Can You Really Retire Early?

What to Know Before Leaving Work at 63 (or Sooner)

A reality check on health insurance, Social Security timing, and making your savings last.

There’s something deeply appealing about the idea of retiring early.

You’ve put in the hours, done the work, and now you want to enjoy the fruits of it while you’re still young enough to make new memories. Maybe that means mornings without alarms, time with the grandkids, or finally taking the road trip you’ve been talking about for years.

But before you hang up your hat, it’s worth slowing down long enough to ask: Am I really ready?

That question isn’t just about the balance in your accounts; it’s equally about peace of mind. Retiring early takes more than money. It takes planning, purpose, and an honest look at what life will cost, financially and emotionally, once the paycheck stops.

The Health Care Gap No One Likes to Talk About

If you leave work before age 65, there’s a simple but heavy reality to face: you’ll lose your employer health insurance before Medicare begins.

That gap—sometimes two full years or more—can be costly if you’re not prepared. You can bridge it with COBRA or a private plan through the Marketplace, but both can be expensive. And while it’s easy to assume you’ll stay healthy, life has a way of surprising us.

A recent Milliman study estimates the average retired couple will need nearly $395,000 for healthcare over their lifetime. And those numbers don’t go down when you retire early—they often go up.

When I meet with clients thinking about retiring early, health coverage is usually the first topic that brings silence to the room. It’s not fun to plan for, but it’s a part of doing what I call “the right work.” Preparing for what you hope won’t happen, so you can enjoy what you hope will.

Social Security: A Lifetime Decision

When it comes to Social Security, timing is everything.

Many folks assume they’ll start collecting as soon as they stop working, at 62 or 63. But what they don’t always realize is that claiming early can permanently reduce benefits by up to 30%.

That reduction affects both you and your spouse’s survivor benefit later on.

I once worked with a couple who were ready to retire in their early 60s. On paper, it looked perfect. But when we ran the numbers, delaying Social Security by just three years increased their lifetime income by over $150,000. The difference wasn’t just in dollars—it was in freedom: they had options.

You’ve worked too hard to give up options just for the sake of leaving work a little sooner. Sometimes, the best move is waiting just long enough to make your financial freedom truly last.

Longevity: Planning for a Longer Life, Not a Shorter Retirement

When my father ran our family’s dairy farm, he taught me something that stuck: “You can’t control the weather, but you can be ready for it.”

Retirement is no different. We can’t control how long we’ll live, but we can plan for the unexpected.

Today, the average 65-year-old will live well into their 80s. Many live much longer. That’s three decades of retirement to prepare for.

That’s why I tell people: early retirement isn’t about leaving work, it’s about doing the right work ahead of time. That means creating sustainable income, balancing growth and protection, and building a plan that considers healthcare, inflation, and legacy.

Because while no one likes to talk about running out of money, what’s even worse is running out of choices.

The Heart of It All

There’s another layer to this that doesn’t show up on a spreadsheet. It’s the emotional side of “enough.”

Most people don’t retire when they’ve hit a perfect number; they retire when they feel ready to trade security for freedom. But real freedom doesn’t come from guessing. It comes from clarity. From knowing your income, understanding your risks, and being confident that the life you’ve built will continue to serve you long after the paychecks stop.

If you’re dreaming of retiring early, don’t rush the process.

Take the time to think and plan. Make sure your decision reflects not just what you can afford, but what truly matters most to you.

A fulfilling retirement isn’t about escaping work; it’s about stepping into the next chapter with purpose, peace, and gratitude.

And when that’s the goal, it’s not just early retirement.

It’s the right retirement.