The Promise of Planning Software: Lessons From a Food Journaling App

When you open a food journaling app for the first time, your motivation is usually simple: track calories, maybe lose a little weight. But as you stick with it, the app begins to surprise you. You discover that your diet is high in sodium, low in protein, or tilted far more toward processed carbs than you imagined. The very act of logging and seeing connections changes the way you eat, shop, and think about health.

Financial planning software (FPS) holds the same promise. At its best, it’s not just a calculator or a tool for checking a box, it’s a living system that reveals the hidden relationships between our financial decisions. Just like nutrition, money is never about a single number. Choices in one area ripple across every other area.

But here’s the catch: while food journaling apps have become mainstream, accessible, and intuitive, financial planning software is still catching up. To understand why, let’s step back and trace how planning technology has evolved, where it’s fallen short, and why scenario planning may finally unlock its full potential.

From DOS Screens to Digital Journeys

When I first entered the fintech industry 25 years ago, financial planning looked nothing like it does today. The “big guys” in the space were 600-pound gorillas. They were powerful, but sometimes intimidating, and lumbering. Their software experiences were clunky DOS interfaces, straight out of a computer lab.

Back then, financial plans were more rare. They were almost exclusively for high-net-worth households and required a mountain of data entry. The deliverable was a thick, glossy paper report that sat on a shelf more than it guided daily decision-making.

Fast forward to today: everything has gone digital. Advisors and clients alike now expect software that runs smoothly on desktop and mobile, integrates data seamlessly, and produces elegant visuals instead of paper bricks. The most important change, in my opinion, is the democratization of the experience. Though we have a long way to go, we’re building more plans now and for a larger % of the audience. A better planning experience that focuses on education and collaboration will be a big part of that continued march forward, but at a much faster pace.

However, while delivery formats have evolved, the core experience of financial planning software still hasn’t caught up to the everyday digital experiences that shape our expectations.

Think about it. Every other industry, from food delivery to fitness to entertainment, is constantly training your clients on what a “good” digital experience feels like. Why would they expect less from their financial advice?  

Calculators vs. Planning Software

At first glance, calculators and planning software can look similar. Both give you numbers. Both provide answers. But the similarity ends there.

• Calculators are transactional. They’re built for one-off questions like “What’s my mortgage payment?” or “How much will I save if I refinance?” Once you close the calculator, the insight disappears.
  
  
• Planning software is relational. It’s built to store, connect, and cross-reference data. Decisions in one area, such as saving more in a 401(k) can be viewed alongside ripple effects in debt management, insurance needs, or retirement projections.
  
  

This distinction is crucial. Imagine using a calorie calculator every time you ate a meal, but with no record of what you’d eaten earlier. You’d never see the whole picture. A donut at breakfast wouldn’t matter if the app “forgot” it by lunchtime. You’d miss the big health story: how small daily decisions accumulate into long-term impact.

That’s exactly how planning software rises above calculators. It reveals the interdependencies of financial health. Without that connective tissue, financial decisions get made in silos and opportunities are lost.

The Food Journaling Analogy

Most people who download a food journaling app start with one goal: track calories. But within days, the app is telling a deeper story. You discover you’re only getting 60% of the daily protein you need. You realize nearly every packaged food you eat contains added sodium. Maybe, you see how much sugar sneaks in through “healthy” drinks. At first, these insights feel jarring or even discouraging. However, over time they empower change. You begin to shop differently, plan meals more intentionally, and experiment with new foods.

This is exactly how financial planning software should work. Advisors might begin using it for one reason such as to model an insurance sale, compare investment options, or run retirement projections. But once data is in the system, the software can illuminate bigger truths like a client may be over-insured in one area but dangerously exposed in another.  Maybe an aggressive debt payoff may conflict with building a safety net or seeing how college savings choices may ripple into retirement readiness. The promise of planning software is that one motivation opens the door to many revelations.

Where We Are Today

Despite this promise, financial planning software hasn’t “arrived” in the way food journaling apps or fitness trackers have. Why? Several reasons stand out:

1. Complexity of data. Unlike food, which can be logged with a barcode scanner, financial data is fragmented across banks, brokers, insurers, and payroll systems.
   
   
2. Advisor adoption curve. Many advisors still use software tactically to support a product sale or client meeting rather than holistically as an engagement platform.
   
   
3. User experience lag. Clients are accustomed to apps that are sleek, gamified, and intuitive. Financial planning tools often feel like spreadsheets in disguise or the experience is too simplistic to actually empower them to play.
   
   
4. Fear of overwhelm. Just as food journaling can shock a user into quitting, financial planning can expose uncomfortable truths. The challenge is to surface insights with empathy and guidance, not just cold numbers.
   
   

The good news is that momentum is building. More firms are embracing integrations, open APIs, and client-facing portals that move software beyond a “behind the curtain” advisor tool. And as consumers grow more accustomed to interactive experiences, advisors are recognizing that planning software is no longer optional, it’s expected.

Why Engagement Matters More Than Speed

For decades, planning software has been optimized for speed: faster data entry, quicker outputs, instant graphs. But the real value isn’t speed, it’s engagement.

Consider the difference between a doctor handing you a strict diet plan versus an app that helps you discover your own patterns. How about an advisor handing you a 50-page plan versus software that helps you explore your own “what if” scenarios. The second option isn’t just faster, it’s stickier. It creates buy-in. Clients don’t just receive advice; they internalize it.

This is why scenario planning is so powerful. It shifts the narrative from advisor-driven answers to client-driven exploration.

From Calories to Cash Flows

The analogy between food journaling apps and financial planning software isn’t just an idea, it’s instructive. Both reveal hidden patterns. Both turn isolated decisions into holistic insights. And both have the power to transform behavior over time.

The key takeaway is that we’re not there yet. Financial planning software has made tremendous progress, but the true breakthrough lies ahead. Scenario planning is the foundation that will make planning experiential, engaging, and empowering.

Just as logging meals transformed the way millions of people think about food, the next generation of financial planning tools will transform the way millions of families think about money. And when that happens, the promise of planning software may finally be fulfilled.

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