9 Secrets of a Happy Retirement

Table Of Contents

    Retiring and living out your golden years experiencing peace and contentment are things we each should aspire to. But like most things in life, there is the hope, and then there is the reality. This can be a serious bummer.

    Fortunately you can have a real impact on the retirement you end up living. This starts well before the big day when you walk out of the office. Working hard, setting goals, diligently adhering to a retirement plan that includes disciplined saving/investing. All are key components that can go a long ways in terms of ensuring you can live comfortably once you retire.

    But all the money in the world won’t matter if you can’t find contentment and happiness in retirement. Doing so can take some serious work…and a plan!


    You find yourself sitting in your favorite chair in the den, across from your spouse happily chatting away. The two of you are pinching yourselves, grinning ear-to-ear and trying to get your arms around the notion you have finally entered the next stage of your life – retirement.

    Yes indeed, the day has finally come and now the two of you can focus on devoting your lives to doing things that will bring you satisfaction and fulfillment.

    It’s time to break out your plan and set about doing the things that you’ve long imagined.

    Wait, which plan are we talking about?

    No, not your trusty comprehensive retirement plan you have been adhering to during your pre-retirement years and now intend to use as a roadmap to guide you in retirement.

    How about the plan you got from George the neighbor. Better yet, the one from Cousin Frankie who promised it offered a surefire path to nirvana.

    Frankie’s plan has you getting up every day at 10ish. Then it’s toast and coffee on the porch, along with mindless chatter about the weather and general gossip about the different neighbors.

    At that point you get in a round of golf most days starting early afternoon. Then it’s time for some tele and then some web surfing to catch up on the news. Eat dinner. Watch some more TV. Engage in a little conversation with your spouse or George the neighbor. Then you fall asleep in front of the TV. Finally you wake up and lumber blindly into bed late at night.

    Frankie’s right. This plan does offer nirvana. Months go by and you feel more fulfilled than at any time in your life. You look forward to another 5, 10, 20 years or more…of the same routine.


    No, we’re talking about the plan that will guide you in terms of how you will live your life. The plan centered on the things the two of you have talked about and looked forward to doing. Passions, travel, hobbies, starting a biz, volunteer work, working on causes you care about, enjoying the arts, going back to school, spending time with family and friends (especially those grandkids you love so much), et. cetera.

    You know, the plan that you worked on together for a fair amount of time that was created to help ensure that retirement would be everything you both wanted it to be.

    Yes, the Happy Retirement Plan.

    Ah, there it is, tucked into the couch. Thank goodness you found it! A happy retirement would have been tough without it.

    Just in case you couldn’t find your plan…or never got around to creating one, today we are going to focus on some proactive things you can do to ensure your happiness in retirement.

    Happiness plan

    Kidding aside, you do actually need to create a plan for what you will do in retirement in order to make it happy and fulfilling.

    Did you think a great retirement filled with bliss was going to just happen on its own or without planning. You’re much more likely to fall into the rut that would naturally ensue by following Cousin Frankie’s plan. The one that sees the two of you settle into being nothing more than couch potatoes. Eventually losing your health and finding yourselves unable to get out and enjoy your golden years.

    No, to make this happen you will need to treat this seriously, just like any other plan where you spend time talking and thinking it through before putting pen to paper. Working diligently to ensure that what you create has been well considered and is comprehensive.

    Why so serious an approach? It’s just retirement…

    Remember the context. You hope to enjoy your retirement and find a lasting measure of peace, harmony and happiness during your golden years. As the saying goes, hope is not a plan.

    Shooting from the hip and making things up as you go is actually a recipe for the opposite of what you want. It will likely lead to frustration, anxiety and a general feeling of malaise. Unhappy that you’re not enjoying this special time of life and doing the things you daydreamed about for so many years.

    So, yeah…you need a “real” plan. One with concrete measures.

    Getting started, the first thing to do is create some general categories that you can think about and discuss. Doing so will provide some structure to your planning and begin to help organize your effort.

    Among the categories you might want to consider:

    • Passions/hobbies/bucket lists
    • Fulfillment activities
    • Learning and creating
    • New adventures
    • Associating with people
    • Me time
    • Travel

    Passions/hobbies/bucket list

    We start with this category because it should be fun and not seem like work. Don’t try to be exacting and exhaustive. Simply add things as they cross your mind.

    Start with passions that you each have, collectively (if that’s the case) and individually. Maybe it’s your faith. Going to the theater or symphony, or better yet, playing a musical instrument. It could be museums, visiting baseball parks throughout the country, painting, photography, et. cetera.

    These aren’t things you sort of want to do or are hobbies you can take or leave…these are things you would feel less complete as a person if you didn’t have them in your life.  There may only be one thing, and probably no more than a couple that you really consider to be passions.

    Now list your hobbies. Since you now have more time to devote to such things, it’s time to get busy doing them. This could include things such as sport (playing golf or pickle), bird watching, hiking, stamp collecting or anything else. And as time goes by you will probably add more things to the list.

    Remember, these are things you enjoy but you don’t have to do all the time. The more you develop over time the better, as more hobbies provide greater variety, which will make life more interesting.

    The bucket list is for the items or experiences that are one offs – things you’d like to do just once if you had a chance. Obvious possibilities include things like skydiving (yikes), hiking the Appalachian Trail (be real, a small doable portion of it), maybe it is putting together and hosting a family reunion for 500 people, staying in a castle, going to a Super Bowl/Olympics/Master’s Tournament just once, et. cetera.

    Try to make them achievable, even if the stars will have to align almost perfectly in order for it to happy. Going to the beach when you live in Florida is fun…it’s definitely not a bucket list item, so be very selective in terms of what you place in your bucket list.

    Fulfillment activities

    These are activities you may have participated in during the past, but definitely want to spend some time doing during retirement. Think volunteer, philanthropic or giving-back type activities. Working a food bank or soup kitchen, helping young at-risk kids and families, joining the volunteer fire department, volunteering at the local theater house, participating in Make-A-Wish or similar organizations, church work, et. cetera.

    Get your kids and grandkids involved so they learn the importance of giving, plus there’s the added benefit of spending more time with them.

    Fact is there is so much need in the world and countless opportunities to give of your time and efforts (even dollars) in order to help others. Such selflessness is rewarding beyond anything else in life. The fulfillment you experience may well be the most important thing you can do when it comes to obtaining real happiness in retirement.

    Learning and creating

    While we usually are ready to step away from hard work when we retire, that’s not always the case. In fact, for some retirement offers the opportunity to reengage with past desires, such as continuing an education, starting a new career or even opening your own business.

    While these can be very fulfilling in and of themselves, you do want to be careful not to let them overtake your time and ability to do other things. Going back to work, or doing so for yourself, and ending up having to devote 60 hours per week is not something you should probably allow to happen. Retirement really should be about balance.

    New adventures

    This is where you try to break your own mold a bit and force yourself to do some things that you normally wouldn’t. Things that may well make you uncomfortable. These are definitely not passions, bucket list items or even hobbies.

    Think instead of things you’ve never done but that might be appealing or that your alter-ego might dig doing. Taking cooking classes or doing stained glass or pottery, learning a language and planning an eventual trip around doing so, starting cycling or taking time to learn to ride a horse (or bull riding – more yikes than sky diving), et. cetera. Or heck, get busy writing that book you always thought you had in you. Variety is truly the spice of life, and there’s no better way to spice it up than stepping outside of your comfort zone and routine.

    Retirement party theme ideaAssociating with people

    Even if you are naturally shy or tend to keep to yourself, as human we are social animals and can’t really go “hole up” in a cave and live out our lives in seclusion. You have to associate with people in order to avoid getting stuck in your own head and overthinking things too much. Doing so is a recipe for bad things, like anxiety and depression,

    This can include time spent with your kids and grandkids, other family, friend and neighbors, people at your church or other organizations you belong to, et. cetera.

    Consider activities like sports or playing cards, book reading groups, watching your favorite show together each Thursday night with George the neighbor, going to bet on the ponies with Cousin Frankie, hosting a bible study or an investing club with the girls or guys, or myriad other options.

    Bottom line, you need to associate at least some on most days to avoid loneliness, which is something many retirees experience if they don’t spend time with others.

    Me time

    Let’s face it, while associating and doing things with others, including the spouse, can be healthy and rewarding, you definitely need some time to yourself – in fact you need it each day.

    This should be time set aside daily where you can turn off and do only what you want to do. Not have to entertain or help carry a conversation. Nor is this about chores or completing the “honey do” list, or any other type of obligation. This can be a walk by yourself, doing a workout or some yoga, sitting on a swing for a half hour simply existing, closing your eyes and letting go of thoughts or any anxiety, day dreaming, et. cetera.

    Be sure to build 20 to 30 minutes or more into your schedule each day devoted to your “me time,” during which no one can interrupt or bother you.


    We place this last, despite the fact most people place it first on their list of things to do in retirement. Fact is when doing so, they tend to treat it in an abstract manner versus really taking time to think about and plan the travel they wish to do.

    We aren’t talking about a picnic or day trip to the beach or heading to your sister’s place for the holidays. This is all about heading off somewhere – anywhere – where you really want to go. It can be domestically or to any of the far corners of the globe.

    This is more about the special travel you wish to enjoy together (or even separately), or with family or friends, or as part of a group. You know, the cruise to Alaska or traversing the rivers of Europe, checking out the Pyramids, hoisting a pint in Dublin, riding a motorcycle up the Pacific Coast Highway or through the picturesque Blue Ridge Mountains, enjoying adventure in the Outback, et. cetera.

    The planning can be just as fun as the actual trip if you really get into doing it together. Keep in mind that you may only have a limited opportunity for travel of this nature during your retirement, so be sure to make the most of it.

    Bringing it all together

    After you’ve spent time (which probably will take days to weeks or longer) listing out everything for your happiness plan, it’s time to set it to paper. You have to do this versus simply thinking about it or you’re likely to not carry through on any of it.

    Man enjoys retirement partyFrankly you’ll probably forget many of the things you thought of and discussed. And in the end you’ll fall into relying on Cousin Frankie’s plan.

    You can’t let that happen. You retirement is too important, so you have to treat it as such – approach it as if it is the most important thing in the world to you. It is! It’s essentially your treasure map that will help ensure you live out the best retirement possible.

    Aside from committing your plan to paper, be sure to create a schedule. Be as sparse or packed on details as you feel comfortable. Daily works best for some, while others are more comfortable with a weekly calendar, as well as one for each month. This can provide motivation and helps you stay on top  things, and it spurs you to do or try new things with regularity versus always doing the same thing.

    A word of caution here – don’t attempt or even set out to pack each day with a bunch of activities. Add items so you have quick options for most days and so you don’t end up sitting around wondering what to do. Plan to cross things off, move other items around, and on some days completely rip it up and just binge watch favorite shows from bed.

    Absolutely remember that a happy retirement isn’t about constantly running around and always being on the go. Balance! Relax! Enjoy!

    Oh, yeah. Remember that attitude tends to set the table in terms of how happy we can be each day. Choose to be positive no matter what’s going on – appreciate what you have, focus on what you can control and let the rest go. That’s a recipe for real happiness in retirement.


    Now that you’ve created your happiness plan, we do need to turn back to your financial plan, given this is a practical world in which we exist.

    Truth is that your financial security will play a big role in how happy you can be in retirement. We’re talking about a plan that covers all the bases, ranging from desires and goals such as sending your grandkids to college, passing on wealth to family and causes you care about, minimizing taxes, addressing estate issues, and more.

    Yes, you definitely need to have that trusty retirement plan always at the ready to guide you as you traverse retirement.

    If yours is outdated – geared toward saving versus actual life in retirement – then you need to have it reworked. Or it’s time to have a new one created.

    Given all the factors and variables involved in retirement planning, it’s best to work with a qualified financial professional, such as a retirement planner or financial advisor who will be there to help you navigate the myriad decision that come with retirement .

    We here at Oak Harvest can assist you in reviewing an existing plan to ensure it works. Or we can assist by building a holistic, comprehensive retirement plan addressing relevant issues, utilizing strategies that cover Social Security, taxes, income, spending, healthcare, LTC, legacy, and more, customized to your family’s specific scenario.

    A plan created with the goal of ensuring you have the best opportunity to live out the retirement you and your family envision.

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

    Let Us Help You Achieve the Retirement You Deserve!

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