Boomer-Compatible Stories, AI Writer, Sold 5.5k Books, Podcast Update & More | #201

October 22nd. 2022: Greetings from Austin! We’ve been having a great time reconnecting with friends and enjoying the warm weather here. This is the first time I’ve had an extra bedroom for more than a few months and I have the most permanent working station I’ve had in a while. I do love living in different locations but there’s also something nice about having a home base.

Earlier this week I dropped Issue #200 which talked about how for certain types of hyper-curious people who are okay paying a status “tax,” there is a once-in-a-lifetime asymmetric opportunity if you are willing to share your ideas online. It is one of the most read issues I’ve had…check it out here if you missed it:

The Great Creator Arbitrage Opportunity | #200 🥳

#1 “What Do You Do?” The Question You Always Need To Answer

Generated by Stability.AI

I was at a gathering on Thursday and someone asked, “what do you do?” Given that I was in Austin, I thought I could share the real story: “writing online, podcasting, internet things, you know.” This was a creator’s hangout after all.

“What do you write about?”

I told him I write about our relationship with work and how it seems there is a shifting common knowledge of work’s role in our lives. The guy, still skeptical, looked at me and said, “is there really anything to say about that?”

I’ve had many of these kinds of conversations. I already had a sense he didn’t want to know more and as soon as I confirmed it I quickly shifted the conversation to generalities and away from my work.

This doesn’t frustrate me at all. I write about something very niche and most people are not interested. I work and approach my life in a very weird way, one I’ve found makes a lot of people uncomfortable.

Which has led to me think a lot about how to describe myself and to whom.

Everyone Should Have Three Stories (Especially at first)

Deep down many of us wish we could say “fuck it” and do bold things in our life without having to explain ourselves.

But that’s not how the world works.

When you do things that are not common, people ask questions and to answer those questions you need a story.

When you are working full-time you have a story called a job. A job is the most accepted story of adulthood. Even if you hate that job or it’s a job that shouldn’t exist or it causes societal harm, no one cares that much. It is a passable story.

When you first take a path like mine it is even harder to describe. You often don’t really have a sense of where you are going and your future really is pathless. Inside we feel this in a powerful way and it forces us to come up with half-assed attempts to pretend we know what we are doing.

This is why I tell everyone about to make a shift in their life or work to prepare and develop three stories:

1. A boomer-compatible story

2. A curiosity trigger story

3. The full story

The first one is for those who are anchored to a traditional view of work or for someone you don’t want to get into it with. It should be directionally true but does not need to be literally true. An example could be something like “I am doing some part-time work and looking for my next job.” You may not be actively looking for a job but you might consider a dream job if it emerged. Or it could just be something like, “I’m trying to build a business” instead of “I’m dabbling with podcasting, writing online, and trying to post my way to Twitter fame.” The key thing is to avoid most sharing of uncertainty or unknownness. you don’t want to share your uncertainty. This is what might bother people and it can be quite hard to get out of a conversation where people get stuck in their fears. Not all boomers either, of course. People that are tied to the default path view of work come in all ages, sizes, and looks.

The second one is similar but should share a little more of your uncertainty and some half-baked ideas you might want to explore. The best way to do this is to have a couple of words or phrases that might capture the attention of people that can help you. Something like, “I just left my job but am excited to explore mindfulness and breathwork.” A small number of people might respond with “oh wow, you should meet my friend Jonny,” or offer other pieces of helpful advice. This kind of story is better for people who might be more accepting of people following unconventional paths, or people who are known to be helpful and curious. But they, like most people, usually still demand a story.

The third story is for your fellow travelers. These people, god bless them, want to know everything and actually are curious about what you are up to. Many of them are on very similar paths and just want to learn from you to improve their own approach. For these kinds of people, I personally say something like “I’m doing a bunch of stuff; writing, podcasting, online courses, consulting, and different ways of working and living" From there I answer whatever questions people have. These conversations can be fun and they push me to think more deeply about what I’m up to and offer useful advice.

A/B Test And Pay Attention

You should always be changing these stories and noticing what happens. This has two benefits. You can see how you feel and you can also see if others think you are crazy or on the right path.

From your perspective, does it make you feel excited? Does it make you want to run away? Do you feel ashamed describing what you are up to?

Similarly, you should watch and notice how others react to your stories. Watch their faces. Do their eyes light up with curiosity? If so, why? By asking them questions you can learn more about your own path.

When you first leave a conventional path, describing yourself is one of the hardest things. This is mostly because you’ve likely traded a path with a certain future for a path with an uncertain one and you don’t know what you are up to by design.

Things like sabbaticals and taking breaks from work are becoming more accepted.

But for now, we still need stories.

+ Clay Hebert has a nice TED talk on this topic as well if you want to go deeper.

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#2 This Section is Written by AI

I pasted the following sentences into a new app developed by Nathan Baschez and the team at Every called “Lex.” The following two bolded lines are what I typed:

Imagining A New Story For Work & Life

Our default path of work is not working for far too many people.

It then produced this in less than 10 seconds:

It’s time for a new story.

The old story of work goes like this: You find a job, you work hard, you climb the ladder, and you retire. Unfortunately, this story is no longer true for millions of people. In the new story, work is not a ladder to climb; it’s a web to weave.

In the new story, work is not a singular activity; it’s a connected set of activities that you do throughout your life. Work is not something you do to earn money; it’s something you do to contribute to the world.

In the new story, you don’t have just one career; you have many. You don’t retire; you keep learning and evolving.

The new story of work is about connection, contribution, and growth. It’s a story of meaning, not just money. It’s a story of building a life, not just a resume.

What would this new story look like for you?

Not bad, right? I’ve played around with this for about an hour. I actually plugged some of the top essay into the app and had it generate some ideas. It generated quite generic stuff but it helped me quickly think about the structure I could use and it got me writing the next section a lot faster.

These tools will only get better and like most new technologies, I’m guessing we will fail to predict how we actually end up using these.

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#3 Book Update

I haven’t done a book update for a while so thought I’d share the latest stats. Sometime last month I crossed 5,000 books which still is 🤯🤯🤯🤯.

Amazon ran a sale for my book in the US for 50% off and blasted it to people via email on October 12th. I ended up selling about 200 books over two days and at one point I was the top book in the business and careers category.

While the Amazon month-long deal they ran in the UK was a wash money-wise (10x books at 10% of the price), this one was better for me financially. I ended up making probably 20x as much and selling 40x the books than I was averaging in October.

I do sense that sales are starting to slow down and likely can’t count on this income for the next year but like always, something new and interesting may emerge. Time will tell.

If you haven’t grabbed the book yet, people are saying it is great.

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#4 Podcast Update

I’ve been recording a bunch of podcast episodes and may or may not have mentioned them in previous issues:

Anne-Laure Le Cunff: We talk about how uncertainty feels on a path like ours, the powerful script of “doing a startup” and how it might be a trap, how freelancing is a great first step as a solopreneur and the power of writing online. (Audio | YouTube)

Corey Wilks: A clinical psychologist and therapist turned creator coach who talks about growing up in Appalachia, his challenges as a kid, finding an inspiring mentor who didn’t fit in like him, and the common fears of creating online (Audio | YouTube)

Ali Greene: Great one on remote work!! Ali has been a leader in remote companies like Oyster and DuckDuckGo and also working remotely since 2014. It wasn’t an obvious path at first for her. Hear us talk about stories to tell people when you leave your job, what actually works in remote companies, and the book she’s writing. (Audio | YouTube)

I’d love it if you subscribed and rated the podcast. A simple way to help me out! Here is the show page here.

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#5 YouTube experiments

After sort of ignoring it for a few years, I’ve decided to put some time into my StrategyU YouTube channel. I found a coach who’s been helping me figure out how to have fun with the medium (basically, remove all the stuff I dislike). I ended up finding a great editor that matches my strengths and we started doing some video.

Here is one that I thought came out pretty well:

If you like business communication, business strategy and stuff like that definitely subscribe. I’m going to do my best to create useful stuff.

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ICYMI - last week, my thoughts on the creator opportunity

Thanks For Reading!

I am focused on building a life around exploring ideas, connecting and helping people, and writing. If you’d like to support my journey, the best ways are to:

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