14 Lessons I Learned That Can Help You Have a Successful Retirement

When we think about what makes for a successful retirement, financial security is often the first thing that comes to mind. However, there are other aspects of retirement to consider beyond retirement accounts, pensions, and 401ks. The emotional and personal aspects of transitioning into retirement are often overlooked as important parts of retirement planning and they can be just as challenging as the financial side.

As you reflect on the past few years and look ahead toward retirement, you may realize that your expectations and reality don’t always match up. 

In this article I’ll share 14 lessons I learned from personal experience during my own transition into retirement. I hope that reading about my lessons learned will help you come up with your own ideas for ensuring a successful, fulfilling, and happy retirement.

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14 Lessons for a Successful Retirement

As I mentioned, these 14 lessons are based on my own experience. Your experience might differ. It’s important to remember that retiring is a major transition, so be patient with yourself and take things as slowly as you need to. 

1. Keep a Schedule

Congratulations on retiring! You might be thinking, “Finally…I can do whatever I want, whenever I want!” While it’s true that you have more freedom now for plenty of leisure activities, having no structure at all can lead to feeling unfulfilled. Having some kind of schedule is essential to ensure you’re spending your time doing what matters most to you.

You might wonder, “But isn’t retirement like being on vacation all the time?” Well, imagine going on an amazing dream vacation and not seeing the best parts of your destination because you didn’t plan anything. You’ve worked hard your whole life to get to this point, so it’s crucial to make the most of it. Don’t miss out on the opportunities that retirement brings by not having any structure. 

It’s important to take advantage of each day and make it what you want it to be. Don’t use “living for today” as an excuse not to have a plan. By creating a schedule that works for you, you can have a fulfilling and enjoyable retirement.

Need help getting started? Be sure to check out:

• 3 Benefits of Having a Schedule in Retirement
• Learn How to Embrace Each Day With Purpose Using Block Planning

2. Plan Your Joy

Michelle Obama once said something that really resonated with me: “Plan your joy.” This sounds simple but it’s so easy to forget once you retire. After years of working, we often view structure or schedules negatively. However, planning your joy is the best way to ensure that you have plenty of it.

Consider these two scenarios:

Scenario 1 – You wake up on a rainy Thursday with nothing planned and nothing to do. You end up binge-watching a show all day and feel lousy and guilty by evening.

Scenario 2 – On Sunday evening, you plan your week ahead. You fill Monday through Wednesday with social activities, physical activity, errands, and outdoor time since the weather looks decent. You set aside Thursday as a day of rest, knowing the forecast calls for rain. When Thursday comes, you enjoy your planned day of rest, feeling grateful for the chance to unwind. You earned it after all your hard work earlier in the week.

Both scenarios involve the same activity on Thursday, but the difference is that in Scenario 2, you planned for that day to be your day of rest. You earned it because of all the activities you did earlier in the week. In other words, you planned your joy!

Regularly take time to plan meaningful activities that bring you joy: hobbies, spending time with loved ones, or simply taking a day to relax, for example. By planning ahead you’ll be giving yourself a retirement filled with joy and purpose.

3. Stay Active with Projects

It’s important to find projects that bring you joy and a sense of purpose in retirement. Not because you need anyone’s approval, of course, but because it feels good to have something to talk about when someone asks, “What do you do all day now?” Plus, it’s a great way to keep your mind and body active.

A project could be anything, from a hobby or home improvement task to a side business, part-time work, or volunteering. It could even be something as simple as reading or taking an online course. The key is to find something that excites you and build a plan around it. Even a tiny plan, such as a list of books to read or steps to take toward your goal, can be a great start.

Tackling your project step by step will feel rewarding and empowering because it’s something you truly want to do, so find your passion and create a plan to pursue it. Your projects are for you and you alone, but they’re also an excellent way to stay engaged and fulfilled in retirement.
For help getting started finding a project that excites you, check out Bye-Bye Boredom! 5 Ways To Conquer Boredom in Retirement.

4. Challenge Your Mind

It’s important to find ways to keep your mind active and engaged in retirement. Push yourself to learn something new by embracing a new skill or subject that you never had time for before. Learn a new technology or hobby, or take a deeper dive into a subject you’re already familiar with.

You can easily combine this with the previous lesson by taking on a project that is mentally challenging, like learning a new language or taking a photography course. There are many resources available to develop new skills and learn new things, such as Skillshare, Udemy, and The Great Courses.

Managing my website has been a great way for me to keep my mind sharp and engaged. Learning technical skills, marketing strategies, content writing, and managing a team has been challenging at times, but always in a good way. It’s been a great source of fulfillment for me.

 Challenging yourself to keep learning and growing in retirement will keep your mind active and your spirits high.

5. Improve Your Social Network

Staying connected to people you care about is definitely one of the keys to a happy retirement.  Don’t worry about whose turn it is to reach out. Focus on what matters, which is staying connected.

One great way to keep in touch is by scheduling regular meetups, whether in person or virtually. For example, you could plan to meet on the first Tuesday of every month. Someone may need to take the lead on organizing these gatherings, including deciding on the location and sending out reminders. Why not you?

Another socialization option is to check out your local community center. Many community centers offer programs and events to help you meet new people and stay engaged with your community. You can attend classes or workshops on topics that interest you or join clubs or groups with like-minded individuals.

Staying connected is about bringing more joy and fulfillment to your retirement and improving your emotional health, not about keeping score. Just take the initiative and make a plan to stay socially active. 

6. Keep Building Good Habits

When you were working, you took your daily routine for granted. Each workday you likely got up at the same time, ate the same thing for breakfast, left the house at the same time, caught the same train, did the same job…and rinse and repeat. Many of these habits were necessary for your job, like being at a desk or in a classroom at a certain time each day.

Now that you’re retired, you have much more control over your time. However, it’s human nature to resort to ritual. If you don’t intentionally create new habits for yourself you may find yourself falling back into old, unwanted habits.

This is why it’s important to establish good habits in retirement. Habits can help you stay active, engaged, and healthy. For example, waking up at a consistent time each day and establishing a morning routine can help start the day off on the right foot. Eating a healthy breakfast, taking a walk, or doing some light exercise are also positive habits to build.

Other good habits include setting aside time for hobbies, learning new things, or volunteering in the community. Intentionally creating these habits will help ensure that your retirement is fulfilling and enjoyable.

7. Maintain Good Health

Maintaining strong physical health is essential, especially in retirement. An experience with a couple of pinched nerves that required physical therapy was a wake-up call for me. Seeing people who were not much older than me struggling with their health in the therapist’s lobby made me realize the importance of taking care of myself.

Your doctor can be an excellent resource in this area. Work with your doctor or a trainer to develop a balanced workout routine that includes both strength training and endurance exercises. Simply walking or running may not be sufficient. Staying up to date with necessary medical tests—such as bone density tests and colonoscopies—and maintaining a healthy diet are also important aspects of maintaining good health.

Make a list of topics to discuss with your doctor at your next checkup, and don’t hesitate to ask questions or raise concerns you may have about your health. Remember, it’s never too late to start taking better care of yourself.

8. Live for Today but Be Prepared for Tomorrow

Living for today is a wonderful philosophy, but it’s also important to be prepared for tomorrow. While you shouldn’t spend time obsessing over the future, you should think about retirement as a process that doesn’t end when you leave your job. 

Setting aside time to think about your future self can be a valuable exercise. It allows you to create a vision of what you want your future to look like and identify the steps needed to achieve that vision. These steps may include financial planning, planning for future healthcare, or making lifestyle changes to support your future goals.

Living for today doesn’t mean ignoring the future. Setting aside some time to plan for tomorrow will allow you to fully enjoy the present.

9. Don’t Rely on Any One Thing for Your Retirement Happiness

Retirement planning goes beyond just finances. You’ll want to give serious thought to how you will spend your time once you retire. A clear plan for your retirement years is critical for enjoying a happy and fulfilling retirement.

One common mistake is placing all of your retirement eggs in one basket; that is, relying on one activity or one set of plans to provide all of your happiness in retirement. For example, someone may want to travel the world, and as such center all of their retirement plans on this idea. However, unexpected events such as a pandemic or health issues could completely derail this plan.

This is why having alternate plans and ideas for your retirement is important. Instead of relying solely on one activity or plan, consider diversifying your retirement portfolio of goals and activities. Include a variety of hobbies or interests, activities, and relationship-building opportunities.

In short, don’t rely on any one thing for your retirement happiness. Instead, develop a variety of retirement plans and goals to ensure that you have a happy and fulfilling retirement no matter what unexpected events may arise.

10. Enjoy The Silence

One thing that you might not have considered in your retirement planning process is the need to get used to silence. No more office chatter or subway rumble…at times, just the sound of your own breathing. This can be a little unnerving for some people. 

But don’t worry, you don’t have to fill the silence with mindless noise. Resist the urge to turn on the TV just for some background noise. Trust me, it’s a slippery slope. Before you know it, you’ll be hooked on daytime soaps and game shows.

Instead, embrace the silence and find ways to enjoy it. Maybe it’s by reading a book, practicing yoga, or even just sitting outside and listening to the birds chirp. Who knows, you might even find that you prefer a quiet life.

11. Be Financially Prepared

I know, I know, talking about money isn’t the most exciting thing in the world. But trust me, being financially prepared is key to having a stress-free retirement.

First things first, find a financial planner you can trust with your nest egg. They can help you create a solid financial plan and figure out how much you’ll need to save to achieve your retirement goals. And speaking of savings, make sure you have a healthy retirement fund and an emergency fund set aside. You never know when unexpected expenses will pop up, like medical bills or home repairs.

It’s also important to get a handle on your spending habits. Are you a big spender or a penny-pincher? Knowing your spending habits and annual retirement expenses can help you create a budget and stick to it. This will give you a better idea of what you can spend and what you’ll need to earn in retirement.

Remember, the goal is to be financially prepared so you can enjoy your retirement life to the fullest. Don’t let money worries hold you back from doing what you love. By having a solid financial plan, retirement savings, and emergency fund, you can rest easy knowing you’re financially prepared for whatever life throws your way.

12. Assess Your Retirement Readiness and Trust Your Instincts

Retirement can be an exciting, yet nerve-wracking time. Despite all of your careful planning, you might still be questioning whether this is the “right” time to retire.  

There’s no magic formula or crystal ball to tell you when to retire; it’s all about trusting your instincts. You know yourself better than anyone else, so listen to your gut. If you feel like it’s the right time to retire, then it probably is.

Of course, that doesn’t mean you should make the decision lightly. Make sure you assess your retirement readiness, including your financial plan, retirement savings, and any potential projects or activities you want to pursue. And don’t rely on just one thing to bring you happiness in retirement. Explore different interests and hobbies to keep things fresh and exciting.

But at the end of the day, trust yourself. If you have that feeling in your gut that it’s time to retire, go for it! Remember, retirement is all about enjoying life on your own terms, and that includes trusting yourself and your instincts. So take a deep breath, trust your gut, and get ready for an exciting new chapter in your life.

13. Take Time Each Day to Reflect, Congratulate Yourself, and Forgive Yourself

The transition into retirement can be a big adjustment. Some days will feel like a breeze, while others might leave you feeling frustrated or even angry. But don’t worry, it’s all part of the process.

One important step in navigating this transition is learning to celebrate and forgive yourself. It might sound easier said than done, but trust me, it’s worth it. One great way to do this is through journaling. Set aside some time each day to reflect on your experiences.

Take a few moments to write down at least three things you want to celebrate. These can be anything from personal accomplishments to connections with others to good habits you’ve developed. Celebrate those wins and give yourself a pat on the back!

Then, take some time to reflect on anything you wish you had done differently. Think about what you can learn from those experiences and take those lessons into the next day. But don’t beat yourself up over mistakes or missed opportunities. Forgive yourself and let it go. Remember, every day is a new chance to start fresh and continue on your retirement journey.

14. Live With Intention

While living a life of intention should be the goal whether you’re retired or not, retirement is a time to focus on the things that matter most to you. It can be easy to get carried away with the newfound freedom and forget about what truly brings you joy, but by living intentionally you can make sure that every day counts.

What does it mean to live with intention in retirement? It means being purposeful and deliberate about your actions and decisions. Whether you’re planning a trip or taking up a new hobby, approach your goal with a clear intention and a plan to make it happen. This will help you avoid aimlessly drifting through your retirement years and instead create a meaningful and fulfilling life.

Living with intention also means being mindful of your choices and taking responsibility for your own happiness. Instead of waiting for things to happen to you, take charge of your life and create the experiences you want. Whether it’s spending time with loved ones, pursuing a passion, or volunteering for a cause you care about, be intentional about making it happen.

Retirement can be a major transition, but with proper planning and the right mindset, it can also be a fulfilling and enjoyable new chapter of life.

I hope these 14 lessons I learned will help you with your own transition into retirement. The most important thing to remember is to embrace and enjoy the experience, whether you’re dancing out the door on your last day of work or are a little reluctant to say goodbye to the 9-to-5. 

Retirement is an opportunity to pursue your passions, explore new interests, and cherish the people and experiences that matter most to you. With these lessons in mind, you can have a successful and fulfilling retirement.