The Entitled Son

Thinking Outloud: Musings and reflections from our adventures in succession and leadership coaching.

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The Entitled Son

I was flying home from a client meeting in Washington state the other evening and had been upgraded to First Class. My seatmate was already boarded – a robust grizzly-looking man in his mid-40’s, still dressed in his yellow slicker jacket that had KODIAC across the front. Unlike most, he offered his hand and introduced himself the moment I sat down. Now I don’t mind being friendly, but frankly, after a long day of wrestling with someone else’s issues, all I really want to do is plug in my earbuds, relax with a good book, and have a glass of wine to unwind. This man, who I’ll call Jake, then proceeded to tell me all about his fishing trip up in Alaska.

What could have been a very interesting story turned strange rather quickly.

Instead of extolling the virtues of the wild, the excitement of the helicopter ride into the deep wilderness or even how incredible eating fish so fresh you were almost eating it right off the hook, he proceeded to tell me each and every detail of what he spent on the trip. From the cost of the room (overpriced, his roommate had stinky boots and snored), how despite over tipping, service was unsatisfactory (each and every person), and what he spent on every single gift for the staff (from the $300 moccasins for the housekeeper, etc). Mind you, I didn’t encourage this with enquiring questions like, “And then what did you buy…?”, he just kept adding up the astronomical bill for me over the next 30 minutes.

I asked my first real question, already knowing the answer, “What is it you do that provides this kind of opportunity?”

And he replied matter-of-factly, “Oh, I don’t do anything. My father started a business sixty years ago, built it up, and sold it for a bundle when he retired. I get my paycheck no matter what I do. My 92-year old dad grew up in the Depression, never spends a penny and always tells me that I could have bought a piece of property with what I spend on these trips. I guess I should, but my business manager tells me I need to go have some fun and relax, so I do.”

Money Can’t Buy You Love
Continuing with my seatmate’s story, Jake then told me that his wife had cheated on him and left him for his best friend, despite buying her extravagant gifts of cars and jewelry every year they were married (yes, he told me how much), that his 21-year old daughter won’t talk to him unless she wants money (despite him buying her a house) and that he didn’t have many real friends.

Curious, I ventured into certain territory where I feared I would never have the peace of my earplugs. “Why on earth do you feel you need to tell me all of this?” And he simply said, “I just can’t trust anybody anymore.”

This 48-year old represented every parent’s nightmare. Living large and in charge, this man didn’t have a clue how to capitalize on a golden opportunity that had been given to him by his well-intentioned father. Unfortunately, his behavior was completely predictable and was fulfilling the Alfred E. Newman mantra, “What, me worry?” that we warn parents about. These are the kids who have a guaranteed income, no incentive to work, be productive or do something meaningful with their lives. Why work when you’ve got an allowance or at the very least, a safety net when you get into trouble?

Jake’s well-intentioned dad probably had meant to make sure his son could take care of his family and wanted to provide him with the security he never had when he was growing up. Times are tough now, it can be difficult to buy a house, job market is tough – whatever. Jake doesn’t need to have a job where he is fulfilling responsibilities, being held accountable or even keeping a regular schedule. Not only is he not investing in himself, his community or the world, he isn’t investing in people – he’s trying to buy them. The classic Beatles tune, “Money Can’t Buy Me Love” seems appropriate here. The vultures can smell greenbacks, and you can be sure that Jake is always surrounded by smiling, friendly and highly accommodating people with their hands out. (“I loaned my friend $8,000 so he could go on the fishing trip with me. Once we got home, I never saw him again. I think he moved.”) Jake is suffering from low-self esteem fueled by a padded bank account.

Jake’s entire self-worth was tied up in his net worth.

Everything his father worked so hard to build, acquire and create financial stability is being squandered by his son in record time. How does something like this happen?

Best Intentions Gone Bad
We all want the best for our children. We want to give them a head start in the world and make sure they can be provided for in a way that they will feel happy, loved and secure. When our children venture out on their own, we help them get started as they marry and begin their own families – and make sure our grand babies have everything they need whether their parents can provide them or not.

If we can reflect back on the challenges we faced as young adults struggling to find our way through the world, fighting to make ends meet as we lived on PBJs and ramen soup, what do our children remember of that time in their lives? Doting Baby Boomers have paid great attention to providing their children with everything they (the parents) thought they wanted, especially if overcompensating for a lack of personal time or split families. This generation is just beginning to find out who they are and what they are really capable of doing on their own. They may be just beginning to learn how hard you have to work to build and maintain a business. We, as parents, made it look easy.

Some kids get it, and they make us proud. I know I am. However, not all kids do. Tough Love is difficult, but it can be even tougher to have to continue to rescue a “dis-abled” child (in the literal meaning of the word) for the rest of his or her life. To be able to offer a helping hand and get your child off to a successful start in life is a dream every loving parent should want to provide. The key is in being able to recognize the difference between the strengthening experience of empowerment over the disabling power of entitlement.


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