Free One-on-one Chess Assessment
Sign Up

Spotlight: Failing Forward with Robert Dugoni

March 25th 2023

At the center of a Venn diagram of law, writing, and chess, you’d likely find Robert Dugoni. He is a bestselling author who impacts millions of lives through his writings and integrated chess into his latest release “Her Deadly Game”. He’s also spent time as a professional legal practitioner before returning to writing, his original career path.

The beginnings of a dream

Robert wasn’t always this well-rounded and successful. Like many other children, he often found himself getting into trouble at school. Some of his teachers requested that his mom get him into reading to help with these behaviors. At an early age he fell in love with books and became a voracious reader as well as a passionate story writer. As early as seventh grade, Robert knew what he wanted to be: his passion was writing stories and his dream to be one of the best story writers in the world.

Bumps in the road

Robert set off on his journey to pursue his goals. He began writing stories in middle and high school, and continued to develop his writing through his education. Robert majored in journalism and creative writing during college which earned him a job at the LA Times, where he not only worked as a reporter but also got a chance to build his writing career. It seemed that he was well on his way to his dream.

However, the pressures of life soon swayed Rober from his path. He went to law school and became a lawyer to pay the bills, though he knew this was not his passion. In his words, he “chickened out” of his dream career path.

Robert practiced law for a full 15 years before he realized he could not follow this path anymore: he was afraid of losing his dreams of writing. Despite the risk and his fears, he knew it was time for a change. With the support of his family, Robert made a courageous move. At 39 years old, he switched his vocation and began to focus on writing full time.

A waste of time?

Robert could have viewed his 15 year break from his passion as a failure. He could have written it off as a waste of time. However, one of Robert’s life philosophies is to always fail forward. At Chess4Life, we call this Win.Draw.Learn. In chess, there is no true losing: you can win, you can draw, or you can learn. Robert chose to learn from his time as a lawyer and use it to make him an even better writer.

Robert faced another test of this lesson early in his writing career. When Robert made the jump to writing professionally at the age of 39, at first he thought that everything was going to be rosy for him. But soon he ran into roadblocks. For the first three or four years, things were pretty bleak. Robert went from making a solid income to making no income, and even received 43 rejection letters on his first novel.

But Robert did not give up. Instead, he took a step back and talked to people who in turn led him to great books that furthered his understanding. It turned out that failure after failure led him to learn important lessons about the craft of writing and how to succeed as an author. Robert discovered the importance of maintaining a positive attitude. As long as you are learning from your mistakes and always improving, your chances of success will get better and better. Robert knew that one day he would write a good novel that someone would pick up and buy.

This is why Robert sees such benefits to the game of chess. According to Robert, the game of chess can impact many lives because it teaches the mindsets of success, such as the importance of embracing failure as a learning experience, building the willingness to not give up, and developing the willingness to take a chance and try. Chess can lead to confidence and a positive attitude towards the things you do.

Chess in “Her Deadly Game”

So how did this writer-turned-lawyer-turned-writer end up writing a book centered around chess?

Although he had never been a chess player before, Robert became fascinated by it during his time practicing law because some of the best trial attorneys he knew played chess. He discovered that his colleagues saw important connections between chess and their work. When a trial lawyer puts a witness on the stand, they must be prepared for four or five different answers that person could give them. Robert’s colleagues saw this as the same as how in chess, when you make a move, you must be prepared for the four or five countermoves your opponent could make.

This inspired Robert to write a novel in which the main character is both a lawyer and an excellent chess player. Being a novice chess player himself, Robert reached out to Chess4Life’s Elliott Neff for assistance in crafting the chess game that is key to the novel. He consulted with Elliott about realistic chess scenarios to best capture the important connections between chess and law. This unique story idea is exciting for readers and chess enthusiasts alike!

The benefits of chess

As in practicing law, Robert also finds benefits from chess in his writing. He tends to write his books without an outline, so he does not know how it will end from the beginning. Instead, he discovers it along the way with his characters. Therefore, he must be able to think through multiple pathways. Similarly in chess, players must be able to consider multiple pathways and make predictions about what impact their next move will have on each one.

Robert sees connections to chess in his personal life too. Chess skills help you to analyze any situation and choose from the various options in front of you. Robert sees this as especially beneficial when you are faced with a myriad of unexpected situations in life. Just like in chess, we cannot always predict what will happen in life. We must be prepared to problem solve whenever problems arise.

One of Robert’s key life lessons is: don't be afraid to try just because you think the worst can happen. After all, competition is not just about winning. You're never going to win everything. Any good chess player will tell you they have lost many, many games along the way. Instead of focusing on winning, Robert advises that whenever you play, learn to win with dignity and lose with grace. Whether you win or lose, you are able to learn a lot from your opponent and there is much to be appreciative of.

For Robert, hard work and persistence has earned him everything he hoped for in life. His advice to the young people is to find your passion and then find a way to make a living from it. Pursue it and never give up when it doesn't work the first time. Do not be afraid of failure; in life you are either going to win, draw or learn your way forward.

You can learn more from Robert Dugoni through his website at

Check out the full interview below!


Online Chess Classes for Kids That Prepare Them for Life.

© 2022 Chess4Life. All rights reserved.