It Takes More Than Money to Retire Early Interview: Financial Freedom Countdown

When we think about early retirement, we tend to focus on the money part of it. That’s natural because we need money to retire early. Building up a portfolio is a crucial step to early retirement. When I was trying to retire early, it was all about how much we spend and how much passive income we need. However, it takes more than money to retire early.

We have done well over the years and saved up a good amount. That’s true for lots of people. There are over 18.6 million millionaires in the US now. Most of these millionaires are still working hard. Clearly, money isn’t the only requirement for early retirement. Some people just aren’t a good fit for early retirement. Finance is a big part of the equation, but there is more to early retirement than that. I thought it’d be interesting to see what that elusive something is. That’s why I’m doing this interview series.

Today, we have John from Financial Freedom Countdown. He immigrated to the US with only $1,000 and became a millionaire in just 12 years. That’s amazing. He lives in the San Francisco Bay Area and enjoys travel and weight training.

*Please volunteer to be interviewed for this series. I’d love to feature more early retirees.

Q: Can you give us a brief background about yourself? What career did you retire from?

I retired from a career in software. Everyone living in the Bay Area works in technology, so not unique?. I always wanted to pursue genetic engineering. However, since I was born in India and we were poor growing up, the only way to go to the US would be to pursue computer engineering.

My career was hobbled because I was an immigrant working on a visa. The US visa system’s challenge is that the visa is tied to the employer, unlike in Canada or Australia, where it is tied to the person and his or her skills.

In the US, as an immigrant working on a visa, you can’t switch jobs easily since every new employer needs to file papers with USCIS to get another working visa for you. Anyone who has dealt with any government agency knows how long that takes! Not many firms are willing to pursue this process and wait. Also, an immigrant can’t work for exciting startups or smaller firms since the firm needs to post their job first in newspapers, bulletin boards, etc., for others to also get a chance at applying.

Long story short, although I did well in my career, I never worked for any of the fancy companies in Silicon Valley. I switched from programming to managing projects and teams and slowly improved my career prospects.

I was fortunate early in my career to realize that the best way to thrive was to improve my human capital.

Here are six specific areas I tackled

  1. Learn new skills.
  2. Add value outside of your team.
  3. Ask for that promotion.
  4. Network with recruiters.
  5. Attend interviews for jobs one level above your current title.
  6. Keep your bridges open.

I highly recommend considering your career as an investment in yourself. I am biased towards STEM (Science Technology Engineering Mathematics). Even if you never work in a Tier 1 company, you will still have plenty of career options in either engineering, management, or support and can achieve Financial Freedom comfortably.

The other advantage of the technology sector is that formal education is not placed on a high pedestal, unlike in different industries. As a result, you are not compelled to pursue expensive higher education degrees to make more money. Silicon Valley is rife with stories of drop-outs being highly successful. The Thiel Fellowship gives $100,000 to young people who skip college to build new things instead of sitting in a classroom.

I only have a Bachelor’s degree in Engineering but never felt that limited my career potential in any manner. I do consider education important since that was my only asset. Still, I would strongly encourage everyone to look at the return on investment of the particular degree you are pursuing. Spending $100K on liberal arts vs. $100K on an engineering degree would yield different outcomes.

My advice is always to pursue the higher probability outcome.

Q: Early retirement means different things to different people. Many people don’t think I’m “retired” because I blog a few hours per day, and I’m a stay-at-home dad. That’s perfectly fine. Everyone is entitled to their opinion. What does early retirement mean to you? Do you work at all?

I do not work at all. My blog is a loss-making hobby at this point, with ads and affiliates helping break even. My CPA has warned me that I risk audit if I do not continue making money. ? 

Q: What were your financial goals, and how long did it take you to achieve them? 

I was not a spendthrift, but I also did not have a concrete financial goal for several years. My first job in the US offered a 100% 401K match, yet I never contributed anything to my 401K.

I never truly embraced Financial Freedom and how it enables one to stop trading time for money until an event in my working career helped reshape my beliefs. I remember my VP, who was in her 70s, mentioning that her sister was not doing well. I naturally assumed she would visit and asked about her travel plans.

However, she did not want to take time off, given that we had a massive product launch coming up. Two weeks later, when we were in a meeting, she received a phone call. Her sister had passed away. ? The fact that although she was a VP, earning at least 3X more than me, yet was still a “wage slave” hit me like a tidal wave.

It was at this point I was also reading a book on five regrets of the dying. Although it is not technically a retirement book, I have included it in my ten early retirement books.

My financial number was $1M + paid-off house. At a conservative 3% rule, the monthly $3,300 withdrawal of principal is enough for occasional dining out, groceries, and travel.

Q: When I was planning my early retirement, I was consumed with the money part of it. I didn’t put much effort into the other details. I’d say it was 90/10, financial/non-financial. What about you? Did you put much effort into the non-financial side of early retirement planning?

To pursue early retirement involves a certain mindset and the focus I believe is detrimental to other aspects of life. I remember hearing the Mad Fientist in one podcast episode talking about how he became miserable with the singular focus of early retirement.

I would say my planning was also 90/10 in terms of financial and non-financial. On the bright side, I did not rush to early retirement and took my own sweet time. I had a plan of activities and hobbies I would pursue in early retirement.

Q: Where are you in your life cycle? Most people retire around the traditional age – late 50s to early 70s. Their children are grown, their partner and friends are stepping back from work, and their parents may have passed. In short, you have a lot fewer obligations at a later age. To go against the grain and retire in your 30s or 40s can be lonely and challenging. Do you think it is difficult to retire early with all these obligations? 

It is challenging to retire, having so much responsibility for other people. I am single, but my parents are older (above 80). They have limited savings in India and might manage, but I would be stressed not knowing how they are. I have asked them to live with me to take care of them as they grow older.

Besides the financial perspective, I am also wondering about the logistics of it all. I know you have written about the challenges of taking care of your mom, so those aspects are still on my mind for long-term care, making my home more accessible, etc. I expect to research these topics and write a few posts on my findings.

No matter what happens, I am glad that I retired early and spent time with them. My parents came for a visit last year and continued to stay with me due to the ongoing lockdowns. The beauty of early retirement is that we get the freedom to decide how to spend each day. And time is our only precious resource.

It takes more than money to retire early

Now let’s focus on the intangibles. To be blunt, lots of people have more money than you. Most of them aren’t retired. They still work and contribute to the economy. 

Q: What makes you special? How can you retire when almost everyone else in your position continues to work? Why are you different?

Well, said Joe. A lot of people have a lot of money more than me. Most of my coworkers believe that my early retirement is a phase, and I will work again after a “gap year” or two. Given that I live in Silicon Valley surrounded by multi-millionaires and billionaires, it is hard to retire.

I already talked about my VP and her pursuit for the next promotion or award. Everyone needs to define what is enough for them.

When I got serious about early retirement, I made a list of the best retirement calculators and plugged my numbers. I have not led a frugal lifestyle, and housing has been my most significant expense after taxes.

I got serious about learning various tax planning strategies and significantly bumped up my personal saving rate. If you can track only one metric, I urge everyone to focus on this one and make sure it gets higher every month.

Develop a Financial Freedom Checklist to track your early retirement. Personalize the checklist so you have a list of activities for you to focus on.

The only reason I would consider myself different from everyone who is still working is that I stumbled upon the wonderful FIRE community. As an immigrant not knowing a credit card, all the OG blogs, including yours, have helped me learn a lot. I am glad that even after more than a decade, you are still putting out great content.

Optional questions from the readers

Q: How is early retirement going? Are you enjoying it as much as you hoped? What are you doing with all your time? 

To be honest, early retirement has not been going well. 2020 was the worst year to retire. The lockdowns have been hard on everyone but harder on single people. The San Francisco Bay area has had one of the longest lockdowns. There is only so much human interaction you can get via video and audio calling. The fact that you are not working removes any further contact. I was so focused on the “when can I retire” part that I did not plan for activities that would keep me engaged without travel. Now I know better and I’m working on other areas to prepare for early retirement.

From a financial perspective, I was lucky that all markets are back to their all-time highs. But for anyone else planning an early retirement, it is an excellent opportunity to prepare both the financial and non-financial aspects. 

Q: Now that you don’t spend 8-10 hours working in a full-time job, what are you doing with your time? What’s your typical day like? Do you have a problem finding things to do?

Early retirement means we have the freedom to not wake up to an alarm clock and set our schedule. Not sure if it is only me, but growing up, I always hated the alarm clock.

Early retirement helps you realize time is precious and everyday can be a weekend.

My typical day would involve waking up and heading to the gym, followed by a home-cooked lunch.

Afternoon nap and some work on projects which inspire me. My blog is one of the projects that is keeping me intellectually stimulated.

Evenings would be to catch-up with family and friends.

I would devote nights to reading/listening to learn something new. Occasionally, nights could be at bars and clubs, depending on the company.

This is my ideal routine when I am at home and not traveling. Over the next year, my goal is to incorporate a modified version of this schedule into my life, even when I travel.

I had no travel last year except for the one international trip in February. However, things are looking brighter. I have planned my trips for late summer and fall this year. Super excited about it

Q: Would you change anything about the way you retired from your job? Sometimes, I wish I stuck around for 6 more months. I could have worked out a deal and get a severance package instead of walking away with nothing.

I wouldn’t change anything with my early retirement timing. I had a number in mind but more importantly, I had an age goal to retire when I am 40. Severance packages are typically not common in my field. If you are in a customer-facing sales role and have built relationships with key customers then I have seen the severance part come into play.

Q: Did you make any big mistakes? How can we avoid them?

I have made tons of mistakes financially. As I mentioned I try different investment strategies and fail at some of them. In fact, one of my most popular posts documented my four worst investments. And each of these resulted in over $100K loss. My cliff notes version of my mistakes post is as follows.

Buying stocks like Sears Holdings based on TV guru recommendations.

Lesson Learned: Don’t take stock tips from TV personalities. It is wrong to assume success in one field translates into expertise in another. Lampert’s hedge fund success was extrapolated to his expertise as the CEO and Chairman of Sears. Also, the backstop was the real estate on which the stores were located. The Great Financial Crisis decimated the real estate market and retailers.

Investing in UNG without realizing that it was a poor proxy for the actual price of Natural Gas.

Lesson Learned: When investing, make sure you anticipate any technological changes that may result in your thesis not being valid in the future. Also, make sure you understand the instrument used to invest/speculate. The usage of futures contracts turned out to be my undoing.

Investing in ICOs.

Lesson Learned: In hindsight, most of these tokens did not have a strong business case. Since Bitcoin is already decentralized money, you could use Bitcoin to pay for all these services. I could see a point with respect to decentralized and anonymous internet being a fair use case since Bitcoin does not offer anonymity yet. The lack of adoption should have been a major red flag.

Investing in Lithium stocks.

Lesson Learned: Not anticipating the new supply was my biggest mistake. I have limited knowledge of the commodities market and need to do more research before investing in the future. Also, we need to consider jurisdiction risks and the fact that assets outside of the developed world do not have much protection.

I am sure I will make many more in the future. As long as you make enough money, none of the mistakes will be catastrophic. You will survive and live for the next battle. 

When you are working, be aggressive and take as many risks as you can handle. Position sizing is critical, so you do not lose it all. Accumulate assets and diversify as needed. I did a risk-reward profile for each of those assets listed. Once your nest egg grows larger, dial down the risk, and capital preservation becomes more important. 

Q: How much time do you spend (per week or month) reviewing your finances, or reading about retirement finances/investment/etc., now that you’re retired?

I spend around 20 hours a week reading about investments and finances. For the average early retiree, it is excessive. However, I love investing and learning. My portfolio’s bulk is in traditional investments like index funds and real estate syndication, but I do have several exotic investments. 

As an immigrant who had experienced sectarian violence as a kid, I was always fascinated by Bitcoin. I wrote about my Bitcoin investment thesis, which was less about price appreciation and more related to the censor-less transactions and ability to cross borders when fleeing persecution. I was so happy when two of my readers wrote back to me that they bought BTC at $8K when I had published my post.

Similarly, I was investing in SPACs, and while it has now become frothy, I still believe they offer an asymmetric risk compared to IPOs. After some trial and error, I developed a framework and now feel comfortable investing more considerable sums. 

While index investing works well for everyone, I do invest in moonshot companies. Although the data for active fund managers is not favorable, I do like to invest in companies I believe will do well in the future.

I also change my investments based on when facts change. For example, I own a rental property along with my primary. However last year I realized that residential rental property is no longer a good investment and wrote about what caused me to change my mind.

But of course, I have made plenty of investment mistakes as well. Even in real estate crowdfunding, I did lose a lot of money before I developed a checklist on how to evaluate real estate deals. I started farmland investing with the hopes that I get some produce annually. Yes, grape harvesting is very lucrative for farms, and I live an hour away from Napa ?

TLDR: If you have only index funds, then you need only one hour a year to rebalance. I don’t consider the time I spend learning as work. All my posts will articulate my investment thesis with pros and cons before I take the plunge. So after retirement you do not need to spend time reviewing your investments unless you like it as I do.

Q: What are you still not getting done/postponing, even in retirement? Perhaps some goal or something you said you’d always do when you have more time

When I thought about retirement, I always assumed I would have lots of free time. I would spend my days researching and writing. However, I have been slacking off, and my publishing frequency is now less than a week. I do plan to write more often.

I also love weight training but never managed to compete professionally. One of my goals this year or next is to enter a natural bodybuilding competition. I attended a couple of seminars and have hired an online coach after appropriate due diligence. 

I do plan to travel a lot more. In 2020 I only managed one international trip before everything was shut down. I have already booked three international trips this year and will spend late summer and fall on travel. 

Q: Looking back on your journey, any regret?

I don’t have many regrets. As Steve Jobs said, “You can’t connect the dots looking forward; you can only connect them looking backward. So you have to trust that the dots will somehow connect in your future. You have to trust in something — your gut, destiny, life, karma, whatever.”

It is easy to look back and wonder how life would be different if you made another decision in the past. However, you never know If that would have resulted in a different outcome, which could worsen. 

Q: What’s your next big dream?

I plan to take one day at a time for the next year and enjoy my early retirement. No major dreams at this point

Thank you, John!

That was a great interview with Financial Freedom Countdown. I hope you enjoyed it as much as I did. It’s always great to hear a story about an immigrant who came to the US with nothing and thrived.

Ok, I need your help. I love this interview series, but I need more people to interview. The problem is this is a long post. It’s a lot of work! Please volunteer to be interviewed. I’m desperate to continue this series.

Let me know what you think of this interview series. If you have any questions you’d like to ask, leave them in the comment as well. I’ll add them to the interview. Thanks!

Previous Interviews

The following two tabs change content below.
Joe started Retire by 40 in 2010 to figure out how to retire early. After 16 years of investing and saving, he achieved financial independence and retired at 38.

Passive income is the key to early retirement. This year, Joe is investing in commercial real estate with CrowdStreet. They have many projects across the USA so check them out!

Joe also highly recommends Personal Capital for DIY investors. They have many useful tools that will help you reach financial independence.

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21 thoughts on “It Takes More Than Money to Retire Early Interview: Financial Freedom Countdown”

  1. Enjoyed the interview and hearing other people’s stories, ideas, and perspectives. Will look forward to reading more in the future.

  2. John. Could you inform the audience how much you earned as an engineer to further shed some light on how your high income helped facilitate your journey to FI. And what percentage of it you saved on average. Thank you.

  3. Thanks John for the interview. Do you find, since you were in software, that you miss the technical aspects of your work? I used to find the challenge of solving a technical problem hugely enjoyable. Do you have any further plans to get involved in any new software, vs the blog? Personally I’m finding the lure of acquiring a SaaS company to develop further quite exciting.
    Thanks again for the interview, was great!

  4. Great interview, realy enjoyed reading and learning about other people’s early retirement approach.

    Joe, I’d love to get interviewed. Not US based but there should be enough similarities between US and Canada. 🙂

  5. So it’s not only me who takes afternoon naps after retiring!
    I retired from teaching last December at the age of 57. As a single parent of 4 boys who (so far) have not had children themselves, this is the first time since early childhood that I have total freedom to do what I want, when I want.
    To say I’m loving it would be an understatement…
    (I consider that I’ve retired 10 years early, since the pension age in Australia is 67. Feel free to send the questionnaire if you think I qualify. One of your questions mentions retiring in the 30’s and 40’s, so maybe I don’t???)

  6. Hi Joe,
    My boyfriend would like to possibly be interviewed by you if appropriate. Please send the questionnaire (to me?). I didn’t want his email out there.

  7. Congrats on early retirement, John! Even though 2020 was a rough year without a doubt, being in the position you were in financially, likely made it a lot less stressful than it could have been, right?

    I was so thankful that we didn’t have to worry about money with all the uncertainties that were out there as the pandemic grew. Although a lot of job recovery has already taken place, there were a lot of folks scared of what would happen.

    Enjoy your upcoming travel plans and I hope FIRE does you well over the years! 🙂

  8. Thanks John and Joe for sharing, I find these real life examples fascinating. A great take-away is that even with some investment mistakes along the way, it’s still possible to get to FIRE. I also enjoyed the Steve Jobs quote which I hadn’t heard before but made a lot of sense.

    By the way Joe, I’m happy to volunteer for your interview series, but realise that I might not be the best fit for much of your audience as I’m not US based. No worries either way.

  9. You say that you would like to interview other people. How about Mike Drak who wrote “Victory Lap Retirement.”

    Mike has written a new book called “Retirement Heaven Or Hell: Which Will You Choose?” You can read about the book here on

    Incidentally, I wrote the Forward to both of Mike’s books and I still have not got a copy of the lastest one. I will email Mike’s contact info to you.

    As an aside, because I have written 3 retirement-related books, I get a lot of emails and letters from people who are glad that they retired when they did. A little while ago Daniel Richards of Andover, Massachusetts posted this on my Facebook Timeline.

    “So Ernie Zelinski I read your book “How to retire happy wild and free” several times prior to my early retirement at age 59. Based on your suggestions, i did a lot of pre-planning for my retirement making sure i had plenty of activities to keep me busy. One of my interests was genealogy which i have been doing for several years. Recently however i wanted to some how to give back because i have had such a great life. I started to volunteer at a non-profit called It’s a company that finds the biological parents of adoptees. My first case was a 51 year old women who has been searching for her parents for 30 years. After 3 short weeks, I identified her mother via DNA search techniques and she made contact with her. They are going to meet next week for the first time in 51 years. Thanks to you for encouraging me to retire early, I have the time to profoundly change people’s lives forever.
    Your book profoundly changed mine forever.”

    In short, retirement is what you make of it including during the pandemic. As an 82-year-old man recently said in an interview with the “Toronto Star”, “I am so busy every day that I have no time to look for diseases.”


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