Waiting Until It’s Urgent

I first came across Stephen Covey’s 7 Habits of Highly Effective People early in my career, back when I was a trying to absorb everything and anything I could to become a better advisor. At the time, the “Four Quadrants” of time and priorities stuck with me, but only in a surface-level way. My understanding was limited to my own life experience, and frankly, I didn’t fully grasp the weight of the concept.

Fast forward a number of years. I was having a conversation with a retired advisor who has been something of a mentor to me. (Strange as it may sound, I think it’s still valuable to have mentors—even after 22 years in the business.) He asked if I remembered Covey’s quadrants. I said I was vaguely familiar. He then shared his perspective on them, and it completely reshaped the way I thought about the framework.

Since then, I’ve often found myself returning to the Four Quadrants. And I’ve realized something: the biggest financial mistakes I see in retirement usually come from ignoring Quadrant II—the place where things are important, but not urgent.

The Four Quadrants

If you’re not familiar, Covey’s Four Quadrants divide activities into categories:

• Quadrant I: Urgent + Important 
• Quadrant II: Not Urgent + Important 
• Quadrant III: Urgent + Not Important 
• Quadrant IV: Not Urgent + Not Important 

Quadrant II is where the magic happens. It’s the space for proactive decisions that shape the future. But it’s also the easiest quadrant to ignore.

When we delay Quadrant II activities, they don’t disappear. They eventually migrate into Quadrant I. They’re still important, but now they’re also urgent—and that’s where stress builds, options shrink, and mistakes get made.

How Small Choices Become Big Emergencies

Think about health. We all know we should eat well and exercise. That’s Quadrant II behavior: important, but not urgent. Nothing bad happens if you skip the gym this week or order the double cheeseburger tonight.

But push it off long enough, and Quadrant I takes over. Suddenly you’re dealing with high blood pressure, diabetes, or a doctor warning you about serious risks. At that point, the choices are limited, more expensive, and harder to manage.

The Same Thing Happens With Money

I see this same pattern in retirement planning:

• Saving for Retirement
  It doesn’t feel urgent when retirement is 15–20 years away. But every year you delay means saving more later. By the time it becomes urgent, the math may not work without drastic sacrifices.
• Roth Conversions
  The sweet spot for conversions is often the early years of retirement, before Required Minimum Distributions (RMDs) kick in. Wait too long, and you’ve lost the flexibility to act at lower tax rates. What could have been a thoughtful Quadrant II strategy becomes a Quadrant I scramble.
• RMD Planning
  Too many people wait until the year they must start withdrawals. Suddenly, large distributions push them into higher tax brackets and raise Medicare premiums. With planning years earlier, those problems could have been avoided.
• Estate Planning
  This is the classic Quadrant II activity. Waiting until a health scare or crisis forces decisions means choices are made under pressure and often with fewer options. Families that work through these questions earlier are far better prepared.

Why Quadrant II Matters

Quadrant II is where the best financial decisions get made. You have time, clarity, and the ability to choose wisely. Quadrant I is reactive. It’s stressful, costly, and narrow.

You’ll never avoid Quadrant I completely—life will always bring the unexpected—but you can reduce how much time you spend there. And every bit of preparation you do in Quadrant II buys you peace of mind later.

The Payoff

The biggest mistake I see isn’t picking the wrong stock or fund. It’s waiting until something is urgent. By then, your choices are fewer, and often more expensive.

But here’s the good news: when you build the habit of focusing on Quadrant II—the important but not urgent—you actually reduce the number of Quadrant I crises you’ll face. That opens up space for something even better: more time in the quadrant that matters most in retirement—the one where your hobbies, passions, and relationships live.

The more you invest in Quadrant II today, the more room you create tomorrow for the life you want to live—not just the problems you want to avoid.