“Day 1”, Jeff Bezos and Vertigo (#15)

How I’m using Jeff Bezos’ philosophy to rebuild myself Better, Faster, Stronger

“Day 1”, Jeff Bezos and Vertigo (#15)

Every Sunday I publish a newsletter featuring the best hacks and insights I discover on my journey as an entrepreneur and investor.

I write this newsletter from my bed in Barcelona. The last few days have been tough. I’ve been suffering from vertigo and unable to do pretty much anything. I had vertigo for 1 month last summer and, because it’s a viral infection, it comes back to bite me in the ass from time to time. 🦠

I suspect, on this occasion, it’s no coincidence. After months of travelling between countries, cities, apartments and friends’ sofas, I’m exhausted. My lifestyle caught up with me and the virus got the better of me.

Last weekend I read Jeff Bezos’s final letter to Amazon shareholders. It reminded me of his “Day 1” philosophy. Incapacitated in bed due to vertigo, I’ve been thinking about how to apply Jeff’s philosophy to rebuild myself Better, Faster, Stronger. 💪

What is Jeff Bezos’s “Day 1” philosophy?

The idea was born in the very early days of Amazon. They occupied a building called “Day 1”, named as a reminder that the company should always be in “Day 1” mode. In contrast to “Day 1”, Jeff sees “Day 2” as stasis, irrelevance, decline, or death.

As Bezos wrote in his 2016 Letter to Shareholders, “Staying in Day 1 requires you to experiment patiently, accept failures, plant seeds, protect saplings, and double down when you see customer delight.” 📈

How can we apply “Day 1” to our lives?

No matter where you are or what you’re doing in life, it’s Day 1 for the next stage. The current moment is perpetually Day 1.

Day 1 is a reminder that we’re not slotted into fixed paths. At any time, we can take stock of our lives, assess what we’re doing and where we want to go, and head in any new direction.

I know that’s not entirely true. We all have certain family obligations or business commitments to see through. But it’s more true than I generally observe people to believe. I think people can restart and redirect themselves in so many more ways than they believe. You can do it with your personal behaviours, thoughts and habits. You can reallocate time where you choose. You can redirect love and energy when priorities. You can break free of self-destructive patterns and toxic environments. 💫

While studying Economics at University, I learned about “sunk costs”. These are costs we incur that cannot be recovered. The primary insight of sunk costs is that they should not impact our future decisions. They’re sunk and should thus be irrelevant going forward.

But our human psychology has an irrational attachment to sunk costs. Even though our investment is “sunk”, we remain invested to a certain path in life. For example - you spend a tonne of money on education in a particular field and later lose interest. You then feel obligated to stick with that path just because you invested so much time and money in it. 🧐

Instead, we must let go of such attachments to sunk costs and investments. Our assessment should be future opportunities versus future costs.

How I’m using “Day 1”

Starting from the basics, I’m examining my habits and routines. There’s not much to change - I’ll continue to meditate, journal, fast and exercise every day. But I’d also like to explore new ways to train cardio and be more mindful and present. I’m thinking about the Barcelona marathon and registering for a meditation or psychedelics retreat. 💊

I’ve also been considering the big decisions in my life: where I live, who I’m with, and what I do. 🔮

I’ve got a clear idea of the people that bring the best out of me. I’ve met so many people since finishing school, but most of my friends are still the people I’ve known either since birth or the age of 10 - and I’m really just doubling down on that.

In terms of work, I love reading, I love writing and I love analysis. I also love to stay on the bleeding edge of trends and study technology and business. So I’m spending more time following my intellectual curiosities and investing in early-stage projects and opportunities. 🤓

While I’ve got a clear idea of the people that bring the best out of me and the work I find most enjoy, I’m still figuring out where I want to live long-term. 🌍

I love the culture and vibe in Europe, and Barcelona is one of my favourite cities in the world. It’s got the beach, the mountains, skiing, culture, history, soul, food, and a young, energetic and international community. But the business, legal and financial rules and regulations in Spain are cumbersome and bureaucratic. On the other hand, while countries like Portugal and Croatia are more economically innovative and welcoming to entrepreneurs and investors, cities there don’t have the pull that Barcelona has. I’m not sure I could live in Lisbon or Dubrovnik for 365 days/year, for example. 🙈

With that being said, I’ve still got plenty of time to decide before I settle down (if I ever settle down!). I’m keen to explore more of the world to get a better understanding of my personal preferences while also experiencing new and interesting cultures and people. I’ve never been to Miami, Taipei, Playa del Carmen or Cape Town. I’d also like to travel to Singapore, Lisbon, Bali and Bangkok again. With my visa in Barcelona running out on 26 June - it’s anyone’s guess where I’ll end up next! ✈️


I believe it’s important for us all to think of today as "Day 1" and to consider how we can reset and reboot for a fresh start. I also think it’s important for us to periodically assess things from a Day 1 perspective.

Thinking from a Day 1 perspective doesn’t mean we should jump around erratically and never finish anything. Momentum creates opportunities, and Day 1 encourages us to be flexible in order to direct our momentum most productively. If we don’t, life will make these decisions for us. And we’ll enter “Day 2”.

I’d love to hear from you

Your future is unwritten and you hold the pen. How will you use Jeff Bezos’ “Day 1” to restart and redirect? You can reach me on Twitter or email: anthony@djangodigital.co.uk.

What I’ve Been Reading

💸 Is BlockFi the Future of Finance. For anyone struggling to understand how BlockFi is paying out 8.6% APY, Packy McCormick does an excellent job of explaining this, plus the broader landscape of financial institutions. (6,500 words).

🇺🇸 The New America, The Biden America. My 17-year-old cousin Freddie just started a blog on Politics. His inaugural post discusses whether Biden’s saved or sacrificed the soul of the USA. (3,700 words).

🤑 Bitcoin Origins and Cultural Significance. Cameron and Tyler Winklevoss explain the birth of Bitcoin and how this marks a paradigm shift in the finance world — with philosophical, technological, and economic implications that continue to expand. (1,800 words).

🚀 Nasa's rover makes breathable oxygen on Mars. An instrument on Nasa's Perseverance rover on Mars has made oxygen from the planet's carbon dioxide atmosphere. (450 words).

🤫 What Networks Whisper. This article builds on the idea that cities whisper. LA tells you to be famous, Boston tells you to be smarter, and New York tells you to be richer. Now, social networks are like cities. Twitter tells you to be witty, Reddit tells you to be clever, Facebook tells you to share your everyday life, Instagram tells you to be glamorous, and TikTok tells you to be entertaining. (800 words).

What I’ve Been Listening To

🐦 Matt Mullenwegg interviews Jack Dorsey, the CEO of Twitter and Square. They discuss remote collaboration,  executive management, and decision making. (01:15:47).

🇮🇳 Jason Calacanis interviews MetaKovan, the acquirer of Beeple’s $69M NFT. An inspirational podcast - offering insight into the psychology of someone frustrated with Indian capital rights and who used Crypto as an escape. (00:55:50).

🌐 Bankless interview Joel Monegro, an investor in decentralized networks and companies democratising access to data, wealth, and power. They dive deep into the relationship between Governance and Capital. Essential listening for anyone interested in Politics. (01:53:35).

🐦 Excerpts from the Twitterverse

Thank you so much for reading this article. If you enjoyed it, be sure to share it with your friends and spread the word.

I want to be able to deliver the best content I can to all of you. To that end, I’d love to hear your thoughts on what’s working, what isn’t, and what you’d like more of. You can reach me on Twitter or email: anthony@djangodigital.co.uk.