Recently, several people have asked me how and when I’d recommend they should prepare for retirement.
Some are decades away from retirement, and others are just a couple of years away.
It’s encouraging that people are beginning to understand that successfully navigating the transition to retirement requires some preparation and thought.
You don’t just quit work one day and successfully retire the next.
It’s much more complicated than that.
What can you do to prepare for retirement, even if you’re years away?
What Retirement Preparation Actually Looks Like
1. Get Real About What Retirement Is
Too many people only play the retirement highlight reels in their minds—endless sunny days, zero problems, perpetual contentment.
Of course, that’s ridiculous.
We understand now that retirement is a major life transition.
In fact, it’s one of the top ten transitions in life, and ranks right up there with the stress of divorce, marriage, or having a baby.
Successfully navigating retirement isn’t about picking the right date—it’s about preparing for one of the biggest transitions of your life.
2. What You’ll Lose in Retirement (And How to Prepare)
Most people have never anticipated major losses during the retirement transition.
A. Identity is often the first casualty of retirement.
For many people—especially men—work isn’t just what they do. It’s who they are.
You don’t have to abandon that. Some people argue that we shouldn’t have our identity wrapped up in our jobs.
I think that advice sounds nice, but it doesn’t match how real people actually live. We’re going to identify with our jobs when it’s a major part of our lives.
We need to think about the fact that when we retire, that identity will go away. We’ll have to figure out who we’ll be after retirement.
As Joshua Becker writes in his book, Things That Matter,
“‘The key to a happy retirement is to have something that you are retiring to, not just something that you are retiring from.”
Joshua Becker goes on to say that to be happy, retirees need to have a purpose.
B. To find a purpose after retirement, you’ve got to follow your curiosity.
Many people have things they’re interested in and curious about as they go through their working lives, but just don’t have time to explore.
In retirement, you have the opportunity to explore those things and experiment. You can make pacts with yourself, in which you say, “For X amount of days, weeks, or a month, I’m going to do so-and-so.”
And then, at the end of that period of time, you evaluate. You decide, is this something that I want to continue? Is this something I want to continue, but with modifications? Or is this something I’ve decided really isn’t for me, and I don’t want to continue?
C. Social relationships can also be another area of loss. We tend to have many of our relationships at work. Those relationships rarely survive retirement.
Pre-retirement is the best time to build non-work-related relationships. So, you have those relationships in advance, and you have social support as you go through the retirement transition.
3. Your Spouse’s Retirement Vision Probably Doesn’t Match Yours
There are very often huge differences in retirement readiness and expectation between life partners.
The retirement presumptions of both partners need to be explored. Each needs to answer the question, “What does a good retirement look like to you?”
If there are big differences, then there’s going to be a need for yet more communication and possible compromises or thinking outside the box. You may also need to renegotiate time, space, and roles with a spouse.
4. Create a Financial Plan (Not a Fantasy Budget)
You can’t expect to magically have the finances to retire when you want to.
Many find they don’t have sufficient income when they want to retire and have to continue working into their 60s, 70s, and even 80s.
Our culture advertises retirement as a life of luxury, filled with spa trips, expensive vacations, and cruises. For many people, that’s just not even realistic.
Money doesn’t create a good retirement—but it limits or expands what’s possible.
Meet with a financial advisor as early in the process as possible. Find out what your financial goals are for retirement, and then let an advisor craft a plan with you that will get you there.
Of course, the hard part is following that plan. You’re going to have to make some sacrifices along the way to save for your retirement. The earlier you start, the better and easier it will be, thanks to the wonder of compound interest.
5. Build Your Health While You Still Can
We all understand that our average life spans have increased.
On the other hand, we don’t often realize that our health span hasn’t kept pace with our lifespan.
It’s very possible that we may spend, especially if we have neglected our health, a decade or more in poor health.
Therefore, we need to invest in our health before retirement. We need to focus on areas like weight control, healthy eating, and exercise.
6. Decide When, Where, and How You’ll Retire
A. When you retire is when you’re financially and mentally ready.
But a warning here, don’t wait too long or wait for the perfect circumstances. I have friends who have been talking about retiring for years now, but every time the economy takes a turn for the worse, they put it off.
I’ve also known of people who kept putting off retirement until they reached what they considered the perfect situation, and then a year later, were dead. They never got to enjoy that retirement they worked so hard for.
The goal isn’t to rush into retirement—but to decide deliberately instead of drifting into delay. Keep in mind that no one will ever be 100% ready to retire, and that to some extent, it’s a leap of faith. You just have to go when you think you’re ready.
B. How you retire is now an option for many people.
Back in the old days, almost all retirements were cliff-edge. You were working full-time one day, you had the retirement ceremony, and then the rest of your life, you didn’t work at all. It was like falling off a cliff.
However, people now have other options.
Depending on the circumstances, you can choose to have a phased retirement. You start out full-time, ramp down your hours, go to part-time work, and then eventually phase into full retirement.
Other people have different dreams. Some want to fully retire so that they can devote 100% of their time to starting their own business or a new career.
C. Where you retire is also a factor to consider. You can retire in place or move, and there are factors to consider for both options. See my post, Where Should I Retire? A Practical Checklist.
7. Test-Drive Retirement Before It Starts
We have no idea what retirement will be like for us until we retire.
We can imagine and fantasize about it, but we really don’t know how retirement will feel until we retire.
However, one way to get a better idea is to run some trial runs before retirement. Things like extended vacations, sabbaticals, or mini-retirements. You can volunteer before you retire to see what that feels like.
Sometimes people dream of turning a hobby into their daily routine—golfing every day, fishing every morning. That might work for weeks or months, but it often grows stale. Test these assumptions before you retire.
Retirement works best when it’s treated as a series of experiments, not a single irreversible decision.
Different Ages, Different Preparation Priorities
Now let’s look at how these priorities shift depending on where you are in life.
Retirement coaches Roberta Taylor and Dorian Mincer, writing in The Couple’s Retirement Puzzle, state,
“Financial experts and retirement specialists encourage people to begin planning for retirement at least five years ahead of time, if possible.”
What should people who are in different periods of their lives do to prepare for retirement?
How you prepare for retirement depends less on your personality and more on where you are in the life cycle.
• People in their 30s and 40s have two or more decades before retirement. You’re often busy with careers and family responsibilities at this time of life.
I recommend you gain a realistic understanding of the issues you’ll face in retirement. Instead of focusing on the highlight reels and fantasizing about luxury retirements, get realistic about what retirement may actually be like.
The two areas that you want to focus on during this period are finances and health.
If you haven’t done so already, start building your financial profile for retirement and making concrete plans. Invest more in your health, so you have a better chance of maintaining it in retirement.
• People closer to retirement age, in their 50s or 60s are going to have to play some catch-up.
If you haven’t been preparing by funding a financial retirement plan, you’re likely going to have to hustle and start saving or investing a lot for retirement.
You’ll need to learn about the realities of the retirement transition (and the losses you can expect) and start preparing to lessen their impact.
If you’ve been neglecting your health, it’s time to get to work. Lose that extra weight, get on a healthy diet, and start regular exercise.
The best time to start preparing for retirement isn’t five years before you leave work—it’s when you start thinking seriously about who you want to be next.
Retirement Rewards the Prepared, Not the Lucky
A good retirement isn’t the result of luck or perfect timing.
It’s the result of intention.
Those who thrive in retirement are rarely the ones who planned the fanciest lifestyle. They’re the ones who prepared for change—who thought about identity, purpose, health, relationships, and money long before the last day of work.
If retirement is anywhere on your horizon, start preparing today.
Learn what’s ahead. Try things out. Adjust your expectations. And give yourself permission to shape a retirement that fits who you are, not who you used to be.
AI Note: I wrote this blog post myself, using my own words and thoughts for the initial draft. I used AI only to suggest headlines, section headings, images, and text improvements.
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