Looking back at 2019

This has been a year of ups and downs for me.

I’ve achieved a modicum of success in my independent career, but I haven’t found a sustainable way to create a consistent output yet.

I started the year relatively unaware of my burnout, coming out of a few months where California was on fire and my girlfriend’s family home burned down. My girlfriend also got a new job, leaving me to work truly solo at home for the first time at the beginning of March.

On the work front, my first few months were plagued with major sync issues in the Shortcuts app that left my growing collection unmanageable. I managed to get a few videos out, but just managing my own library of Shortcuts was a Herculean task and I barely scraped through. Then came WWDC, and while I had a blast, Shortcuts’ beta transitions were even more unstable and I fought daily uphill battles, culminating in the complete and total crashing of Final Cut Pro on launch for the final weeks of the summer.

With my entire strategy falling apart, I changed gears. I focused on my shortcuts first, building out an entire Airtable database of all my shortcuts so that I could manage (and share) my toolkit.

From there, the Shortcuts Library was born, leading to amazing links in places like Lifehacker that sent more traffic to my personal website that the total views up to that point.

I also consider my “Whats new in Shortcuts in iOS 13” livestream on YouTube a big success, where I spent an hour (and all of my energy) detailing every thing I could thing of that was new.

And, back in March, I will definitely not forget my Tim Cook tweet, where he quote tweeted my account after I shared an article with 100 apps with Siri Shortcuts.

On the podcast front, Supercomputer unfortunately saw its end as my cohost Alex Cox recovered from hand surgery. I will also admit that I never found my footing with the show – I felt our dynamic was great, but simply preparing for and our conversations about what I was doing ended up focusing more on what I hadn’t yet gotten done.

Thankfully, Mikah Sargent reached out to me and Smart Tech Today on the TWiT network has been going strong for 12 episodes now – in contrast, we have a very specific format and it’s been much easier to integrate it into my weeks. We’ll also be releasing it as a video podcast from now on starting in January, but the show is still a podcast and will lean towards audio listeners – you can just see our pretty faces now.

This newsletter slid back a bit, and I’m formally deciding I bit off more than I could chew in both calling it a biweekly newsletter, thinking it should be weekly, and really not having much to say via email except for maybe once a month on average. So I’m swapping it to “at least once a month, but also more if I feel like it” because there’s no reason to limit myself either direction – I’m also considering plain-text only, like this one is.

On the writing/iMore/video front, I’ve adopted a new mindset after indecision plagued me for much of the year. Instead of separating topics for each “vertical,” I smashed all my content ideas into single projects that can evolve naturally into the best distribution channels. I suffered so much from “context switching” where I felt like I had to decide “where” I should be focusing my efforts, rather that “on what” – working on videos made me feel guilty for not writing more iMore articles, and working on articles felt like a distraction from my videos, a truly vicious cycle.

Now, I’m pursuing ideas from gestation, letting them grow naturally, and picking which channel to use based on what the topic calls for – I’m taking the context shifts as they come, rather than forcing myself into a randomly chosen area of work each day.

That means I’m blogging and writing pieces more often, sharing quick links to shortcuts on my website way ahead of when/if they might appear in a video, and making good progress on a significant number of ideas that’ve been ready but waiting.

I’ve also worked on a large number of personal, over-detailed checklists. I’ve been tweaking many daily routines that I’ve built up from scratch this year, developed multiple “master” templates for different types of work, and have truthfully spent too much time managing tasks – but I’ve done so in a way that’s finally starting to pay off.

Going into 2020

One of the biggest lessons I’ve learned this year is that you can’t optimize something until you’ve gone through it at least once. It’s infinitely harder to plan something new that it is to just try it once, write down the steps you took, and then brainstorm on ways to improve it the next time. 

Sometimes that means a single task, sometimes that means a week-long project, or sometimes it means observing trends over more of your whole year. And, you must to wait until the time period is over – you can’t fix a weekly process in a day, by nature it must take at least one week and often times three or four weeks.

That means developments come in months and quarterly gains, not daily. And hanging your hat on daily improvements will almost guarantee disappointment.

And along those lines, I stopped worrying about what I’d be doing during any single day and instead either focused on exactly what I’m going to do right now as my next action, since that’s all that matters in the moment. I’ll admit this part of this is unique to my work situation, but it’s a practice in focus that has taken me almost a year to improve on.

I found myself excited to work through all of this December, which didn’t match my feelings last winter when December was the month I disappeared for a bit.

Many projects are still in progress, but I’m looking forward to what 2020 will bring. I have a limited set of videos I’ll be producing at first, filling in any “white space” with blog posts, live-streams, and some new things that are still in the works.

I’m also open to appearing on podcasts, in videos, or whatever form might fit – I want to connect with more people directly whether to talk about, work on, or join forces on technology-related projects. I have unlimited topics to cover in regards Siri Shortcuts, and a whole host of other things I’m interested in too – reach out and maybe we can find time for something fun.

On the personal front, I plan on making time for one big trip, successfully keep new plants alive, move my exercise efforts up one notch, and see my nephew as much as possible.

Living life at 30 in Berkeley is going well and I look forward to developing personally alongside whatever 2020 has in store for my life as an independent creator – maybe now that I’ve been doing it a full year, I can learn and optimize properly this time around.

Hope your year goes well too.

Thank you for reading the 12th issue of my newsletter! It was great to have you.

If you're interested in past issues, check out the full archive.

Copyright © 2019 Matthew Cassinelli, All rights reserved.

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