ProductivityRetirement PlanningSelf-Improvement

Don’t Give Yourself So Much Time That You Constantly Run Out of Time

REGULAR CONTRIBUTOR

One of the biggest surprises for many people in retirement is not how much time they lose—but how much time they suddenly gain.

And yet, ironically, time can feel like it keeps slipping through our fingers.

I hear this often in coaching sessions:

  • “I thought I’d finally get to that travel scrapbook, but it’s still sitting in a drawer.”
  • “I planned to volunteer after I retired, but I haven’t even looked into it yet.”
  • “I always thought I’d write that book. Now I have the time, and still—nothing.”

Sound familiar?

Here’s the paradox: when we give ourselves too much time, we often end up doing nothing at all. And before we know it, another month—or year—has passed.

It’s not because we’re lazy. It’s not because we’re forgetful. It’s because time without intention doesn’t create results. And without meaningful structure, time expands in all directions—and often disappears into distractions, doubt, or decision fatigue.

This is where deadlines come in. Not the hard, corporate kind that made you dread performance reviews. But personal deadlines—retirement-friendly timelines that serve one purpose only: to help you do the things that matter most.

Why Deadlines Still Matter in Retirement

Many people entering retirement are excited to finally break free from the constant deadlines of working life. No more meetings at 9. No more quarterlies. No more rushing for school pickups or battling traffic to get to appointments.

This new freedom is liberating—but it can also be disorienting.

Without structure, it’s easy to drift. Without urgency, dreams become “someday” goals. And someday goals are the ones most likely to fade away entirely.

Deadlines give you a way to anchor your time to something purposeful. They invite you to:

  • Take action before doubt creeps in
  • Move forward even if it’s imperfect
  • Break larger intentions into manageable parts
  • Rebuild momentum after a pause or loss
  • Treat your time as a precious, limited resource

In short, deadlines help ensure your intention becomes action.

The Danger of the “Endless” Deadline

Here’s something I notice often in coaching sessions with retirees: when people are finally free to do whatever they want, they often set very generous timelines.

“I’ll start that memoir in the new year.”

“I’ll look into volunteering later this summer.”

“I want to downsize, but probably not for another couple of years.”

“I’ll get healthier now that I have more time.”

But when deadlines are too far away, they don’t motivate us—they lull us. They allow the rest of life to crowd in: household chores, last-minute family needs, minor errands that stretch into entire days. Time fills up, but not with what we intended.

Soon enough, the generous deadline you set feels just as rushed—or even more rushed—than if you had started sooner.

The truth is: it’s not more time we need. It’s better use of the time we already have.

What Proper Deadlines Look Like in Retirement

So how do you use deadlines in a way that motivates, not intimidates?

As a retirement coach, I encourage a few key principles:

1. Make the Deadline Meaningful

Deadlines shouldn’t feel arbitrary. Tie them to a real reason:

  • “I’ll finish my photo project by May so I can gift it to my granddaughter for her birthday.”
  • “I’ll explore three volunteer options by the end of the month so I can start one by next season.”
  • “I’ll walk three mornings a week for the next 90 days to boost my energy before summer travel.”

When the “why” is personal, the “when” feels motivating.

2. Make the Deadline Short Enough to Act, Long Enough to Succeed

Too short, and you feel overwhelmed or paralyzed. Too long, and the urgency evaporates.

The sweet spot? A deadline that pushes you just enough to begin—but gives room for life’s pace.

Ask yourself:

  • Can I realistically work toward this for 30, 60, or 90 days?
  • Is the deadline clear enough that I know what I’ll do this week?

3. Break Down the Steps

A meaningful retirement project (like writing a memoir, starting a garden, learning a new skill, or launching a side project) can feel daunting.

The fix? Don’t just set one big deadline—set micro-deadlines.

Example:

  • Big dream: Start a memoir.
  • Deadlines:
    • Week 1: Create a list of chapter themes.
    • Week 2: Write one childhood memory.
    • Month 1: Draft 3 short stories or vignettes.

Every mini-deadline is a little “yes” to yourself—and the journey builds from there.

4. Track Your Progress and Adjust as Needed

Deadlines should be a compass, not a whip. If something shifts, adjust—but don’t abandon.

Missed a deadline? Reflect:

  • Was the task too big?
  • Was the timeline too tight?
  • Did I lose motivation or support?

Then reset. Don’t wait three more months. Start again this week—with a shorter, clearer, more compassionate goal.

5. Celebrate Completion—Even of Small Things

When you reach a deadline, no matter how small, pause to celebrate.

This reinforces the belief: I follow through. I do what I say I’ll do. I respect my time and my dreams.

This is especially important in retirement, where progress is often self-defined and self-directed. You may not have a boss to recognize your effort—but you can become your own cheerleader.

Final Thoughts: Use Time as a Tool, Not a Trap

Retirement isn’t about doing everything. It’s about doing what matters.

And deadlines—loving, realistic, well-chosen deadlines—can help make that possible.

When used wisely, deadlines do more than manage your time. They protect it. They preserve space for what you love. They move your dreams from “someday” to “now.” And they remind you that your time is still valuable—even more so now that it’s truly yours.

So don’t give yourself so much time that you run out of time.

Give yourself just enough time to act.

Then take the first step. Start small. Keep going.

Because this next chapter? It’s not just open—it’s yours to design.