2020 in review

by Randy Gingeleski

11 minutes to read

Annual recap of what happened in my personal life (2020 edition).

Post featured image

For new readers, I’ve traditionally done year-end posts here on the blog that chronicle my own life.

This year shined a light on a lot that might’ve otherwise stayed hidden.

For example — anyone who thinks 2020 was “the worst year ever” is revealing valuable information about themselves. If you’re in that camp then please study some history instead of my writing.

In general, we might concede that the year positively…

  • Unveiled a lot about the nature of people, politics, and life
  • Catalyzed certain changes to happen maybe 5 years faster than otherwise
    • Transition to remote work may be the clearest example
    • Cryptocurrency as a legit investment vehicle is arguably another

I appreciate this was a difficult year for certain groups especially. Older folks in certain parts of the world. Many small businesses.

Playing the cards dealt to me, 2020 was an excellent time despite several hiccups. I can only explain what happened around me for your possible insight.


Let’s talk about “best laid plans”.

This was going to be my biggest travel year of perhaps the decade, then it wasn’t.

My girlfriend of January is now long gone here in December. Had you asked me back then if we’d be getting married, I would’ve guessed yes. We were together ~3 years.

2020 not only clarified what I want out of life but also that it wasn’t going to happen with her. This was all a learning experience, for the best.

My “day job” of January is now long gone here in December. That’s another change I would not have predicted and another ~3 year thing dissolved.

To summarize some other points quickly, in no particular order —

  • Spent lots of time with family and friends
    • Difficult to quantify but may be greater than any year since 2017
      • As long as you count virtual/phone time
  • Conducted significant business through my company Kapotel
  • Re-did this website/blog twice
    • All “legacy” content from old.gingeleski.com has now been migrated
  • Increased net income 50%
  • Doubled one-rep max on the barbell back squat
  • “Found God”
  • Presented at a major cybersecurity conference
  • Started working towards my private pilot’s license
  • Did more reading and writing than any other year in recent memory
  • Further embraced my predominantly Polish heritage
    • Began studying Polish as a foreign language - my proficiency is now A2
    • Pending Polish citizenship by blood
  • Got decent travel mileage on the books despite COVID-19
    • ~18,800 miles by commercial air
Randy Gingeleski in November 2020
Flight school in November

Before getting too drunk on my own Kool-Aid, I’ll restate that this was a year of big changes all around.

These aren’t necessarily good or bad —

  • Became disenchanted with New York City
  • Spent perhaps an unhealthy amount of time living with my parents

Then as already mentioned —

  • Split from my girlfriend of 3 years
  • Left my job and “work family” of 3 years

We’ll go chronologically to cover everything as it came up.

Act one

At the start of the year, I was traveling a lot for my consulting job. Minneapolis 5 or 6 times. Denver once.

A vacation was mixed in there to Las Vegas with my then-girlfriend. My parents were there for a couple days at the same time. I love(d) these 3 people — and Vegas — dearly.

The Las Vegas strip

The trips were all interesting stuff but did not allow appreciable time to do “side business”. This period certainly detracted from self-development.

As luck would have it, though, the make-up was about to reverse. COVID-19 started to pick up speed.

Before most other people got freaked out, I did some preparation work. Food, a new squat rack, medical supplies, masks, cash, gold, bitcoin, safes.

Half of that stuff went to my parents’ then half came to Jersey City. And as someone who had worked remote for years already, I was then set for COVID-19.

Was this me being super prescient? No, this is a credit to Mike Cernovich writing about would-be scenarios relatively early.

Scarcity, fear, and lockdowns swept the New York metro area. My girlfriend lived with me briefly at my apartment.

Then it became clear we’d be better off at my parents’, so Mom came to get us. Supply stockpiles merged.

Now in upstate New York, I was living quite comfortably. Even during the lockdown peak. My whole approach to “pandemic living” got captured in this other blog post.

Day job switch-up

Before initially settling in at my parents’ to ride out the quarantine, a friend had broached a job opportunity with me. It was casual, brief, and over coffee.

At that time I fully did not take it seriously but didn’t outright reject either.

There’s not a humble way to say this — if you have legit information security skills, you’ll get solicited every day for opportunities. Even now. There’s automation to spam everyone, after all.

Of course these jobs from strangers aren’t as serious as with your friends. The point is, though, if I was outright unhappy in my consulting post, it wouldn’t have ever been hard to go elsewhere.

Still — in thinking on where my consulting career was, and how I’d been struggling to grow it — this new job offer got to me.

I did a “virtual on-site” interview of 4 video meetings. I talked to my friend who brought this to me (also now sort of my boss). I talked to my boss at that time. My decision was made to change jobs.

May 18 was my first day with WarnerMedia. As security for their direct-to-consumer org, my core product is HBO Max, which would launch May 27.

This ensured the whole summer would be busy in just those obligations. In August, I shared those details at Hackers on Planet Earth (HOPE) 2020, a major infosec conference.

There are recordings of me on YouTube and Livestream if you’re interested.

Has this new position been as I expected before joining? No. That’s not necessarily bad.

But it is all I will say about my “day job” in this post. 🙃

The Road Less Traveled

This year seemed to break a lot of people in a lot of different ways.

Mentally, spiritually, psychologically. News and social media. Disinformation.

Financially. Many Americans suffered from business restrictions, unemployment, sick time. The markets went wild in some parts and annihilated in others. Wacky stuff started happening with monetary supply.

Physically. Outside the viral stuff, I imagine time spent indoors and sedentary spiked. Gyms closed. Home exercise equipment was scarce for a long time.

I captured this stuff early-ish with my quarantine survival guide, yes. Bigger picture, though, it’s all self-improvement.

The last decade or so of life I’ve been obsessed with self-improvement. Maybe the start was reading The Four-Hour Workweek in high school. Maybe it was all the vain things I started doing to attract girls towards the end of that.

Regardless of when it started — it’s something internal I cannot turn off and cannot really explain. Like feeling compelled to journal and write out essays on this blog.


As we entered June, all the goings on of this year had already clarified certain things for me. One of those was that I love my whole extended family and want to have a family of my own.

Another was that I shouldn’t — and wouldn’t want to — make that happen in a major city. Not in my New York metro residence.

I was coming around to the reality that my then-girlfriend was not an ideal partner for life and/or raising children.

But weirdly — there’s so much beautiful and good in life. Even despite the virus and civil unrest right then, early summer. Which turned me off from urban family planning.

The good and the bad are clashing constantly. Yin and yang. Like Alan Watts goes over in The Book too, how you can’t have light without dark.

Family is good. Honest work is good. Nature is good. That’s about where I was at in June and felt this all quite strongly.

Then I read M. Scott Peck’s The Road Less Traveled, which put words to those feelings and 2020.

Much more eloquently than in my rambling here. I may sound nuts.

The earlier “Found God” bullet point is from the conclusion of Dr. Peck’s book. It sounded about right to me but I will not preach any further. Or perhaps even mention “God” here ever again.

Just — that would be the one book I recommend this year. It’s barely religious so do not let that turn you off. Also, very interesting, it is from the 1970s and reads like it could’ve been written this summer.

2021 may see a review/recommendation post on The Road Less Traveled. In the meantime, this is it.

Upstate NY summer

Besides that, much of the summer was spent dining out in Sylvan Beach or enjoying family time at my grandma’s river house.

Summer and Sylvan Beach
Summer and Sylvan Beach

My sister, long-time friends, and a rotating cast of others also started to do a weekly Jackbox Games night. This was technically facilitated through Steam Remote Play and/or Google Meet.

Jackbox Games

I helped get my ex-girlfriend back to New York City in the mid-summer and would go to visit every so often. At first it was strange being back in my own apartment, after so long co-habitating.

Amtrak train
Amtrak’s rooms being great for this commute.

Neon Moon

In certain ways I reverted to being 10 years old during the middle of 2020. Much of the summer was spent living with my parents, the Nintendo 64 releases of Mario Party were played a lot amongst friends, and I rediscovered late ‘90s to early 2000s country music.

At 10 years old, yes, I listened primarily to country. What a weird, pudgy kid I was.

One of my favorite songs of that musical era — Neon Moon by Brooks & Dunn.

It never held any deep meaning to me until my girlfriend of 3 years and I broke up in September. Then suddenly it did.

And the words of every sad song seem to say what I think …

The end of a long romantic relationship hurts. Not just how you miss someone after, but also your visions of a certain future.

To watch your broken dreams dance in and out of the beams / Of a neon moon …

It is what it is. The time before the end was positive. Revelation was positive and necessary. Overall, a net positive.

I won’t dwell too much because obviously no one cares about matters of your heart like you do.

Back to business

Suddenly it felt like I had a lot more free time and a lot more to prove.

This recommitted me to developing Kapotel properties, doing some miscellaneous security jobs, investing more actively. I overhauled this blog after one overhaul in 2020 already.

Computer desk

The other thing that came up is my pilot training. One of the phases I went through as a kid was wanting to fly planes for a career. Obviously, that didn’t happen, but it’s a desire that never 100% went away.

Without a reason to go back to the city at a regular cadence, I invested myself in November to getting my FAA PPL.

Aerial view of Oswego county in New York state

It’s been cool — overwhelming or scary at times, but one of those experiences where you feel yourself growing. Which just goes back again to self-development.


November through Christmas, I did a bit of (unsuccessful) hunting …


… then I drove my grandmother and one of her friends to Florida.

Oh plus the friend’s two cats, stained glass collection, etc…

This was a situation where just my grandma intended to drive this other woman there from upstate New York. That — didn’t seem like a great idea to me. So with a free conscience, I picked up a rental car to make the trip.

After dropping off this friend, the two of us went on to stay with family for a week.

I had put some thought towards moving to Florida, before we made the trip. A lot of New York City tech people seem to be deciding that way. The trip was quite enjoyable and reminded me of my other Florida vacations as a kid.

Florida lounging

This is a life decision I am eyeing for 2021.

We flew back and never caught a virus or anything. The rest of the year went off without a hitch.

Randy Gingeleski in December 2020
Alive and well in Florida

Closing thoughts

2020 saw a lot of change in my life and forced me to rethink all visions for the future I had at the year’s onset.

2021 may end up as a “sexier” year to write/brag about, but 2020 showed me a lot.

I am just trying to enjoy the journey and continue hustling along. Very thankful for my true family and friends.

Here’s hoping you and your loved ones are well. If 2020 was bad to you, I’ll plug my habits for uncertainty post one last time.

After relaunching this site again, you might expect more frequent updates from me in the new year.

Or not. I can’t see the future and we’ve learned many — most? — “experts” can’t either.

To your continued success.🥂

Related content

2019 in review
2022 in review
2021 in review