The Grasshopper 3/5/23, a Sunday note to my readers

This article is not paywalled like normal Sunday Editions

A major strategic mistake is to reinforce things that are not working. Like many Substack writers, I’m trying to make paid subscriptions work, and normally this would be a paid Sunday Money Edition. My plan was to devote it to Content Marketing, and I drafted a good part of the guide.

But I stopped. I’m not getting validation that the Sunday content is compelling enough to upgrade from free to paid and I am doggedly working to find a way to make it more compelling. The plan is to do one comprehensive Money Edition monthly and to use the other Sundays to explore the mindset of writers who want to go pro, i.e. get paid for our work.

I am one of those. But I also want to offer readers something interesting enough to have you consider upgrading. So I’ll be experimenting here for the next few months, trying to crack that code. Thanks for your patience.

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That ‘follow your bliss’ thing

A lot of the work we do as paid writers is not always scintillating or rewarding beyond that payment. I’ve written about business freelance writing, writing on Medium, going viral, and Substack newsletters as micro-businesses.

I’ve done all these things fairly successfully but they never felt like I was following my bliss. And that was alright. Any writing improves you as a writer and some paid work is just that, work. A craft if you will.

But money has never been my primary goal as a creative and I don’t think it can be in the long run. Prior to the Covid lockdown in early 2020, I had decided to leave a lucrative long term contract writing job for a great small company. Without planning it, lockdown gave me and many of us a time of reevaluation, whether we wanted it or not.

After I quit the contract job in the fall of 2019, I took a train trip across the country to the West coast, and up and down that magical coast, a bucket list item for me. But that trip was not what I had expected, as much because of my state of mind as from outside events I experienced.

There was a dark side I was not prepared for and its theme was the homelessness I seemed to witness everywhere I went. It didn’t help that it was November, a cold time of darkness before the Winter Solstice. Tip: don’t take scenic train trips when the days are too short to appreciate the views.

I was gone for a month and spent it largely alone on the train and in brief stays in Chicago, Denver, San Francisco, and Santa Barbara down the coast. It may be that my awareness of the extent of the unhoused, the current term for that plight, was because train tracks often run through the backsides of the world, places where a person can avoid the appearance of failure.

So, darkness,and being a witness to a human disaster of a different sort, I returned a bit shaken and began wondering how I could find my bliss as a writer. I had freelance work and my writing on Medium was paying a little something, enough to scratch by while I considered my options.

Then the world changed. I think every one of us has a store of stories of that time when the world was put on hold. Because I had demonstrable steady income prior to lockdown I was able to apply for a generous unemployment income and money was temporarily not an issue. 

Though, of course, there was not much to spend it on. Like many Americans, my savings grew through that strange 18 months. And I had the luxury of time to consider what my bliss might look like. The world had changed and with it my priorities.

Freelancing dried up at first in 2020, but as businesses rethought how to work, it came back full strength. Being a remote resource was now much more the norm and I happily took on projects from two European software companies marketing to US markets. I wrote blog posts, website copy, white papers, sales letters, and the typical content marketing stuff.

I liked my clients and the money, but I still had not dealt with that bliss thing. But that was a time when there was less urgency to the world and I felt less pressure from myself to drive forward. There were few places to drive to.

So, like the rest of us, especially those without children, I cooked, made cocktails, and obsessively watched the news. I was often shocked by the political climate with a President denying a pandemic because it interfered with his re-election plans. He dithered while millions died and I got pissed off.

And the focus of my writing, politics, climate, and global events, changed. And it turned out I was not alone in my opinions. I was writing about something I was passionate about and enough others were reading it that it started to become a legitimate source of revenue.

Some of that bliss crept back in as I realized I could write on my own terms and glean out a living in the process. So, I decided to go all in with online writing and that eventually resulted in, among other things, The Grasshopper. It’s now been a year since I started writing this thing and it has been a gratifying experience.

I eventually cracked the code for finding subscribers and started to build a second stream of online readers in addition to my growing following on Medium. I still haven’t found the formula for making the paid version work but that was always going to be an experimental process. It’s one that is ongoing.

I’m only doing my own writing these days, having gradually stopped freelancing when it became possible. I won’t say I’ve completely followed my bliss but I’m much closer to it. There are other things in life that contribute to that and they are ongoing.

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That’s my Sunday meditation on where I am right now and how I got here. If you think there is value here, consider upgrading to paid. But keep on reading the free issues. Sundays will continue to be part of the paid package, along with archive access to over one hundred articles like this. 

It’s really quite amazing to me that starting the Substack has worked out as well as it has. It’s hard to complain about it. And someday it may start to pay for itself. I just need to remind myself that some things are best left to the universe, and it generally takes care of its own!

Did you write today?

Martin

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