All that money and nowhere to spend it. Literally.


Because he doesn’t know how to have fun. He wants to have fun. He just doesn’t know what he finds fun. Isn’t that a shitty problem to have? It’s like handing a kid a PS4 and he doesn’t know the first thing to do with it.

Believe it or not, many executive men suffer from what I like to call “defectus funtopia”. I know, it sounds like a term out of the wizarding world of Harry Potter, but trust me, it’s a thing. Don’t believe me? Take a look at the conversation I had with one executive below about what he does to have fun (he’s a doctor – grey bubbles):

executive man explains fun
A doctor explains what he does for fun

Defectus funtopia has affected friends of mine who are executives and exes of mine who are executives. It seems to plague men more so than women and often a specific type of man. If you haven’t read my post on The Two Types of Executives, do it now. Bubbles are more likely to suffer from defectus funtopia for the reasons explained in that post.

However, as promised, here is the story of a dinner my boyfriend at the time and I had with a CEO of a multimillion dollar technology company and his wife. Before we get started, here is some context about the characters at the dinner table:

CEO: We’ll call him Nick.
Wife: Amy, works in the healthcare industry.
Boyfriend at the time: Service provider to Nick’s company (so Nick is his client). We’ll call him Andrew.
Note: Everyone at the table was of a different religious and cultural background.

Amy and Nick had prepared a wonderful spread for dinner at their home. I was silently freaking out because the food looked delicious to a food loving adult like myself, but Andrew was a pickier eater than a teething toddler. After Andrew and I finished negotiating which items would make their way on to Andrew’s plate with a bit of help from Amy and Nick, Andrew and Nick began talking business. Typical.

In an effort to be polite, I sat there silently clearing my plate while the guys went back and forth on what Joe Shmoe did and how it wasn’t in the best interest of the company at the time. Amy noticed my silence and at the first opportunity, put an end to “work talk”. Being a team player, I jumped in and took the lead to take the conversation in a different direction, one that both Amy and I could participate in.

“So, Nick, you sound like a pretty busy guy.” I said, “What do you like to do for fun?” Amy and I exchanged looks like celebrating athletes who had just scored a goal. Nick looked like a deer in headlights. “I mean to destress and take your mind off work.” I offered a bit of encouraging clarification to him. “Do you read, play sports….?” Andrew knew exactly where I was going with this.

“Oh, yea, well I don’t have a lot of time, but when I do, I like to travel.” Nick swallowed hard, knowing there was more questioning to come.

“Nice! So, how often do you travel? Once or twice a year? More than that? Do you prefer fewer long trips or multiple shorter trips?” I continued what felt like the line of questioning that Harvey Spectre and Mike Ross would ask a witness when they were leading them to slaughter.

Long story short, I got Nick to admit that he had just gotten back from Italy with Amy. It was the first trip they had taken in 5 years. Naturally, I did the asshole thing and asked why he hadn’t travelled in 5 years if that is how he liked to have fun. Amy jumped in and confessed that since he was the company’s second CEO, he had a lot of cleaning up to do after the first CEO left. This mean he couldn’t really take any time off for the last 5 years. Then, when the company was sold and he was relieved of his position, he decided to take some time off before starting a new company. At this time, he and Amy decided to go to Italy.

In hopes that Amy and Nick wouldn’t kick me out before serving dessert, I volunteered an explanation for choosing to take the conversation in this direction.

Andrew suffered from a serious case of defectus funtopia, I explained. He didn’t know how to turn his brain off and relax. And if he couldn’t stop thinking about work, he couldn’t have fun. I had trouble getting Andrew interested in doing anything even remotely fun. Think of Sheldon from the Big Bang theory. Every time I’d suggest doing something fun, like going skating or trying a new restaurant or taking a trip, it would get shot down with one word: boring. It’s not just that Andrew didn’t want to do what I was suggesting, he also wasn’t contributing any fun ideas. Because all he did was work all day. He didn’t see the value in sitting there like a normal procrastinating human being and fantasizing about what he’d do when he punched out at the end of the day…because he never. Ever. Punched. Out.

Nick, being quite a bit older than Andrew and I, explained that burnout and deteriorating health were very real repercussions of failing to destress.

That didn’t seem to register with Andrew. Nick noticed. He also added that tightly wound leaders would often not be in the ideal frame of mind to make the best decisions for their business. Since Andrew ran his own firm, he began paying attention. Then a miracle happened. Andrew asked Nick how Nick discovered that travelling was the best way for him to have fun.

Amy and I held back jumping in and interrupting because we didn’t want to spook Andrew. We hoped that Nick would say the obvious answer. He did. The only way to find out what you find enjoyment in is by trying new things. He further explained that Amy always liked travelling, so he piggybacked on her interests. I saw a lightbulb turn on over Andrew’s head. All those months of having ideas shot down and all I had to do was get him a mentor.

And ladies, if finding your executive a mentor doesn’t work….

Wait for him to get bored!

Stop being the one who suggests or plans date night. When he starts complaining about it, tell him you ran out of ideas for him to say no to and that you’d be happy to plan an activity that he suggests. For the first little while, whatever it is that he suggests, just go with it. Some will be hits, while others will be misses. Be sure to point out to him it’s important to try different things in order to find something you both find fun. Who knows, hell might even freeze over and he may suggest trying that new restaurant called The Cheesecake Factory, which opened up at Yorkdale Mall recently. But only if he manages to crawl out from under the rock that is his email app on his work phone first.

If he likes to read, put this book in his hands to see if it’ll get him to stop being a workaholic change his outlook on fun: Bored and Brilliant by Monoush Zomorodi

So now that you’ve got the first of 10 challenges of loving executive men sorta kinda somewhat handled, are you ready to tackle challenge number two?



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