A funny thing happens when you become a writer: People ask your advice. While the primary topic is writing and, given my non-fiction endeavors, career management, the topics have a surprising span. Over the years I’ve been asked about love, politics, health, family life, sex, finance, technology, and even spiritual well-being. While I have some experience in these, I’m by no means an expert. Frankly, learning mindfulness from me is like learning to ice skate by listening to an accordion.

I warned readers to no avail and ultimately relented by penning a duo of sarcastic self-help books. I thought that would do the trick, but the questions kept coming. Here’s two I received recently and a slightly more thoughtful response.

How can I talk with my friends about money? 

Short answer: Don’t. Mind your business. Okay, assuming you’ll ignore that, try these three largely harmless actions:

  1. Swap Advice: It’s impossible to keep up with every financial instrument: 401(k)s, IRAs, 529s. Swapping knowledge about longer-term vehicles is a great way to get comfortable with money as a topic of conversation. This can lead to open discussions about near-term saving and investing strategies. Granted, it may not be a staple of your happy hour convos, but this strategy will allow it to occasionally ease into the rotation.
  2. Share Your Values: Obviously money helps you secure things, but if you don’t value them they are worthless regardless of the price tag. Letting your friends know what is important to you can help ease the awkward feeling when the proverbial check comes. If you don’t value the big night out, suggest something smaller. And if you can’t afford it at all, say so. There’s always a free way to hang out with friends. Your honesty will let you keep the connection, but on your terms. If they don’t flex occasionally then they’re probably not real friends.
  3. Be the Voice of Reason: You wouldn’t think twice about saying something if your drunk friend reached for his keys or your buddy used a piece of gym equipment bassakward.  If you see a pal doing something overwhelmingly stupid with money, say something. Yes, it will be weird and yes, he’ll probably get mad, but friends don’t shrink from tough conversations.

How to a break up with a boy/girlfriend?

This is 2019. Ghost the hell out of them. Kidding. Never do that. Man or woman up and break the news…ideally in person.

So, here’s the deal. Breaking up with someone personally is similar to “breaking up” with someone professionally. Hopefully there is more emotion involved on the romantic side, but if you’re not married, there’s considerably less paperwork, which is nice.

In either case being respectful, honest, and direct is the way to go. Remember, you’re not devaluing the person. You’re just noting that the “fit” is off. Sometimes it’s helpful to illustrate that gap.  For example, you could say, “One of the many things I love/like/appreciate about you is (fill in the blank). And while I’ll always look fondly on that, what I really need at this point is (fill in the blank). I don’t see that happening with us.

This strategy places the blame on the fit rather than the person, so it eases the blow without being disingenuous. It can work for big issues i.e. I want kids/marriage and you don’t or smaller things like, I enjoy our wild evenings out, but want to focus more on my career now.

Getting “dumped” is never easy, but having an understandable reason makes it easier. It also prompts the person to reexamine his/her needs and wants which can help them in the long run.


Okay, kids. That’s my best Dr. Phil impersonation. (I was about to say Dr. Ruth, but that would make me seem like 1000.) Anyway, next time I get a question here, I’m going back to full sarcasm mode.  Bring your helmets.

We’ve all had someone drop a turd in our Zen Garden.  Laugh it up with these books or give the gift of off-beat humor to that special sarcastic someone.


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