Why subscribe?


Honestly, I don’t have a good answer. This is an experiment, and some experiments go badly. Things blow up, or melt down, or just kind of fizzle with very little fanfare. This experiment may be no different. So you probably shouldn’t subscribe yet.

But if you’re curious or long-suffering or just a masochist, then you should sign up to see what happens. Because even if most experiments fail, every now and then something transformational happens, and it’s pretty magical to witness that if you can.

I’ve been blogging off-and-on since 2006 (first post), and I’ve gone through numerous periods where I posted on a daily or near-daily basis. Looking back, those periods were both stressful and incredibly engaging. There’s a clarity in my thinking and writing that emerges after I write on a daily basis for awhile. I find my voice, I start seeing patterns around me, I get more focused. I’m better able to synthesize my thoughts.

Unfortunately, I haven’t found a shortcut to getting to that point other than grinding out a lot of writing that isn’t great, based on thinking that’s even worse.

And I need to get back there somehow.

I’ve been working with clients since 2007 as a freelancer, and I’ve done pretty well at it, so a few years ago I started writing about that. I appeared on a bunch of podcasts, I started coaching other freelancers, I sold a course, I launched a service to help freelancers find work. It was all going so well that I rebuilt my personal brand around freelancing and built an email list of tens of thousands of people. I built complicated systems to acquire, nurture, and convert those subscribers into customers of my products. I stitched together complex systems for marketing automation, analytics, managing ad campaigns, and partnerships. I learned a lot about copywriting, analytics, ecommerce, conversion rate optimization, sales, coaching, product creation, pricing, and managing staff. It’s been both exhilarating and crushing at times.

But I think through it all I lost my writing voice. There’s so much stuff between me and my audience now. The words aren’t just the words anymore. Everything is a commodity. Readers become an “audience”, writing becomes “content”, persuasion becomes “copywriting” or the dreaded “conversion rate optimization”.

I used to login to Wordpress, write a post, and hit the publish button. Now there’s a whole marketing automation stack involved, subscribers are on different automated campaigns, and they signed up to get emails from me about freelancing a few times a month. Now I’m going to start sending them daily emails on other topics?

So to sum up, this list is two main things:

  1. It’s me declaring online marketing bankruptcy. I want to focus on the actual writing and as little else as possible. No promotion, no custom technology stack, no analytics, no sales, no bullshit. Just the words, in the simplest channel I can imagine. I write a short daily email, and I send it to you. That’s it.

  2. It’s me giving myself some space to play, to write about whatever I feel like writing, and to see where it takes me. Right now I feel nothing more than a vague fog about what this newsletter should be. But I know from experience that writing here daily for a couple months will wash most of that away.

That still doesn’t tell you what kinds of things I’m going to write about, does it? So here you go: this is a list of some of the topics I’ve been jotting down over the past couple weeks to potentially write about:

  • Building something for others vs. building something for yourself

  • Why doing the wrong thing is usually better than doing nothing

  • The psychological danger of betting against the happiness of others

  • How do you find ways to add unique value to the world?

  • Why don’t independent workers have better representation in government?

  • Is the middle of a pandemic the best time to start a new venture?

  • We hear about how a “scarcity mentality” holds you back, but what about when there’s actual scarcity and deprivation in the world around you?

There are a bunch more ideas in my notebook, but these are the ones that make sense to me at first glance. I need to take better notes.

If there’s a common thread, it’s the idea of navigating your life without a roadmap, or even a road. I’ve always been a lot more interested in a lifestyle that does not follow a defined path. That’s why I was drawn to entrepreneurship in the first place.

But carving your own road through the jungle of life is scary. It’s dangerous sometimes too, in the oh-god-my-rent-is-due-and-this-client-wont-pay-me-oh-god-oh-god-why-didnt-i-take-that-corporate-job sense.

I wish I could write that going your own way is worth it, but I don’t even know if that’s true. I think I might be happier if I could just settle down and live a “boring” life. But I can’t. Some of the reason is clearly psychological damage that I’m working to heal from, but part of it is not. That is a thread worth pulling at.

And since I know there are many others out there who don’t quite feel like they fit in, but who also aren’t sure if they want to, I offer you a short, daily (-ish) email from someone who gets it, and would love to see what we can learn together.

But seriously, you probably shouldn’t sign up yet.