9 Things You Wish You Knew Before Retiring


By Louis Horkan
Reviewed by Nathan Kattner

Table Of Contents

    Last Updated: February 20, 2024


    Retirement is a big transition in life and involves all types of issues and challenges you have to learn to deal with and navigate. Knowing some of those things in advance can save you time, frustration and money.


    Retiring is something we all think about. Many of us actually dream of that event for years, longing to enter that phase of life where we can live out our lives in a manner that is full of peace, relaxation, contentment and fulfillment.

    That does sound wonderful…

    Wait, what’s the catch? There has to be some sort of caveat. No way can you simply ride off into the sunset without a care, or problem, in the world.

    Aah, yes. You’re right. Time to get real. There are going to be challenges, some quite serious, that you will deal with during the 2nd act of your life. In fact, some of these issues are unique to retirement.

    Some will require that you simply deal with them as they arise, but others you encounter will in fact have been avoidable. Especially if someone had warned you in advance or you had at least contemplated their possibility ahead of time.

    Today we are going to focus on a handful of issues retirees before you probably wished someone had made them aware of before retiring. Hopefully this will help you as you prepare, or even if you’ve already retired.

    Think twice – you may have to unretire

    Of all the pieces of advice you could receive prior to retiring, this one might be the one least appreciated at the time. But it might be the one that most resonates now that you’ve already retired or are contemplating doing so.

    According to a 2023 study by Paychex, roughly one in six retirees are considering “unretiring” and returning to work. Of those, 65-percent preferred full-time work versus 35-percent who wished to do so part-time.

    Approximately 53-percent were contemplating the return to work because they needed the money, while roughly the same percentage reported that they were doing so due to boredom.

    A bit more startling is the fact that on average the respondents to the survey had been retired for four years. It’s a safe bet many of them wished someone would have told them to stop and really consider their choice to retire before they did so.

    Needless to say, if you have retired and find yourself looking at “unretiring,” then you are not alone. If instead you are not yet retired but are considering doing so, it makes sense to slow down and really think things through before pulling the trigger and walking away…just yet.

    You’re going to spend more than you expect

    Despite best laid plans, there’s a good chance you will spend more in retirement than you think. More importantly, you’re likely to spend more than your retirement plan allows for.

    According to the 2022 Spending in Retirement Survey: Understanding the Pandemic’s Impact issued by the Employee Benefit Research Institute (EBRI), approximately 27-percent of retirees report they are spending at least, “a little more, to much more, than they can afford.”

    This is obviously a problem, given that today’s overspending turns into tomorrow’s budget shortfall. The more this occurs over time, the more likely you will outlive your assets, which is a nightmare scenario for any individual or family in retirement.

    The unpleasant truth is that either your spending or your lifestyle will have to be adjusted to ensure that doesn’t occur.

    Ignore focusing on the pile of money

    When you retire it can be a bit overwhelming and disconcerting to see the pile of money (in the form of various assets) that you’ve actually been accumulating for all those years.

    For some reason it goes from being theoretical to real. And temptation can easily set in.

    Whether you’ve saved $500k, $1.5 million, $5million, or more, it’s easy to see that amount and feel “loaded.” Even fall into the trap of feeling you can afford to spend lavishly given all the money you’ve amassed.

    Fact is you have to look at your assets in the mindset of what you actually have budgeted for the given year. If your budget allows for $50k for that year, that is what you have, period! Not the $1.5 million that you see in your financial statements. That money is probably meant to last you 30 years or more. Be disciplined.

    You could easily live decades in retirement – which gets expensive

    Longevity is a tough issue. There’s no way you can know how long you will live, but you do need to plan for the potential eventuality that you could live for decades in retirement.

    What that equates to is the fact you may have to pay your bills for a longer period of time. Your retirement savings may potentially have to last decades. Now that you’re retired you are probably asking if you are financially set to handle that possibility.

    Looking at the statistics, the Center for Disease Control and Prevention (CDC) reports that life expectancy declined for Americans recently, to 76.1 in 2021 from 77 in 2020. For females the average life expectancy in the U.S. as of 2021 is 79.1 years, while that of males is 73.2.

    So if you are 60 now there is a good chance you will live 1.5 to 2 decades more (on average), and perhaps much longer. The “perhaps much longer” element is the thing that can really start to weigh on your mind in retirement.

    To provide perspective: In simple terms, if your retirement budget calls for annual spending of $50k, just one extra year of longevity beyond what you planned for will cost you $50k. Several years will require an extra $150k. A decade longer than expected and you are looking at $500k. Wow!

    You simply can’t know how long you will live. But you have to remember that you will need more money to simply survive retirement (without outliving your assets) the longer that you actually end up living.

    Healthcare in retirement isn’t cheap

    A major benefit for most retirees in the U.S. is that of being covered for medical insurance by Medicare when they turn 65. Despite receiving Medicare, there are still additional expenses that are incurred related to healthcare costs that many fail to consider.

    A recent healthcare study by HealthView Services estimated that the average monthly cost of insurance, in addition to Medicare, for a “healthy” couple (age 65) would be approximately $1,023. It’s obviously more for those with medical issues. That’s exclusive of long-term care. And that amount is expected to continue rising over the couple’s lifetime.

    Then there is the issue of long-term care itself. LTC is an area where many people tend to make one of their biggest mistakes in retirement, simply failing to account for the expense. Many do so thinking they won’t need it. Truthfully, that’s more of a hope.

    That’s a mistake. According to the Kaiser Family Foundation or KFF, 70-percent of people aged 65 and older will require LTC at some point.

    This can range from home health care to living in a facility of some type, such as assisted-living, traditional nursing home, skilled nursing  (much like the level of care in a hospital), and end-of-life hospice.

    LTC insurance is expensive, but the alternative is paying for the care yourself out of pocket.

    The American Association for Long-Term Care Insurance (AALTCI) estimates that a 55-year-old male will pay an annual premium of $950 for a $165,000 level-health policy. The same policy for a female will cost an average of $1,500, and for a 55-year-old couple the combined cost is just over $2k annually.

    If you wait to purchase any of those same policies until age 65, those costs nearly double. And they go up from there.

    But if you don’t have LTC insurance, the ALTCI estimates your annual out-of-pocket cost on long-term care could range from $20k to $100k, depending on the type of care needed.

    An inconvenient truth

    There’s no easy way to put this, so might as well jump right in. If you’re married or significantly involved, you have probably come to notice that while you’re retired and supposedly have all the time in the world, you seem to have less time for yourself. Or even by yourself.

    The two of you probably spent a fair amount of time apart most days due to work and other issues or activities during your pre-retirement years. Nowadays, it might seem like you are constantly together.

    While there can be upsides to all that added “us” time, it can be a challenge – maybe more than is healthy or that either of you ever thought about before retiring. That added time together – think 24-7 or thereabouts – could definitely test the bonds of being a couple over time.

    Testament to this very real issue is the rising incidence of “silver divorce” (aka empty nest or gray divorce) that occurs between couples aged 50 and older. In fact, the U.S. Census Bureau estimates that the divorce rate for people over 50 has doubled since 1990.

    In 2021, they estimated that 34.9-percent of all Americans who got divorced were aged 55 or older. For people aged 55 to 64 the rate was 43-percent, while those 65 to 74 remained elevated at 39-percent.

    Fair chance that nobody walked up and mentioned this to you at a party or gathering, but it is a real issue. To counter it you will both need to program “me” time into your regular routine and recognize it will take time and work to find the right balance so that you avoid becoming a sad statistic.

    Boredom due to lack of plan

    Retirement can certainly be a great time of life for you and your significant other, especially if you have your health. Playing golf, seeing the grandkids or other relatives and friends, travel, ticking items off your bucket list, et. cetera.

    And then a couple years pass and many of those things start to lose a bit of their allure.

    This is when it really sinks in that just as with most things in life, you probably need a plan. In this case a plan for how you are going to be happy and fulfilled in retirement.

    Staying busy and engaged are big factors, as well as finding balance. Sports, volunteering, travel, mentoring, going back to school, engaging in passions and hobbies, and much more.

    While boredom is probably the last thing you expected to encounter and deal with when you were retiring (you were just happy to have reached that critical life stage), it is a real issue – one that can and will impact your life.

    If you haven’t done so already at this point, now’s the time to create your plan for actually LIVING in retirement.

    Pay down that dang credit card debt…for real

    No way can you say you wish someone would have told you this before retiring. We all know intuitively that carrying around expensive high-interest-rate credit card debt (or charge card, such as furniture, store cards, other retail shopping cards, et. cetera), especially into retirement, is a bad thing.

    And yet many people do so.

    Once you begin living on a fixed budget that debt can seem especially exorbitant. And daunting to address.

    At that point it becomes harder to set aside extra money to tackle the debt and kick it to the curb. The net result is you continue to pay minimums and carry high balances for years on end, resulting in much of your hard saved money simply going down the drain.

    This robs you from spending in other areas that really matter to you. That debt can also preclude you from investing so that you can have more available later in retirement.

    Bottom line, that debt is a burden that directly impacts your quality of life. Even if you didn’t do so before, you have to make eliminating it a priority now.

    Investigate where you will live before making the move

    When retiring many people decide they are going to change things up some. This can be for myriad reasons, ranging from a desire to downsize their home, living somewhere cheaper, more exotic, closer to family, and more.

    And at the time the change can be exciting, just like the change of pace and new experiences associated with retirement. Wow, we live on a golf course, or by the ocean, on a mountain, et. cetera. This is the life!

    It’s not till you’ve been there a bit that you start to realize there’s some things you don’t like so much.

    They can seem little at first, but they might start to gnaw at you over time…big time.

    You’ve been a pizza lover all your life and now there’s not a place to get a decent pie within 500 miles. You have to drive three or four hours to be able to enjoy performing arts or a museum, or to catch a ball game. Coming down off the mountain for groceries takes hours each time up to several days per week, and can be impossible when there’s bad weather. Ouch!

    If you’ve already moved then you’ve probably figured out the “not so pleasant” things you don’t like so much regarding your new home or area. In which case it’s a matter of figuring out how you will deal with those things over the long haul.

    Or you may find you will have to move again because you simply can’t do without.

    If you haven’t done so yet, but are contemplating making a move, do yourself a favor and really take the time to investigate what you might gain, and lose, in the process of doing so. At least you will do so with your eyes wide open.


    There’s so many things that go into the decision to retire and then actually doing so that it can be overwhelming. There’s simply no way to know everything in advance.

    That said, there are areas you’d best consider before the time comes…or you will likely wish you had done so thereafter. Some of which come with nasty or lasting consequences.

    The list above is but a handful – you will definitely come across many more as you proceed through your retirement.

    Hopefully in examining some of these you can adjust and avoid (or at least mitigate) potential pitfalls and ensure your retirement doesn’t get sidetracked. That it is in fact the success you hope to achieve.

    At Oak Harvest Financial Group we can be here for you as you address these issues and more, to help you navigate what can be the difficult journey of retirement.

    If you are currently utilizing a retirement plan (either your own or one created for you) our team would be happy to review it to determine if it is capable of really meeting your goals.

    Or we can assist you by creating a retirement plan capable of helping you to retire with confidence. We can build a holistic, comprehensive retirement plan addressing relevant issues, utilizing strategies that cover taxes, income, spending, healthcare, legacy, and more, customized to your family’s specific needs.

    A plan created with the goal of ensuring you can successfully live out the retirement you envision.

    If you are ready to take the next step and talk to a team of retirement planners who can advise on all your retirement needs, and who will put your interests first, Schedule a call today!

    Let Us Help You Achieve the Retirement You Deserve!

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