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What Crossword Puzzles Can Teach Us About Life & Business

Crossword puzzles are my diversion. I do one almost every day. It’s both a brain stimulant and meditation for me. When I’m doing a puzzle my mind is focused, not wandering or multi-tasking. What’s your diversion? For some of you it’s Sudoku, or maybe a game on your phone or tablet. For others it may be yoga, or reading a book.

As my family and I live in the New York area, I get The New York Times delivered daily. I rarely get to read more than a few articles in a day, while eating breakfast, and I can get the same news on my NYTimes iPhone app. I get news alerts on my phone, so I’m up to date on the latest in world happenings. I find that reading the actual newspaper, as with reading a physical book, is a different experience than reading on a screen.


Involve more senses

When it comes to crossword puzzles, I like doing a physical puzzle versus using an app. I can do the same New York Times puzzle, the same day, on their app. I’ve tried it and I get too easily bored and distracted. It’s too easy to flip between the puzzle and email or social media. That’s why I like the analog version (pen and paper).

Even my millennial age son now does the crossword puzzle on paper. He gets The Wall St. Journal delivered, so we have both puzzles to do. Our daily ritual is to make copies of each of the puzzles, so we can all do both of them (and don’t worry—we always recycle them when we’re finished).


A few years ago, I watched a documentary called Wordplay, which is about The New York Times crossword, and the people who make the puzzles, edit them, and solve them. You can probably find it on Netflix or a similar service. One thing I learned from watching it was that Monday is the easiest day for The New York Times puzzle, and—as it turns out—also for The Wall St. Journal. The puzzle gets progressively more difficult each day through Saturday (which is the most difficult). I always thought Sunday was the hardest. The Sunday puzzle, while bigger, is the equivalent difficulty of a Thursday puzzle.

Bolstered by this knowledge, I started doing the Monday puzzles, in pen (with a tube of Wite-Out close by). Once I was able to finish the Monday puzzles, I started trying Tuesday. When I was able to finish the Tuesday puzzles pretty regularly, I went on the Wednesday, and so forth.

A fresh set of eyes

Often, I’d have to walk away from a puzzle, and come back to it. Answers, that had previously eluded me, were suddenly clear. The puzzles towards the end of the week are particularly challenging. While the answers are often familiar, the clues become more obscure. There are times when I want to just give up and toss the puzzle in the recycling bin. After all, what’s the loss? It’s just a crossword puzzle, and no one will know (except me).

It’s just like life

And that’s when it hit me, crossword puzzles are just like life and business. Some days the answers are obvious and easy, and some days the answers elude us. Some days we want to throw in the towel and call it quits, and other days we revel in our accomplishments. So, what’s the difference? If I can come back and solve a puzzle that eluded me, why couldn’t I solve it the first time? After all, I must have already had the knowledge and skills to get to the answer, so why didn’t they work for me the first time?

Some days will be more challenging

When I first tried solving the Friday and Saturday puzzles, it was very humbling. I would get a handful of the answers at most. Looking at all of those unfilled boxes was depressing; but, something told me to keep trying. What I discovered was that there were always some answers that I could get, so I would just work my way out from those. In the movie WordPlay, they filmed different people (actors, ex-Presidents, and other notables) doing the same puzzle. They talked about how some people have to go in order, doing all of the Across clues in order, before doing the Down clues. While others went more randomly, working off a completed answer, going across and down, until they couldn’t go any further.

Structure or random?

Isn’t that just like life? Some people have to go in order, and others go more unstructured. They may come to the same conclusion, they just get there in different ways. The other thing that’s just like life, is that some people walk away, while others stick to it. Which are you? Do you walk away when things get tough? Do you come back and give it another shot, or toss it in the metaphorical recycle bin of life? In my book “Your Attitude for Success,” I say that the difference between those who succeed and those who don’t isn’t ideas or money, it’s action.

Action, action, we want action

Ideas don’t get you anything, unless you act on them; and, it’s not just acting on your ideas, it’s sticking to it. If it was easy, someone would probably already be doing it. And yes, sometimes we need to walk away, and come back with a clear head. Often, we need to get out of the environment to clear our heads. Have you ever come up with the elusive answer in the shower, or at your kid’s soccer game? I'm sure there’s a good psychological reason for this, but for the purposes of this article, let’s just accept that it’s happened to all of us before and it will happen again. Sometimes we just need to keep our eyes open, and sometimes we need to stop thinking about it for a while, and then come back.

The answers aren't always where we’re looking. Artists and product designers get their inspiration from everywhere. The answers you seek may very well come from outside your industry. You have to be willing to look for them, and ready to adapt them to your needs. We have a phrase in the National Speakers Association, “Adapt, don’t adopt.” It means don't take someone else’s idea, adapt it and make it your own.

Be an original, not a copy

Too many people in our industry are trying to copy a competitor’s ideas, instead of adapting what they see, and coming up with their own ideas. It’s hard to copy someone else, because you’re living their reality, not yours. You’re actually copying their history. What you’re seeing is their past ideas, brought to fruition. You don’t know what new ideas they’re working on. By the time you copy what you’re seeing now, they may very well have something newer. So, are you an original or a copy? Do you give up, or do you stick to it and see your ideas through - especially when the going gets tough? The next big idea is waiting for you, don’t give up.

Alan Berg has been called “The Leading International Expert and Speaker on the Business of Weddings & Events.” He speaks at every Catersource conference—including the 2018 conference in Las Vegas, as well as conferences around the world. Visit to find out more about his speaking, sales training, website reviews, business consulting, books, and audio presentations.


Alan Berg

Alan Berg

Marketing Guru,, Kendall Park, NJ

With more than 20 years in wedding & event related sales and marketing, Alan Berg has been called "North America's Leading Expert on the Business of Weddings & Events". He's uniquely qualified to help caterers achieve success in this most important sector of the business. As a highly regarded industry expert in all aspects of marketing, his knowledge and expertise can help practically any caterer move to the next level. As the author of the popular books "If your website was an employee, would you fire it?" and “Your Attitude for Success” (both in their 2nd editions) and the mini-book “Don’t Paint The House”.

Weddings represent the...