From the Editor’s Desk: Just One Piece of the Success Puzzle (Premium)

We’ve all heard some version of the advice “do what you love” or “follow your passion” from some well-meaning family member, friend, or outsider. Compared to the equally schlocky “everything happens for a reason,” which is just a call for the passive acceptance of those things you cannot change, it is at least an action item, a to-do.

The problem, of course, is that it can be bad advice. And I bet it’s given, most often, by those who are even not doing what they love themselves, because that’s how advice usually works. It’s sort of a to-don’t, when you think about it. But most work requires some set of skills, and those skills don’t always align with one’s passion. Perhaps it’s better to focus on what you’re good at, with an emphasis on those areas in which you can make a difference.

Granted, none of this even applies to me, as I’m in the very lucky position of doing something that I love that I’m good at, and, in its own small way, can make a difference. And because this thing, writing, can just as luckily be done anywhere at any time, I’m also in the very lucky position of being able to indulge some of my other passions, like travel, without them getting in the way.

This wasn’t supposed to happen. Coming out of high school, I was never going to do anything other than “be an artist,” whatever that meant, or slightly less vaguely, “do something with this skill” that I had. But it didn’t take me very long into my first semester in art school that fall to realize that I was on a fast track to never making any money at all. My response was to give up because it just felt so futile. I dropped out after one year, and about four months after I had quietly given up internally.

I didn’t see it this way at the time, but this, too, was lucky. As it turns out, I was interested in other things too, and it was clear that one of them, my love of what I’ll now call personal technology, could lead to a lucrative career. And so my post-art school years involved part-time and then full-time study with the aim of becoming a computer programmer. And then life took me in another direction, albeit a related one, and here we are. More luck.

Which is a problem when people come to me for advice. At various times over the years, I’ve been approached by others asking how I ended up doing what I do, and what they could do to get similar work. This is impossible to answer on one level because so much of my experience was circumstantial coincidence (luck), not any grand plan on my part, and so the story, interesting or not, can’t be used as a blueprint. (And things change. Were I starting out today, I’d probably be making YouTube and TikTok videos, not writing, and would be less successful. Even my timing was lucky.)

But I do have some advice. I’ve noted many times that it’s easy to start something—a blog, a website, or a YouTube channel, whatever, anyone can do that—but the trick is to keep going. And for that to work, you need to have some skill and offer something unique, be able to rely on the support of those around you, and, on some level, wait for it, you have to get lucky.

There’s so lot more to it, of course. But this past year, there were a few incidents related to success that reminded me of something important. That in addition to adapting to what life hands you in bad moments, it’s just as important to seize the moment when things are going really well. This is the “success breeds success” theory, and similar to another familiar bit of advice, that to accomplish a big set of goals, you need to start with the small things first so you can build momentum as you succeed with each.

That sounds reasonable, but it’s not for everyone. For example, some will argue that this strategy works particularly well with paying off debt—always tackle the smallest debt first so you can quickly succeed at paying it off—while others believe that starting with the debt with the highest interest rate is a better strategy. But maybe we should look at this as we do with diet and nutrition: we’re all different and so different things will work depending on the person.

But the commonality here is that success can be inspiring. And even the smallest successes can lead to exponentially bigger successes over time, especially when you’re tackling something big. And I have, in my own way, written around this topic already in response to those two incidents.

The first happened back in March. My wife and I spent most of that month in Mexico City and specifically led normal day-to-day lives there, with no sightseeing, to experiment with the viability of spending more time there. Meaning, we worked every day, just as if we were at home. One of my goals going into the trip was to do as much as possible to get the book Windows Everywhere, which is based on my Programming Windows series, ready for publication. This seemed like an ideal, distraction-free time to do this work. But as with all big projects, I wasn’t sure how much of it I’d get done.

It went better than expected. A lot better. As I wrote in Windows Everywhere: Hitting a Wall at the time, I found myself in a weird combination of frenzy and fugue state—I guess most would describe this as “being in the zone”—in which time disappeared as I made incredible progress on a tedious project that I’d tried and failed to do multiple times in the past. Where I was initially going to be happy with making at least some progress, it suddenly seemed that I’d get a good chunk of it done, maybe even half. But as the successes racked up, I stopped settling and started dreaming. Maybe I was actually going to finish this thing. I began measuring my progress against the calendar, not whether I’d finish, but how quickly.

Unfortunately, I eventually hit a wall, as hinted at by the name of that article: technical issues at Leanpub, which couldn’t at the time handle a book this big, slowed me down and then stopped me completely, as I could no longer generate previews of the book. This experience was important, and it’s tied to success and satisfaction (work-related or otherwise): as good as things can be, there’s always a potential roadblock out there. I got by that one with the help of a friend, as noted in Windows Everywhere: Some Good News. (And seriously, surround yourself with people who can help, not those who get in the way. That applies equally well to tools, processes, and lots of other things when you think about it.)

The second experience is ongoing. After moving from a big house to a small apartment earlier this year, I was once again struck by the need to declutter, and in May I wrote that I would finish my earlier photo decluttering work (when, four years earlier, I had scanned in my entire paper-based photo collection and thrown out the originals) by scanning the remaining loose photos and other personal items. But by the time I started the work in early August, I had expanded the scope of these efforts. I was also going to declutter my digital photo collection and my work-based documents archive.

Or at least try. As with the book work back in March, the goal was just to get something done, and make some amount of progress on a task with which I was very familiar: any decluttering work, physical or virtual, peters out at some because it’s tedious and time-consuming, and it doesn’t always seem important at that moment. I knew what was going to happen: I’d get some of it done, and then I’d give up for a while. Probably for some number of years. Until the declutter bug struck again.

That’s not what happened. I ended up doing far more work on this project, and I have seen much more success than I’d imagined was possible. And over the course of the next five weeks, I actually finished the work, which you can read about if needed over a series of several articles I wrote during this time period. I’m sure that it’s all a bit much for some readers, but the repeated success I experienced in doing this work was inspiring. I wanted to keep going, get more done, and share that success with others. Maybe in writing about it, I can inspire others to at least think about this stuff, and a few to make positive changes of their own. It’s enough. (And rewarding in its own right.)

But there is one big difference between this decluttering work and my March book experience: I never ran into a decluttering roadblock that was big enough to stop me cold, not once. I had serious issues with File Explorer reliability and performance, for example, a potential momentum killer when you’re dealing with 10s and 100s of GB of files being transferred over the network and to and from the cloud, but I just moved to a better solution (Directory Opus) and just kept going. And there were a few other issues. But nothing major.

In fact, this work was so successful, I’ve expanded the scope to encompass more digital decluttering projects—music, home videos, other videos, online services, getting another NAS, and so on—and will be writing about these topics soon. (Actually, my article about music collection decluttering is already up because I finished that task. Again, success breeds success.) I am going to emerge on the other side of this in much better shape, organizationally, than I’ve ever been in my life.

And I have to tell you, this feels good. There is something inherently satisfying about getting this work done, and putting it behind me for good. And each step of the way has had its magical moments.

Lost in the literally 100s of GB of unorganized image files spread across multiple locations, I found random photos, individual and in sets, some of family and friends from years ago, that we’d either never seen or forgotten because they were never digitized. But now they’re among the cherished images that pop up on our kitchen smart display, triggering smiles.

Similarly, I went through our DV and 8mm tape-based home movies (and, ahem PDC 2003 and 2005 videos), intending to re-digitize it all in a higher quality than was possible 20 years ago But I discovered there was a DV tape still sitting in our 20-year-old camera. That my wife and I had never seen. I hooked up the camera to my computer—I’ll be writing about this soon—and we watched, for the first time, our then-young children enjoying Christmas morning in 2005. That’s not just a smile, it brings tears to my eyes.

And it keeps me going. Like some decluttering Terminator robot, relentlessly on-mission.

I wish I could summarize this whole thing with a pithy Michael Pollan-like phrase, like the slogan I came up with for my Twitter profile and this site: “Personal technology, with a focus on productivity, mostly Microsoft.” But it’s impossible, and I’ve only touched on the outside edges of what constitutes success on any level. Learn from your mistakes and setbacks, sure. But also let success take you along with it, get caught up in it. There are always more wins to be had.