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My brother and I were playing chess they other day. He had a winning move that we both missed. After the game we found it, and why we both missed is the inspiration for this article.

The move we missed involved moving his Rook next to my King. My King would have been in check, and the only option I had was to take the Rook (it wasn’t defended by another piece). And that’s why we missed the move.

When we saw that my King could capture his Rook, we dismissed the move out of hand. In other words, we failed to ask one of the most important life question one can ask–what if?

If either of us had asked that question, the beauty of the Rook sacrifice would have revealed itself.  What if the King takes the Rook? The answer was a beautiful two move combination that either resulted in checkmate or the loss of my Queen.

What if. . . .

The application of this to our finances and life are limited only by our imaginations–

What if you started saving 3% of our income in a 401k or IRA?

What if you got rid of one of your cars? All of your cars?

What if you paid cash for your cars, limiting how much you spent to the money you had saved for the purchase?

What if you downsized not at retirement, but in your 30’s, 40’s, or 50’s?

What if you canceled cable?

What if you moved to a less expensive area of the city (or country)?

What if only one spouse worked so the other could stay home with the kids?

What if you took a year off from work and took the family on a trip across the country or around the world?

What if you voted for politicians not because their proposed policies would make your life easier, but because they would make our country better?

What if we put down our picket signs asking for a $15 minimum wage, and instead through training and education found a job that pays two or three times the minimum wage? It’s a lot harder than holding a picket sign, but far more rewarding.

What if you spoke up during the next company meeting?

What if you come to the end of your life with feelings of profound regret because you had never asked the simple question–what if?

Author Bio

Total Articles: 1083
Rob founded the Dough Roller in 2007. A litigation attorney in the securities industry, he lives in Northern Virginia with his wife, their two teenagers, and the family mascot, a shih tzu named Sophie.

Article comments

Sam says:

Best of Luck with your “living without a car” experiment. I wish I could. I would love to ride my bicycle to work, but its just not practical in Southern California. I also totally support your thoughts on being debt free. No mortgage is totally liberating, speaking from personal experience.

My “What if?” thoughts are on downsizing and moving out of state. I would love to downsize and de-clutter. Focus on quality, not quantity. Bigger is not always better. Wow, what a big difference 10 years makes. I was all about supersizing in my early 30’s. Having a big house and even bigger mortgage. Using Other people’s money (OPM- Robert Kiyosaki) to acquire leveraged assets. Boy, I wish someone would have given me the definition of RISK, back then….LOL

Kelli B says:

Good job posing some tough “what if” questions here. I especially like the one of going down to 1 car or 0 cars. It’s hard to believe that not that long ago most families only had 1 car… and now most of us have 2 or even more!

Deb S says:


Thanks for a thought-provoking podcast. Everyone should make a point of challenging their assumptions as often as possible. I know it’s difficult for me, and you’ve inspired me to work harder at this.

What if we took the premise of What if.. a bit further? I think that folks may need to give themselves permission to think differently – to explore different avenues. For some, it’s really tough to open up that thinking.

A friend of mine wrote a beautiful book about this topic “I’ve Been Down Here Before But This Time I Know The Way Out” by McDowell Graham. It contains stories of individuals who came to a crossroads in their lives and choose a new path. It’s available on Amazon.

Thanks again, Rob. I’m off to share this post with my social media friends!