Jacob's Journal #1: Prototyping the Writer's Lifestyle

Yet another relaunch of my newsletter. Stay tuned for more Journal entries!

Hello there. It’s been a while.

Welcome to Jacob’s Journal, my humble attempt at (once again) relaunching my newsletter (previously known as Undringer). A fresh start, clean slate, new beginning, if you will.

This very first edition is partly a meta-newsletter (a newsletter about itself), and partly the beginning of prototyping a lifestyle I want to try out.

To introduce both parts, I must write about writing for a second.

The Paradox of Writing on The Internet

In this very moment, I am writing on the Internet, which is a somewhat weird thing to do. Writing online takes a lot of time, effort and energy, yet most of what is written is never read by anyone else than the writer’s mum. Despite this, writing online can turn lives upside down, start revolutions, impact millions of people, or even change the world.

This is the paradox of writing on the Internet. It’s not worth doing for the most part – until suddenly, it can become extremely worthwhile.

Writing online – like most good things in life – is ruled by the iron law of compound interest. Nothing explains this better than this simple image from Jack Butcher, which has been my phone and desktop background image for the last few years.

I’ve seen countless people transform their entire lives through the written word via Twitter, newsletters, blogs, e-books or Medium posts over the last few years.

Ben Thompson started writing about tech as a side project – now his site Stratechery is read by everyone with a pulse and a hint of ambition in the tech sector around the world.

Paul Skallas started a niche Substack about the Lindy Effect (one of my own favourite ideas from Nassim Taleb!), built a cult following on Twitter, then got featured in The New York Times, all in less than 12 months.

Erik Torenberg writes “Erik Torenberg’s Thoughts”, plain and simple, about education, tech and venture capital, which leads people, startups and opportunities to him, to his company OnDeck, and to his VC fund Village Global.

Tim Ferriss, James Clear and Mark Manson all got started with simple blogs. Ramit Sethi started with a shabby e-book. I could go on and on.

This fascinates me. All of these people started from zero, and through a combination of novel thinking, clear writing, persistence over time, and compound interest, they created their own serendipity machines in the form of written ideas on the internet.

Through the magic of Google searches, social media posts and people’s incessant desire to share quality content with others, these published ideas, blog posts, newsletters and Tweets attract new readers and new opportunities day in and day out.

OK, cool, but what does this have to do with me?

Prototyping My Ideal Lifestyle

If I didn’t have a job, I’d probably make an attempt at making a living off of writing on the Internet.

It seems like an absolutely ideal situation for me and my personality. I’d get to spend all day every day reading, thinking and sharing ideas, without being confined to the prison walls of academia where most other full-time readers/thinkers tend to be found. With a self-built audience, I’d be completely free to write about anything I want, and I wouldn’t have to cater to anyone or anything other than my own curiosity (and the law). I’d have unlimited upside, control my own time, and be an utterly antifragile sovereign individual. Perfect.

That being said, I do have a job. And I intend to keep it, because it’s fun, engaging and meaningful. But as a quintessentially entitled millennial, of course I’d like to “have it all”.

Fun job AND creative outlet.

Building a business AND writing online.

Creating value for customers AND sharing ideas with strangers on the Internet.

So here we are. This is yet another attempt at the writing game. Just as businesses should use cheap prototypes to test new product ideas, we as evolving individuals should prototype different lifestyles to learn about what we truly want and enjoy. This newsletter is my attempt at prototyping the “online writer’s lifestyle” in my spare time, so I can get feel for what it’s actually like to live that way.

I’ve tried this before, of course. But never with serious dedication (nor accountability). I hope and believe this attempt will be the dedicated one, and I hope you’ll want to follow along for the journey.


What You Can Expect

This newsletter will be in perpetual beta, which means I will experiment with the format, content and style on an ongoing basis. But right here, right now, this is what I think it will look like:

Language

I’m back to English for a very simple reason: English is the lingua franca of the Internet. English is the language we use to play the Great Online Game in all its glorious forms.

It just doesn’t make sense from a scaling and ROI perspective to spend time writing in Norwegian anymore. The time and effort spent writing is the same regardless of language, so with a global rather than a national potential audience, the upside calculus is obvious. The Queen’s Good English it is.

Content

I’ve tried separating my online “personal self” from my online professional self for a while. Undringer were from “me-me”, about things I personally found interesting, while Braver’s newsletters (here & here, both in Norwegian) were from “work-me”, and are about professional themes only.

This separation will come to an end in this newsletter. That makes sense, because there’s no true separation between these two selves for me anyway. After all, I’ve worked very hard to align what I’m personally interested in with what I do for a living, by building a company that literally only does things that I think are cool.

I’m also actively trying to show up as “just me” across all areas of life, because putting on a professional façade just because you enter an office seems like an outdated and inauthentic way to operate in the world. (To be blunt, if you can’t bring your true self to work, you probably have one of two problems: either, you’re ashamed of who you really are, or you work in a toxic, non-inclusive workplace. For the first problem, the solution is called personal development. For the second, it is called finding a new job.)

Therefore, Jacob’s Journal will be about whatever I’m exploring and find interesting at any given moment, personally and/or professionally. Right now, this includes business building, philosophy, productivity, the emerging cryptoeconomy (DeFi and NTFs), biohacking, innovation, writing, tech, interior design, game theory, minimialism, mental models, personal development, the Enneagram, remote work… or anything cool I find on Twitter.

If any of this sounds remotely interesting to you, tag along. If you read that thematic list and felt utterly disconnected from all of it, feel free to unsubscribe. No hard feelings :)


Two Public Commitments

Starting a new project is easy. See, I just did.

Sustaining a new project is difficult. That’s where you come in.

All habit change research highlights the immense power of accountability. Tell someone about your goals, and you’re way more likely to follow through on them. If those someones actively keep you accountable, even better. For whatever reason, presumably thanks to our evolutionary history as a social species, it is just so much easier to not let other people down than to not let ourselves down. I intend to capitalize on that bias of ours.

Publish 20 Editions of This Newsletter

That’s why I’m making a public commitment right here, right now, to publish at least 20 Jacob’s Journal newsletters going forwards. They may be short, the may be long, but there will be at least 20 of them put out there.

Why 20? I think that’s enough to find answers to two important questions:

  1. Do I enjoy this enough to continue? This is a prototype, remember. If I really enjoy it, great, continue writing. If no, I give myself permission to quit after those 20 editions, because then at least I’ll know I gave it a serious attempt.

  2. Does anyone care? Compound interest takes time. Building an audience takes time. Finding a voice and a set of topics to write about which resonate with people takes time. I think 20 newsletter sendouts is enough time to see at least some indications of traction. The harsh truth is this: if I can’t make a serious number of people care after 20 editions, I should probably take the hint and go do something else with my time. Life is too short to keep doing things that don’t reach product/market fit.

Provide Radical Transparency

I wish I could have seen behind the scenes as Tim Ferriss or James Clear or Shane Parrish started out on their writing journeys.

How long did it take them to get any traction?

Where did they find new readers?

What were the ups and downs along the way? When were they in doubt about the whole enterprise?

If this newsletters works out in any way, if it among all odds becomes anything worthwhile, something to look back on with fondness from some future vantage point, I’d like there to be a paper trail showing how we got to where we ended up.

That’s why I intend to be radically transparent about how this writing project goes. I’ll share subscriber statistics, my own motivations (or lack thereof), reader feedback (anonymised, of course) and other things that happen behind the scenes of Jacob’s Journal.

You’ll get to see an honest attempt at becoming some kind of online writer play out in real time – the good, the bad and the ugly.

I hope this transparency will accomplish two things: first, to inspire you or someone else reading this to give your own creative projects a serious try. Second, to keep myself honest, as a form of self-accountability scheme. Because as legendary physicist Richard Feynman says, “you must not fool yourself, and you are the easiest person to fool”.

The End

That’s all I’ve got for now. Thank you for reading to the bitter end! Feel free to hit reply to say hello if you’d like – I read every reply.

Upwards and onwards,


Newsletter Statistics Right Now

In the name of transparency, here’s where I stand at this very moment:

  • Subscribers: 307. Aiming for 500 by end of August (help me out by sharing! 🙌)

  • Open rate: roughly 60% over the last few issues of Undringer. Very happy with this number.