Can you relate to this scenario: You’re hanging out with a group of friends. Someone in the mix (not you) starts to vent about something that really isn’t working out in their life, and they are frustrated.

You and the others listen intently as “Jane” gives you details about what’s wrong, and paints a picture of why she thinks things aren’t working out. And then she asks for advice.

So, you and the others start providing ideas and sharing your own experiences or the experiences of others whom you know have dealt with similar circumstances.

But for every example proffered, the person who asked for advice comes back with a reason why they simply cannot do whatever anyone has put on the table for them to consider.

Ugh…doesn’t this just drive you crazy?!

I know it drives me crazy. It’s like why did you bother to ask for help if all you were going to do is say, “no?”

Here’s the funny thing: In the same week where I rolled my eyes because “Jane” resisted every suggestion offered, I realized I had behaved in the same way only a few days later. Oops! -:)

Different underlying issue; different group of people; same result: We resisted.

That is what we humans tend to do.

It doesn’t matter if the issue is related to work, a personal relationship, or finances, just because you and I want something about our lives to be different, that doesn’t mean we are fully prepared for the metamorphosis the change usually requires.

A New Reality

I remind you of this because of the confluence of seemingly random yet interconnected factors that will bring about a financial difference in your life: 2017 holiday season, healthcare costs, tax reform, the stock market, and 2020.


When doing research for my book, “Financial Intimacy,” in 2007 and 2008, I remember coming across studies that said by 2020 anywhere from forty to fifty percent of the American workforce would be freelancers. Back then,13 years seemed far into the future; now it’s just a little over two years before we hit this benchmark.

Why does this matter? Because if you haven’t already experienced a downsizing or unintended career shift due to the shifting economic conditions and employment landscape, you might want to brace yourself – financially and emotionally. Especially if you’ve never envisioned yourself as an entrepreneur or independent worker.

The stock market

Yes, the Dow Jones Industrial Average is at an all-time high of over 23,500. Extraordinary when you consider where it was in early 2009 (a little over 7,000), when the bull market started. And yes I am happy with the current market value of my Betterment account, but here’s a truth we all need to remember: markets don’t stay high forever.

Plus, if you’re following the investing adage of “buy low, sell high,” it is important to remember that high prices are good for people who are selling, not for people who are buying.

Tax reform

There is so much we still don’t know about what will become of the final tax reform bill proposed by the GOP. But, it is pretty fair to say the ripple effect will be far reaching and significant – on individuals, families and businesses. Because (a) tax cuts don’t pay for themselves, and (b) the fact sheet refers to “low and middle-income” earners as those earning $450,000. FYI: The median household income in the U.S. is $59, 039!

Healthcare costs

I don’t know anyone – whether you self insure like I do or get your insurance through your employer – who isn’t complaining about the rising cost of healthcare premiums.

At the Family Table

What do healthcare costs, tax reform, the stock market and 2020 have in common besides a healthy dose of uncertainty? They represent what will impact and be impacted by an ever-evolving financial reality.

They represent the dance and the friction between what changes when things are different.

And they represent the perfect reason you and yours should take advantage of the holiday season to talk about money! I know, I know – crazy idea! I suggested it last year around this time, too.

Because these interconnected factors are a great way to frame a conversation about unspoken guilt and shame, and unchecked expectations and obligations with family, extended family and “friends-as-family.” It’s a great way to break through the wall of financial silence that exists in many families.

Sharing insight, informed decision-making skills, and key financial habits is a great way for families to build greater financial health and wealth. Something that every individual and family is going to need more and more of as the economic conditions and employment landscape continue to shift into something we’ve never seen or experienced before.

Back to “Jane”

“Jane” (and I) were initially resistant to the suggestions of others – even though they were offered with our best interest and goals in mind regarding what we wanted to be different. So, you’re likely to encounter resistance when you suggest to your family that you carve out time for a meeting about money.

This resistance could be due to any numbers of factors. Maybe it’s a misunderstanding about your motive for suggesting it; maybe it’s a fear of being judged or coming across as not knowledgeable; or perhaps it is a general discomfort regarding all things money (family or not).

Here’s my suggestion for how to respond to the resistance with grace:

  • Think about who is likely to resist the idea of a family “money” meeting, and how that resistance is likely to play out.
  • Acknowledge that resistance, and ask what if anything you can do to make them feel safe.
  • Figure out what creating a safe space looks like for you and yours — and then create it.
  • Create ground rules that support your safe space – which includes avoiding the temptation to tell people what they should/should not do. (Even if you’re a financial expert, don’t wear that hat at the table.)

It is true: Some families navigate conversations about money with aplomb. They don’t let that it’s uncomfortable stop them from discussing the full spectrum of financial experiences, results and expectations.

For other families, just the idea of having this conversation is stressful as hell!

And in case you can’t tell, I want families to do it anyway. As I said last year

“I wish more families were less silent when it came to talking about all aspects of money. That’s because I believe the emotional and financial costs of avoiding these important conversations are often greater than they need to be. It’s also because I wholeheartedly believe that together, we can break the money taboo – one family at a time…one conversation at a time.”

Because each conversation represents an opportunity to proactively get ready for a new reality that awaits us all.

So, if you need help initiating that conversation, if you’re looking for strategies and tactics to help you set the tone; if you’d like a framework for broaching sensitive topics; and if you’d like to role-play, I invite you to join us for the next and final Comfort Circle™ dinner for 2017. Click here for details and to RSVP.

p.s. The Comfort Circle™ dinners is where we talk about money, business and life – over food and wine. Our next dinner is scheduled for November 13th, at 6:30pm. I’d love to welcome you to the table! The theme: Talking About Money With Your Family…With Ease. To join us >> CLICK HERE TO RSVP

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