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My Investing Journey, Just Do It

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AUTHOR: Dan Smith on 11/28/2025

I began contributing to an IRA in the 80s, buying certificates of deposit at the local bank. Pretty soon I began thinking about investments. I knew almost nothing about the stock market, still, I knew I needed to be in it. I remember watching the nightly news, where the anchors always reported what the DOW did that day, never a mention of that other thingy…. What was it called…. The S&P500? 

I started reading up on the stock market, learning only enough to be dangerous to myself. The thought of investing was infesting me. At some point I was contacted by a smiling and dialing registered rep from IDS. 

I soon rolled over my IRA CDs, all $3500 of them, into a mutual fund and an Real Estate Investment Trust (REIT). Soon after that Black Monday happened. My mutual fund was down hundreds of dollars. Was the world coming to an end? I felt I would throw up. Still, I held on and soon learned that what goes down, usually goes back up pretty quickly. As for the REIT, I watched it go down with every quarterly report. There was no secondary market for it, no buyer for several years. When I was finally able to dump it, I lost about 40%. No more REITs for me. 

In the 90s I took over managing my own money. I spread my investments out in several managed mutual funds. I wish I had known Jonathan back then, because the hot managed funds I chose were nearly clones of each other. By the time the 2001 bear market came to an end, most of the stellar growth from the 90s had evaporated. 

Around that time came a period when I became securities licensed. I briefly worked for a financial company that was owned by a large insurance company. We had an investment specialist, and he taught me much about analyzing mutual funds. He was, however, all about selling managed funds with front end loads and 12b1 fees, and seemed convinced that he could beat the indexes. 

By the time the 2008 financial crisis rained down on the market, I was using either balanced funds or target date funds, still all were managed. They proved superior to my fund picking skills, largely because they dealt better with controlling allocations. 

It’s only been in the last five or so years that I have switched most of our investments into index or ETFs. I stubbornly hang on to a few managed funds, but in total they represent less than 30% of our portfolio. 

Earlier I posted about consolidating most accounts into Fidelity. That has worked out very well so far. I like the  platform and find the website intuitive enough; their phone reps have been perfect whenever I needed them. 

I leave about 20% of our assets with an advisor, whose referrals were a huge help when I was building my income tax practice. He does not charge me much, and uses ETFs in my account.

Over 40 or so years of saving/investing, I have made plenty of mistakes. Still, I kept plugging away, and although I surely could have made better decisions along the way, things turned out okay. The old Nike slogan comes to mind; Just Do It.

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DAN SMITH
2 months ago

Lester, thanks for commenting. 
I have a few thoughts regarding your appreciated stocks. 
One solution would be to leave them for your beneficiaries, who would (under today’s tax laws) receive a step up in basis to their value on the day that you die.
Another course of action is to calculate exactly what the tax would be on the gains. The long term capital gain tax rates are O%, 15%, or 20%, depending on your income and filing status. The 20% rate doesn’t kick in until income rises to between $533K and $600K. 
If it were me, I’d open my tax software, estimating the  best I could, current income along with the anticipated capital gain from the appreciated stock. The tax might not be as bad as you fear. Depending on the outcome you could consider selling all of the shares now, or selling a portion of them each year in order to stay in the 0 or 15%  brackets. 
If you are using Medicare, be aware of the IRMAA triggers.
Good luck.

Lester Nail
2 months ago
Reply to  DAN SMITH

Thanks Dan

Lester Nail
2 months ago

Thanks for sharing your experience. I’m sure I’m the only one who made every possible mistake in investing. My biggest regret is trusting several “investment advisors” until they proved to me they were not worth my trust. Finally at 65 I believe I know enough to handle my own money. I no longer need or want to chase high returns, Index funds in the broad market are sexy enough for me. Since have two many stocks that have hugh gains so not sure what to do with them because I’m not going to pay big capital gains to to move them into a index fund. Yes they are in my taxable account. But I think it’s a good problem to have. Thanks

Olin
2 months ago
Reply to  Lester Nail

Lester, I think the only way to avoid mistakes is to make mistakes. Most people can do their own investing, but at some point you need a tax strategy, or a very good tax advisor who can see the big picture, to prevent under or overpaying taxes now and in the future.

We sometimes get caught after the fact that I wish I knew the mistake back then to what I should know now in taxes. Our tax system has become too complicated unless you have one source of earned income and some interest.

As you say “have two many stocks that have huge gains so not sure what to do with them because I’m not going to pay big capital gains to to move them into a index fund.” This might be a case to seek out a professional (if there is one) for some guidance. But I’m afraid such person will make the situation too complicated that I wouldn’t understand it. I have a tax preparer with 50+ years experience and was a former IRS agent, and this person is not savvy enough in tax strategies…in my opinion.

I can input my age and personal financial data into AI to get a hint of suggestions, but yet when I read the advice of well known professionals (I won’t name them) on the web, I get different recommendations. Seems to be a catch-22 and all you can do is all you can do.

DAN SMITH
2 months ago
Reply to  Olin

Olin, I have known a few preparers who claimed to be former IRS agents, but were actually no more than telephone customer service reps for the service.

Olin
2 months ago
Reply to  DAN SMITH

This person does have their IRS credentials framed on the office wall. Hope it isn’t a fraudulent certificate, and they were a former Special Agent…if that has any bearing.

normr60189
2 months ago

Good job. It is likely that if we invest consistently over long periods of time that we’ll earn 5% or more on our money. Within that context of consistent investing what would be a mistake? Over reliance on bonds at an early age could be one. Trading rather than investing is another.  Inertia is yet a third. Improper allocation is a fourth, and so on.

Today, some are willing to continue to let their stocks ride, ignoring the impact of a 30-40% decline on their stock portfolio. Such a decline could erase 5 years of gains. Saying “I could handle that” would be a mistake for many of us who could not bear white knuckle stock declines.

The WSJ ran an article “Meet the teens investing in stocks for their future home and retirement”. There have been similar articles in the past, but many of these “investors” bail when the bear market or a sharp downturn occurs. As I recall earlier articles indicated how young investors became disillusioned by the 2021-2022 downturn. 

Today, after the S&P 500 nearly doubling in 5 years, there is a lot of interest in the stock market. Buying at the top is a mistake, unless one is willing to hold for 10+ years. That could allow a recovery.

Individual stocks can also be a trap.

Today with a handful of tech concentrated stocks dominating the S&P 500 this is not the index I remember.

Last edited 2 months ago by normr60189
Patrick Brennan
2 months ago

Great post Dan, thanks. We’ve all made mistakes investing. In my view, investing is about the future, and because we don’t know what the future will bring us, we’ll always find ourselves in situations where we could have done better. I’ve been trying for some time to evaluate my decisions based on the information I had at the time, not the information I have after the fact. But that’s not easy. The worst mistake I made was trusting an advisor who sold me front end loaded mutual funds and whole life insurance when I was single. It was my first effort at investing and I had to learn the hard way the concept of the sunk cost fallacy. That fallacy made for several years of inertia before I finally exited those two bad decisions.

Patrick Brennan
2 months ago
Reply to  Dan Smith

Thanks Dan!

Oscar Barbarin
2 months ago

It is reassuring to hear about mistakes and lessons learned. It makes me feel a little better that I am not the only one who made many mistakes along the way to finding out that simpler is better. For me the lessons learned like many of you were:

  1. The most sure way to accrue resources is to SAVE, SAVE, SAVE. Live below your means but still enjoy life. Avoid debt at all costs.
  2. Build core long term investments around low cost passively managed funds. Don’t be to fancy or complicated: 2-4 funds should do it.
  3. If I need the funds in the next year or two, money markets or CD’s is the option. If definitely needed in 2-4 years bonds are a decent place to park it. Anything beyond 5 years in equity fund
  4. Although I have bought into the idea that I should stick with funds rather than individual stocks, I get tempted by what I thing are attractive opportunities. Sometimes I feel a need to implement an investment idea that I think will do well over time: biotechnology, dividend growing companies, a well run company that has a moat but is underappreciated by the market. I hold firmly to the “only funds” strategy for my retirement finances. For my Roth which I intend not to spend from but to leave to my heirs, I still give in to these temptations but restrict these to less than 20% of the total. So far this has worked out well.
  5. My last lesson is that it is very difficult to impart these lessons to my family. For them it seems like they have to go through their own cycle of mistakes.
  6. Places that grow and develop human capital are attractive . Don’t restrict investment to the domestic market. Over a 30-40 year period that my kids and grand kids will be investing places like India and Africa will experience growth and provide handsome returns if patient.
Oscar Barbarin
2 months ago
Reply to  Dan Smith

Thanks for your supportive comment. You are right that it may time for the lessons learned to manifest themselves. I will check out the Winker book.

Fred Beck
2 months ago

We all have made mistakes.

But over time, dollar cost averaging uniformly reaps benefits.

Edmund Marsh
2 months ago

Thanks for your story, Dan. It seems most of us here have arrived at a similar destination, though we may have started from a different point and followed a different route. I’m thankful I stumbled on indexing before I got too far into the weeds.

David Lancaster
2 months ago

I started my self investing journey in the late 90s when I left a job and had to roll over my retirement accounts. Luckily I discovered Vanguard and John Bogle. Ever since I have followed their philosophy and as a result I have been saved from making bad investment decisions.

baldscreen
2 months ago

Thank you, Dan, for sharing this. I am sure it helped some of our young friends. It helped me, as we made a lot of mistakes along our way too. But it all turned out ok in the end. As I learned more, we did better. Chris

Gary Klotz
2 months ago

Good post.

Many kinds of personal investing journeys can lead to the final destination of a financially secure retirement.

Trial and error, including a variety of investing errors, can provide experience that can result in future knowledge and success.

In a decades-long investing journey, a perfect record or a completely optimized plan is hard, if not nearly impossible, to achieve.

Yes, just do it: save and invest regularly, focus on the long-term goal, make reasonable asset allocation and asset location decisions, stay invested, and let compound interest work for you over time.

congratulations on your successful journey and for sharing your personal experiences.

Mark Crothers
2 months ago

The tortoise eventually beats the managed fund hare. I ran my business for nearly thirty years, and many times I had no clue what to do and needed to think deeply. But I can tell you—in some ways, that was easier than trying to figure out what on earth to invest in for my retirement accounts. The market was opaque and difficult to understand in the 80s and early 90s, but eventually I discovered the simplicity of indexing.

Bogdan Sheremeta
Admin
2 months ago

I love your story! Just have to stick to your plan & think long term. Thanks for sharing!

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