You’re Already in a Relationship With Money — Is It a Healthy One?
As you may know, the title of my signature keynote is, “Financial Success Doesn’t Start in Your Wallet.”
So named because before the money…
ever reaches your wallet,
becomes the balance in your banking or investment accounts, or
shows up as credit you can access,
a whole lot has already happened — none of it directly tied to the actual dollars and cents.
Financial success isn’t just built on strategy or numbers alone — it’s shaped by a multitude of relationships.
In 2026, I’m glad to see that fewer people are skeptical about the idea of having a relationship with money. That wasn’t always the case. And maybe you can relate — because you, too, were once the skeptic.
When I talk about pricing, I often explain that what you decide to charge is a confluence of the relationship you have with money, yourself, your business, and your buyers.
In other words, before money ever shows up in your personal or business accounts (in any capacity), it shows up in your relationships.
And while acknowledging that money is relational is a meaningful step, lately I’ve been thinking it’s time to go a little deeper and explore:
What makes any type of relationship a healthy one?
What makes a choice good versus great?
And how do you measure results in the context of your answers to those questions?
I don’t come at these questions — or the process of answering them — as a licensed therapist, psychologist, or psychiatrist.
Those credentials aren’t required to recognize that not only do you have a relationship with money, but also with earning, enough, success, and uncertainty.
That every financial decision and choice is relational — even the ones you believe are purely logical.
Which raises three important questions — about the health of your relationships, the quality of your choices, and how you evaluate the results.
Question 1: Is It A Healthy One?
I’ll be the first to admit that I used to believe a healthy relationship was one that was perfect. (I know…ridiculous!)
Thankfully, I’ve outgrown that belief (yay to therapy!).
What I now understand — more clearly than ever — is this:
A healthy relationship — with money, with work, with success, with others — isn’t one that’s perfect. It’s one that’s functional.
A healthy relationship has three big-picture components:
Clarity
You understand what the relationship is for — and what it isn’t.
Money: What role is money meant to play in your life right now?
Business: What is your business expected to carry — and what is it not?
Self: What expectations are you unconsciously placing on yourself?
Others: What expectations are you consciously or unconsciously placing on them?
Lack of clarity is often where overextension begins — and misalignment surfaces.
Boundaries
There are limits — emotional, financial, energetic.
What gets access?
What doesn’t?
What requires a pause before a yes?
Boundaries aren’t restrictions; they’re definitions.
Reciprocity (or Sustainability)
The relationship gives something back — not immediately, but consistently.
Does this way of earning support your life?
Does this choice replenish — or only extract?
Can this relationship continue without resentment?
Your answers can reveal whether you’re taking a short-term perspective or evaluating your relationships through a longer-term lens.
Question 2: What Makes a Choice a Good vs. Great One?
While I tend to take a “both/and” approach to most things, there are moments when thinking in binary terms is actually useful. The distinction between a good choice and a great one is one of those moments.
A good choice:
solves the immediate problem
reduces short-term discomfort
makes logical sense in isolation
A great choice:
holds the full context — meaning you’re considering your actual capacity, your current season, your existing commitments, and your values in practice and asking: Given the life I’m already living, what does this decision actually ask of me?
considers second-and third- order effects — what happens after the immediate result…and then what happens after that? What does this choice quietly create over time? What becomes easier — or — harder — to sustain?
aligns with where you’re going, not just where you are
In other words, good choices often answer the question, “Will this work?”
Great choices answer a different — and more enduring — question: “What will this require me to live with?
And while great choices aren’t always the most impressive ones in the moment, they tend to be the ones that age well.
Question 3: How do you measure the results in this context?
Measuring numbers is relatively straightforward — they either went up or down. And ideally, the right numbers went up (sales, revenue, profit, savings, investments) while the right ones went down (debt of any kind).
But if money is relational, then results aren’t just quantifiable — they’re experiential.
Here are a few ways to measure what can initially feel abstract:
Clarity: Do decisions take less mental energy?
Consistency: Are you experiencing fewer internal reversals? (Oh, the self-talk…)
Regret: Are you questioning decisions less often?
Resentment: Is it decreasing — or quietly accumulating?
Capacity: Do you feel more spacious — or more compressed?
I journal almost every day, which helps me notice patterns. But even if you don’t journal, simply paying closer attention to these experiential results can help you make decisions that support the kind of financial success you want — and don’t require recovery later.
About Jacquette
I love to ask questions and spark aha moments. I love to talk about why success with money is about more than just the numbers, and how the cultural impact on the intersection of money, business, and life matters–A LOT! And, I really hope I help people feel seen, heard, and not judged—especially since money is emotional and personal.
