Are there Lessons to be Learned after 3 Years of Early Retirement?

Time flies. It’s been 3 years since I said goodbye to the corporate life and a twice monthly paycheck. My wife and I had a dream. We wanted to retire by the time our kids went off to college so that we could travel and enjoy life while we were still young and energized.

So how did we do it? We built a software business with personal savings of $10,000 and sold it 10 years later. It wasn’t easy. It had its ups and downs. Months when we didn’t know how we would make payroll and flying high after landing a large account that could sustain us for months in the future.

In the end, we exceeded our own expectations. 3 years prior to our kids graduating high school, we got the call from a larger company that saw value in acquiring our product line. Shortly after, I said sayonara to the daily grind.

After 3 years of retirement, it’s time to reflect and share with you lessons I’ve learned.

1. Early Retirement Conjures Up Unexpected Emotions

Literally the month after we retired, we saw our boys off to college and began traveling. Starting in Canada, we visited the maritime provinces of New Brunswick, Nova Scotia and Prince Edwards Island.

Prince Edwards Island

Prince Edwards Island (Canada)

We then made our way to the Galapagos Islands, Machu Picchu and the Bahamas. We saw extraordinary things. We watched a tortoise painstakingly dig a hole for her eggs.

Galapagos Islands

Galapagos Islands (Ecuador)

We saw the handiwork of the Incas, appreciating the architecture and incredible surroundings of a civilization that’s now long gone.

Machu Picchu

Machu Picchu (Peru)

And we watched professional divers descend into Dean’s Blue Hole not to come up again for 5 minutes.

Dean's Blue Hole (Bahamas)

Dean’s Blue Hole (Bahamas)

After returning from this incredible 3 month trip, something weird happened. We started settling into our retired life and I began to feel sad. Before I retired, my employees and peers needed me. They were constantly asking for advice, calling and texting for help and now the phone was silent.

I began to mope around and waste my days fretting about what was next in life. Had I made a huge mistake by retiring early?

2. Boredom is Self-Inflicted

After a few weeks of licking my wounds, I read about this phenomenon known as “retirement depression“. It is common for new retirees to go through this because they are left with lots of time to reminisce about the days when their schedules were full and others depended on them.

After a bit of self-reflection, I came to realize that these feelings were driven by boredom. After working really hard all those years to retire early, I needed to get out and enjoy hobbies that I never had time for before.

I found all kinds of new hobbies. I began golfing, working on photography, cycling, hiking, boating, fishing, and blogging. A few weeks later, I couldn’t figure out how I ever worked because my days were so full with things I enjoyed. Depression was fleeting, I was now enjoying life more than ever.

Challenged myself to cycle 50 miles

Challenged myself to cycle 50 miles

3. Traveling provides a World of Amazement

Since retiring, we’ve enjoyed some incredible travels. After our first 3 month trip, we spent an entire summer traveling the western United States. We started in the Grand Tetons and went on to visit California, Oregon, Washington, and British Columbia. We capped that summer trip off with an Alaskan cruise.

Grand Tetons

Practicing Photography in the Grand Tetons (Wyoming)

Hot Springs in Yellowstone

Hot Springs in Yellowstone (Wyoming)

Bigger than life Sequoias in California

Bigger than life Sequoias (California)

Majestic Crater Lake (Oregon)

Majestic Crater Lake (Oregon)

Glaciers (Alaska)

Glaciers (Alaska)

Last Summer, we took our youngest (college aged) son to Europe. We built our itinerary around the Running of the Bulls in Pamplona, Spain and capped off the trip in the Italian Riviera. We also visited Paris and Portugal.

Running with the bulls (Pamplona, Spain)

Running with the bulls (Pamplona, Spain)

Italian Riviera

Italian Riviera

As much as we’ve traveled, you would think we had seen it all. Not true, every new place we visit amazes us with something we’ve never encountered before.

4. You can still Fuel your Entrepreneurial Spirit after Retirement

Even though I retired early, I truly loved building my last company. It never really felt like work — it was fun, intellectually stimulating and invigorating. You don’t have to give up that feeling when you retire. You can choose to challenge yourself by starting a new business, a blog or working on pet projects.

I’ve recently done just that. I wanted to learn more about mobile app development so I started a project to develop an iPhone app. Since I love to travel, I built an app to provide peace of mind when traveling. It tracks things that are easy to forget (passwords, passport numbers, banking information, software licenses, etc.). I called the app aMemoryJog because it does just that – it securely tracks things that are easy to forget.
Learn More:

Developing this app was not about making money. It was about doing something that stimulates me intellectually and provides an outlet for my entrepreneurial spirit. I’ve enjoyed it so much, I’m working on my next app. It will be called Count Us Down and will allow you to count down the days to your next big event (like a vacation or even retirement).
Learn More:

iPhone Apps for Travel

5. Volunteering yields a Great Sense of Satisfaction

My wife motivated me to begin volunteering. She has volunteered for many years and genuinely enjoys helping others. Based on her example, I started volunteering last year with Habitat for Humanity (HFH). HFH builds homes for low income families and each family must contribute a significant number of hours helping to build their home or help build one for another family.

I belong to the Walton County Florida chapter and last year we renovated 1 home for a family and built 2 homes from scratch. Not only is volunteering incredibly satisfying, you get to know the family you are building for and you understand the how important it is for them.

Habitat for Humanity Volunteer work

Habitat for Humanity Volunteer work


Retirement is just another phase of life. Don’t over analyze it. Embrace new hobbies, travel to new places, experience other cultures, stimulate your intellect and enjoy life — you’ve earned it!

About the Author

Steve and his wife built a software company, sold it and retired early. Steve enjoys blogging about about lifestyle freedom, financial independence and technology. If you like this blog,subscribe here to get an email each time he posts.

Steve uses Personal Capital to manage all of his finances and investments because it is free and very robust. If you would like to download a free copy of Personal Capital, you can do that here.

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19 thoughts on “Are there Lessons to be Learned after 3 Years of Early Retirement?

  1. dthaggard

    Great post Steve! This is Paula. I went through that, I didn’t know it was normal:)

    Life is great now here too!

    *David H. ThaggardParagon Construction Co., LLC.* PO Box 1492 Cleveland, TN. 37364 (423) 284-2596

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  2. smiller257 Post author

    Hey Paula! I know life is great there too, we are looking forward to getting back to Florida and spending some more time together. Take care!

  3. rcharlto

    Thanks Steve for your honest insights. We agree, retiring early doesn’t equate to instant happiness or endless bliss, and suddenly having lots of free time can be a bit intimidating at first. We think it’s all about finding that personally right balance of travel, “fun” work, family, and leisure. We’re still working on getting the balance right for ourselves, but we love the freedom to make our own choices in that regard.

    1. smiller257 Post author

      I agree it takes adjustment but I can honestly say it is much better being retired and planning your own day than sitting in an office or cubicle dreaming of the day you can have lifestyle freedom.

  4. lukeythekid

    Great post! I’m far from my own retirement (I’m 22, haha), but this is something I’ve wondered about, and I’m glad to see you’ve managed to really take advantage of your retirement. Good luck!

  5. Derek

    Steve, your story is inspiring. It’s very gratifying to have played a small hand in helping you realize your goal of early retirement. I’m so thrilled that you and Lynn are living out your dreams – there are not two more deserving people.

    For me you have set a bar – a bar in which I’m also committed to achieving. I know I’ll get there (someday :)) and it’s very encouraging to know that you will be a resource to guide me through the transition when I finally throw the blackberry in the river. All the best – Derek

    1. smiller257 Post author

      Great to hear from you Derek, and thanks for your influence in purchasing my company in 2009! Looking forward to the day you and Sue visit us in Florida!

  6. Mr. 1500

    The “retirement depression” scares me a bit because I saw it happen to my parents.

    In my current working life, I’m very busy. My days our packed. It will be nice to back off a little, but I really can’t stand sitting still either.

    I think I’ll be OK because I’ve spent so much time thinking about it. I’ll be doing all of the same stuff I do today, just more of it. 30 mile bike rides squeezed in after work will turn into 60 mile morning rides. The hour of reading before sleep will turn into 2 or 3 hours in the afternoon. Our hectic, week long vacations will turn into month long adventures where we’ll actually have more time to explore our surroundings.

    In any case, I should find out very soon how I’m going to adapt. I can’t wait for that next chapter…

  7. our next life

    Just found your blog. We are about 2 1/2 years away from our early retirement, and love hearing your perspective on what the transition was like for you guys. We wrestle with a lot of these questions — how will we define ourselves? will money become a source of tension? what will the perfect day look like? — but of course nothing replaces the real life experience of those who’ve done it!

    1. smiller257 Post author

      Thanks for finding our blog. You will wrestle with a few issues when you retire but they always seem to work themselves out. The first year of retirement, I really stressed about lots of things (will the money last long enough, why do I not feel fulfilled, etc.). I didn’t wallow in that long and you won’t either. 6 – 12 months after retirement, everything falls into place. If you have any burning questions you’d prefer to ask in private, email me at and I will be happy to answer them.

  8. Pingback: How I Retired Early- Steve Miller - Just One More Year!

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