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There’s a saying that goes something like this: To feel rich, take whatever you earn and triple it. Once you get there, triple it again. In other words, due to hedonic adaptation, it’s impossible to ever feel rich!

But I’ve noticed on my path to financial freedom there were several times when I felt incredibly rich. And money wasn’t the only factor. Perhaps you can share when you finally felt rich as well.

When Do You Finally Feel Rich?

Looking back, here are all the times when I finally felt rich. Each moment of richness felt a little different and lasted for different lengths of time. I think these type of moments will make you feel rich as well.

1) When you visit a lower-cost country.

I used to live in Malaysia from 5th grade to 8th grade in the early 1990s. At the time, the exchange rate was ~2.3 Ringgit to 1 USD. When I finally paid a visit more than 20 years later, the Ringgit had depreciated to 3.7:1. One Ringgit bought the equivalent of $1 worth of stuff in the States.

Therefore, I suddenly had almost 4X the amount of purchasing power during my week-long stay. So perhaps making 3X more doesn’t really make you feel rich, but making or having 4X more does!

In addition to the increased purchasing power aspect, it felt particularly moving to visit my old house. It was overgrown with weeds. All the rich memories came rushing back of me skating boarding in my driveway and inviting friends over for fun.

It also felt good to realize I didn’t fall through the cracks. Back in middle school, I was an undisciplined kid who got into way too much trouble. If I was my own father, I’d have considered sending myself to military school.

Unfortunately, within a couple weeks after returning to the United States, I no longer felt richer than normal. I can completely understand the lure of being a digital nomad in a place like Malaysia, Thailand, or Vietnam. In a different life, being a digital nomad is exactly what I would have been.

Pulau Redang, Taaras Resort & Spa
Taaras Resort at Pulau Redang, Malaysia was the bomb.

2) When you finally hit your passive income target.

It took 17 years to achieve my passive income target of $200,000. When I finally got there, I felt rich. There was no more fear of running out of money anymore. Growing up in developing countries and experiencing many boom bust cycles working in finance always makes me a little paranoid about losing everything.

Passive income feels like free money because you’re not doing much to earn it. In a way, you almost feel guilty, even though you spend a tremendous amount of time building your passive income portfolio.

The amount of passive income generated is less important than whether or not it can cover all of your living expenses plus a nice cushion. Once it can, you will feel rich.

Another reason why you will feel rich once your passive income is high enough is because you can finally freely speak your mind. You don’t have to suppress your true opinions about anything. You’re less concerned about displeasing somebody. You’re also not afraid to lose your job any longer.

Unfortunately, once we had our son in 2017, $200,000 no longer felt like enough. With the cost of health care, housing, and college education rising far quicker than income, I felt like I needed to generate more. There has to be some type of biological trigger that switches on in all people once they have a child.

Today, if we do not have a third child, our current passive income is enough to provide for a steady rich life.

When Do You Finally Feel Rich?

3) When a new income stream comes out of nowhere.

None of us are maximizing our income potential. I’m going to guess that if we could make a maximum of $100 a month, most of us are really making only an average of $30. It’s kind of like how none of us utilize more than 20% of our brains. If we did, perhaps we’d find a cure for all cancer already.

One of my issues for years was not caring about revenue maximization on Financial Samurai. I already had enough passive income. Therefore, I wasn’t constantly hustling to find new business deals. When some of my peers would hire a team of writers to write affiliate posts, I was busy focusing on writing about fun topics that made little-to-no money.

But in 2018, I decided to become more entrepreneurial because I received poor feedback on a post I spent a lot of time on. I figured, if people didn’t really care after reaching my 10-year anniversary, then I might as well start being selfish for myself. Besides, I had a baby boy to take care of and we planned to have another child.

Today, I feel rich whenever a new income opportunity appears on Financial Samurai because I’m still not proactive. I’ve just been more open to offers. It feels great to produce income from what I already enjoy doing.

4) When you don’t sell assets at suboptimal times.

Back in 2012, I listed my San Francisco single family house for $1,700,000. I didn’t get any official offers, only whispers from a couple real estate agents saying their clients were willing to pay closer to $1.5 – $1.6M. I refused and took it off the market until I had an opportunity to re-list the home again in mid-2017.

My tenants had given me their 30-day notice. I figured I might as well test the market for both rent and sale again. My hope was to get at least $2,300,000 or $8,800/month, the same rent as my previous tenant.

Instead of getting $8,800/month, the best I could get was $7,500/month, a big 15% decline. At the same time, my realtor found a prospective buyer off-market who offered $2,600,000! After much back and forth, I was able to get them up $1,040,000 more than I would have sold it for just five years earlier.

When do you finally feel rich?

Not selling an asset at a bad time will make you feel richer and richer as time goes on. That asset can be real estate, stocks, or anything that would have continued to go up in value. The only way to counteract the bad feeling able selling is if you reinvested the proceeds in something that also went up.

Holding On To Something You Created

Perhaps more important than not selling an asset you did not build is not selling an asset you did build. I feel rich for not selling Financial Samurai back in 2018. I was very tempted, but I wanted to reach the 10-year mark. The site has collected two years more of revenue and valuations are higher.

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In a low interest rate environment, you want to hang onto your income-producing assets for dear life. Any business that can operate unimpeded during a pandemic has also become more valuable.

Just look at the NASDAQ, up more than 40% in 2020 alone. Finally, Financial Samurai has given me something meaningful to do while stuck at home.

5) When something comes true after trying for so long.

The longer you spend working on something, the richer you will feel once you succeed.

This rich feeling is why you don’t want to just give your children everything. It’s better to make them earn their success. Please don’t envy the person who inherits everything. Feel bad for them instead.

Here are some good examples that take a long time to achieve, but once you do, you will feel rich:

  • Studying for the MCAT, LSAT, Bar Exam, CFA, and passing.
  • Writing a book for years and finally getting it published
  • Working on building a relationship with a client for a year and the client finally agrees to do business
  • Coaching your players for three years and finally winning a championship
  • Dating for eight years and finally finding the one
  • Trying to have children for years and finally giving birth to your first child
  • Practicing for hours after school and finally making the team
  • Diligently saving and investing for years until you finally come up with a down payment for a house without any help from your parents

Delaying gratification and demonstrating grit go hand-in-hand.

6) When You’re Surrounded By Loved Ones

Friends and family are everything. Having friends to joke around with brings so much joy. Having family that supports you in your endeavors feels priceless. We recognize this importance more than ever before.

As a father of two young children, I feel incredibly rich. It took years to conceive our son. Then to have a daughter a couple years later felt like a miracle as 39 and 42-year-old parents.

I wish someone told me in my 20s and early 30s that having children would provide so much love. If I had been told, I would have tried to have children at least five years sooner and not been so focused on trying to achieve financial independence.

If we could not have children, then we would spend more time nurturing friendships. Great relationships mean so much more than having a lot of money.

7) When You Become A Time Billionaire

A time billionaire is someone who has full mastery of his or her time. There’s no greater feeling of wealth than being able to do whatever you want, whenever you want.

Even after my income plummeted by 80% once I left my day job in 2012, I felt richer. Sure, the unknown was a little scary. But I was excited to have taken the leap of faith while I was still relatively young.

Being able to sit in the park and read a book on a Wednesday afternoon is nice. Being able to conquer your FOMO that you should be out there hustling for more money is truly rich.

Once you experience being a time billionaire, unless you can earn more than a billion dollars, you will no longer be willing to grind as hard at work or at building a business.

8) When You Wake Up Each Morning Without Any Ailments

One of the biggest epiphanies I had after leaving work was that I had internalized all my chronic pain. I just lived through my TMJ, teeth grinding, allergies, sciatica, plantar fasciitis, lower back pain, and tennis elbow for over a decade. Then, about a year after I retired from finance, practically all my chronic pain went away!

Some of us work in such stressful occupations that we forget what living a pain-free life feels like. I remember seeing my first gray hairs at 33. The dam had finally broke, I had thought to myself. But 10 years later, the gray hairs went back into hibernation and have stayed there, probably because I’m less stressed on average each day. The health benefits of early retirement are priceless.

Unfortunately, I’ve noticed more and more random physical issues that are nagging me as I’ve gotten older. If it’s not a sore lower back, it’s a rickety shoulder, or an itchy ear.

Most of these problems have to do with me playing sports too often. Now I wonder whether being unathletic is better for living longer and having a more comfortable life. At the extreme, you hear about major health problems to NFL players.

Cherish your health and your youth folks. You not only want to have full control over your time. You want to have full control over your time while you are healthy. This means travel and explore while you can. Have the time of your life in your 20s and 30s. Health issues will inevitably pop up as you get older.

9) When You Learn Something Meaningful For Free

I love the internet because you can learn practically anything you want for free. You just have to focus your time reading and watching sites that are most helpful.

And because I love learning things for free on the internet, it’s only right to share on Financial Samurai what I’ve learned along my journey as well.

It feels good to help people on personal finance matters without a paywall. Money consistently ranks as a top 1 or 2 stressor in people’s lives. If I can help strangers solve difficult problems or give readers the courage to act, it feels really satisfying.

2020 has probably been the most difficult year in millions of people’s lives. As a result, it was important to regularly publish posts and write more nuanced newsletters to help folks through muddy waters.

Feeling Lucky Makes You Feel Rich

The common theme to feeling rich is when you start feeling lucky. We can all work very hard to try and get rich. However, I truly believe luck is the main reason why some people are able to amass an extraordinary amount of wealth. They either were lucky to meet the right people, have the right parents, or be in the right place at the right time.

Spend some time going through your lucky breaks. The more you are aware of your luck, the richer you will feel.

A couple of my lucky breaks include:

  • Getting into The College of William & Mary and meeting my wife my senior year. If I had attended the University of Virginia or had been one year older, I never would have met her.
  • Getting handed the phone by my VP. On the line was a recruiter who ending up getting me a job at a competitor three months before I was to be laid off. That phone call brought me to San Francisco in 2001.

Of course, I’ve also had plenty of bad luck and failures along the way. However, by focusing on the lucky breaks, I feel richer.

Other Examples Of When You Might Feel Rich

Here are some other examples when you might feel rich.

  • If you walked away from a car accident unscathed.
  • If you find a $100 bill on the ground with nobody else in sight.
  • If both of your parents live to hold their grandchildren.
  • If you were diagnosed with a terminal disease and are still living past your due date.
  • If you found the love of your life early.
  • If your job is something you’d happily do for free.
  • If you’re making a difference in other people’s lives and also getting paid.
  • If you were a C-student who now lives an A-lifestyle.
  • When your investments return more than your income.
  • When your children achieve something you did not expect.
  • When you come out of a global pandemic richer and with your health intact.

If you focus only on an absolute dollar amount, you’ll never truly feel rich. The reason is because there is always someone with more money than you. I have friends who are worth over $100 million who keep grinding because some of their old peers are now worth over $1 billion. Can you imagine?

Therefore, if you can focus on your lucky breaks and the good fortune you are currently experiencing, you will feel like the richest person in the world.

Readers, I’d love to know the times when you felt rich. How long did that rich feeling last? What are you doing to feel rich more often?

Feeling Rich, Staying Rich

One of the best ways to feel rich and stay rich is to track your net worth with Personal Capital. I’ve been using Personal Capital’s free financial tools to optimize my wealth since 2012. It’s the best free money management tool on the web. Just link up all your financial accounts to measure your cash flow, x-ray your portfolio for excessive fees, calculate your retirement income, and more. 

Get you finances right the first time around. There’s no rewind button in life. Once you do, you can focus on the other things that truly matter in your life.

Personal Capital Retirement Planner Free Tool
Personal Capital’s Free Retirement Planner


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