and-a-half years had paid off and I was finally seeing the rewards in my success a recruiter, I knew deep down that recruitment just wasn’t “it” for me, and I’d started to read about folks who had changed career. I remember stumbling across the world of blogs, and coming across these folks who were making a full-time income as bloggers. I think I also just really enjoyed connecting with other people’s stories through their blogs.

Towards the end of my time in recruitment, I would attend evening meetups at places like Google Campus (to immerse myself in and learn more about this exciting ‘startup’ world I’d heard about), and Escape the City which was a community for disillusioned worked in the City who wanted to find work that they cared about.

I still remember well the moment when the penny felt like it fully dropped for me… I was at the 2014 Christmas party, I’d just been jointly awarded the Employee of the Year prize with a fellow colleague, and I just felt worn out and empty, whilst everyone else around me was drinking and being merry and having a good time. I skulked off earlier and I knew that my time was up. I’d had a “successful” year in recruitment, I’d proved to myself that I was capable of sticking at something and doing well at it. And I knew that I didn’t want to “rise up the ranks” and manage, nor did I want to do exactly the same… i.e. bust my balls and have another “successful” year as a recruitment consultant.

Going into January the following year, I’d pretty much made my mind up. And the huge “pipeline” of possible deals I’d accrued proceeded to collapse into nothing. It might’ve been a little test of my nerve to walk away from a wad of commission money, but with each of my interviewing candidates not receiving an offer, I wasn’t faced with any such test. To the contrary, it was as if the Universe was saying to me “Yep Jas, I’ve got your back, your time is up… trust in yourself”. In February I went away on vacation with my family and was doing Headspace every day on the beach, and with the stillness that that afforded me things became real clear.

It was time for me to move on, and… in the last few months, I’d gotten into reading Positive Psychology books, around the “science of happiness”. I was fascinated by this field, and I wanted to know how I could live fully and by happy in my work and in my life, at a time when I was feeling pretty meh and increasingly disillusioned by the work I was doing.

I got myself onto a Masters course at a university in London (yep, it was totally fine that I didn’t have a Bachelors degree… it was a pretty new course which wasn’t heavily applied-for and, more importantly, universities are businesses that will happily take your money), and I handed in my notice the very same day I had written confirmation of my offer. In fact, I remember the day I was waiting on my offer and, after a few weeks of being pretty switched off from my work, I actually resigned before the email had come through (it actually arrived in my inbox whilst I was resigning).

My notice period in recruitment was, as is pretty typical, just a week and I think I was out of there a couple of days after I had resigned, after I’d done a little handover. I feel like they wanted me out of the office before I could tell too many people I was “leaving to figure out who I was and what I was passionate about”.

Studying (again) and the start of figuring things out

Around the same time as leaving, I started writing and posting some of my thoughts on LinkedIn and then on Medium.

And soon after that I started the first of many little blogs, A Happier Introvert.

The next couple of years after leaving my job were this fuzzy, stick, disorientating period of coming back to centre and figuring out what on earth to do with my life.

Truth be told, this process of self-discovery had begun in a more theoretical manner about a year or so before quitting my job, whilst I was reading various career change, psychology and self-help books (from Quiet by Susan Cain, to The $100 Startup by Chris Guillebeau, to Happier by Tal Ben-Shahar). But the big difference was that at this time I still had the solid ground of being in my corporate job, even if it was increasingly becoming ground I didn’t want to be on, and also the busy day-to-day rush of commuter life had meant I was too busy to let myself truly be still and really sit in the discomfort.

For a long time, I had just been carried along in the currents that whooshed me along through school, university and then into work… I’d lost sight of who Jas even was. Isn’t that crazy? That little guy was still there inside of me though.

Even though the safe ground I mentioned had started to crumble from beneath me as I realised just how much I no longer wanted to be standing there, I wasn’t yet brave enough to leave with no ground beneath me. Doing that Masters for a year was to be my safety blanket whilst I spent that year figuring out what Jas was going to do with his life.

Alongside the Masters, I took part in a 3-month ‘tribe’ with Escape the City, the community I mentioned earlier for disillusioned folks who needed a career change. It started around the same time as my Masters did in the September of 2015, and we’d meet one evening each week. I was one of the few who had actually left my job at that point; most of my tribe-mates would venture to class after working in their day job that they had fallen out of love with.

Early morning sober-raving at MorningGloryVille with some of my Escape Tribe, November 2015

📝 9 things I learnt during the Escape Tribe (written: February 21st, 2016)

Beyond that, my so-called “full-time” year-long Masters had just a couple of days of in-person lectures every three weeks, a couple of hours away on the other side of London.

Which meant I had in-person stuff to attend one evening in the week (Esc the City tribe) and a couple of days of lectures to attend on campus every 3 weeks (at the University of East London). Which meant I had a lot of free-time. Going from the structure of those long days in my full-time job to much emptier days was quite the shock to the system. I had a lot of time to think. At the time, it felt like too much time to think. It felt like I was spending much of my waking hours low-key figuring out (and freaking out) about what I wanted to do with my life, I was desperate to figure out what it was and having the “magic answer”, to have a new purpose and identity. All of that time to feel angsty about my life actually made me unhappy and probably provided the embers that would eventually lead to my depression diagnosis (more on this a little later).

In an attempt to figure out this answers and make use of all this free time I had (I had far too many hours in the day for this supposed full-time Masters, and pretty much everyone else in my cohort was doing employed work of some kind), I started my first business, Thriva Programme, an alternative to university which I worked on and ran a pilot for the summer after I’d left my job, in July 2016.

📝 Higher education: Creating a new story (written: September 5th, 2016)

Something else that happened that Summer was I attended World Domination Summit, hosted by one of the first bloggers I had come across and whose The $100 Startup book was one of the first ‘business’ books that introduced me to this concept of doing my own thing as a “company of one”, embracing slower growth over time, not needing to be a big company that took investment, starting with no overheads, and just generally being able to have a business that fit around me and my lifestyle and that kept me close to doing the work I cared about.

LYL meetup at WDS 2016 — my head is small (I’m at the back) but my smile is wide. (photo: Live Your Legend)

The conference had a bunch of familiar speakers and meetup hosts (like Chelsea Dinsmore and Corbett Barr), and it was attended by folks who wanted to do work they cared about and, more specifically, be doing their “own thing” as a solopreneur (or they were already doing so).

If you like, it was like the Escape the City community but these folks had decided that they wanted to do their own thing, and were at different stages of the journey, and there were a bunch of talks, meetups and social activities (connection 🙌) for a week in Portland, Oregon.

I had an amazing time, but I was to come back after the high of this trip to the miserable reality that I was still some way from where I wanted to be and was also figuring out exactly what sort of solopreneur business I wanted to focus on. I’d had blogs but they’d always quickly fizzled out and making the jump from “fun blog” to “making money from a blog” seemed like a big hurdle I was yet to overcome.

There was a glimmer of hope on the horizon, though.

📝 WDS 2016: The experience of a lifetime (written: August 26th, 2016)

Therapy and travels

Shortly after I ran that pilot programme, the Masters programme officially came to an end with the handing-in of my thesis, and it had become apparent that Thriva wasn’t a sustainable business for me, health-wise, nor — whilst I was passionate about the mission — was it the sort of business I actually wanted to build. All the moving parts were overwhelming, and took me awai from what I was actually passionate about. It was my first experience running a business (if you don’t count the tutoring work I had also done at that point), and I’d learnt a few things but mostly what I didn’t want.

Honestly, I knew deep down pretty early on that Thriva didn’t have the legs. I find that when I start things, pretty quickly my intuition gives me a sense of how realistic or sustainable something is. At the time, I ploughed on with Thriva and — hey — I’m glad I ran that pilot programme, but another reason for why I stuck with it for a few months was because I felt under lots of pressure to make a success of whatever I chose to do after leaving recruitment, I held this weird and irrational belief that my ex-colleagues, friends and family on social media were all keeping an eye on me and were judging me… if Thriva failed, it meant maybe I was a failure and hadn’t I been a silly boy for leaving recruitment… looking back, I know now that this was most certainly irrational, but it felt strangely real at the time.

All of a sudden, there was no business and no Masters. I had no structure again in my life, and I was freaking out even more about what I would now do with my life. I felt lost and overwhelmed and alone. And, looking back, anxious. As we moved into the last quarter of the year, the days were getting shorter and darker. It was only later that I would realise that I seemed to get some sort of Seasonal Affective Disorder, and no doubt with everything going on this wouldn’t have helped.

Before I knew it, I didn’t even want to leave the house, not even to go the gym which had long been a trusty place that would raise my mood. I didn’t want to see any friends (or strangers), and I barely wanted to talk to my closest family I shared a home with, my mum, dad and brother. I didn’t want to burden them with my low mood and I felt like such a failure — as a son and older brother — for putting them through all my sh*t and dropping out of uni twice, quitting my job, going through a wobble during the Masters where I was threatening to quit, Thriva not working out, and then after all of this still having no clue about what I wanted to do with my life.

(Though, deep down, I did have a clue. I knew what I wanted in an ideal world. I just wasn’t brave enough to follow-up on it and didn’t believe that it was possible for little ol’ me).

I’m not sure I’d ever felt that as low and depressed like that before, and thankfully my perceptive mum realised something was up and, after some persuasion, I agreed to see a psychiatrist. So we took a train together into West London to see one who had been recommended to her by someone.

Long story short, I filled out some forms, was given a generalised depression and anxiety diagnosis, and was prescribed a low dose of an SSRI called sertraline, as well as a course of group therapy and individual therapy. The group therapy ended up being several days’ worth over a number of weeks at a private therapy centre… thank goodness we had private medical insurance as a family (again, thanks mum and dad) as this would have been very expensive to have paid for out-of-pocket. I was an out-patient, but there were also in-patients at this clinic. I got to meet folks from different walks of life who had been diagnosed with different ‘mental health’ conditions, and it was interesting to spend time folks who were on the one hand different to me, but on the other hand strangely similar… it was interesting to connect some dots when it came to our temperaments, experiences and patterns.

So I took a few months off for therapy which, as well as being a useful place to explore inner stuff, gave me some much-needed routine, stability and community. All things I realise I need as constants in my life, wherever I am in the world or whatever my life circumstances happen to be. After starting to feel better, and with the days of spring joyfully returning (this always make my soul happy after the period of dark winter months), I did some travelling.

I stayed with a friend of mine and her family in Luxembourg, she was someone I had met during the Masters course along with Mat. Her name is Angie, and Mat, Angie and I have fond memories of the three of us meeting up for breakfast before our day’s lectures. In fact, I ended up dedicating my debut book, The Indie Author, to Mat and Angie for their friendship, love and support during this period in my life when I needed it the most. I will forever be grateful to the both of them.

My debut book, published in November 2021 under my own imprint: Indie Writer Press

I hopped on a train to Luxembourg from Paris, where I had spent a couple of weeks watching the tennis at Roland Garros (known as the French Open if you’re into your tennis). And later that Summer I went to Las Vegas of all places for the ‘fight week’ that was Floyd Mayweather vs Conor McGregor. Watching tennis started out as just being this fun thing (I still love watching tennis to this day), but somewhere along the line I thought I could be some kind of sports coach. When I happened to bump into the CEO of the US Tennis Association during one of the matches I thought the universe was trying to tell me something… and when I later met the CEO of Mayweather Promotions at a weigh-in event in London, I went up to him and asked him for a job. A story for another time, but the whole sports coach thing didn’t materialise.

Another example of, even on fun travels, how much I was still trying to solve the whole what do I do with my life? thing. I didn’t manage to find the solution that summer, but I had a fun time being away and travelling on my own for the first time. (Note: being away in Las Vegas alone is… interesting. And I can confirm it’s possible to be in that crazy desert city without doing an ounce of gambling. The boxing helped… and I was having fun posting to a sports blog — I thought I might be able to become a sports journalist slash coach or something — and, for the first time, a little youtube channel).

📝 I’m in Vegas. And I’m excited. (written: August 21st, 2017)

Mat’s company

When I got back home in England, and summer was drawing to a close, I again needed a healthy dose of structure in my life. My good friend Mat who I met through the Masters, and really helped me when I had my I’m-not-I-want-to-complete-this-thing wobble, then helped me even more when he offered me a job at his financial services startup. So I had about a year of working remotely, with monthly-ish train rides to Manchester, where I’d stay in a budget hotel overnight (handily in the same little complex as a Nuffield Health gym, where I had — and still have — a membership that lets me use most Nuffield Health centres in the UK). I’ll always be grateful to Mat as a dear friend and mentor who saved my bacon in giving me that job (and persuading me to finish the Masters) — just what I needed at the time to provide me that solid ground and community I’ve talked about.

During this time I got the experience of working a) remotely and b) for a startup with a decent culture, and run by a good friend of mine. I felt pretty fortunate, and it was nice to be a part of a startup in a suburb in (south) Manchester, as opposed to one of the several I applied to in the friendly beast that is “the city” aka London.

I found myself doing sales, though, rather than more content and marketing stuff away from the sales I’d done for five years in recruitment and ideally wanted to step away from. So, ultimately, I got bored. By now I’d started and stopped various blogs (aside from the A Happier Introvert one I mentioned earlier, there was always Quarter Life Introvert and Awkward Brown Guy), and around the summer of 2018 I started this blog called Introvert Jedi* whilst I was working at my friend’s startup.

*are you noticing a theme here?

A guide I created for my IntrovertJedi blog subscribers, and the first ebook I ever wrote.

I ended up leaving the startup at the beginning of 2019, and by now I was beginning to realise that maybe the employed world, even one with the freedom of remote and a decent culture, just wasn’t for me. I took a couple of weeks off in Slovenia where I brainstormed my next business idea.

It was around this time that I really began to look into how I could do this whole writing thing as a career.

So my next step was to try being a freelancer and I started HonestContent, to help write guides for financial services clients I’d gotten to know during my time working in sales for the startup. I properly started working on this business after getting back from Slovenia and taking a month’s trip to the Canary Islands for what was to be my first official stint as a “digital nomad”. Smartly, knowing my need for structure and community, I stayed at a co-living space and had a great time.

So I want to write things. Now what?

I didn’t really know exactly what I wanted to “do” for my clients… I was trying to find the right way to pitch to clients but, truth be told, I didn’t want to write for anyone else. I realised that even doing writing gigs on more fun things I was into like travel or psychology just wasn’t for me. I didn’t want to have to write under rules or guidelines, or be at the mercy of writing for just a specific topic or theme…

I feel like I had to go through this process of “ticking things off and realising they weren’t for me”, to ultimately realise what I had known deep down all along, ever since I had come across those bloggers making a living prior to leaving my corporate job a couple of years previously…

Honestly, what I’d really wanted to do all along was write things freely and make money as a writer, it was just a case of:

a) exhausting all other options (and bringing this dream of mine into focus)

b) finding the confidence to pursue this dream (and proactively work towards making it happen)

After trying the freelance writing thing, sending lots of pitching emails and attending lots of networking events and securing literally zero clients (again, less of an indicator of my abilities and more of a sign from the Universe to say — “nope, Jas, this isn’t it”), I also tried working as an intern in a publishing house for a couple of weeks. This was after attending London Book Fair and attending various meetups and sending out a bunch of emails to folks who were working in publishing.

I had also thought about being a journalist (see my summer of 2017 travels and foray into the world of tennis and boxing, above) in, say, sports or something like working for online publications focused on things I cared about.

But, ultimately, I discovered that I did not want to “play the game” and “work my way up” in the world of traditional publishing (especially as I didn’t even want to do this in the first place — I wanted to write!), and that any sort of freelance/journalist gig would mean me having to write about particular things, under certain guidelines and to particular deadlines and constraints… in an organisation which — even if it was a friendly one with a great culture — would involve some level of office politics and “playing the game” and (at that time before the pandemic happened and remote/hybrid working become more of a thing) a commute and going into an office.

📝 How I came to work as a writer. (written: January 25th, 2022)

By now, I was starting to realise that I wanted:

1) to write

2) for myself

3) with freedom

In other words this blogging thing I had been doing for fun in the background, and trying to ‘figure out’ how to make money from, was what I wanted to do.

I re-joined a community started by Corbett Barr (another of the first bloggers online I had come across) called Fizzle, and started Introvert Jedi in the Summer of 2018, before this became INF Club a few months later in 2019, and for the next couple of years I got more serious — and consistent — about my blogging. I focused on this blog alongside a tutoring business (tutoring was something I had been doing on-and-off now for years), which worked well because my tutoring was local (through leafleting I picked up a handful of clients who lived near me), and then when the pandemic happened tutoring went online which was even more convenient for managing my time and energy.

That blog was moved to Substack, where I started a paid newsletter, and then I co-hosted an online summit with Lauren Sapala, someone who I’d connected with over twitter, we’d read each other’s blogs, jumped on a couple of video calls, and then decided to host this Summit together. Lauren has since become a dear friend and mentor of mine. And in fact, as I write this, we’re just finishing up putting our second online summit together.

That first summit involved us inviting a handful of folks to chat with us about their experiences being introverts — the Summit was called the INF Summit, and most of those we interviewed identified as being INFP and INFJ personality types, and everyone identified as being somewhat introverted and/or sensitive or creative. It was great fun, and it was actually after having so much fun recording those interviews that I started the INF Club podcast, which I went on to run for nearly 2 years and more than 60 episodes.

In the next year or so INF Club had a membership community, a Mastermind programme I ran, a couple of workshops I ran, and 1:1 coaching. There was something special about earning those first few dollars before the Summit, and then my first $100, and then $1000. Those early milestones are so big and special, when you see someone somewhere else in the world offer you money for something you’ve created. It really is special. And so I experimented with offering different types of services and ended up making more than $6000 from INF Club.

I was some way off this making a full-time, sustainable income but making some money from INF Club was enough to psychologically shift me into another gear and realise that this whole ‘solopreneur blogger’ thing was possible for me.

As the Summer of 2021 came around I was working pretty much full-time on INF Club with a couple of hours of tutoring a week. After a long year of pandemic and several months of winter and then a really cloudy-and-not-so-sunny spring, I was in need of some adventure and a boost in Vitamin D levels #SADproblems.

I was looking to spend another stint as a digital nomad somewhere, having had a good time at the co-live in the Canary Islands a couple of years prior. I was looking for someplace in Europe where I could work, roam, and be surrounded by community. I was aware of a digital nomad podcast run by a previous member of Fizzle, and I came across this digital nomad village initiative in Madeira which was amazing and exactly what I needed. I love islands (the size, the beach, the climate) and this place was being set up as a place to foster a digital nomad community in a way that integrated with and supported the local community.

After some interactions in the group on Slack, and a quick video call, I committed to staying for a month in a spacious house with five fellow housemates. I lucked out — the house was beautiful and spacious, and nearly all of us were thoughtful introverts and ambiverts. We had a happy month together with a shared car, we had “family” movie nights and weekday trip and hikes, as well as integrating with the wider community via the co-working space and the various activities going on in the village on the beach, and at the nearby beautiful hotel where some nomads stayed, but had its facilities open for us all to use and enjoy (like the weekly Friday sunset party, or the various meetups that would take place on the grass there… one that stands out was the wonderful music jam session).

That time in Madeira was just what I needed. Time away from regular day-to-day patterns tends to give me clarity, and this trip helped me realise that INF Club had been an amazing phase of personal growth, self-belief, and meeting many warm introvert friends as well as actually committing to a blogging practice (I published a post nearly every week for two years), and also made my first $5000 from blogging.

My book, The Indie Author, was soon to be ready for eBook release and my intuition was telling me it was time for a new chapter.

So I started a new site, The Indie Writer, and closed off my INF Club blog and podcast.

This chapter still feels pretty new, and one I’m gently navigating.

Some final words

Thank you for reading all the way to the end.

I had no idea I’d write as much as I just did, but it’s been a really interesting and reflective experience to process and simmer over everything that’s happened for me so far, right from the beginning to the most recent couple of years where, looking back, more has happened than I’d expected or realised.

I feel like I’ll need to write some kind of annual summary every year, as I’ve now realised just how much has happened for me and it’s nice to process and (re)connect with it all properly through writing about it.

Apparently, lots has happened in the last 7 years since I walked home from that Christmas party and knew that something had to change.

I suppose I shouldn’t be that surprised, as more than two thousand days have passed since then.

Here’s to the days, the weeks, and the months ahead…

See you around ✌️


Taking a rest during a hike in Madeira, Summer 2021. (📷 by a friend + fellow hiker I met on my travels, Zdenek)

Thanks for reading my story.💛

I’m Jasraj, a writer who likes coffee shops, mini-adventures and autobiographies.

Growth, connection and freedom are things that are important to me.

The rest is still unwritten… but I’ll be sharing it as I go :)