3 Lessons I Learned this Week


Quick announcement before we dive into this week’s email – Black Friday is (nearly) here and for the first time ever, we’ve decided to run a deal for the Part-Time YouTuber Academy. I’m not a huge fan of discounting our products – we’ve never done it before – but since a few people have been asking if we’re doing a discount for PTYA, we decided to create an exclusive offer for Black Friday. Starting next Tuesday 21st November, instead of the usual $995, we’ll be offering the Part-Time YouTuber Academy for $695, only for a couple of days and only this one time of the year. If you’ve been thinking about enrolling for PTYA but it was never the “right time” or the price was an issue, this is the best moment to enrol. You can click here to join the Black Friday Waitlist and I’ll let you know when the promotion goes live.

Anyway, and on a totally unrelated note, I’ve spent the last few days hanging out with an incredible group of entrepreneurs and creators in Cabo, Mexico. There were 7 of us, and everyone there had built a much bigger business than mine, and was way wealthier than I am, so it was the perfect group for me to learn from.

Through various structured and unstructured conversations, I picked up a few learnings that I’m taking away, that I thought I’d share in this email.

Takeaway #1 – Money doesn’t buy much more happiness beyond a certain point

Okay, so everyone knows this… but it’s still one of my favourite things to ask about when I meet people with way more money than me – in this group, some of the guys had sold their businesses for tens of millions of dollars, and some for hundreds of millions of dollars, so they were literally at least 10-100x wealthier than I am.

They all said, pretty candidly and without trying to virtue-signal, that making more money basically made no difference to their happiness levels. Yes, one of them was able to buy a house for his parents, which was pretty fulfilling. And another was able to move into a fancier house and buy a nicer car. But broadly, making tens to hundreds of millions of dollars didn’t seem to have much of a before-and-after effect on their day-to-day happiness.

This is MEGA REASSURING – we all know that pursuing money at the expense of health, relationships, balance or enjoyment is probably not a sensible thing to do. But in a world that encourages us to want more and more and more, and where “success” is still often measured through numbers, it’s easy to forget that and make decisions for the sake of more money – decisions like staying in a job you hate, or getting into a business that you don’t particularly enjoy, or making lots of sponsored YouTube videos…

All the guys in the group basically confirmed that “doing something for the sake of more money doesn’t buy happiness, and in fact, it detracts from it if you’re doing something you don’t enjoy and find meaningful”.

Obviously, all of this is with the caveat that if you’re struggling to pay your bills, making more money will substantially change your life because it removes the stress of not being able to pay your bills. But beyond the point where you’ve got your basics taken care of, money buys a lot less happiness than we think it would.

Again, this is nothing new – if you’re into personal development, psychology, finance etc, you (like me) already know all this. It’s just nice to be reminded of it (at least for me lol).

Takeaway #2 – Happiness comes from working on something meaningful

All the guys who sold their businesses for tonnes of money said they were much happier when they were working on building the business, rather than when they sold it.

When you’re working on building a business, you wake up everyday excited to build something with a team of people you like hanging out with. But when you sell a business, becoming a “person of leisure” is a lot less fulfilling than you think it would be.

Without exception, every one of the gentlemen in the group returned, post getting rich, to building a new business. And they’re all happier and more fulfilled as a result.

Again, this is VERY REASSURING. It shows that if you’re enjoying your work (and obv, making enough money to comfortably sustain your family’s needs), then there’s not a huge difference between where you and I are at, compared to where people with 10 or 100 or 1000x as much money are at.

So if you’re enjoying your work, don’t sacrifice that for the sake of more money. And if you’re not enjoying your work, don’t think that making more money is going to make you much happier – instead, find a way to enjoy your work, and if that doesn’t work, consider moving into a role that you find more fulfilling. If you’re looking for practical tips on that front, my upcoming book Feel-Good Productivity has plenty 😉

Takeaway #3 – Prioritise your Health and Relationships

One of the gents in the group shared an experience of hitting rock bottom. His business was doing great, but his personal live was falling apart. He said: “No one ever wakes up one morning and thinks ‘you know what, I’m going to screw up my life today’. Instead, their life gets screwed up by the micro decisions they make over many months and years – and often those decisions are when they’ve over-prioritised their work and under-invested in their health and their relationships”.

Again, you probably know this. I certainly do. But it’s SO HELPFUL to get the reminder. Because even though it’s sort of obvious that “don’t screw up your personal life for the sake of your work because it won’t be worth it”, plenty of us don’t act in line with that.

For me, the more people I meet who’ve experienced this first-hand, the more it sinks in that work shouldn’t be the only thing we care about, and that a balanced and healthy life where we take care of our physical and mental health, and prioritise our relationships with friends and family, is WAY NICER than a life predominantly spent in the pursuit of riches.

This is a very useful reminder to me too, as I write this. I’m writing this email in a taxi from Cancún to Tulum in Mexico. It’s 8pm, and because I had some time to kill on this 2h drive, I thought “great, let me bust out the iPad and write this week’s newsletter”. I didn’t think “great, let me bust out the iPad and plan the next weekend road trip with the boys”. I didn’t think “great, let me bust out the iPad and figure out which gym I can use when I’m in Tulum”. I thought “great, let me do some more work”.

I had some spare time, and my default action was to do more work, rather than to think about taking meaningful action for the sake of my health or my relationships. Kinda funny how that happens…

Have a great week!

Ali xx

PS: If anyone reading this has any experiences to share on the topic of money vs happiness and fulfillment, either your own or someone you know, please do reply and let me know – I’d love to curate some of these and share them. If you’d like you or your story to be anonymous, that’s totally fine too 🙂

❤️ My Favourite Things this Week

  1. Movies – In the pursuit of relaxation over work, I decided to watch some movies on the various flights I’ve taken this week. I watched The Big Short (a great film about the 2008 financial crisis), A Beautiful Mind (a wonderful film about the mathematician John Nash), and The Batman (the 2022 one with Robert Pattinson). All three were excellent, and I’m glad I watched them. If you’re looking for something for your downtime, I’d recommend all three.
  2. App – I’ve started keeping track of my movie, TV show and video game consumption on an app called Sofa. It’s beautifully designed, and makes it feel like a bit of an accomplishment to actually relax and watch something. Not sponsored, I just think it’s a cool app.
  3. Video – I loved this new video by Veritasium, another absolute banger as usual – What the Longest-Running Study on Happiness Reveals. If you enjoyed this week’s email, you’ll love this video.
  4. Article – After the various discussions with the gang in Cabo, I decided to re-read a blog post that had enormous impact on me earlier in my entrepreneur career – “The Day I Became a Millionaire” by DHH. He comes to exactly the same conclusion: that having a lot of cash is nice, but doesn’t move the needle for meaning and fulfilment.

✍️ Quote of the Week

“In my experience, high-achievers focus a great deal on becoming the person they want to be at work—and far too little on the person they want to be at home.”

From How Will You Measure Your Life? by Clayton Christensen. Resurfaced using Readwise.

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