Getting to Checkmate – My Journey into online Chess

By McLaughlin Thomas, MTI Contributor


I have friends who played chess seriously back in middle or high school, or who started training recently because they finally “got around to it,” or who have a chess set but don’t really use it. All these little blips were subconsciously building until the day the prompt arose in my mind, “I should learn chess.” I had been feeling the itch to find and take on “the next thing” for maturity, personal development, and broadening my skills.

My workdays could vary greatly in pace, some days are longer and actually non-stop. Other days, it’s hurry up and wait, executing some functions at a server and waiting for it to do its thing. So I would feel uneasy at these gaps in my day and wanted to fill the time with something constructive and stimulating that I could engage with alone. If I have to be “in the chair” and largely independent during my work hours, what are my options for something new to learn and practice on my own time, effort, and presence? Online chess was a great candidate. I can play on my mobile device, against a computer or someone else in the world, with access to performance reviews and continuing-education resources to develop my game. All by myself! 

Further, I had heard over the years, and more recently through Instagram posts, about chess’ esteem through history, how it was regarded as an almost exclusive measure of intellect and social insight, so that gaining such perceived “status” was also attractive. I leverage my Instagram account to fuel and edify what’s important to me in life, so I follow several  accounts that post puzzles, feature a “move of the day” from some landmark chess match in history, and even show full games played by chess legends as far back as the 1800s (and even further back).

Getting Started

I started on the iOS app. has been instrumental in my initial learning, continuing education, and competition thanks to the on-demand nature of online chess. The application makes chess super accessible to anyone.To play entire games and practice specific scenarios and skill sets, I don’t require another person physically in the room with me, or a certain scheduled time frame, but I can bring anyone in the world into the room with me at any time through my mobile device! 

Thus farI haven’t taken any formal classes or courses, dedicated study under a paid mentor or as part of a club, or devoted time to practice from a book – all my chess playing and learning has been via the app.

I am still discovering just how vast and diverse the chess community is. There are almost endless leagues and dozens of tournaments for various modes and rule sets of chess. For example, there was a recent tournament for the Fischer Random mode of chess, where games are initiated from one of over 600 possible pre-arranged piece placements. At any given time, one can watch over three dozen tournaments taking place in real time and enjoy the matches unfolding. 

Chess is truly the universal game, played by all genders, ages, nationalities, and professions at all times of day. I always figured as much, but seeing the outrageous volume of games progressing in real time absolutely impressed and captivated me. 

Online chess provides the ability to condense a large volume of practice into a smaller time frame at a much more rapid pace than anyone could manage in person. While nothing replaces the holistic experience of an in-person chess game or the suspense and energy in the air of an in-person tournament, online chess affords you higher-tempo practice with targeted scenarios and drills for polishing specific factors of your game, especially if you’re limited or isolated in some way on your chess journey.

Once I developed competence with building thoughtful pawn structures that reinforce my special pieces, I started playing my friends in person. One of my best friends played a lot in high school, and he’s still got it. Every time I visit him on the west coast, we play a few games and he still wins confidently (though it’s getting closer and closer). I also work closely with our power plant’s Security team, and they have a chess set in one of their standby rooms. So I always ask if they want to play. Once in awhile someone will accept. I win against some, and others wipe the floor with me.

Playing and Training.

I play a dozen games against challenging computer opponents every day or every other day to stay trained up and measure my proficiency. One day, I’ll also watch a lesson or two and do the practice drills; another day, I’ll practice one of the many scenario drills available, such as starting with differing special piece matchups, starting at a loss, starting from an advantaged position, or mastering an endgame situation. 

Once a week, I’ll devote a full 1-2 hours of practice to test myself against stronger computer opponents, play some quick games against other live people, learn better strategy, and read the board faster to make smart moves more quickly.

The competitive chess world uses one of several points-based ranking systems. For examples, amateurs will be ranked anywhere from 0-600 points; intermediate players will be ranked around 1000 points; and grandmasters will be ranked well over 2000 points. Learning skills and tactics will get you up to 1000 points in due time. In my experience, leveling up past 1000 points requires taking on a new brain and entirely new frameworks of thought, strategy, and foresight! It’s a different world up there. I took screenshots when I finally beat the 1100-ranked computer player, I was so excited! Now I can defeat a 1100-ranked computer regularly, but I’m banging my head against the wall trying to beat the 1200-ranked computer player. However, no computer player is a replacement for a real human opponent, who can be spontaneous and unpredictable.

Masters and chess coaches offer free instruction through YouTube channels. They will also stream match play Twitch as well, which is a great avenue for remote mentorship as it offers a grand volume of on-the-field, real time analysis and insight into the game. I pay a small subscription fee to follow certain masters and chess coaches on Twitch. 

The masters and coaches I follow are very skilled at explaining their thought processes and exploring multiple decision-making paths very quickly and simply. That’s incredible value worth paying for: distilled, specific knowledge and experience over minutes, instead of expensive battle scars (in time and money) over years of trial and error. Here are the resources I’ve used: 

Eric Rosen (RosenChess) is a thoughtful teacher, family friendly, and it’s easy to follow his discourse; he streams on Twitch ( and posts lessons and highlights to YouTube ( 

Daniel Naroditsky is another grandmaster who streams on Twitch ( and posts highlights and commentary from his streams to his YouTube ( He evaluates his own matches from online everyday play and from tournaments so he provides quality practical insight. 


Hikaru Nakamura, widely regarded as the #2 player in the world as of this writing, is another phenomenal resource, streaming on Twitch ( and posting a variety of lessons, footage, and commentary on YouTube ( His weaponized ADHD style of commentary offers considerable entertainment value and supports a teaching proverb, “if they’re laughing, they’re learning.” He can simply and rapidly explain diverse decision-making paths and the pro’s and con’s of each. If you want to drink from a firehose, study Nakamaura’s videos and streams. 

Levy Rozman of GothamChess is another great teacher, who streams on Twitch ( and posts on YouTube ( a variety of lessons on openings and tactics, commentary, and match and tournament reviews. He recently hosted a collaboration video with Nakamura, evaluating and solving some historical chess problems “that made grandmasters cry.” They would individually mute their video feeds and talk through their thought processes to their individual stream audience to devise the solution, come back and speak together about how they thought through the problem, and finally consult the book for the ultimate solutions found by grandmasters in history.

Chess intrigues me because of the equal starting positions. Both players get the same pieces in (mostly) the same positions, same rules of time limits, taking turns, moving, and capturing. Yet one player uses their pieces and commands the game flow more effectively than the other. One way to think of chess is as a puzzle we’re both shaping as we go and presenting to the other, back and forth, that we’re both trying to solve faster and before the other person. As we try to solve the puzzle and defeat our opponent, this again changes the puzzle, move by move. It’s the OODA loop dogfight on a two dimensional board. I heard a funny rule about what constitutes something as a sport: “if you sweat, it’s a sport.” I can’t say I’ve gotten to the point of sweating playing chess yet, but it’s come close. 

As I’ve grown wiser on the chessboard, I’ve come to realize how few moves I really have available at any time. All moves are possible, but very few moves are wise and advantageous. Often, there’s only one sensible move to play! And the eternal task is finding it in time. Playing chess well requires a command of the fundamentals, respecting principles, using some “pro tips” like “castle before move #10,” and mental agility to evaluate the board conditions rapidly and repeatedly as the game evolves. 

Playing Chess forces me to “improvise, adapt, overcome” in the war of nerves. “Improvise” in the sense that I have a starting plan and openings in my toolbox, while knowing that my plan won’t survive first contact with the enemy, and so “adapt” in response to your opponent’s play to finally “overcome.”

Lessons Learned

I learn more about myself every time I play, whether that’s being more patient and taking more time to evaluate the board conditions, or playing more aggressively, risking captures and trades to open an attack path.

Pawn structure is everything. “Pawn structure” refers to how you have your pawns organized and progressed across the board. With sturdy sturdy pawn structure, you can put up a fight against almost anybody. Learning this is one thing. Once you respect pawn structure as the foundation for offense and the life-line between victory and defeat, apply it and you’ve crossed the first threshold toward advanced play.

Moving as a team and mutual reinforcement are other painfully important lessons I’ve learned. I’ve typically been an independent performer in life, and it showed on the board. I’d send out special pieces to attack with no reinforcing pawn structure to retreat to, and I’d lose knights and bishops quickly. I’ve learned to move as fast as the team can move, not how fast I want to rush around the board and take, take, take. There’s a balance and proper pace to building a pawn structure and developing special pieces onto the board amongst the framework to control travel lanes and suppress the opponent’s options. 

The more I play and learn, the more my interest and fervor to improve grows and evolves. I came in with optimistic curiosity, no idea what to expect, just open to learn and start trying stuff and explore the resources. Now I know enough to be dangerous (mostly to myself) and my interest has changed from learning how to play, to how to play well and wisely. Now it requires sharpening specific tactics, like practicing scenarios with different special piece matchups and mastering endgame conditions, as well as developing broader personal skills, such as observation and thinking multiple moves ahead – “if this piece moves here, it threatens me there and there.” When I lose a game, I can usually find my mistake 10 or more moves in the past. 

Chess has had a mirror effect – it’s taught me about myself. Noticing my feelings and thoughts during a game, reveals my tactical strengths, and weaknesses. Reviewing my own chess performance has shown me how impulsive and reactive I can be, driving me to invest more time observing and fully evaluating the board, not panic when I get attacked, thinking through my intended move and how that influences my opponent’s next moves, and balancing my offensive and defensive intentions.

Getting Started

I recommend starting an account on and use the app. It’s worth paying for a middle ground membership if you want to improve because it opens up several resources and functions for practicing drills and scenarios, game reviews, and chess community news and tournaments. 

Start with the Lessons module, it’s the best resource I’ve found for starting from zero knowledge. The tactics and strategy they present ramps up at a modest pace, and you can always replay any lesson and its exercises until you get it. You can also play against a large variety of computer opponents with different play styles and proficiencies, some based on real people.

As mechanical as chess may seem, that’s only 20% of the game. 80% of chess is dynamic, organic, and a war of nerves, so invest the time to play against other people, study the masters who came before, and learn from coaches and champions explaining their thinking and talking through their decisions.

If you’re one to dive in with both feet, explore this article for a broad lay of the land. Everything You Need to Know About Chess Culture ( 

McLaughlin Thomas leads the Bedrock Rucking ruck club and works as a Computer Engineer at a nuclear power plant.


Want to be a paid, MTI Contributor? Email a current resume and 3 topic ideas.


Subscribe to MTI's Newsletter - BETA