Shalllow focus photo of chess set

Life Lessons You Can Learn From Chess

You do not have to be a chess player to appreciate today’s advice. As you gathered from the analysis I drew from Monopoly, I love finding ways we can learn from tabletop games beyond the moving pieces.

If you missed my introductory post on chess, check it out here.

And now, in no particular order, here are nine life lessons we can learn from playing the great game of chess.

1. Make Your First Move

Many opening strategies hinge on the first moves. White pieces have an advantage in setting the tone of the game. As a casual player, I believe a good game will be a good game no matter the opening. This is probably why I will never be a grand master. In the beginning, it’s enough to take a deep breath, move out a pawn or knight, and prepare yourself for a good time.

Life Lesson: Before I got into investing, I spent a lot of time reading books and articles. I was afraid of losing money. I didn’t want to make irreversible mistakes. The truth is, unless someone was tempting me with a Ponzi scheme, the likelihood of making an irreversible mistake was extremely low. Even if the stock market had crashed the next day, it would have rebounded eventually. The amount of time I spent fretting over which funds to purchase is time I could have been earning interest on my first investment.

Stop overanalyzing. Jump in there. If you make mistakes along the way, good. It means you’re going to learn from them. Ask that girl out on a date. Start that blog or podcast. Take those dance lessons. The time you spend planning life is time you could have spent living it.

2. Protect Your Assets

Throughout the game, you want to move your pieces in such a way as to create a protective sphere. It’s easier to move your bishop to the center of the board if you have a pawn diagonally behind to cover its back. It’s even better when you can move that bishop to the center of the board and enjoy the queen’s protection from afar.

Life Lesson: Before taking a job with the government, I worked in financial education and advocacy. I had a stable job. It was also a remote position, which meant optimal flexibility. I had to think long and hard before deciding to completely rearrange my work schedule and environment.

Don’t make decisions that leave you unnecessarily vulnerable. Don’t leave your career to plunge headfirst into freelancing unless you have the resources to sustain yourself. Don’t go back to school unless you can secure funding and can commit to seeing the goal through completion. Every risk will leave you vulnerable to some degree, but take stock of the impact your decision would have on your health, your wealth, and your loved ones.

3. Take Risks

Recently I played a game in which I deliberately placed my queen in the direct path of the opposing queen. I did not give my queen the protection she required to fend off an attack. I was betting that my opponent would choose a different strategy. I would kill their queen. Sure, the king would have immediately killed my own, but my entire objective was to play a game without queens to show my opponent how to play without them.

Instead, my opponent killed my queen. It took several more steps to exact my revenge and achieve my original goal. I don’t regret the move though, because it showed me my opponent was paying attention and taught me something about their style of play.

Life Lesson: The advice here may appear to contradict what I just said about protecting your assets. On the contrary, you protect your assets so that you can take risks. For instance, going back to school in order to advance your career is not a bad decision, but make sure your partner is willing to step up their game if going back to school means taking a hit to your finances.

A better example of this point is starting something new, whether it’s a blog or a podcast or something more tangible like a business. People will tell you there are millions of them already out there. That is true, but no one would be doing it exactly like you will. Don’t let complacency keep you from believing in your own abilities.

4. Learn to Make Sacrifices

Even though you will try hard to hold on to all your chess pieces, you will eventually start losing them. Losing pieces is part of the journey to meeting the opposing king. The best you can do is control how the pieces are sacrificed for the greater good of your game strategy.

Life Lesson: The hardest part of parenting is reaching that point when you know you can no longer protect your children from the challenges of life. They need to scrape their knees to learn from their mistakes, and sadly, this process of letting go comes ahead of their eighteenth birthday. The hope is that we raise them well enough to make good decisions.

There is value in learning how to hold on. There is equal value in learning when to let go. Learn the difference between surrendering and sacrificing, and you will reduce the regret in your life.

5. Do Not Undervalue What Matters

Beginning chess players view pawns as the dispensable pieces. In truth, they are the glue that hold strategies together. Never sacrifice a pawn unless you need to. Remember, they are the only piece that can slowly move across the board and convert to a queen if they make it to your rear rank.

Life Lesson: My Seeing Eye dog, Matthew, will never be considered the world’s greatest worker. I sometimes wish he would walk faster. I wish he did not cling so fiercely to his patterns, but despite these shortcomings, his sweet disposition and quiet temperament make him the best companion. If I had to do it all over again, I would still choose him.

The shiniest weapon does not make it the best weapon. The loudest speaker does not make them well-spoken. Sometimes the best solution stems from the most overlooked option.

6. Think Ahead

Not even the best players think twenty moves ahead. That’s just a silly misconception, but dedicated players learn to study patterns and learn to read their opponent.

Life Lesson: I wanted to move to DC after college. At the time I thought I wanted to go into politics, but entry level jobs on Capitol Hill would have made living in DC difficult considering the cost of living. Instead, I got into AmeriCorps. The stipend was minimal, but since my housing expenses were covered, I could afford to live in the District and use my year of service to network. The experience turned out to be more rewarding than I could have anticipated.

Sometimes you’re not going to get what you want when you want it. It doesn’t mean you will never get it. It just means you may need to take a different route to reach your goal. With a little forethought, you can use the intervening period to learn more about yourself and determine whether the original plan is still your desire.

7. Small Moves Yield Huge Impacts

The queen is a powerful piece. There is nothing more satisfying in chess than pouncing on an opponent from across the board, but the best moves in chess are not long range attacks. Sometimes the entire tone of a game can shift by moving pieces by one square.

Life Lesson: You’ll often hear people say employment opportunities are all about who you know. I’m sure there is truth to that observation, but one of the best business contacts I developed started with a cold call. They knew nothing about me. To be honest, I didn’t really know them, but one day I got a wild hair to reach out to them and pitch my services. They replied shortly thereafter, and nine years later we still have a business arrangement.

Every decision you make, from the restaurant you choose for lunch to the person you choose for a life mate, will trigger a chain of events. Understand that even the most fleeting of choices will have a ripple effect, and no, not every ripple will be a positive outcome. Think carefully before you make that small move.

8. Educate Yourself

Chess is not a linear game. There are numerous ways to bring down an opponent, but the only way to get good at executing those strategies is to keep playing.

Life Lesson: At the time of this writing, I am learning how to use Reaper, a digital audio workstation. I am still at the beginning stage where I get frustrated at my inability to execute what, to me, seems like a simple task. Despite these frustrations, I am buoyed by the reminder that one day I will be able to do for myself what others pay to get accomplished.

I would like to believe that if we keep challenging our brains, we will never truly grow old. Learning should be an active part of our development, and hell, the more you learn, the more marketable you become. The larger your skill set, the more money you can charge for the privilege to tap your potential. I never saw myself as an audio engineer, but by golly, at this rate I may end up producing soundtracks like a pro! Or not, but I am loving the learning process.

9. Learn From Your Victories

Conventional advice says to learn from your mistakes. While true, there is also value in learning from your winning games. No matter how well you think you did, I promise there is something you could have done to win faster.

Life Lesson: My senior year in high school my partner and I won the regional mock trial competition. The victory was sweet, but we would have done better at the state level had we learned to gel better as a team. We should have spent more time strategizing against new opponents. We could have done more to think outside the box.

There is always room for improvement. Never become complacent and believe your strongest effort was your best effort. You always have a little more to give. Give that, and then figure out how to give a little more.

Final Thoughts

If you let it, chess can be a phenomenal instructor. You just have to humble yourself enough to let it teach. We haven’t scratched the surface of the valuable lessons to be derived from this classic favorite.

What parallels have you drawn from playing? If you have not played, what’s keeping you from doing so? And, again, here’s a shameless reminder to check out my other post on Monopoly. I’d love to have it out with you on either board! 🙂

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My blog is a collection of advice I wish someone had shared with me when I was young and targets subjects like personal finance, careers, and relationships. It publishes Mondays with the occasional bonus article. Sign up to have fresh content delivered straight to your inbox, no SPAM!


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