Celebrating 2 Years of Early Retirement

two canvas tents in the desert
Manuel Antonio, Costa Rica (Photo Credit: AR)

Today, I am officially celebrating my 2 year anniversary of leaving my CEO gig to retire early!!!

Wow. Just WOW.

I can’t believe it’s been two years, even though in some ways it feels like three? Ya know what I mean?!

When I left my cushy CEO gig for my mini-retirement, I really had no idea where it would lead. I just knew I needed some time off.

Now two years later, I can say with even more certainty than last year, that it was 1000% WORTH IT.

Two Years Later –> The Details

Last year for my 1 year early retirement anniversary, I went in depth on the good/bad/ugly. This year I’ll try to follow the same format!

As you can expect, early retirement is mostly good. But it’s not without its stressors and problems.

At the end of the day, I am a stay-at-home parent, and that job is hard as hell.

And on top of being a stay-at-home parent, I bought a website last year and have been heads down busy with that.

In fact, in many ways it feels as if I am working full-time. So much so, that I declared myself as “un-retired” earlier in the year.

Financial Samurai hit the nail on the head with this piece in which he called his retirement a “fake retirement.”

Either way, when you’re working, even on your own terms, it feels weird and even disingenuous. But all the weirdness aside, at the end of the day…

No matter how messy it is sometimes, early retirement is waaaaay better than heading into an office, reporting to a boss, meeting with employees, and worrying about if you are going to hit your goals and deadlines. Period.

Doing what you want, when you want.

That is early retirement.

Early Retirement: I Wouldn’t Change a Thing

At the end of the day, I would not change a thing.

Yes, you adapt to a new routine, and that new routine can get old.

Yes, you sometimes get stuck at home with a sick kid when you wanted to go out on a hike or doing something else fun.

Yes, you may end up working more than you thought.

All of these things can and do happen.

And this is early retirement.

It is ALL better.

Early Retirement: Year 2 Review

Let’s get into the details.


Earlier this year, I revisited if early retirement had an impact on my happiness.

My Good Days increased near 28% year over year in 2021.

And my Great Days went up 10%.

But the best part, is that my Bad Days went down 50% from 2020.

So yes, early retirement did improve my happiness. I am not soaring high on great days all the time, but my bad days have been marginalized.


Health wise things remained very similar to last year’s update.

Steps – I’ve had a slight improvement from 7,319 in my first year of retirement to 7,738 steps per day in my second year.

It wasn’t quite as much as I thought it would be, but still a slight improvement.

Diet – Probably the biggest change is that I stopped eating breakfast sometime last summer. I was a) curious to see what would happen and if I would lose or gain weight and b) wanted to see how it felt.

My intermittent fasting from 8pm every night until 12pm for lunch every day turned out to be a fairly easy adjustment. Only a few days of being hungry until my body adjusted.

And what happened…nothing. Absolutely nothing.

I am perhaps slightly hungrier at lunch, and that is about it. But I didn’t lose or gain any weight. Nothing happened.

However, I found that I didn’t really need breakfast anymore, so I’ve kept this practice up.


Net Worth – Well you’d think this would be all bad right now. It’s not. Compared to when I retired two years ago, my investment portfolio is flat. However, our total net worth is up 3%.

Look, it’s not something to get super excited about when you take inflation into account, but zooming out, it’s not bad.

The market will recover, and I have a solid plan to help stave off sequence of return risk.

Expenses – Our expenses are up this year. I’d like to chalk it up to just inflation, but that isn’t the case.

We’ve traveled more, our kids have done more extracurricular activities, and combined that with inflation, we are up about 15% YoY.

Taxes – My goal for 2020, was to pay $0 in taxes. And my plan worked…but my accountant and I had a mixup, so we ended paying a good chunk of change to the government, half of which they will keep for this year. Doh!

Alas, I have a limited idea of how they will play out this year, due to the website. If it continues to bring in more money, we’ll owe some taxes, but it is too early to tell. Any taxes we owe, can hopefully be paid with the money the government still has. I’ll know more in a few months as we get closer to the end of the year.


Writing – Last year, I was able to keep to a pretty torrid pace of writing 2 articles per week at a minimum.

However, this year has been a different story. I’ve had to shift down to once a week, and even that has been hard some weeks.

My hope is that I can get back to 2 times a week real soon and keep up the practice.

Consulting – Last August and September, I had a larger consulting gig.

It was nice, because it helped to create a little buffer in cash account, but boy was it hard for me. I just don’t think I am cut out to work for other people in that situation. I like to run my own ship and have some control issues.

The folks I was consulting with wanted me to joint heir team full-time. But I declined. I enjoy doing things my way after 10 years of having business partners.

Buying a Website – This was one of my big goals last year, and in October, right after we parted ways on the consulting gig, I was finally able to find a website that fit all of my criteria on Empire Flippers.

And it has indeed ended up being a better purchase than a real estate investment.

But it has also taken up a ton more time than I ever expected!

Thus why I feel like a fake retiree right now. I am working full-time on the business!

However, my plan is to start to shift into using more contractors and doing less of the work myself. This way I can focus more on AR and having fun.


Travel – This is where year 2 really shined. We really have amped things up in the past year.

We’ve been to Disneyland twice, had an amazing staycation at a local resort, and recently just got back from Costa Rica.

Plus we are planning even more in the coming months. It feels good to be back on the road!

Hobbies – This one was a bit of a letdown. I did not hit my goal of playing 2-3 rounds of golf per month.

I also didn’t get out on the trails as much as I thought.

With my time being spent on my web investment, I opted for more walks around my neighborhood.

Plus our kids started to do more of their activities and that really takes up quite a bit of time!

Books – I continue to read at the pace of 20 books a year or so, and had some great reads in the last year. I’ve tried to review many on AR, and here are some of my favorites:

On top of that, I also really enjoyed The Alchemist and Project Hail Mary.


I hit many of my early retirement goals from last year, but they can all continue to be improved upon. So my goals remain largely the same.

In no particular order:

  1. Continue to manage my finances and grow portfolio by 10%
  2. Grow the web business to offset 50% of our expenses
  3. Manage capital gains and income to pay $0 tax for the year
  4. Improve my relationships all around; family, friends, kids, wife, etc.
  5. Have fun and enjoy running AR. Write what I want, when I want.
  6. Play more golf – 2 times a month
  7. Go on more hikes – 2 times per month
  8. Continue to travel and check off things on my bucket list
  9. More date nights – and find a new sitter!
  10. Be more present and mentally available with everyone

And that’s that.

Thanks to all of you who have been following my journey and who I have connected with along the way!

Looking forward to all that year 3 has to offer!!

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  1. Congrats on your second year anniversary! I like your 20 books a year ago. That is a really good place.

    Given I’m about to publish a book on July 19, one of the perks of being an author is getting other books from the imprint for free. Some of the books I’ve read by fellow Portfolio Penguin authors include from Strength To Strength and The Practice Of Groundedness. I think you will enjoy both.

    I an sending you a hard copy of my upcoming book right, I think so. The final prints finally hit the warehouses this week. If not, shoot me an email with your mailing address and Portfolio will send!


  2. Great stuff. I FIRE’d at the end of 2021 and after some time detoxing from my career am both learning more about myself and starting on my next phase in several different areas. I like your measurement sticks!

  3. Congrats on your two years! Funny how time flies faster when we are busy what what we WANT to do and not work.

    I find it intriguing because everyone agrees retiring early beats going into an office and working for someone else, but what about people who have jobs with meaning and autonomy? We sure still need construction workers, hospital staff, and chefs and more. Probably part of the reason there are still help wanted signs everywhere.

    Anyway, congrats and it’s impressive how much work you’re doing being a “stay at home” parent, you don’t give yourself enough credit!

    Just got my hands on Atomic Habits from the library, look forward t reading it.

    1. Thanks Gary!

      No doubt that we need many critical jobs and I think the FIRE movement will always be niche, because let’s face it not many people have a solid handle on their finances.

      But if you love your job and you are getting meaning from it, then there is absolutely no reason to leave. If you have to work, which most do, then I think it is best to do something you enjoy and that challenges you.

      I loved my job for 10 years. In fact, I tried to buy my company back – it just didn’t quite work out. So now onto new things and it helps that I already have the security of being financially independent.

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