15 Lessons Learned From 10 Years of Investing

It’s been a little over 10 years since I started investing in equities through my retirement plan at work. At first, these dollars were like tiny drops that dripped into a bucket. It didn’t feel like they were amounting to much, but every pay cycle kept filling up the bucket a bit more.

Fast forward to a decade later, and this bucket, along with Tatiana’s equally sized bucket, is almost big enough to declare us financially independent.

I began my investing journey by contributing enough to get the 4% employer match in the 401(k) plan. Even though the company wouldn’t start matching my contributions a year after my date of hire, I started contributing right away.

Why would I contribute right away when there was no match?

I took immediate action because I didn’t want to get used to the extra money. I thought it would be much harder to adjust to a lower take-home pay a year later.

In retrospective, that 4% savings didn’t reduce the paycheck by much since the money was pretax but one can always find an excuse to not save. That’s why saving should come first in households that tend to overspend, and let it run on autopilot.

Savings rate and retirement

Paying yourself first should be the key action to take if you want to become financially independent. Not many people do that in this country and, by default, we suck at saving.

As a country, our personal savings rate has been hovering around 5% for the past five years.

Why should we even be concerned with this low number?

Well, because your savings rate will determine how soon you can retire. With a tiny savings rate you can expect to work for a very long time. It would take 62 years to retire with a 5% savings rate! (You can play around with this calculator to see how much time you have left until retirement.)

So pump up your savings rate, so that you don’t become one of those haters that despise others who have the option to retire early. 🙂

Looking back to my pre-FI days, with the employer contribution and my 4% contribution, it would have taken me up to 39 years to retire!

There’s nothing sexy about that. JMoney would agree!

I also wouldn’t have the same endurance that I have now. It’s a lot harder to hike mountains in your seventies.

I didn’t discover FIRE until later, so I thought I was doing great by contributing the minimum back then.

I even thought I could stand showing up to a 9-5 until my sixties.

What the heck was I thinking?

Saving was not always a priority

If I had the mindset that I have now at least 10 years ago, I could’ve had enough money to retire by now, but I was caught up in the same nonsense as the average American.

I was having a spending problem. I had cash that was flowing mostly into the home, transportation and finance charge categories, leaving very little for savings.

“It’s not your salary that makes you rich, it’s your spending habits.”

Charles A. Jaffe

With the new job also came lifestyle inflation: the house with a pool, the new car, the 52” flat screen TV and home improvement projects. My paycheck was depleted by material things and most of these expenses could’ve been avoided.

I don’t like to dwell on the past, but if saving during my initial investments years would’ve been as disciplined as my most recent ones… Damn!!! I’d be writing a different story now.

But this is my story and it had to unfold like this in order for me to be in this situation now. And it’s an awesome situation to be in.

I’m living a life of gratitude that brings me true happiness with the love of my life. Have you found your formula for true happiness?

My initial investment years (2006-2011)

I didn’t know jack about investing in equities when I started. I didn’t get some stocks as gifts when I was a child from an uncle or grandparents. There were no family members who knew how the stock market really worked.

My parents invested in real estate and farmland, but the stock market was a complicated and untouchable world to them.

Little did I know that a whole different world of investing was about to unfold in front me when I opened my first investment account.

During my first 5-6 years of investing, I continued with my minimum 401(k) contributions into a target date fund. Choosing a target date fund was a smart decision during that time because I didn’t know much about investing.

A target-date fund is a mutual fund in the hybrid category that automatically resets the asset mix of stocks, bonds and cash equivalents in its portfolio according to a selected time frame that is appropriate for a particular investor.


Once you choose a target date fund close to your retirement date, the fund allocation in your portfolio becomes more conservative as you get closer to retirement.

Saving for retirement sounded boring to me until FI came along

I kept saving for a retirement that seemed very far away because, in my mind, I thought it was something that you reach when you become a senior citizen. I knew I had to save something for retirement, but I wasn’t enthused about it.

There were no bloggers who retired in their 30s talking about early retirement, nor was I interested in reading about the topic. Retirement was something that I could look forward to, somewhere in the year of 2035.

Now, the definition of retirement has totally changed for us and it’s something that we look forward to. We’ll retire from a job to do things that we truly enjoy.

Who doesn’t want that?

Two years after I started investing, the market tanked and took half of my 401(k) balance with it. Fortunately, it was a small amount of money at the time, otherwise I would’ve been worried desperately without knowing what to do next. I had little investing experience.

That period known as The Great Recession made its mark.

The savings that were left of the carnage were locked up in a 401(k). There was no good way to free that money without penalties. Selling and running was not a viable option. I wasn’t going to withdraw money and deal with a 10% penalty!

I kept pouring money in and it took me a couple of years to recoup my losses, just like everyone else that stayed put and didn’t sell in a panic.

During the downturn, I also opened a brokerage account and bought a few stocks, but I wasn’t investing. Rather, I was speculating and learned some valuable lessons in that arena.

In 2009, I decided to get more educated about investing and play a more active role in my investments. I took it upon myself to learn about investing as much as possible.

I read some books. I learned about the market and the mutual funds in my plan. It’s amazing what you can learn on your own when you put your mind to it.

“Invest in yourself. Your career is the engine of your wealth.”

Paul Clitheroe

By 2010, the wheel started to turn. I switched my contributions from the target date fund to other index funds that were in my plan.

The best investment years, so far (2012-2016)

How things have changed since I started saving for retirement. We are now looking to an early retirement date no later than three years!

And how did I advance the retirement date by 16 years?

First, I had an epiphany, second, I realized that my relationship with money needed to change and, third, I met a partner who shares the same goals in life as me. We’ve been working hard by delaying some gratification to be able to invest all that we can. The only caveat is that we make sure that we enjoy the journey.

The past four years have been the best so far, financially speaking. After realizing that the most important luxury money can buy is our freedom, I paid off all my debt and started maxing out my 401(k). No more saving a minimum for a match and hoping for the best.

The chart below shows the steady progress made throughout the years. In 2006, I accumulated 1% of my current balance all the way through 100% in 2016.

A well-oiled FIRE couple

By investing in our retirement plans, Tatiana and I have become a well-oiled FIRE couple! Her numbers are not included above but are pretty similar since she started working a year after me.

We do our own investing and have an asset allocation that works for us.

And the most important thing is that we know the why of our investments. We don’t just buy an investment because someone recommends it–it needs to make sense for our goals. There’s a valid reason why we own every investment in our portfolio.

I enjoy investing and continue to learn about rate of returns, tax harvesting and the different market sectors.

However, I didn’t get to this point without making mistakes. They were not huge, but significant enough to teach me valuable lessons.

“An investment in knowledge pays the best interest.”

Benjamin Franklin

Some mistakes that I made, such as buying a few stocks instead of index funds, caused me losses and I choose to see these losses as the cost of learning.

I’ve also learned a great deal along the way just by being invested in the market.

I feel that most of this stuff is basic, but sometimes we complicate it by not applying the basic principles of investing.

Lessons I learned in my first decade of investing

1. Don’t speculate, invest

I didn’t grow up around people who invested in the stock market and, therefore, had limited exposure to stock market investing. Latinos, by and large, become wealthy by pursuing entrepreneurship and business ownership.

Anytime I’d hear about the stock market, it would be because of: a) News of a guy who lost a fortune or committed suicide due to a market crash. b) Someone or a friend of a friend who made a killing with stock trading. c) The Spanish channels sounding off the alarms that la bolsa de valores (the stock market) is crashing.

I wasn’t exposed to the good stories of long-term investing so, to me, stock market investing sounded like a gamble. A place where you place bets on a rising stock and plan to dump it once you make gains. I learned that this is not investing, but speculating.

Speculating and investing are so not the same. I learned this lesson the hard way. In late 2008, I bought a few stocks and traded them back and forth looking for a quick profit. I was looking for short-term gains, and there were good days and then there were bad days.

By early 2009, as the market continued to hit bottom, I grew impatient, gave up on that game and took my losses (I lost about a couple of thousand dollars). After that, I decided to concentrate on my 401(k) investments and invest for the long-term.

2. A stock is not just a ticker symbol

As Warren Buffett says: “Price is what you pay. Value is what you get.” When I invest in a fund, I look at the stocks and bonds in the fund because all the stocks in the fund represent businesses. When I’m buying a stock, I’m buying a piece of a business.

“Investing simply and in strong companies may not be the sexy way to invest nor will it produce the amazing returns that off stocks produce or that option income can produce. But, it will help you build a strong portfolio of companies that you know, understand, and know are capable of rewarding shareholders over the long run.”

Bert, Dividend Diplomats

I don’t do any individual stock-buying nowadays, but if I do decide to buy them in the future, you bet that I’ll be looking into the business behind the stock.

I wouldn’t just buy by only looking at its price history and name familiarity or simply because someone at a supermarket thinks it’s going to increase in price without sound reasoning.

“The stock market is filled with individuals who know the price of everything, but the value of nothing.”

Phillip Fisher

3. Use proper investment vehicles according to time horizon and risk level

There are so many schools of thought when it comes to where to allocate your money. A rule of thumb that I follow is that if I need the money within 5 years, I don’t put it in stocks. We could have it in bonds, CDs or any other low-risk investment vehicle, but not in stocks.

4. Allocate assets properly

A proper asset allocation helps in reducing the risk of being overweight or underweight in one asset class over another. Without a proper asset allocation, I was doing some market timing a few years ago.

One of the mistakes I made was putting a big chunk of the investments into cash in the 401(k)s, thinking that after such a bull run the market was destined towards a correction.

Then, the next year the market had great returns!

I missed out a bit by retreating from the market instead of following an asset allocation. I didn’t lose money but I could’ve gotten some dividends from that portion of the portfolio at least. After that I decided to just put the money back into the market and let the market do its magic.

We spent about a year studying different asset allocation models to see what would work for us and, once chosen, were happy to just invest our money accordingly.

With an asset allocation, there’s no more guessing on where the contributions should go and no temptation to make irrational investment decisions.

5. Market timing is a fool’s game

It’s almost impossible to win at market timing. The problem with trying to time the market is that you have to be right twice: when you sell and when you buy.

When I decided to put a portion of the portfolio in cash, I couldn’t figure out when to go back in because the market kept going up. No one has a crystal ball on the market.

I also learned that is about time in the market, not market timing. If we don’t need the money right away, let’s say within five years, we rather have the money in the market yielding dividends and expecting a longer-term return than sitting in a money market fund.

6. Stock market long-term trend is up

The market can be down for days, weeks, months, years, even a decade but it you look at the stock market trend for a longer period, you realize that the trend has always been up.

This tells me that as long as I’m investing for the long term, I should not worry about the short-term trends. I don’t pay attention to the headlines or even listen to the daily news cycle.

7. Pick a specific day to invest

It’s important for us to have a specific day to invest whether if it’s weekly, monthly or quarterly. By investing on a certain day, we don’t worry about the ups and downs of the market.

If I just invest on any day without any rules, I might feel tempted to wait and see if the market is up. As I already mentioned, we don’t know what the market will do the next day. It could be up again, and again.

So we invest on payday and move on with our lives.

8. Investment fees matter

We’ve always been DYI investors and always will be. We’re very cautious of investment fees and realize that what one can pay in fees can really impact returns.

One feature that I like about the Personal Capital investment tool is that it lets us know how much we pay in investments fees and gives projections of fees over time.

9. Have multiple sources of income

Besides investing in equities, we also have a rental property that provides monthly cash flow. We might sell it before retiring, but that doesn’t mean that our income will only come from our portfolio of stocks and bonds.

One sure way to bulletproof our cash flow after retirement is by taking advantage of other investment opportunities. We’ll take the next two years, before we retire, to research other investments, possibly in real estate.

“The real key (to wealth) is to have multiple flows of income that are indestructible due to economic conditions or technological developments.”

Grant Cardone

10. Take advantage of tax loss harvesting

Tax loss harvesting is the practice of selling a security that has experienced a loss. By realizing, or “harvesting” a loss, investors are able to offset taxes on both gains and income. It can be hard to comprehend at first and there are rules to follow to make it work.

I wasn’t familiar with tax harvesting until I saw bloggers discussing the topic. This year we’re implementing this strategy on our non-retirement accounts.

11. Keep learning

I keep learning and the more I do that the more I realize there’s always so much more to learn.

Sometimes I drive Tatiana crazy with new investing strategies, but I don’t mind changing my mind based on new information.

It’s about finding new logic and new ways of thinking. Also, I like to make informed decisions when investing because it helps me take calculated risks and improve performance.

12. Keep tabs on asset diversification and net worth allocation

We have a diversified portfolio now, which is important, but having diversified assets will be even more important in retirement.

We’re building a portfolio that needs to last at least 60 years and having different kinds of assets would allow us to sell some while others might be down. The key will be to continue to buy low and sell high.

I also keep a tab on our net worth asset allocation. It’s good to get a view of the entire panorama.

We still have a long investing path ahead of us and, as our assets in the stock market continue to grow. We’ll eventually move some of the gains into tangible assets, such as real estate.

13. Asset location is just as important as asset allocation

It’s important to know where we hold our assets in our portfolio for tax purposes. This was a good lesson to learn as we formed our asset allocation.

Different type of investments get different tax treatments. We make sure to keep most of our bonds in our retirement accounts, so that the interest doesn’t get taxed as ordinary income. That just one of many ways to save on taxes.

14. When dumb money follows smart money, the party is over

This header was a quote that I picked up somewhere along the way and it stuck with me throughout the years.

Whenever you have a supermarket clerk handing you their realtor business card, you know that the party is over.

Whenever you have 100 personal finance bloggers popping up every day and showing how well their investments are performing, you can tell that the party is just about over.

It’s a lot easier to make money in a good economy or when in the middle of a bull market. I’m not trying to put down people or discourage PF blogging.

On the contrary, I like it when I see more blog launches and I tend to follow many of them on Twitter. That means that more people are waking up, taking better care of their finances and want to share their story to help others.

My challenge to all of us is: let’s not follow the smart money, let’s become the smart money!

When people are running for the door, the smart investors are coming in to snatch opportunities.

One of my favorite smart money bloggers is Sam from Financial Samurai because this guy is always hustling and showing how he finds investment opportunities.

15. Practice the KISS Method

Probably the most valuable lesson has been to “keep it simple, stupid”.

Investing doesn’t have to be complicated. I’ve learned that more complexity doesn’t equal higher returns. At times, I found myself complicating it and realized that investing just needed to be kept down to basics.

Just because an idea sounds sophisticated and almost like a foreign language, doesn’t mean that it will make money.

Screw having so many confusing spreadsheets to prove a point or holding a ton of funds in a portfolio, that replicate the same results.

Simplicity makes life more enjoyable. I choose to invest to live not live to invest.

Final thoughts

I can sum my first investment decade into this: slacking on the first half and getting my act together on the second half. It’s like that college student that buckles downs come junior year, to be able to graduate with a GPA above 3.0.

It’s been a great investing journey so far and I can’t wait to see what the future holds for us when we retire and live off of our investments.

Even though I had a learning curve, we still managed to get over an 8% rate of return during our first decade of investing.

I’m very optimistic about our second decade of investing. I’ll be learning more about other investments vehicles and start switching part of our allocation into tangible assets.

Tatiana, my partner in crime and shareholder, is there with me along the way. What else could I ask for? 🙂

I’d like to end by commenting on one last quote:

“People value and spend their money more wisely when they acquire it by their own efforts – also known as work.”

Larry Elder

When you work hard to become financially stable, you’re going to appreciate the freedom that your efforts provide a lot more than if money was just given to you.

The journey is more enjoyable when you forge your path with your own hands.

When people go around spending and thinking that a dollar is just a dollar, they’ll never have a hundred dollars. So take care of that dollar and the bigger bills will take care of themselves.

We want to hear from you. What investment lessons have you learned over the years? 

Risk disclosure: All investing involves risk, including the possible loss of principal. The material contained on this website is for discussion purpose only and should not be misconstrued as financial advice.

This article has been featured on: RockStar Finance and Physician on FIRE


José worked at Vanguard for 12 years, helping create electronic and print educational materials for 401(k) participants. He retired at 44 from corporate America and loves to spend time with his wife and daughter, discovering new adventures or just sharing a meal in their backyard.

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16 thoughts on “15 Lessons Learned From 10 Years of Investing

  1. An excellent read, and your timeline mirrors mine in that the vast majority of my investing has occurred over the last ten years and I’ve learned a lot in the process. I also started with target date funds and actively managed funds-of-funds, but have “graduated” to owning nothing but simple passive index funds.

    Keep up the good work, and I hope Mr. Market is kind to you over your remaining months to the ultimate goal.


    1. Hi PoF-
      I also noticed that our investing styles do have a lot of similarities, after reading your asset allocation post. It’s good to be in great company!

      I’m not sure what to expect from Mr. Market (and never will be) but it will all depend on how we define kindness. Maybe he’ll give us a gift of a 20% drop so that we can buy more before we conclude our accumulating stage? As much as we don’t like to see our net worth drop, a correction might be the best thing to come our way now.

      I’m glad you liked the article and thank you for commenting!

  2. Tnx for helping others! My personal decision to leave wall street and their manipulations to move into physical assets that pay passive income, real estate, rentals. The comment that real estate is not for everyone does not take into account that everyone is capable of learning and excelling. I did most folks can too.

    5 yrs ago my wife retired from teaching so we moved her 30 yrs of hard saving a meager $203k of 403b savings into a Self Directed IRA, with check book control and started buying rentals in good school districts of Atlanta. With rent re-investment the fund went geometric (hocky stick) in valuation. Just 5 yrs later it can be liquidated for $900k and today throws off $7k of rent / month. Easily enough to live off. The math on this gain should be impressive.

    I’m certain I did not have the skill and temperament to replicate this in the stock market. I seriously doubt anyone could do the same in the stock market. It is true we bought at the low of real estate, but historically it still is great time to buy. Typical real estate cycles are 15 yrs up, 6 yrs down. The hedgfunds jumping in and buying shortened the 6 yrs to 4 yrs. With the en mas conversion of past buyers into future renters and worsening ave income stats I don’t see anything but great predictions for buying rentals. As long as close to growing jobs and good schools. Best of luck.

    1. Hi Curt,
      I agree that most folks are capable of learning real estate investment. We have a rental property that provides a 10% ROI but and it’s much less risky than the stock market. However I bought the property a while back and didn’t make the best of it due to its location. I learned some lessons since then which is making me think about doing a part two of this post to include real estate investments.

      That sure is an impressive gain. You more than quadrupled your initial investment in 5 years! Congratulations! I’m interested in learning more about Self Directed IRAs. I think that it is a great option to pursue so that you can have total control of your investments. We’re keeping our options open and are willing to look into those options at some point.

      I’m not familiar with the RE cycle so this is great info. As long as you make money when you buy and yes, have a criteria such as a growing job market and good school district, you certainly can’t go wrong with RE investing. Awesome comment! Thanks for dropping by.

  3. Great story! I went through many of the same phases on my journey to FI. Early on I was not maxing out my 401k, and actively trading stocks. After spending too much time trying to beat the market, I finally learned it’s easier and more effective to just make regular investments in index funds. Then down the road, I got a better with optimizing taxes and investment fees. Wish I would have learned sooner, but mistakes are a big part of learning, and I am sure I still have more to learn 🙂

    1. Hi Mr. CK,
      It’s good to understand how important it is to be able to optimize taxes early on. Maxing out the 401(k) is our most effective way to lower our tax bill.
      We all have a lot more to learn and I’m sure more mistakes will be made! So I’m glad that we have this medium to learn from each other. Hopefully the mistakes will be small in nature as we find ways to mitigate risk. Thanks for dropping by.

  4. I like your point about picking a day to invest. Despite the fact that I totally agree with you that timing the market is next to impossible, I spent some fruitless time researching “What is the best day of the month to invest?” There really is no consensus out there. So starting now I’m going to have to set up an automatic transfer. I’ve always just invested ad hoc each month.

    1. Hi CoupleofCents –
      The only “market-timing”, if you will, that we sort of do is to rebalance with the new investment cash to keep our intended asset allocation. This minimizes the risk of being under/overweight in some assets.

      Picking a specific day it’s a great strategy that takes away the guessing of whether we should jump in or not. On “investment day”, which falls on the same day as payday, we look at the bills that are due before the next paycheck, set that money aside and invest the rest. Rinse, repeat.

      Thanks for stopping by.

  5. I can say from experience that it is much harder to increase pension contributions, than it is to start on a certain amount. I started a job with a scheme that I could contribute 4% and my employer would match it. Then (and contrary to every other employer), they launched a new scheme that was way better, but you had to contribute 8%. It was a no brainer, and it wasn’t quite losing a further 4% once tax and national insurance was factored in, but it was still a big adjustment to make.

    1. Hi Sarah –
      I agree, it’s a lot harder to meet the match when companies have schemes that offer a match but require a contribution higher than 4%. What I would do in that case if I can’t meet the full match right away, is increase the contribution on an annual basis by certain percentage until meeting the full match or maximum contribution. But of course, the FI crowd that wants to reach FIRE sooner rather than later would want to sacrifice a little more to max out ASAP. Thanks for stopping by!

  6. Thanks for sharing your lessons here. The lessons resonate very well with me and it is all stuff I have thought and considered over the years too. Being in the online community, I have watched others change their investment styles and try to one-up the market, aka find the next best way to beat the market. Investing simply and in strong companies may not be the sexy way to invest nor will it produce the amazing returns that one off stocks produce or that option income can produce. But, it will help you build a strong portfolio of companies that you know, understand, and know are capable of rewarding shareholders over the long run.

    Thanks for taking the time to share your experiences, again. Lots of good stuff in here!

    Bert, One of the Dividend Diplomats

    1. Hi Bert –
      This is such a great statement about investing in great quality companies that I made it part of the article. Thanks for sharing your knowledge.

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