2018 was actually pretty great for me.
Unlike seemingly most people, 2018 was actually a pretty great year for me — today, a look at how it went, and my plans to build on it in 2019
Greetings, users! Like most other Twitter members, I’ve been seeing an alarming amount of tweets this week from all my friends about what a shitty 2018 it was for them, and how they can’t wait for it to be over and how they’re desperately hoping 2019 will be better. Unlike them, though, 2018 actually went pretty well for me, so I thought I’d get a journal entry up here on a quiet New Year’s Eve and review why, as well as look at my plans for building on these successes in 2019.
The main reason, of course, is that for the first time in 15 years, I actually generated revenue in my life during every single month of 2018; and that’s because, for the first time since attending a coding bootcamp three years ago, I finally gave up on the idea of trying to get a full-time job in the tech industry, and decided instead to try to make a living for the first time as a full-time freelancer. The simple fact is that, although I learned a lot of lessons about myself and about soft skills by attending DevBootcamp* in 2015, trying to get a job because of it turned out to be kind of an unmitigated disaster, for a variety of interrelated reasons — partly I was discriminated against for being in my late forties while apply for entry-level positions; partly I was old enough that I could see all the red flags at the various companies that did interview me; partly I was ethically disgusted with most of the positions I had even the tiniest chance of getting; partly those various positions started drying up a couple years after my bootcamp experience, as more and more tech companies started realizing that hiring bootcamp graduates was turning out to cause more trouble than help.
[*It’s also worth noting that DevBootcamp is now out of business, one of the half-dozen such organizations that bit the dust during The Great Coding Bootcamp Purge of 2018. It was kind of an open secret within these bootcamps, in fact, that the clock was already ticking as far as your window to get anything useful out of the experience; although the official line was that “There Will Be Endless Coding Jobs In Our Glorious STEM Future For Everyone!,” it was clear even in 2015 that the industry was soon going to reach a point of unsustainable critical mass, and this was even before the bloom fell off the rose of tech companies actually hiring bootcamp graduates, and realizing that most of them weren’t getting nearly the kind of education they needed to be decent ongoing employees.]
At first I decided to combat this by switching my job search to front-end developer positions, instead of the full-stack positions that DevBootcamp prepared its graduates for, since I’m already a veteran of graphic design, HTML and CSS; but it turns out that you can’t get a front-end dev job unless you’re competent at modern front-end Javascript webapp frameworks like React, Angular, Ember, VUE and others, which I’m not. Then after starting to meet people in the tech industry that were doing this, I decided to switch my focus again now to product management, since I already had self-taught experience in my life at helping creatives and tech people communicate with each other, the main thing that people in that position do; but unlike coding positions, no one wants to hire product managers based on them having a bit of self-taught experience, which meant I was going to have to go back to school yet all over again if I wanted any chance of getting even an entry-level position. And I had already spent $12,000 to attend DevBootcamp, so wasn’t thrilled by the idea of spending yet another $12,000 with still no guarantee of a job.
So out of desperation more than anything else, I decided back in January to sign up for some of these third-party freelancing websites, like Upwork.com and Freelancer.com, just to see if I could pick up some quick easy work doing my old pre-bootcamp jobs like personal assistant, copy-editing, proofreading, data entry, document layout and the like. And that’s when I discovered something interesting that I would’ve never guessed — that the eclectic set of random skills I’ve happened to pick up over the years because of my own personal interests (graphic design, website development, manuscript editing, marketing, mailing lists, managing people, high-level strategy, ebook creation, podcast production, etc etc) just happens to be the perfect combination of skills to bring to full-time entrepreneurs who are usually hiring half a dozen different people to fulfill these roles in their lives.
I’ve had a policy for many years not to mention online the people and companies I work for (people who get pissed off at me online tend to retaliate by trying to get me fired from my jobs, and I don’t need the headache anymore); but basically the kinds of people I’ve been picking up this year as ongoing freelance clients are what are typically called “thought leaders,” with Malcolm Gladwell probably being the most famous example — people who write bestselling books about the intersection of business and intellectualism, then use the books’ popularity to speak at events like TED and SXSW, then use the popularity of the events to get paid gigs consulting for C-level executives at Fortune 500 companies, then use those consulting connections to interview famous CEOs for their next bestselling book, thus starting the cycle over again once very couple of years. Despite all the successes, these people are essentially just doing what I’ve been doing over the years, going it solo and working from home and with no office peers to fall back on when it comes to things like maintaining their newsletter subscription lists, their personal websites, their booking calendar, their Google Adwords, their podcast, their blog, etc; and I’ve been finding a lot of surprise success at getting hired by such people to basically do all those things for them, a job category I would’ve never realized even existed if I hadn’t stumbled ass-backwards into it this year.
I also decided this year to up my game over at my rare-book dealership at eBay, with more success than I was expecting. I’ve been collecting rare books since 2011, mostly as a personal hobby, and over the years have had maybe 20 to 40 of my books for sale online at any time; but this year I’ve been making a concentrated effort to get all of them finally photographed and listed, a daunting prospect since it takes around three hours to do each and every listing (that is, to do it correctly, with a dozen high-dozen photos and deep research on the book’s history, significance and previous sales records). As of today, though, I finally have almost 200 of my 300 books now listed; and more importantly, sales for 2018 is going to top just about $2,000 by the end of the year, about twice as much as the thousand bucks I was aiming for. For someone like me who lives off just $25,000 a year, that’s a significant amount of money, and way more interesting than $2,000 worth of secretarial work, a positive experience I’m hoping to build off of in 2019.
And what else? Well, it was a good year for spending a significant amount of quality time with my friend Carrie’s twin sons, including one of them coming and living at my place full-time for two and a half weeks, which was a much better and more fun experience than I was expecting, despite the sudden preponderance of way more Kanye West in my life than I ever wanted to have. This is important to me right now, because the boys were 15 this year, which means there’s only a few years left before they’re off to college and will never live full-time in Chicago as kids again. That makes me want to spend as much time with them as I can these days, which directly clashes with most teens’ wishes to spend as little time around the adults in their lives as humanly fucking possible; so I’m glad that I got to have the experiences I had, learning about the videogames now in their teenage lives and the friends now in their teenage lives and the music now in their teenage lives, without having to pull any teeth to get the information.
And other than these things, you can generally say that 2018 was a good year simply because of maintaining the status quo in many respects of my life, which always counts as a positive merely from not slipping into a worser position. I didn’t get any fatter this year, for example, although I also didn’t really get any thinner (still hovering between 185 and 190 pounds, when the goal for years has been 175); I still got in my Fitbit step count and bicycling goals most days, although I didn’t come close to my weightlifting or swimming goals; I meditated a few days per week, although not the seven days a week I would like to achieve in a perfect world; I generally ate healthily, but not as healthily as I could; I got to travel a bit, but not as much as I wanted; I maintained an even keel with my elderly parents, and finally convinced them to take their first Uber ride as a hopeful first step towards the day soon when they’ll no longer be able to drive, although I failed at convincing them to let my brother and me make their home more elderly-friendly. And perhaps most importantly, I maintained another year of strong filters and bans on all my online destinations so that I didn’t receive a single bit of news about Donald Trump and his latest crazy antics, which I suspect is the number-one reason why so many of my friends at Twitter keep proclaiming that 2018 Was The Worst, Just The Fucking Worst. All these things count as positive experiences merely because I deliberately worked on them, regardless of how successful they were.
So what’s on tap for 2019? Well, as always, instead of New Year’s resolutions, I actually created an entire year-long three-page detailed plan for myself, so let me just run down it right now and share the highlights with you…
—A one-year pause on all web development. For years now I’ve been paying $115 every single month in order to have a series of Wordpress builds through the hosting service WPEngine, but then haven’t built out any of the actual sites; so I’ve decided this year to get rid of the account and put all my development plans into deep freeze for the time being, especially since I no longer plan on using these as portfolio pieces in trying to get a full-time dev job. That’s why, for example, my personal journal is still appearing here at Medium.com, when I promised in my last update that it’d be switched over to a dedicated Wordpress site by now. (Obviously if you're seeing this, you know that I've recently started trying the federation-friendly minimalist blogging platform Write.as; but more on this in another post soon.) Also, hardcore fans will notice that the website for my old arts center, the Chicago Center for Literature and Photography, is now entirely offline, since I hadn’t updated it in years and it was essentially serving as an extremely expensive parking space for the 25 or so books that CCLaP still has for sale up at Amazon.
—New revenue opportunities. Inspired by my successes at “piecemeal revenue” in 2018, I’ve decided to push and expand in this direction even more in 2019. Specifically, I’ve decided to invent a new type of handmade bullet journal to sell at my Etsy store; although there’s a growing amount of mass-made notebooks for this suddenly hotter and hotter form of organizational system (which has gotten a big boost in recent months because of the inventor finally publishing his first full-length book on the subject), I’ve noticed that there are almost no cool crafty handmade versions, which I’m hoping will bring some new notice and new sales over at my Etsy store.
And I’m re-opening my personal chef service from my early thirties, “The Slacker Chef!” This was a little experiment I was convinced to try during one of my periods of unemployment when younger, basically cooking for other people’s dinner parties; the money was fantastic, but my heart wasn’t into it at the time because I wasn’t into all the work of going out and hunting up new clients every day. But now that I am in the habit of trawling for new clients every day, I’ve decided to revisit this idea for the first time in twenty years, and see if it can’t generate another couple thousands of dollars in revenue just like my rare books are doing. The more things I can do in my life that will make a thousand or two or three a year, the less I have to worry about freelancing in order to pay all my bills.
And speaking of which, I’m also going to try doing my first-ever physical live events as a rare book seller in 2019; specifically, I’ve decided to get a tax ID and join the Midwestern Antiquarian Booksellers Association, so that I can get a table at this coming year’s Chicago Book and Paper Fair and the Printers Row Lit Fest. I don’t have the slightest idea how much money events like these might bring in; but just to throw out a random number, if I could make a thousand dollars at each of these, that would effectively double my money next year from rare-book sales, from $2,000 to $4,000. That would be exciting, because collecting and selling rare books is easily the most fun thing I do for money these days, and I’d like to be doing a lot more of it if I could.
—New third-party tools to put it all together. Specifically, I’m signing up for a Shopify.com account in 2019, as a central place for selling everything I just mentioned; and I’ve already set up a weekly newsletter called “I Love You Robot” for disseminating new announcements regarding it all, since my activities are going to be spread out across so many different online and physical destinations next year. You can sign up for the newsletter right now at bit.ly/ILoveYouRobot, which on top of everything else will include the most fascinating 10 or 15 news items I linked to at Twitter that week. (It will also announce new journal entries here at my blog, if you’re not a person who uses RSS.)
—The #JPCHI25 Project. Next year will be my 25th anniversary of moving to Chicago! To celebrate, I recently put together a list of 100 “core things” that everyone should do in Chicago at least once before they die, a mix between a bunch of touristy things I haven’t done in decades (go to the top of the Sears Tower; eat at the Billy Goat; ride the Navy Pier ferris wheel; attend the Chicago Blues Festival), semi-touristy stuff that even locals tend to enjoy doing regularly (attend late-night shows at the Green Mill and Buddy Guy’s; eat at the Walnut Room; walk the entirety of the Art Institute; watch a Cubs game from a next-door rooftop bar), a shopping list of various famous but semi-obscure locations to visit (the Driehaus Museum; the Lincoln Square pedestrian mall; Garfield Park Conservatory; the Robie House; Nelson Algren Fountain), and a bunch of weirdo unique things that are fun to say you’ve done at least once (visit the last Chicago street still paved with wood bricks; stop by the Obama Kissing Rock in Hyde Park; attend the turtle races at Big Joe’s; bowl at the vintage hand-set Southport Lanes; see a movie at Facets; have a Malort at Old Town Ale House). I’ll be taking copious pictures at each destination, and tagging them all at Twitter, Instagram and Flickr with #JPCHI25, so I hope you’ll get to follow along all year. And speaking of which…
—My first-ever 52 Week Photography Challenge. For those who don’t know, I received my first-ever DSLR camera as an early Christmas present this year, my first high-end camera since I was a photography major in college thirty years ago; so I plan on throwing myself heavily into this new hobby in 2019, including participating in my first-ever 52 Week Photography Challenge. There will be much more about this at Instagram and Flickr throughout the next year, so I encourage you to follow along at those places for it all.
—New wellness goals. I’ve decided to try a year of tai chi instead of yoga in 2019, which I’m looking forward to; I’m planning on buying my first electric bicycle, which will hopefully let me bike more often and for longer distances now that I’ll be turning 50; I’m going to take my first class in American Sign Language, which it’s just time for now that my hearing is continuing to get worse and worse each other; and perhaps most significantly, I’m getting a driver’s license again for the first time since 1989, almost exclusively so that I can drive around in my parents’ suburban-scrawl community during my increasingly frequent trips down there, but also so that I’ll have access to a car-share program in Chicago, for the rare times I need a car here like the book fairs I’ll be participating in. As always, more on all these things here in this journal as 2019 continues.
—And a new computing system in my life, both in equipment and attitude. Another thing that’s happened recently is that my ten-year-old Macintosh desktop finally died, which is sad but actually lasted longer than I was expecting it to. Even low-end Macs are now just so ridiculously fucking expensive that I’ve decided to try something brand-new for 2019 instead, which is to switch full-time to Linux and start moving more and more of my computing life to cloud services. That will involve buying one of those Windows laptops with a touchscreen monitor that can be flipped backwards to “convert” it to a tablet; erasing Windows and installing Ubuntu; buying a 4K television during Amazon Prime Day next summer to serve as a new home monitor; installing open-source versions of my usual Adobe Creative Suite software, the main thing I’m currently missing by using my cheap little Chromebook right now instead of my broken Mac; buying an external solid state hard drive as a central portable location for all my daily files; and moving my workflow for documents more and more to my Google Drive, and for music to Spotify instead of downloaded MP3s and iTunes. (I actually did this part last week, and am really blown away already by how amazing Spotify’s recommendation service works; this will likely be the subject of my new journal entry here.) Will this finally let me wean myself off the increasingly sour teats of Apple, Microsoft and Adobe? Well, it won’t fucking hurt!
So that’s pretty much it for now; although I should mention that another part of this plan is to start updating this journal a lot more often, now that I’m not sitting around endlessly waiting for a Wordpress conversion that will never come, so I hope you’ll have a chance to come by on a regular basis during 2019 for more. As always, I can be reached at ilikejason@gmail.com, and would love to hear from you about advice or invitations regarding any of these projects. Here’s hoping 2019 will be a chance to build on the successes I had this year, and that your own goes better than apparently the shitty 2018 most of you had!
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