Why Your Goals Keep Failing

January 17th is apparently called "quitter's day." That's the date when most people have already abandoned their New Year's resolutions. This likely means the gyms are probably a little less crowded, and the ambitions of early January have faded into February routines.

But here's what I've been wrestling with: maybe the problem isn't willpower. Maybe it's that we're starting in the wrong place entirely.

I've been thinking about this a lot in my work with families. When someone says they want to save more, retire earlier, or finally get their financial house in order, my first question isn't about numbers. It's about why. Not the surface-level why, like "I want to be financially secure," but the deeper why. The one that actually holds up when life gets hard.

The Foundation Problem

Dr. Jen Dragonette put it well in our recent conversation. She said it's like remodeling a house on top of a shaky foundation. You can have all the plans and budgets in place, but if the foundation isn't solid, everything you build on top is at risk.

The foundation she's talking about is purpose. Or values. Or what some people call their "why." These words overlap, but they all point to the same thing: knowing what actually matters to you before you start chasing goals.

Without that foundation, we end up doing what Jen calls a "flight into health." We try to change everything at once. Eat better, exercise more, save more, spend less, be a better parent, be more present. It's not sustainable because we don't really know why we're doing any of it.

Purpose vs. Objectives

A distinction I've been working on with TAMMA families for the past few years comes from Dan Sullivan's work on The Gap and the Gain. The way I think about it is this: your purpose is like the horizon. You can keep walking toward it, but you never actually reach it. It keeps moving. That's not a flaw, that's the design.

Objectives, on the other hand, are checkpoints along the way. They support your purpose, but they're not the purpose itself. When you finish one objective, you move to the next. The horizon stays where it is.

The problem comes when people confuse an objective with their purpose. They set a goal, achieve it, and then feel empty. "I saved enough. I retired. Now what?" That's the gap Dan Sullivan talks about. You thought reaching the goal would feel like reaching the finish line, but it turns out there is no finish line.

Here's the framework I use: Purpose, Objectives, Actions. Your purpose is the bigger why. Your objectives are the goals that support that purpose. Your actions are the how, the specific steps that help you hit your objectives. As you complete actions and achieve objectives, your objectives can change. But your purpose remains.

Take saving for college. That's an objective, not a purpose. The purpose might be raising kids who make good decisions about their own lives. College is one way to support that. But if your kid doesn't go to college, or if they go and don't get much out of it, your purpose doesn't disappear. It's still there, guiding you toward whatever comes next.

The Kinder Questions

George Kinder is often called one of the fathers of life planning in the financial world. He developed three questions that I keep coming back to because they force you to think about time in different ways.

The first question is: What would you do if you were financially secure? Think big time horizon. It asks you to imagine a world where money isn't the barrier. What would you pursue?

The second question is: What would you do if you only had five to ten years to live? This zooms to the middle distance, where real priorities sharpen against the constraint of time. You're not dying tomorrow, but you know the clock is ticking.

The third question is: What would you regret not doing if you only had 24 hours left? This snaps you into immediate focus. Strip away everything else. What's the one thing that defines it all?

These questions work because they use time as a lens. When you imagine different time horizons, different answers emerge. And where those answers overlap, that's usually where your purpose lives.

The Eulogy Exercise

Another exercise that Dr. Jen shared, which I think is particularly powerful, is asking someone to imagine writing their own eulogy. Or better yet, imagine you could attend your own funeral and hear the people you love most speaking about you. What would they say? What would make you proud?

This isn't about death. It's about living. When you cast out into the future like that, you start to see what actually matters. Nobody's eulogy talks about job titles or how much money they made. It's about relationships, impact, and the way you showed up for the people around you.

I would love for my own eulogy to mention that I raised kids who went on to have meaningful relationships. That I had friends who knew me well. That I was present during the years that mattered most. That's purpose. The objectives, like saving for college or retiring at a certain age, are just the scaffolding.

The Permission Trap

There's something else that keeps coming up in my practice. I see it especially with people in their late 40s and 50s who have the financial means to do almost anything they want. They already know what they want to do. They need someone to give them permission.

Carl Richards talks about this a lot. People come to a financial planner not for the math but for permission. They need someone to say, "Yes, you can do this. The numbers work. Go ahead."

This is particularly true around retirement, which I believe is one of the most underrated life transitions anyone will face. You spend your entire career building an identity around work, then flip a switch, and it's supposed to be over. The financials might be fine. But emotionally? That's a different story.

I've seen what happens when people stop completely. Their health declines. Their sense of purpose evaporates. The last thing any of us wants is to watch someone fade away because they didn't have a reason to keep going.

Sustainability Through Alignment

How do you sustain purpose and direction over time? The answer, I think, is alignment.

When your purpose, objectives, and actions are aligned, things feel easier. Not easy, but easier. You know why you're doing what you're doing. You can weather setbacks because the setbacks don't change the horizon.

When things aren't aligned, every obstacle feels like a reason to quit. That's why so many resolutions fail by January 17th. They were never connected to anything deeper.

Theresa reminded me the other night that the average male lifespan is 77. I'm turning 50 this year. That gives me maybe 27 more years. I hope it's more than that, but the point stands. Time is not infinite. Andy Dufresne had it right in Shawshank Redemption: "get busy living or get busy dying."

The Action Step

This week, try the eulogy exercise. Write down what you would want people to say about how you lived. Don't worry about making it perfect. Just get it on paper.

Then look at your current goals and ask yourself: do they support the life I just described? If they do, keep going. If they don't, it might be time to reconsider what you're actually working toward.

Money is a number. Enough is a story. Make sure you're writing your own.