How to Catch Up on Retirement Savings If 55 or 60 Feels Out of Reach
A few years of runway is worth more than it feels like right now. Here’s how to catch up on retirement savings before the date you’re aiming for, and one lever most people never think about.
Direct Answer: If the number on the 55 or 60 hub page landed higher than what you’ve got saved right now, you’re not the exception, you’re the rule. The good news is the years right before retirement are the most valuable years you’ll ever have for catching up on retirement savings. Your savings are at their biggest, you’re still adding instead of withdrawing, and every year you wait shrinks the income bridge you’d need. There’s also a lever most people never think of: part-time work that comes with health benefits can close two gaps at once, the health insurance gap and the savings gap, without touching what you’ve already built.
Can I ask you something?
If you ran the numbers on retiring at 55 or 60 and came up short, what’s the first thought that crossed your mind?
For most people, it’s some version of “I guess I can’t.” That’s the wrong conclusion, and it’s worth walking through why before you write off the whole idea.
Why the years right before retirement are the best time to catch up on retirement savings
Here’s what nobody tells you. The years right before the retirement age you’re aiming for are the most powerful years your money will ever have.
Your savings are at their biggest they’ve ever been, so growth on that balance does the most work it’s ever going to do. You’re still earning, so every dollar that comes in is adding to what you’ve built instead of coming out of it. And every year you haven’t started the income bridge yet is a year that bridge gets shorter and cheaper to build, since a shorter gap between retirement and Social Security takes less to fund.
That’s not a consolation prize for missing the number. It’s a real plan with a date attached to it. The difference between “I can’t retire at 55” and “I can retire at 57 or 58 with room to breathe” usually comes down to a clear-eyed look at what you actually control: how much you protect, how the rest is positioned, and when each piece turns on.
The lever most people never think about
If the health insurance gap is what scares you more than the savings gap, there’s a move that handles both at once.
Some employers offer health benefits to part-time staff working somewhere around 20 hours a week. Land one of those for a few years and you’ve solved two problems in one move. First, you’ve covered the pre-Medicare health insurance that worries almost everyone retiring before 65. Second, the paycheck from those hours means you’re leaning on your savings less, which shortens the bridge even further, all without touching what you’ve built.
Which employers offer this changes over time, so a quick search for current part-time positions with health benefits will turn up what’s out there right now. It’s worth twenty minutes of looking.
What this actually buys you
Have you heard the saying that the best time to plant a tree was years ago, and the second-best time is today?
That’s the whole idea here. The best time to start positioning for 55 or 60 may have been a few years back. The next best time is now. A short runway used well beats a long one wasted, and the gap between “almost” and “yes” is usually smaller than a general page like this one can show you. It closes faster with an actual plan than it does by waiting and hoping.
Want to see where you actually stand? See Can I Retire at 55? or Can I Retire at 60? for the real savings targets behind these numbers.
Frequently Asked Questions
I’m a few years away from 55 or 60 and my number isn’t there yet. Is it hopeless?
No. A few years of runway is one of the most valuable things you can have. Your savings are at their largest, you’re still earning instead of withdrawing, and every year that passes shrinks the income bridge you’ll eventually need. Most people’s number starts out bigger than they expected. Knowing that now, while there’s still time to act on it, is the advantage.
How does working part-time help me retire earlier?
If the job includes health benefits, typically available around 20 hours a week at some employers, it can cover your pre-Medicare health insurance and reduce how much you’re drawing from your own savings at the same time. That shortens the runway you need without spending down what you’ve built.
Does waiting a couple more years really change the numbers that much?
Yes, more than most people expect. Every year you don’t start the income bridge is a year that bridge gets shorter and less expensive to fund, since there are fewer years to cover before Social Security starts.
About Kurt H. Jackson, Retirement Lifestyle Architect
Experience
Kurt H. Jackson has spent more than 16 years working directly with retirees and pre-retirees in Missouri, Nebraska, Kansas, Iowa, and Florida, helping them turn the savings they spent a lifetime building into a paycheck they can’t outlive. Before founding KJ Financial, he spent 20 years as a Certified Mortgage Planner working with more than 1,000 clients on major financial decisions. He has seen firsthand how a protected, guaranteed paycheck changes the way retirees handle every market up and down, and how it frees them to actually spend on the life they worked for.
Expertise
Kurt is a Retirement Lifestyle Architect and the creator of the Lifestyle-First Retirement Income Planning framework. He is Life and Health Insurance Licensed in MO, NE, KS, IA, and FL. His practice focuses exclusively on insurance-based, tax-optimized retirement income strategies including Protected Lifetime Income design, Roth conversion planning, and the Retirement Tax Avalanche. He does not manage investments or sell securities.
Authoritativeness
Kurt founded KJ Financial and operates MaxMyRetirementIncome.com as a dedicated educational resource for retirees. His Lifestyle-First framework starts with the retirement the client actually wants, builds a guaranteed income floor to make it certain rather than probable, and manages the remaining assets as true long-term money. The research supporting this approach comes from J.P. Morgan, BlackRock, Morningstar, and peer-reviewed academic work by David Blanchett and Michael Finke. The framework connecting them is his.
Trustworthiness
KJ Financial is a compliance-first firm. All educational content on this page reflects current law and research as of 2026 and is subject to change. Kurt H. Jackson is not a securities broker, registered investment advisor, or CPA. Nothing on this page constitutes personalized tax or legal advice. Guaranteed income strategies involve real costs and require careful planning based on your individual circumstances.
KJ Financial
1014 E. 5th St., Maryville, MO 64468
Direct: 816.582.5532
Email: kurt@kjfinancialonline.com
Website: www.MaxMyRetirementIncome.com
Last updated: July 2026
All figures on this page are illustrative and hypothetical, as of 2026, and are subject to change. They are not a promise or guarantee of any specific result. Which employers offer part-time health benefits changes over time; verify current availability directly with employers. Nothing here is investment, tax, or legal advice. Kurt H. Jackson is Life and Health Insurance Licensed in MO, NE, KS, IA, and FL, and is not a securities broker, registered investment advisor, or CPA. Guaranteed income strategies involve real costs and require careful planning based on your individual circumstances.