Two Games to Help Develop Your Entrepreneurial Mindset


Reading the title of this article you might be thinking, ‘how will games help me develop as an entrepreneur?’ and I thought that as well before I started this different sort of mental training. Often times we’re stuck in routines and our minds are moving so quickly that we lose outside perspective. Participating in immersive games gives you the opportunity to solve problems in a new light, and also be exposed to situations that you otherwise wouldn’t encounter. In this post I’m going to go over two main games that have helped me develop myself mentally and I truly believe have helped improve my entrepreneurial mindset.

Two Games to Help Develop Your Entrepreneurial Mindset

Image Credit: Remco Wighman


The history of chess spans back over 1500 years, initially played as an intellectual war game where the stylistic play of tricks, and sacrifices were almost as important as winning. In modern day, chess is often found in school programs ranging from the elementary to collegiate level. As an intellectual game requiring several tiers of psychological analysis and foresight one could definitely agree that you could improve your mind by playing chess, but let’s go over how these developments tie more specifically to entrepreneurship.

Foresight in chess

A very important element of entrepreneurship is being able to take an idea or concept and quickly flesh out whether or not it is feasible. You may have numerous ideas per day and a large amount of them won’t be successful in the long term – so how will you determine which ideas to take to the next level, and which ones to let go? This methodology will be critical to your success as an entrepreneur. The bottom line is you need the capacity to analyze your ideas future potential and decide which ideas to put resources into. As resources and time are limited, too many mistakes in this sense could be detrimental to your livelihood.

Spatial awareness in chess

This will be a bit more obscure relationship to examine, but you will see its applications. On the chessboard you need to be aware of not only the positions of your own pieces, but also those of your opponent. Is their queen lined up to put you in check next turn? Is taking this seemingly open piece a trap? This game and spatial awareness transfers to entrepreneurship through being aware of the risks, and potential directions that your ideas could encounter. Having mental awareness to solving issues in real time will be an extremely valuable skill to have and develop. You will be more well equipped to deal with decisions involving multiple factors after experiencing the depth of spatial awareness and analysis in chess.

Caution and aggression in chess

So you’re developing your foresight to make optimal decisions for the future, and spatial and game awareness to be aware of all potential issues and directions to take your idea. But how do you use this information for the best result? The last way in which chess has helped me develop my entrepreneurial mind is determining when to be cautious or go aggressive. You can be aware of different routes to take, and maybe some issues that might crop up along the way, but when do you push for more investment? When do you scale back and bootstrap your idea? Playing chess can give you new insights into using the information you have to determine whether your next move will be aggressive or more passive and defensive.


The second game that has helped me develop immensely is poker. Poker is one of the few “gambling” style games that you can actually gain an edge on the other players through training and overall game knowledge, with some psychology thrown in there. The basic elements of poker training and playing that have helped me move forward with entrepreneurship are the economics and bankroll management of the game, and the application and adaptation of previous experiences.

Bankroll management and economics in poker

Playing online poker involves having a pool of money that you can play games from called your “bankroll”. It wouldn’t be a sustainable strategy to play a game of poker with all of the money you have to play the game at due to the variance of the game. You want to manage your bankroll and economics appropriately so that you can have around 50 buyins for the type of game that you’re playing. This teaches and deeply instills discipline regarding economics and financial decision making that I’ve found critical to entrepreneurial decision making.

Application and adaptation of previous experiences in poker

Poker is a game that builds on itself. Every hand you play provides you with new information on how different players act when presented with a specific situation. How you choose to use this compounding information and adapt it to new situations is highly related to your success as a poker player. The key takeaway here for entrepreneurs is that it’s okay to fail ideas, and in poker lose hands. What you must do however is take this information and apply it to future scenarios to your benefit. Take what you learn and move forward with it in a positive light.

Some of these ideas may seem a bit abstract but the way my mind works while playing these games has really opened my entrepreneurial mind to more aware and optimized decision making. These are two strong examples that have worked for me, but I believe you can find new mental insights by doing any new activity that requires you focus and be completely immersed in. If you’re interested in more information regarding the deeper strategy behind chess and poker here are some resources that I’ve found useful:

PokerVIP Interactive poker school – PokerVIP has several levels of interactive courses to go through that are great for players at any level.

Chess Tempo – Chess Tempo has a ton of basic information, and several situational tools that I’ve found essential to developing my chess game. – One of the original online chess resources with an abundance of beginner information. You can also play online chess from this site and track your progress.

About the author: Scott Wolowich is a contributor at PokerVIP and PokerTube which are both sites dedicated to providing relevant poker strategy and news.

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