What Would You Do if You Knew You Couldn’t Fail?


Hey friends,

A very good evening to you from London in Summer with a light drizzle in the air.

So last week, I stumbled upon some journaling notes I’d written just over two years ago, in April 2021. I was doing a “designing your life” type exercise, and asked myself the question:

“What would you attempt if you knew you couldn’t fail?”

So in this issue of Sunday Snippets, two-and-a-bit years later, I’m going to go back through what I wrote and offer a commentary on it, for whatever that’s worth.

“What would you attempt if you knew you couldn’t fail?”

2021: I don’t think it’s failure that’s holding me back from doing things. I’m not sure anything’s holding me back from doing things. But okay, let’s have a think. If I knew I couldn’t fail… I would… I’d have boundless confidence to do street magic, I’d roam around the streets of Cambridge and London with a camera crew and do magic for people and film their reactions and it would make for sick YouTube videos. I’d do ‘pranks’ like ThatWasEpic, going up to pretty girls and saying “hey I like you” and seeing where the conversation goes. I’d have zero approach anxiety.

2023: Haha. None of this ever happened but it’s interesting that this was where my mind first went to when I thought about what I’d attempt if I knew I couldn’t fail.

2021: I’d travel around the world, living in a difference city for a few months at a time. I’d be super confident with making friends and meeting girls.

2023: This girls thing is really showing up a lot… guess it reflects my single status at the time, coupled with some confidence issues that I was aspiring to work through. The travel around the world thing is interesting – that’s exactly what I’m planning to do from around November 2023 onwards.

2021: I’d learn more stuff. I think windsurfing seems cool, so I’d go somewhereI could do that, and learn how to windsurf. Preferably in some sort of club where I can hangout with other people too. Or at least turn it into a more social activity. Throughout these adventures, I’d have my mini YouTube studio with me. I’d setup shop in each new place I’d visit, and I’d continue to make videos each week documenting my adventures and the stuff I’m learning, or reading, or thinking about.

2023: Nice, pretty wholesome. Still vibing with that philosophy of trying out random stuff that I think would be interesting. And the plan from November onwards is indeed to pack a mini YouTube studio with me and continue making videos while travelling around interesting places.

2021: I’d do more reading and writing as well. I’d start to read old stuff, understanding how philosophers of the past saw the world and integrating their thoughts with my own.

2023: I really haven’t done much of this. I guess over the past two years, all my writing and reading efforts have either been directed at YouTube videos, or towards the book. I haven’t made the time to read older stuff, philosophy etc, but it’s definitely on the cards now that the book’s finished and I’ll (hopefully) make the time to read and write stuff that isn’t immediately contributing to creative output.

2021: I’d continue to do the podcast each week with Taim. We’d always have stuff to talk about because our lives would be quite varied and fun.

2023: Cute. Weirdly, since my brother and I started living together (Sept 2022), we’ve not at all been consistent with our podcast, despite literally having a podcast studio in our flat. I guess back in the day, when we didn’t live together, the weekly podcast was a way to catch up. These days, it’s felt increasingly like we have the interesting conversations offline, and “saving” something for the podcast feels not-fun. We’ll see how the podcast shapes up over time.

2021: I’d do a lot more writing. Instead of regurgitating ideas from self-help authors, I’d have original insights (sort of), and lived experiences that I’d talk about. I’d probably focus on the personal development side, writing about the things I’ve learned along the journey of trying to live my best life etc.

2023: Cute. Definitely still the plan.

2021: If I knew I couldn’t fail, I’d probably do some level of competitive play in WoW lol. I’d join a guild that raids twice a week, and those days I’d login and raid / PvP etc. That would be quite fun. I’d become friends with these people IRL and it’ll be a blast.

2023: Haha this is still something I fantasise about sometimes. I think “you know, if I won the lottery, I’d spend more time playing video games”. But then I play a video game for a bit, and any sort of semblance of a regular gaming routine gets derailed by work and other social commitments. And I don’t like the idea of saying to friends: “sorry can’t hangout tomorrow night, it’s raid night so I need to be online on World of Warcraft to slay some arbitrary demon”. Maybe I just need to admit to myself that this dream of becoming a competitive WoW player is never going to happen.

2021: I’d continue to improve my singing and guitar skills. I’d do a bit of busking, film myself, teach people how to do the same thing. Teach people how to be more confident when approaching life, how to take more risks, how to ’seek discomfort’ in a way.

2023: Cute. Shoutout to YesTheory.

2021: I’d play squash more regularly. I’d join a club, take lessons, play in competitions. Probably tennis too.

2023: Checks out, would still love to do this, just gotta make the time.

2021: I’d be a jack of whatever trades I wanted. Music, art, writing. I’d be the modern renaissance man. If something strikes my fancy, I’d explore it and document the journey for others to follow along and to hopefully learn something from.

2023: I love how sharing these private journal entries is in itself, an exercise in overcoming the cringe response. “Modern renaissance man” lol, can’t believe I wrote that. But at the same time, as I read this, I’m thinking “tbh that’s exactly what I want to be” and the only reason I’m cringing at the phrase is because you, dear reader, are reading it… as I said, it’s an exercise in overcoming cringe and being okay with being sincere about stuff like this.

2021: On the side, I’d be a tenured professor at a medical school like Cambridge. I wouldn’t have many recurring commitments that tie me to a specific location, but somewhat regularly I’d run lectures and revision sessions for students. They’d go away from those thinking ‘wow that was the best session I’ve ever been to, I learned so much and I was entertained throughout and Ali is a legend’.

2023: This actually still seems pretty fun. I’d love to stay involved in academia / students in some capacity, maybe being a guest lecturer or something that has the benefits of being able to teach students IRL, but without the annoyance of grading papers, dealing with admin etc. If anyone knows what this sort of arrangement could look like, please hit and let me know haha.

2021: I’d be a prolific writer. Every 2 years or so, I’d release a book. Some of them would be NYT bestsellers, and I’d hit #1 on the list with my 3rd book. But I wouldn’t be concerned with the sellability or the bestseller status, or any of these lists. I’d write for its own sake, and publish because it’s fun, and I like seeing my books in the hands of real people. Some of them would be quite niche, but some would have mainstream appeal and get people into being more intentional with the way they’re living. I wouldn’t pretend to have it all figured out, but I’d be experimenting on myself and sharing my thoughts as I went along, and if people want that vibe, they’d get it in the books and on my blog and my YouTube channel.

2023: Awh this is cute, and still the plan. Book #1 is being released this year, so I guess Book #2 comes out in 2025/26, Book #3 comes out in 2027/28 and hits #1 on the list 😂 We’ll see what happens. It’s funny how back then, I was still grappling with this issue of commercialising creativity – on one hand, wanting to write for the sake of sharing a message, but on the other, wanting the commercial success that comes with it. I guess it’s something every professional creative struggles with.

I’d get much better at music. I’d understand music theory, I’d level up on the piano and guitar and any other instrument I’d want to learn, and I’d write my own songs. I’d do covers of other songs that I love but apply my own twist to them, and I’d write original songs that don’t take themselves too seriously. I’d stick these on YouTube, Spotify etc. People would like them.

2023: Cute. Still on the bucket list but not a priority right now with everything else going on.

And now we come to the moment that I start really grappling with the “do I want to continue being a doctor?” situation. If you’ve heard my thoughts on this ad nauseum since then, feel free to skip this bit.

2021: Right, so I’ve written 800 words and honestly haven’t thought about medicine once, beyond the teaching thing. Does Medicine fit into this life story of mine? Well, sort of. Being a doctor is quite brandable. But other than that? Would it be fun to actually work as a doctor? I think it would. If I could have whatever I wanted, if I were a multimillionaire and I knew that my brand wouldn’t be affected by the doctor thing, would I still be a doctor? Definitely not full time. What about part time?

Maybe… again, the idea of 2 days a week seems reasonable. I’d try it out to see if I enjoyed it. I’d get really good at emergency medicine. But I’d also have a deep understanding of general medicine and surgery so that I’d be able to teach medical students. I don’t really care about teaching actual doctors (unless it’s within my own speciality) but I do care about having a broad enough knowledge and understanding of medicine as a whole to be able to teach students effectively. I’d take emergency scenarios that I’d see IRL and turn them into cases that explore the why behind the what.

I’d be a legendary emergency medic, with amazing leadership and communication skills and the ability to lead a high pressure team well. I’d be calm under pressure… Is this what I want? Does that future seem interesting? Yeah it does, in a way. But I think mostly I’m seeing Medicine as a means to an end, as a means to having a better brand, or as a means for being a better medical educator. Rather than as an end in itself, for the sake of patients or whatever. I don’t really care about the patient impact. I care about the teaching impact of what i can do.

Do I need to be working as a clinician to teach effectively? Probably not, but it probably helps. The teaching lifestyle is very suitable for 1-2 days per week clinical. Maybe even less than that if I feel like it. I don’t care at all about being a consultant, I’d happily be a fellow / staff grade / locum for ages. There’s some teaching brand value in being an EM trainee. I guess. I should talk to Nathan H-Peacock, see what he’s doing.

2023: It’s interesting reading this back 2 years later. I remember thinking at the time: “Okay, so my ideal life seems to involve working as an Emergency Medic 2 days a week… so why don’t I just run that experiment and see how it feels?”

So in the aftermath of this journaling session in 2021, I emailed senior doctors I knew at my local hospital and asked if they’d consider employing me as an emergency medicine locum (part-time). They very kindly said yes. I tried out a few shifts, but every 20 minutes during those shifts, I had the thought in my mind of: “What am I doing here? I’d be having way more fun and feeling way more fulfilled if I was hanging out at WeWork with my team and working on the book and making YouTube videos…”

I think I got this method of thinking from Tim Ferriss (thank you for the ongoing inspiration, hope to meet IRL someday). Tim’s whole lifestyle design philosophy centres on figuring out what you think you want, and then running low-friction experiments to see if what you think you want is actually what you want.

So for me at the time, I ran the experiment of “work 2 days a week and see how it feels” and realised “this feels absolutely awful, I’d much rather leave Medicine completely and go full-time on the creator entrepreneur writer stuff”.

It still took several months for me to come to terms with that decision, and a big part of it was an interview I did with Lewis Howes on his podcast School of Greatness. The interview started off with him asking me how I built my YouTube channel and how I’d help people generate passive income. But it very quickly turned into a mini coaching / therapy session where Lewis coached me through my fears around leaving Medicine. Through that conversation, and reflecting on it afterwards, I realised that what was keeping me tied to my job was a combination of identity, prestige and ultimately, fear. And that the life I wanted to lead wasn’t a life that was optimising for either of those things. So I decided to take a break more permanently, freeze my General Medical Council registration, and commit to going all-in on this internet entrepreneur creator writer thing. And so far, touch wood, I haven’t looked back 🙂

2021: What would be a fun life to have a year from now? Living in London, super nice apartment. Social, having friends over all the time. Amazing YouTube studio setup. Working in London, training in EM, but part-time, 2-3 days per week. The rest of the time would be my own for YouTube + writing + reading. I’d travel whenever i feel like it. Could take extended time off work to go to European cities for a few weeks at at a time. I wouldn’t bother buying a place, I’d just rent, to have that freedom of movement.

2023: I ended up moving to London in late 2021, living in a super nice apartment, which was very social and had friends over all the time. We have an amazing YouTube studio setup. I’m not working in Medicine anymore, and I do indeed travel whenever I feel like. So this has worked out in a nice way.

2021: I wonder if I should publish this…

2023: Well I guess here we are, two years later, and this journal entry is indeed published. I hope you took something away from it.

Have a great week!

Ali xx

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✍️ Quote of the Week

“We start off in childhood believing parents might have access to a superior kind of knowledge and experience. They look, for a while, astonishingly competent. Our exaggerated esteem is touching, but also intensely problematic, for it sets them up as the ultimate objects of blame when we gradually discover that they are flawed, sometimes unkind, in areas ignorant and utterly unable to save us from certain troubles. It can take a while, until the fourth decade or the final hospital scenes, for a more forgiving stance to emerge. Their new condition, frail and frightened, reveals in a compellingly physical way something which has always been true psychologically: that they are uncertain vulnerable creatures motivated more by anxiety, fear, a clumsy love and unconscious compulsions than by godlike wisdom and moral clarity – and cannot, therefore, forever be held responsible for either their own shortcomings or our many disappointments.”
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