A lot of tragic creative stories go something like this:
“I always loved writing/painting/singing/sculpture but no one believed in me and they told me I’d never make a living at it, so I put it aside. Now I work as an office manager and I’ll never know what could have been.”
Mine isn’t like that.
I had hugely supportive parents - some of the most supportive I know. When I told them as a child that I wanted to be a writer, they were excited and believed that I could do it. By the time I was a teenager, they definitely would have helped me pay to go to college as an English major, and would have trusted me to figure it out. I had supportive teachers, including a really encouraging community college professor who told me she really hoped that I did something with my writing, and when I told guidance counsellors that I was thinking about journalism, they let me know that they thought it was a good idea.
Right up to a few months before high school graduation, it was the track I was on - figuring out how to become some sort of professional writer.
It’s me. Hi. I’m the problem. It’s me.
At the last minute I decided to low key join a cult instead. Or, uh, go to a fundamentalist college and study to become an evangelical minister.
That decision derailed my writing path for at least a decade, and to this point has meant that I’ve never had formal writing training. (That’s right, all of this magnificent glory is self-taught.)
—
To be fair to my 17 year old self, I didn’t actually have any context for what it would mean to write professionally. I may be forgetting something, but as far as I remember I genuinely didn’t know anyone who wrote for a living. I’d never met an author, and I didn’t know any journalists. In life, you follow the survival strategies that you know, and in my small-town context, I had no model for writing as a means of survival. (And not inconsequentially, I knew a lot of ministers.)
Worse, as an adult I’ve gotten to know writers over the years, and it hasn’t exactly made me feel like it was a mistake to find other ways to make money. By the time I started university in 1998, journalism was beginning its transition from a relatively stable print-based middle-class occupation into an online, freelance subsistence hustle. I've realized that the vast majority of people who make a living wage from books already have some sort of public persona that drives sales. The rest write for passion or principle and figure out how to make the bulk of their living through other means. Magazine editors? Journalists with stable jobs? All of them that I know outside of major New York publications make less money than I do as a nurse (I retrained after I stopped being a fundie), and work longer hours for the privilige.
By the time I’d left the path towards ministry and was in a position to think about putting myself in a writer’s shoes again, it seemed potentially embarrassing. Setting aside a stable career to pursue writing seems something like selling the house to fund an album for your Huey Lewis cover band.
Maybe that’s a little unfair to writers. Also, screw you, there’s nothing wrong with Huey Lewis.
Anyway though, I wish the world wasn’t like this, but that’s the story with pretty much everything that sounds fun, right? Anything in the arts, working as a tour guide, dishing up popcorn in a movie theater your whole life: none are realistic. Every clear path to financial viability is unpleasant, boring or sociopathic, and the decision to pursue a career that actually sounds fun risks both public humiliation and financial failure.
When I retrained after ministry, I didn’t choose writing. I chose an unpleasant path and became a psychiatric nurse. It worked. It’s not publicly humiliating, and I have plenty of income.
—
The thing is though, from the time I was a teenager I never stopped writing. I’ve always had some type of outlet even if I was never, you know, a writer. Theses. Blogs. Copy for websites. A couple of self-published books. I just write things.
So, for a variety of reasons, this year I decided to become a writer.
That might seem weird, but what I mean is that I decided to stop being embarrassed to tell people that I’m a writer, and to start working on getting better at it intentionally instead of brushing it off as a hobby that I don’t really care about. Because the fact is that I do care about it, and I’m old enough to know that isn't going to change.
I could say that it was Covid that triggered that shift, and the whole existential crisis we’ve all just gone through. “If you want to do something, you need to do it now." There’s something to that.
But more honestly the thing that drove the decision was an ego boost and/or an address to my insecurity that happened in 2020, which was the result of my wife Angel’s labor. After writing The Dirtbag’s Guide to Life in 2019 for fun and Boldly Went (our previous business for the uninitiated), Angel spent a few months figuring out how to use Amazon ads to market it during the Covid lockdowns. She is really good at that sort of thing, and sales jumped from something like 15 organic sales a month to more than 400 during mid-2020. Those aren’t blockbuster numbers by any means, and I sell less now, but it was confirmation that the book had an audience and was marketable. For any entry level author that’s a holy grail.
Most books, self-published or otherwise, never achieve that.
It plants a seed. Maybe I actually am a writer?
Like you, probably, Covid killed most of my inspiration in life, but in 2021 I did manage to get through a rewrite of my first book, I Hope I Was Wrong About Eternal Damnation. In case I was a writer, I didn’t want to have this thing out there publicly that was too embarrassing. Or rather, I didn’t want to be embarassed for technical reason. It’s full of damning details about who I am as a person, but readers love that sort of thing. They’ll turn on you though if you repeat the word “very” too often or use dashes where you should’ve used commas. Those are the sorts of things I tried to clean up.
After that, facing down 2022, I decided that for better or worse this was the year that I was going to become a writer. I wasn’t going to try to make a living from it. I was just going to accept that it’s an important part of who I am, and was going to try to get better at it intentionally. I’d stop hiding it in the closet. I’d stop treating it like an ugly birthmark on my upper thigh. I’d accept the embarrassment that might come if I said it out loud.
I was going to start that proverbial Huey Lewis cover band.
How do you transition from not a writer to a writer?
Taking stock of my life at the beginning of the year, for someone who wasn’t a writer I did have a few pieces in place.
I had one moderately successful book with my name on it.
I had a second book that hadn’t really sold, but that I at least liked pretty well.
I had a few articles published here and there.
I had almost 20 years of personal blogging experience and a small group of people who I was pretty sure would read what I wrote (i.e. you).
I had a bit of experience with trying to write things optimized for search engines for Boldly Went.
I had a fair number of incomplete projects in various stages of disarray in my Google Drive.
I had a bit of knowledge about the types of things that people latch onto and the types of things that they don’t.
And I had plenty of financial stability through my job as a nurse (and Angel’s) to fund some time focused on what to do next
I also didn’t have a lot of things though.
I didn’t have any formal training. Let’s be honest, I’m not the worst but I’m no prodigy when it comes to writing ability. I still do a lot of things that scream amateur, and I still leave very many “very’s” in my copy.
I didn’t have any real plan for what I wanted to produce or how I could make writing financially viable in the long term.
I didn’t have any significant “platform” or a clear plan for how to build one.
I didn’t have many friends who were writers or who were trying to become them.
And if I’m honest, I didn’t even have a clear sense of what I meant when I said “I want to be a writer.”
In that situation, there’s nothing to do really but get started.
But get started on what?
The first thing I needed to do was to define what I meant when I said that I wanted to be a writer. What was even important in all of this? If I was going to devote time to it, what would make it worth the sacrifice? We’re all hurtling towards death. What type of writing would be worth giving up the other productive things a person could do before it gets here?
Late last year, an entrepreneur friend named Amer was trialling a free, structured course for people who want to bootstrap a business, so I sat down with his tool to try to hone in on what to do with my writing. It was a good tool, and it helped me identify some important things:
I want to write books, stories and articles that people will find some combination of funny, useful and interesting.
I want to build a few income streams from writing so it feels financially viable to keep working on it.
I want to be more intentional about building a wider audience.
I want to learn to write well and properly instead of continuing to flail around saying whatever comes to mind.
I want to actually enjoy what I’m working on.
I want to build up some degree of community with other authors.
That is still pretty broad, but it was a direction to start, and it allowed me to ask the next important question, which was “How can I get there?” I’m still feeling around in the dark a bit, but it gave me some principles to guide the concrete things that I wanted to work on.
Thanks Amer.
What’s your lane?
If you want to create things that are funny, useful and interesting, and if you want to actually enjoy it, then you have to identify your pretentiously named “zone of genius.” That is, you have to figure out what you like and what you’re good at, and preferably have that be something that is relatively rare but useful.
For me, my natural interests are in travel, the outdoors and adventure. My professional training in both religion and psychiatric nursing, when I boil it down, has been focused on how to help people put together a meaningful life. I’m not the most adventurous or the most widely traveled person alive, but I do think about travel and adventure more philosophically than most. It’s one of the things that people like about the Dirtbag’s Guide. It’s stuff that I think about whether I want to or not. I’m a weird nerd who lives mostly in my head. So I started there.
I’ll write mainly about how to put together a meaningful life through travel, adventure, and the outdoors. That’s my zone of genius.
What will you write?
From there, the question became what exactly should I write?
My goals were building audience, practicing at getting better, writing things that are marketable, and enjoying it, so across the year my strategy coalesced around a few different things.
Platform
I’ve written a relatively popular book, and Angel and I had a decent following with Boldly Went, but at this stage I’m starting from baseline in a lot of ways with trying to build an audience. If I were smart I would’ve figured out a way to develop things like social media following and email lists from those two projects, but I didn’t really so here I am.
So, I spent the first part of the year putting together this website and thinking about how to start using it. I spent some time trying to learn a bit more about search engine optimization so when I post here it’ll be discoverable by randoms on the internet, and migrated and updated a bunch of old posts that were previously popular. I started this email list because it’s a reliable way to stay connected that won’t, hopefully, be impacted by the whims of tech billionaires and their capricious algorithms.
Speaking of that, I also started trying to use social media more intentionally. I admit that this is an area where my motivation and discipline are low, and my timing is bad. The algorithms on Facebook and Instagram this year shifted thoroughly and a lot of the old stuff stopped working. Instagram started heavily prioritizing video, so I’ve made some attempt at learning reels so Instagram won’t hurt my family.
Generally speaking, I’ve been unsuccessful at using either of those platforms for connecting with new people, although I did dink around a bit with sharing poetry and gimmicky little ideas, and a few of them went very mildly viral.
In both cases, the email list is small and my social media following isn’t much different from what it was at the start of the year. So far, I’ll admit that I don’t feel like I’ve been great about building a platform.
What’s internet social failure feel like?
You feel dumb sometimes, writing to a small group of mostly friends and family. Imposter syndrome is a constant companion and sabbateur.
But 70 - 80% of you do open my emails each time I send them out, which I hope indicates that you all at least are finding this worthwhile. Don’t tell anyone, but to make myself feel good, sometimes I go through and look at the names on my email list and think about each of you out there - us quietly connected. That makes writing feel more like the good parts of old school blogging. It feels personal, like we’re talking. It feels less like shouting into the void.
So shut up sabbateur. I’m just getting started. I’m sure I’ll get better at getting more people on board.
Becoming a better writer
Listen, I’m too old for more university. I’m not signing up for an MFA program any time soon. But I am okay at self-directed learning. This year I read a bunch of books about writing, and have tried to implement their good ideas. My seven favorites have been:
Across the year, these books have provided a foundation to start writing stories with more of an intentional structure and process - like this story, for instance, which is roughly following a Hero’s Journey structure. They’ve taught a few tricks here and there. They’ve given a lot of ideas and fodder for growth.
It’s hard to measure, but I do think I’ve gotten better at producing coherent writing across the year. I’ve definitely gotten faster. An MFA would probably help more. I'm still flawed.
I'll keep working
Practice
Ultimately, I guess, if you want to be a writer you have to write, so I’ve tried to get more consistent about just writing things.
I spent a lot of time writing short travel stories to work on some of the mechanics of storytelling, and to create things that are easily consumable. I’ve shared a few here, and I threw some of those in to writing contests - I didn’t win, but I was a runner up in a couple of them. I got a few stories published in the Intrepid Times, as well as a short blurb on The Trek. It’s not much but I wrote a couple of paid publications and something like 20 more stories that will probably contribute to future projects.
I’ve messed around a bit with fiction and poetry, neither of which I’ve ever really done in the past. It’s been fun - like learning a new instrument. I have a ghost story about a place called Crybaby Bridge near where I grew up in Ohio. I like it. I'll probably share it with you in a few weeks.
And I’ve also started formalizing larger projects. I finished a second draft on a guide to pilgrimage on the Camino de Santiago focused on making the trip a transformative experience rather than just providing logistical details. (By the way, if you’re going on Camino or are interested in reading a rough guidebook, let me know - I’m at the stage where I’d love some feedback!) I have at least some general direction on a couple of other book length projects as well - one about Aotearoa/New Zealand and one about the Americas. I’ve been chipping away at both of those in small bits and pieces, and I plan to put some significant energy into the NZ book while I let the Camino book simmer.
A side benefit of hanging your sign out is that it’s at least theoretically possible that you’ll pick up random interest, and a few months ago an old colleague reached out and asked me to put together a training about using storytelling as a therapeutic/debriefing tool for healthcare staff. It was one of those unexpected things - I didn’t think about pulling over storytelling into psych work, but it makes a lot of sense. I don’t have any formal plans yet, but it’s got me thinking that there may be future direction there for useful projects for nurses and other healthcare providers. Stay tuned for CE nurses, and if you know anyone who wants to learn to use writing to process a life challenge…
So am I a writer now?
Concretely, I’ve made a grand total of around $3500 this year from writing. I don’t have an exact ledger (another thing to put on the list), but that’s a bit less than last year. It’s definitely less than 2020. That’s not money in the bank either. I’ve spent most of what I’ve made on ads, websites, and workshops.
By that financial measure, it’s hard to say I’m a writer, but in the grand scheme of things I’ve taken some significant aspects of the plunge. I’ve admitted I have a problem. I’ve started working on it intentionally. I’ve gotten a few publications. I’ve gotten paid for a few pieces. The Dirtbag’s Guide keeps selling. I’m intentionally working to get better, and I’m pretty consistently enjoying it. It was a foundation building year, but I do feel like I have some elements of author infrastructure in place now.
How do you know that you’re a writer?
I’m not sure that there’s been a key moment that things tipped over, but this has been the year where I’ve been more intentional about writing than any other, and when I looked it in the face and said “Right, here are your strengths. Here are your weaknesses. Let’s figure out what to do with them.”
More, the thing that seals it is that this year I started being able to say “I’m a writer” out loud without being worried that people would look at me like I do Huey Lewis covers. I’m not sure why that changed. Maybe I’m getting more secure in my old age. I'm old enough to accept my fate?
Whatever the case, the problem now is that realistically, I need to figure out how to create more things that you people will want to read, I need to figure out how to get it in front of you and all of your friends, and I need to figure out how to make it all financially viable.
So next year, along with creating new projects and continuing to hone my writing skills, I’ll keep working on marketing, audience building, and deciding on routes for publication.
In any case, thanks for being a part of it. Thanks for being in on the ground floor. Some of you have been reading things I write for years, so we have a weird secret sort of relationship, and I don’t want to forget how strange and meaningful that is. Thanks for joining me in this first year that I’ve been a writer.
As I always say in closing:
That's the power of love
If you'd like to read more, there's a lot in these books.
