Here’s My 2020 In Retrospect

I’m lucky to have come out of it relatively better off, but I also wish I could have done more for others.

Derwin Dexter Sy
7 min readDec 31, 2020

I find it funny when I look back at my 2019 retrospective, where I wrote that it was highly unlikely that I could beat that year in terms of being “transformational”. It turns out that was kind of true. But while I’ve personally decided to stay the course for this year, the entire world just happened to change super drastically. A little bit forward to early this year (still pre-COVID) and I wrote this update on where I was at at the time, and even that seems ages away now. All of the changes around us made it impossible and unwise not to adapt.

I’ve had my personal challenges without a doubt, but I strongly feel it’s been nothing quite close to what many people have gone through this year. Even in my close circles — friends and family and people I work with in varying capacities — so many have struggled in unique circumstances. I do feel lucky to have come out of it relatively better off, but I also do wish I could have done more for others (which is why I recently published a starter list of charities I currently support, both to hold myself accountable and to encourage others to consider donating to them, or other charities, as well).

I thought all of this was worth a deep reflection before the year ends, so here’s my 2020 retrospective (and, bear with me, it’s a long one considering everything that’s happened this year).

Working from home

A lot of the situation may have been beyond my control, but the least I could do was face these challenges head on and address questions as best as I could.

At the beginning of the quarantine, I wrote this article about my own experience working with remote teams, in the hopes of helping others make the transition more easily. But despite my experiences, I have to admit, like most people who shifted to remote work, that I’ve been a little bit caught off guard by the scale of a fully remote team.

For context, I already managed one remote team (of three to five people) along with several on-site teams before the pandemic hit. While it did make the decision to go full remote a no-brainer, there were a lot of considerations that hadn’t been taken into account in the transition. As the months dragged on, people started growing weary of the situation — the unreliable personal internet connections, the social isolation, the difficulties onboarding new team members. Admittedly, it turned out I had not done quite enough to make sure things would continue to be smooth after the novelty of working from home faded.

A lot of the situation may have been beyond my control (as were many things this year), but the least I could do was face these challenges head on and address questions as best as I could, even if the answers were not what people wanted to hear. Ultimately, I wish there was more I could do, and as we roll into another year of remote work, I will push on trying to make things better.

Misses and makes

I give myself a 5 out of 10 in terms of accomplishing the goals I set early this year.

Looking back at the goals I set for myself early this year, I give myself a 5 out of 10 in terms of accomplishing them — that is, about half of them made. Not too bad, considering the curveball the circumstances threw in my way.

Financial goals were first and foremost in the miss list, as investments inevitably did not do very well this year and it just wasn’t the year to take very many risks with money. Likewise, I missed my goal to take my daughter on our first international trip, as that was obviously not possible this year.

On the other hand, I’m proud to have made leaps in personal growth goals. The quarantine was an opportune time to spend reading ( here are three of the books I managed to read early on in the year and here’s my recommended reading list for 2020), and I outdid my reading goals for the year by a mile. Likewise, while I hadn’t posted as much on this blog (another personal growth goal), more important channels opened up through the year to publish my thoughts and reach audiences (more on that in the “small wins” section). But perhaps the biggest and most difficult personal growth achievement was actually “losing”… that is, about 30 pounds in body weight. It may sound superficial but these days when health is everything, I definitely think this was a big win for me this year.

In terms of professional growth, I set a goal for this year of taking on a new role at my work with Synacy. This was a little bit delayed, but it’s going to happen at the start of 2021. While I’m definitely excited to share the news, I’ll save that for later. For now, suffice to say, I’m quite eager to start learning in this new role and hopeful about being able to make a bigger impact in our organization.

Small wins

Never have I been as driven to discover and find solutions to market concerns as I have this year.

If there’s anything I’m grateful for in 2020, it’s that it’s given me a new appreciation for my personal situation and how fortunate I’ve been not to have to worry about where my next meal is coming from or whether I would still have a job in the next few weeks. There’s definitely something to be said about how lucky I am just to be able to still accomplish small wins (beyond just surviving) this year.

First off, a plug for the first e-book I wrote, which came out early on in the pandemic. I had always wanted to do it, and eliminating the commute time by working from home as well as all the other free time I suddenly had gave me the perfect opportunity. If you haven’t gotten your copy of “Risk Management Crash Course” yet, you can do so here for free!

Likewise in other entrepreneurial ventures, never have I been as driven to discover and find solutions to market concerns as I have this year. With such an unfamiliar landscape, there was no doubt that new needs would arise and new ways to fill them ripe for exploring. (So, this is primarily why I haven’t been updating this blog as much recently.)

If you didn’t already know, I run two startups that are yet to fully take flight — an independent music label called Melt Records, and a software development firm called ATeam Software. Both were ripe with opportunity as entertainment and software were two differentiators for the year and something people and businesses really needed.

With Melt Records (which I hadn’t been as involved in in the last two years), connecting musicians and fans in a purely online space was a challenge I felt I could make a difference in. And with the launch of our website and a few web video series, I did to some extent find a new channel to provide a richer multimedia experience to our audiences.

Likewise, with ATeam, we pivoted to pursue a few areas we thought might be what the world needs right now — learning management systems, booking apps, and e-commerce. Ultimately, the e-commerce product met some moderate success, and we have now soft-launched one marketplace website, completed building two, and are in development for at least three more.

The best thing about 2020

While we weren’t able to make that first trip abroad, being at home was a journey in itself with so many things happening.

Perhaps the best thing to come out of 2020 and the strange circumstances we faced was that I had an opportunity to be present for my daughter, more than I would have any other year. Being stuck at home both for work and for leisure, I got to spend a lot of time with Harper and in no better timing than when she’s a year old and the milestones just keep rolling in.

In a span of a year, I’ve witnessed her first few words and her first step. I was there when she started to walk more confidently and started forming coherent sentences and counting to ten. Now she’s becoming even more independent and experiencing a lot of new things for herself.

So while we weren’t able to make that first trip abroad, being at home was a journey in itself with so many things happening in such a short time. I couldn’t ask for much more than being able to be there for all of them (something I know many parents have not been as privileged to experience).

That’s it for my retrospective — thanks for humoring my self-indulgence for a while. TLDR; I feel lucky to have come out of 2020 much better than I know many have, and just as many have not even made it out of the year (rest their souls). I definitely wish I could have done more for others and I personally resolve to try and do just that in 2021.

Here’s to a great 2021 for everyone! Happy new year!

Photo by Danil Aksenov on Unsplash

Originally published at https://techmanagement.life on December 31, 2020. Subscribe to my mailing list to get updates and articles straight in your mailbox, plus a free e-book, or follow me on Facebook!

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Derwin Dexter Sy

I’m an engineering manager and entrepreneur who loves exchanging ideas and helping others become better at what they do. I run a blog at techmanagement.life