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The Best Interest » Do You Have a “Deeper Yes?”

Do You Have a “Deeper Yes?”

I was recently listening to Michael Kitces and Carl Richards on their podcast, and they posed an amazing question:

“What’s one thing that you do regularly that you’d like to stop doing?”

What would you stop doing? Each of our answers will vary. It could be a destructive habit, a bad behavior, or the simple wasting of time.

As their conversation continued, Carl posited this effective strategy: saying “no” becomes much easier when you have a “deeper yes.”

Carl used the example of a client who chose not to pay for an expensive parking spot. Instead, that client took the would-be parking money and parked it (ha!) in a bank account. Every few months, those moneys would pay for a family dinner at a nice restaurant.

Family meals at nice restaurants were a much “deeper yes” than the parking pass. It made saying “no” to parking easy.

group of people making toast

Kitces and Carl are both “celebrity financial planners,” and so their message is tailored to other financial planners (like me).

Early on in most planners’ careers, we are incredibly excited by the opportunity to work with any clients. I’ve felt this acutely, potentially because I’m a late-comer to the industry and a career-changer. But like all good businesses and business owners, we need to ask, “What does my ideal client look like?”

What’s an “ideal client?” For me, it’s an individual or family who:

  • needs my help. They want to delegate their financial planning to an expert, and regain more time in their own lives.
  • values my help. They understand the benefit of getting this stuff right, and the costs of getting it wrong.
  • is enjoyable to be around. I don’t want to work with jerks (and I hope my clients share this value!)
  • can pay for my help. The Best Interest is and always will be a free resource. But it only survives because paying clients who meet all the criteria above seek me out. When readers like you refer people in your lives to me, you’re making this whole enterprise possible. Thank you!

My time and bandwidth are finite, though. So if I say “yes” to a non-ideal client (someone outside the center intersection) I’m exhausting my limited bandwidth. I’ll eventually run out completely. I’ll be forced to say “no” at that point, even when talking to a more ideal client!

Thus, my “deeper yes” is truly ideal clients. They’re out there and worth waiting for. While it’s hard to say “no” to people who want my help, it’s easier when I know there is a “deeper yes.” Plus, I can refer my “no” to other fiduciary, fee-only advisors who have a different “deeper yes” than my own.

While Kitces and Carl – and me too, at least so far – are applying this “deeper yes” idea to financial planners and their clients, we should also apply this idea to your personal finances.

Your “Deeper Yes”

One of the great, common frustrations in personal finance sounds something like:

“I wish I had more money for travel…but I guess I did spend $17,000 on a snowmobile last year, hmm…”

photo of woman sitting on boat spreading her arms

Spending money is a constant, alluring tease. It becomes easier to say “no” to overspending when you have a “deeper yes.” We can apply “bimodal spending” to our lives.

There’s nothing wrong with snowmobiles. But do you have a “deeper yes?” If you don’t know your “deeper yes” yet, we’ll discover it right now.

To discover your most meaningful spending, ask yourself the following questions. Some questions will resonate more than others. You can even build a Venn diagram, like mine above, and see which spending falls in your “Ideal Intersection.”

Questions to Find Your “Deeper Yes”

What are my core values? Identify what matters most to you (e.g., family, health, education, adventure).

Which expenditures align with these values? Assess if your spending supports these core values.

Which purchases bring me the most joy or satisfaction? Reflect on purchases that make you feel happy or fulfilled.

What spending do I regret? Identify any expenditures that make you feel guilty or regretful.

Which expenses contribute to my long-term goals? Determine if your spending helps achieve your future objectives (e.g., raising children, saving for retirement, investments in education).

How do these expenditures improve my quality of life? Assess if spending enhances your well-being, skills, or relationships.

woman surrounded by sunflowers

What are my essential expenses? Identify necessary expenditures for living (e.g., housing, utilities, food).

    Are there any non-essential purchases that still hold significant meaning? Reflect on discretionary spending that is important despite not being essential.

    What am I sacrificing to make certain purchases? Consider what you might be giving up when you choose to spend on certain items.

    Would reallocating funds to other areas better align with my values and goals? Think about how redirecting spending could enhance your life or align better with your priorities.

    Do I value experiences over material goods, or vice versa? Do you get more satisfaction from experiences (e.g., travel, events) or material items?

    black and white laptop computer

    What experiences have been most memorable and fulfilling? Identify past experiences that were particularly meaningful and why.

    How does my spending affect my relationships? Consider if/how your spending habits influence your interactions with family, friends, or community.

      Does my spending contribute to causes I care about? Reflect on if and how your money supports charities or social causes important to you.

      Which purchases do I consistently make? Identify regular expenditures and evaluate if they are meaningful or habitual.

      Have my spending patterns changed over time? Consider how your spending has evolved and if it reflects changes in your values or life circumstances.

      How does my spending support my personal growth? Think about whether you invest in things that help you grow, such as education, hobbies, or self-improvement.

      What purchases have had a lasting impact on my personal development? Identify expenditures that contributed significantly to your growth or learning.

      Put Rout to the No’s

      Once you discover your “deeper yes,” it becomes easier to say “no” to other spending.

      I can’t buy the snowmobile. I’m taking my family to Portugal next summer. It’s a “deeper yes” for us.

      Henry David Thoreau famously wrote,

      I went to the woods because I wished to live deliberately, to front only the essential facts of life, and see if I could not learn what it had to teach, and not, when I came to die, discover that I had not lived. I did not wish to live what was not life, living is so dear; nor did I wish to practice resignation, unless it was quite necessary. I wanted to live deep and suck out all the marrow of life, to live so sturdily and Spartan-like as to put to rout all that was not life, to cut a broad swath and shave close, to drive life into a corner, and reduce it to its lowest terms, and, if it proved to be mean, why then to get the whole and genuine meanness of it, and publish its meanness to the world; or if it were sublime, to know it by experience, and be able to give a true account of it in my next excursion.

      A replica of Thoreau’s cabin at Walden Pond

      Spend deliberately! Put rout to the “no’s” in your life, and look for the “deeper yes’s!”

      If that plan “proves to be mean,” then report back about that meanness. But I predict you’ll find it sublime, and you’ll be able to give a true account of such wise spending to the rest of us.

      Thank you for reading! If you enjoyed this article, join 8000+ subscribers who read my 2-minute weekly email, where I send you links to the smartest financial content I find online every week.


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