Retiring is hard, no question about it. You spend decades working, saving, and building up your nest egg, and then one day, boom—it’s time to stop. But here’s the thing: it’s not just hard because of the financial side of the equation. It’s tough emotionally and psychologically too. We’re wired to be productive, to earn, to save, and when it’s time to reverse that…it feels unnatural. 

This is what we hear all the time from people.  Slamming on the brakes is no easy task.

The Grind Doesn’t Stop… Until It Does

Think about it: Most of us start working young. Babysitting, raking leaves, grabbing our first part-time job. Some of us were cutting lawns or delivering papers at the age of 10. Some were wearing department store vests as soon as we could get a work permit. It’s in our DNA. You work hard, you earn, and then you save. But suddenly, retirement comes along, and it’s like someone pulls the cord on everything you’ve ever known. You stop working. You stop earning. You stop saving. And now, you’re supposed to live off everything you’ve saved.  We all hear that phrase “well, you can’t take it with you” – but that doesn’t stop the idea of taking from your stash from being a terrifying concept.

Retirement is the most expensive thing you’ll ever have to pay for, and you can’t borrow for it, right? So when you finally see the cost of what you’ll need, it’s overwhelming.  It’s not just the cost; it’s the entire mentality shift that comes with it.  We understand.

Start Early, Give Yourself a Break Later

So, how do you make retiring easier? First things first—start early. I know, it sounds simple, but it’s critical. The earlier you start saving, the more time you give your money to grow. Compound interest is your best friend here. The reality is, retirement sneaks up on you, and the sooner you start, the more options you’ll have later. If you’re in your 20s or 30s, this is the time to get aggressive about saving. Don’t wait for that “better time” to save. Start now, even if it feels like there’s never enough.

Look, I get it—life’s expensive. You’ve got rent, student loans, car payments. But if you can find a way to push through that discomfort now, the “Future You” will be grateful. Let’s say you’re putting away 10% of your paycheck. That’s great, but why not stretch it to 15%? Get to the point where it stings a bit. It’s going to feel tight, but the more you save early, the easier it will be to relax later. The best time to start saving for retirement? Yesterday.

T-Minus 10 Years Until Retirement: The Final Countdown

Now, if you’re getting close to retirement, that final 10-year stretch is a whole different ball game. This is what we call T-Minus 10. You’re not just saving anymore; now, it’s about protecting what you’ve built. Ideally you’ve been saving for decades, and now your job is to ensure that your nest egg is there for you when you need it.

When you’re 10 years out from retirement, the stakes are higher. You don’t have time to recover from a 30% market correction the way you did in your 30s. You’ve got to think defensively. It’s not all about growth anymore—it’s about preservation. And remember, don’t take risks you don’t need to take. You’ve earned the right to play it safe if you’ve done the saving.

It’s Not Just About the Money

Here’s where it gets tricky: retiring isn’t just hard because of the money. It’s hard because it’s a total life shift. You’re losing structure, routine, social interaction—your sense of purpose. Work isn’t just a paycheck for most people. It’s how we define ourselves. It’s how we’ve spent the better portion of our waking hours our entire adult lives. What do you do when that’s suddenly gone?

This is where we’ve seen people struggle the most. They’ve been working their entire lives, and then one day, they retire, and they’re left asking, “Now what?” You’ve got to figure out how you’re going to spend your time. Will you volunteer? Travel? Pick up a new hobby? You need something that gives you that sense of purpose because trust me, if you don’t have it, you’re going to feel lost. Think about this ahead of time and give yourself something concrete to look forward to. 

And don’t forget to integrate the social side of it into your plan. A lot of your social life is tied to your coworkers. Once you retire, those relationships change. Suddenly, the people you spent 40 hours a week with are no longer in your life, and even if you couldn’t wait for some solitude at the end of your day, when you don’t have it anymore, you’ll miss it. Social interactions will begin to take effort to create, so you’ve got to find new ways to stay connected. Whether it’s community groups, volunteer work, or team activities, it’s critical to keep that side of life alive.

Go Do the Thing

One thing to consider that may come as a shock: don’t be afraid to spend your money. A well prepared retirement should not end up in instant austerity!  You’ve worked your whole life for this. Now is the time to enjoy it. Here is it again – “you can’t take it with you” – so don’t be afraid to do the thing, whatever that thing is for you. Whether it’s buying that vacation home, taking the family on a big trip, or even just treating yourself to something you’ve always wanted.

You didn’t save all this money just to stare at it in your bank account. Retirement isn’t about dying with the biggest number in your portfolio. It’s about living your life.

Making Retirement Less Hard

So, how do we make retiring less hard? Start early. Save aggressively when you’re young, protect your assets as you near retirement, and be prepared for the emotional and psychological shifts that come with this new chapter of life. It’s not just about the numbers on a spreadsheet—it’s about finding that balance between financial security and living the life you want.

The earlier you start, the less jarring it is when you finally do retire.  When that day comes, don’t forget to enjoy it.  After all, you worked hard for this—now it’s time to do the thing.