Have you ever done (or heard of) the 9-dot puzzle? If not, here’s how it works:

  • Draw three columns and three rows of three dots, each.
  • Connect the nine dots using four straight lines, BUT your pen or pencil can never leave the paper.

If you didn’t Google the solution, I’d love to see your result. (Take a photo and DM me on Instagram.) Because, there are several ways to solve this puzzle as instructed. And the one thing each approach has in common is this: you have to extend beyond the boundaries.

The 9-dot puzzle image often comes to mind when I am facilitating abstract conversations about money. I happen to LOVE these kinds of conversations.

However, I’m not always so sure my guests or audiences feel the same. At least not in the moment as we’re having the conversation. 🙂 I had this inkling twice last week: 

First, when I hosted this month’s dinner on finishing strong and asked my guests to explore the type of fear they were feeling and what it may be inviting them to do as it pertains to that “thing” that is unfinished

Then again, when I presented a roundtable discussion about “The Missing Pieces of the Money Conversation,” and talked about transparency, power and intimacy. Without defining transparency, power and intimacy for them! (Don’t worry, I didn’t leave them hanging. I provided examples to help them define what these words mean to them. Because the most relevant definitions are personal and contextual.)

I know people find comfort in “how-to’s.” But neither the dinner nor the roundtable presentation were “how-to’s.” By design, they were more in the vain of “what, what-if, and why.” Meaning: we were diving into uncomfortable – and sometimes, even, unexamined – territory.

Now, don’t get me wrong. How-to’s – or the tactics of money – serve a purpose and are important. But too many in the personal finance industry would have you believe that if you just did the “how-to’s” you’d be in some version of financial utopia. Hmmm…

One of my biggest problems with financial “how-to’s” is this: They lack depth. 

They are too emotionally safe.

They rarely, if ever, invite you to explore and imagine. Or, to think creatively about how to resolve your financial challenges or achieve your desires. Or, to look beyond the numbers.

For example: A couple wants to save more. Yet they aren’t reaching their goal and they don’t realize that the reason has nothing to do with the actual numbers. Rather, it is because one of them has a different definition of what financial security looks and feels like. 

Here’s another: An entrepreneur is rocking it. They’ve grown their business to a coveted seven figures in revenue. So what’s the problem? Their revenue could be even higher, if only they would charge differently and charge more. But, they don’t see how their relationship with money is what is blocking them from doing either. 

All the how-to’s in the world would never have uncovered these deeper reasons.

That’s what I appreciate about abstract money conversations. They uncover the less obvious. And much like the 9-dot puzzle, these kinds of money conversations can spark creative thinking in structured and unstructured ways.

So…to the question in the title of this piece, do you also appreciate diving into the “what, what-if, and why” of money? 

Or, are you in the camp of, “Tell me what to do and when?,” “Give me certainty that I’m doing all the right things?,” or, “I want to take the emotions out of money?”

These are sentiments I hear, often. So if you answered “yes” to any of these questions, you are not alone. 

But as any of my coaching clients and presentation audiences will tell you, I will push back on these and similar statements/questions. 

To the:

  •  “Tell me what to do and when?” I’d ask what if following generic financial wisdom actually creates (more?) financial insecurity for you? It is so much better to follow the spirit of a financial tactic and find what’s suitable for your current circumstances than it is to unquestionably follow a financial rule. Strategic adaptation is key and is what will set you up for success. 
  • “Give me certainty that I’m doing all the right things?” Sorry. But life is full of uncertainty. It is better to seek and prioritize clarity over certainty.
  • “I want to take the emotions out of money?” I’d say it isn’t possible. Everyone reacts to money emotionally. Everyone! Regardless of where you are on the income and wealth spectrums. The question is whether you are in front leading your emotions, or in front being pushed by them? The position is the same; the posture is different. 

When I reimagine how the personal finance industry works, shifting how we talk about money is definitely at the top of the list. 

I especially want there to be a shift from a dogmatic business model that dispenses universal rules to one that inherently promotes the use of frameworks to help contextualize common personal finance wisdom. In other words, make personal finance…personal!

That’s my why, in general, for what makes me so keen on abstract conversations. 

Here’s my why as it pertains to YOU. 

  • If you’re dealing with a financial challenge or frustration right now, do the 9-dot puzzle (or a similar type of puzzle) whilst asking yourself what’s the problem behind the problem? This will not only help you reframe the problem you see, but it’ll help you tap into several possible solutions to the actual problem. 
  • If you’re tired (and who isn’t with everything that is going on in the world?!), and doing what is necessary to meet your goals or fulfill your desires seems like one never-ending-to-do-list, zooming out to go beyond the boundaries will help you reconnect to what made these goals and desires important to you in the first place
  • If you’re stuck, it’s time to look for patterns. (You know I always say you can’t interrupt a pattern you don’t notice.) In the process of looking for patterns, you’ll gain new insight. This, in turn, will expand your perspective on many fronts. 


I am fully aware that abstract conversations about money aren’t easy. Let alone necessarily desirable :).

But, that doesn’t mean you shouldn’t endeavor to have them…or have them more than you do currently. Especially when you consider the role they play in helping you get the results you want, as well as the experiences you want – with as little friction as possible. 

One thing is for sure: you can count on me to do everything I can to make it feel emotionally safe for you to do so. Whether I’m facilitating that conversation on your screen, or in a coaching engagement, or during a presentation.

In other words, you can count on me to be here to instigate the “what, what-if, and why” in all that I do to help you make better, smarter choices with your money.

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