6 Keys to Ensure You Have a Fun, Rewarding & Happy Early Retirement

You may think retiring early is a magic pill that will automatically solve all your problems and make your life amazing and wonderful.  Perhaps you envision a happy-go-lucky life filled with sunshine, white sand beaches, rainbows, and butterflies. On the flip side, perhaps you’re convinced that once you’re retired, you’ll be bored quickly or die faster (Allison’s father is of this mindset).

While I will admit that early retirement beats the hell out of commuting into an office everyday and sitting in meeting after endless meeting, I also know that you have to put in some work to make sure it’s a happy and rewarding retirement.

If you’re not careful,  it’s all too easy to become lazy, unhealthy, lackadaisical, and anti-social when you’re not working.

My wife, Allison, and I have been retired for over three years now, and every day is fun, interesting, and challenging (in a good way). Here are some ways to make your retirement more fun and rewarding:

1. Stay in Shape:

Retirement will not be much fun if you’re unhealthy and can’t get around very well. Here are some ways to keep your body healthy and fit:

Exercise --  The key is to find routines that you actually ENJOY doing, so you’ll stick with them. For us, that means lifting weights, swimming, yoga, and walking. We do at least one of those things every single day.

And it’s important to mix things up.  I know Allison gets bored easily, so I created 8 different weightlifting workouts for us.  Check out health websites like Men’s Health or Shape or Youtube fitness channels for inspiration.

Mission Peak
Allison after hiking to the top Mission Peak

We also aren’t big fans of doing long bouts of cardio, so we do what are called HIIT (High Intensity Interval Training) workouts.  You can get much of the same benefits as a typical cardio workout, but in about half the time.  I use HIIT for my swimming workouts, and Allison does it with a jump rope.

Diet -- Now that you have more time, try preparing your meals at home.  When shopping, focus on whole foods located along the periphery of the grocery store (produce, meats, dairy), and limit your purchases from the interior aisles, which contain mostly processed food items.

Sleep -- Since you don’t have to be in an office at 7am, you can set your own sleep schedule.  Try to get 7 - 9 hours each night for optimal health (I shoot for 9 myself). I also enjoy sleeping in until about 9:30 or so.  A lot of entrepreneurs swear by getting up at the crack of dawn, but I think that’s highly overrated.

Check-Ups & Insurance -- It’s important to get regular checkups with your physician, dentist, and eye doctor.  You make sure your car gets an oil change every 3k miles, so why not do the same for your body.  Also, make sure you have some sort of health insurance, even if it’s just an emergency high-deductible plan.  A major accident or illness could run you hundreds of thousands of dollars if you’re uncovered.

2. Shore up Your Finances:

If you’re worried about money, early retirement will be stressful. Make sure you have plenty of money saved up to cover your expenses. Here are some tips:

Multiply by 25 Rule -- How much money do you need?  The general rule of thumb is the Multiply by 25 Rule (the inverse of the 4% Rule).  This rule states that you should at least 25x your yearly expenses saved up in your nest egg (although we recommend at least 30x).  The higher that multiple, the more likely you’ll have enough money for your retirement years.

Live Frugally -- The previous rule is made up of two parts:  how much money you’ve saved up and how much money you spend each year.  If you want to improve your odds of having enough money in retirement, look for ways to reduce how much money you spend.

Do you still need to live in that expensive condo in the city-center of your previous job?  Or maybe you have a big house in the suburbs, and now you can downsize to something smaller.  

We live very frugally, and actually enjoy living that way.  I wrote about our frugality in the blog post How We Live Comfortably for Under $3k Per Month in the Bay Area.

Sprouts market
Buying in bulk at our local Sprouts market

Investing -- Of course you also need to make sure you’re investing your money intelligently.  You may want to start shifting your mix of stocks and bonds from a growth strategy to a more conservative approach.  Check out our Saving & Investing Resource page for tools to help.

Getting to your money -- We were able to invest a lot of money in a taxable investment portfolio after we maxed out our tax-deferred accounts.  But you may not have been able to do that. Most people retire just with whatever they saved in their 401(k) and IRA.

If that’s the case, then you may need to get a little creative to tap into those accounts early without a penalty.  One common strategy that early retirees use is a doing a Roth Conversion Ladder, where you slowly convert funds from your Traditional retirement accounts to a Roth account.  With a Roth, you can pull your contributions out after 5 years penalty-free.

3. Socialize:

It’s important to keep your social connections after retirement, because you’ll no longer have that built-in network of friends and colleagues from work.  Why is that important?  Well, according to this popular TED Talk, one of the most important factors for living longer is close personal relationships and face-to-face interactions.

Communicate / Stay in touch -- It’s easy to fall out of touch with people when you retire.  Make sure to reach out to people you care about by phone, email, text, or social media.  Just checking in every once in awhile will keep your connections alive.

Meet up with people -- The next step is to actually meet up in person with those connections.  Make it a point to regularly get together with friends for dinner, coffee, hikes, road trips, pool parties, etc.

Project Open Hand fundraiser
At a Project Open Hand fundraiser

Go to events -- Don’t become a social recluse.  You don’t have to go to every party or event, but try to get out to as many as you can.  I tend to be a little introverted, so I’m not always super excited to go to events. But I’m almost always happy that I did after the fact.  It gets you out of your comfort zone. And who knows -- you might have some interesting conversation, learn something new, or make a business or social connection.

4. Travel & Experience:

People don’t travel much when they’re working, because they “don’t have the time.” Now you have the time! So get out there and travel as far and wide as you can.

Book a big trip -- We try to one big trip per year if possible.  Since retiring, Allison and I have traveled to Central & South America, Europe, China, and SE Asia.   These big epic trips are, in many ways, life changing. As soon as we got back from China I wrote 6 Reasons to Travel as Far & Wide as Possible.

Back of the Bike tour
Eating street food on our Back of the Bike Tour in Vietnam

Take smaller tips -- We also try to do 1-2 smaller trips each year.  For us, that usually means going across country to visit family and friends in New York and New Jersey.  We also enjoy doing road trips around California and exploring the Western US.

Do fun things — Just get out and do stuff - experience life!  Splurge a little and go to shows, ballgames, fairs, new restaurants, food festivals, and concerts. Think outside the box.  Volunteer at a local pet shelter or senior community. Send in an audition tape for Survivor or Wheel of Fortune. Go skinny dipping at a nude beach or hot springs.  Enjoy yourself!

5. Keep your Mind Sharp:

When you’re working, you’re forced to think. You may not always like what you’re forced to think about, but you’re still usually using your mind.

When you’re not working, it’s easy to get mentally complacent.  Here are some ways to keep that from happening:

Learn -- One of the best ways to keep your mind sharp is to learn new things.  You can learn how to speak a new language, program & code, play a musical instrument, cook, etc.  The choices are endless. Just find a book at your public library, watch some videos on Youtube, or take a course (online courses or in-person at a local community college).

Vietnamese street food
Allison learning to cook Vietnamese street food

Puzzles & Games -- Solving puzzles and playing games are fun and good for your brain.  You can try jigsaw puzzles, crossword puzzles, and Sudoku, as well as strategy games like chess, Go, Risk, and even card games like poker.

ABC -- The acronym ABC is a sales strategy that stands for “Always Be Closing.”  But I prefer to think of it as “Always Be Creating.”  Whether you’re painting a picture, writing a book, designing a website, or building a house, it feels good to use your creative juices to put interesting and useful things out into the world.

Planning -- Another great way to keep your mind working is to make short and long term plans (and tweak them as you go).  These can be anything from life plans (like where you want to live), to finance plans (how to adjust your investment portfolio over time), to travel plans (how to engineer a 2-month trip around Europe).

Meditation -- Practicing meditation on a daily basis provides great benefit.  It not only reduces stress, but it helps you focus your mind, which is especially important in the ADD world we live in.  Meditation is easy to learn (although difficult to fully master).  You can start with as little as a few minutes a day, and work up to 10 - 20 minutes.


6. Design a Routine:

It really helps you to feel focused and productive after retirement if you create daily and weekly routines.  When you’re working, you follow a pretty set routine to help your productivity. You probably get coffee and lunch at the same time each day.  And you schedule weekly meetings on the same day and time each week.

Productivity -- Routines can sometimes be boring, which is why you also need to break out of them from time to time.  But for the most part, a regular routine will help you feel like you’re being productive and accomplishing things.  

Auto-pilot -- Another nice perk is that you don’t have to think too much about what to work on.  Just as people like Steve Jobs and Mark Zuckerberg wore the same outfits everyday, having a set routine allows you to focus on other more important things.

Scheduling -- You can develop a regular schedule for just about anything and everything, such as your sleep, your meals, your workouts, meditation, time in nature, entertainment, and even sex and romance.  When you schedule these activities, you’re more likely to complete each task, and you’ll feel great about accomplishing so much!

Prioritize by Enjoyment -- I have a To-Do List to keep track of projects I’m working on (for personal projects and site-related projects). Sometimes I’ll look at that list, and I’m not sure what to focus on. And then I’ll think about which projects will I truly ENJOY working on, which ones will challenge me, and make me feel content and fulfilled. I always try to work on those first.



It’s a pretty big leap going from working full-time to having all the time in the world to do what you want.  But if you work on these six keys (or even 4 or 5 of them), I guarantee you’ll be so much happier and fulfilled with your early retirement!  

2 Responses

  1. Steveark

    I’ve been early retired for three years also. Most of those tips ring true for us as well though we prefer distance running and competitive tennis for our fitness activities. We also don’t like cities and prefer living in a rural setting. A third difference is I work a couple of days a week consulting for entertainment and to keep my professional network vibrant. But pretty much we second everything you say.

    • dylinr

      That’s great! Yeah, one size definitely does not fit all. As long as you find what works for you and makes your early retirement rewarding!