What if the difference between a comfortable retirement and one filled with financial stress comes down to a handful of decisions you make in your 40s and 50s?
Financial advisors who work with retirees day in and day out notice clear patterns.
The clients who sleep well at night, who can afford the lifestyle they envisioned, who aren’t constantly worried about outliving their money?
They all tend to have done certain things before hitting 60.
And the good news is that none of these things require a six-figure salary or exceptional investment skills. They’re practical, achievable steps that almost anyone can take with enough planning and intentionality.
If retirement is still years away, or even if it’s around the corner, these eight actions are worth your attention. Because regret is expensive, and preparation is priceless.
1) They maxed out their retirement contributions early and often
The single biggest regret among retirees? Not saving enough, soon enough.
Financial advisors consistently point to one simple truth: compound interest is your best friend, but only if you give it time to work. Every dollar you save in your 30s and 40s has decades to grow. Wait until your 50s, and you’ve cut that growth window in half.
The retirees with the fewest regrets prioritized maxing out their 401(k) contributions whenever possible. They took full advantage of employer matches (which is essentially free money) and increased their contributions with every raise instead of letting lifestyle inflation eat up the extra income.
If maxing out wasn’t possible, they at least increased contributions steadily over time. The goal was always to save more this year than last year, even if it was just an extra percentage point or two.
Starting early matters. But if you’re reading this in your 50s, don’t despair. You still have catch-up contribution options that allow people over 50 to contribute significantly more to retirement accounts. Use them.
2) They created a detailed retirement budget before leaving work
Hope is not a financial strategy.
Financial advisors emphasize that the retirees who thrive are the ones who knew exactly what their retirement would cost before they signed their last timesheet. They didn’t guess or assume everything would “work out.” They calculated.
This means sitting down and honestly assessing what your life will actually cost when you’re no longer working. Housing, healthcare, food, transportation, travel, hobbies, helping adult children, unexpected repairs. All of it.
The magic number for many financial planners is knowing you can cover 80% of your pre-retirement income, though this varies wildly based on individual circumstances. Some people need more, some need less.
The retirees with no regrets also did something clever: they test-ran their retirement budget for six months while still working. They lived on what they projected their retirement income would be and banked the difference. This gave them a realistic preview of whether their plans were actually feasible.
If the trial run felt too tight, they adjusted. They either saved more, planned to work longer, or scaled back expectations. All of this happened before retirement, when there was still time to course-correct.
3) They paid off high-interest debt completely
Carrying debt into retirement is like trying to run a marathon with ankle weights.
Credit cards, car loans, personal loans with high interest rates. The retirees with the fewest regrets made eliminating this debt a priority before age 60. They understood that in retirement, when income is fixed and often lower, every dollar going to interest payments is a dollar that could have gone toward living expenses or experiences.
This doesn’t necessarily mean paying off a mortgage if it’s at a low fixed rate. Many financial advisors note that low-interest mortgage debt is different from high-interest consumer debt. But that credit card balance accumulating 20% interest? That needed to go.
The strategy that worked for many was the debt avalanche method: paying off the highest-interest debt first while making minimum payments on everything else. Others preferred the debt snowball method, tackling the smallest balances first for psychological momentum. Either approach works as long as the debt is actually eliminated.
Once the high-interest debt was gone, these future retirees stayed debt-free. They adjusted their spending habits to live within their means, which made the transition to a fixed retirement income much smoother.
4) They built multiple income streams beyond Social Security
Relying solely on Social Security for retirement income is a risky bet.
Financial advisors often use the analogy of a three-legged stool: Social Security is just one leg. The other two legs might be retirement accounts (401(k)s, IRAs) and other income sources like rental properties, part-time work, or pensions.
Retirees who have no financial regrets built these multiple income streams deliberately and well before age 60. They didn’t assume Social Security would be enough, and they didn’t assume their retirement accounts would grow without effort.
Some started small side businesses in their 50s that could continue generating income in retirement. Others invested in real estate that would provide rental income. Still others simply ensured they had robust retirement accounts across multiple types (traditional and Roth IRAs, for instance) to provide flexibility in how they withdrew funds.
The key was diversification. If one income source underperformed or changed (like Social Security benefits being taxed differently than expected), they had backup options.
5) They planned specifically for healthcare costs
Healthcare is one of the biggest expenses in retirement, and one of the most underestimated.
Financial advisors note that the retirees who sleep soundest are the ones who planned for healthcare costs years in advance. They understood that Medicare doesn’t cover everything, and the gap between retiring at 60 and becoming Medicare-eligible at 65 can be extremely expensive.
So they saved specifically for healthcare. They researched Medicare supplement plans, understood what would and wouldn’t be covered, and budgeted accordingly. They also considered long-term care insurance in their mid-50s to early 60s, when premiums were still reasonable and they were still healthy enough to qualify.
For those planning to retire before 65, they mapped out exactly how they’d cover insurance costs. Would they use COBRA? A spouse’s plan? Marketplace insurance? They didn’t leave this to chance.
They also built health savings accounts (HSAs) when available, which allowed them to save tax-free for future medical expenses. Some financial advisors call HSAs the “secret weapon” of retirement planning because contributions are tax-deductible, growth is tax-free, and withdrawals for qualified medical expenses are tax-free.
The bottom line: healthcare was treated as a major line item in the retirement budget, not an afterthought.
6) They understood Social Security timing and made strategic decisions
When you claim Social Security can make a difference of hundreds of thousands of dollars over your lifetime.
Financial advisors consistently see regret among retirees who claimed Social Security at 62 simply because they could, without understanding the permanent reduction in benefits. Those who claimed early often did so out of necessity (they needed the income immediately) or out of impatience.
The retirees with no regrets took a different approach. They worked with financial advisors years before retirement to determine the optimal claiming strategy based on their specific situation. For many, this meant delaying benefits as long as possible, ideally until age 70, when benefits max out.
Waiting from 62 to full retirement age (typically 67) can increase monthly benefits by about 30%. Waiting from full retirement age to 70 can increase them by another 24% or so. That’s substantial money compounding over decades.
Of course, this strategy only works if you have other income sources to bridge the gap. Which is why it connects back to earlier points about saving adequately and building multiple income streams.
7) They created a comprehensive estate plan
Estate planning isn’t just for the wealthy, and it’s not just about death.
Financial advisors emphasize that retirees with peace of mind are the ones who created comprehensive estate plans before age 60. This included wills, trusts where appropriate, powers of attorney, and healthcare directives.
Without these documents, families face lengthy and expensive probate processes. Worse, without healthcare directives and powers of attorney, family members can struggle to make critical medical and financial decisions if incapacitation occurs.
The retirees who did this right also had clear conversations with their adult children about their wishes. They didn’t leave their families guessing about what they wanted or scrambling to figure out where assets were held.
They also reviewed beneficiaries on all accounts regularly. Many people set beneficiaries decades ago and never updated them after divorces, remarriages, or the death of originally named beneficiaries. This can create massive problems.
Getting this done before 60 meant they could enjoy retirement without worrying about what would happen to their assets or who would make decisions on their behalf if they became unable to do so themselves.
Conclusion
Retirees with the fewest regrets didn’t stumble into comfortable retirement. They planned for it, adjusted their spending to make it possible, educated themselves (or hired advisors who educated them), and took action years before their last day of work.
If you’re in your 40s or 50s, you still have time. Not unlimited time, but enough time to make meaningful changes that will impact the next several decades of your life.
Start with one thing. Maybe that’s increasing your 401(k) contribution by 2%. Maybe it’s scheduling a consultation with a fiduciary financial advisor. Maybe it’s finally creating that estate plan you’ve been putting off.
One decision leads to another, and before you know it, you’re on track to be one of those retirees who looks back with satisfaction rather than regret.
Your future self is counting on the decisions you make today. Make them count.
