Income Investing Results

I would not make that assumption for everybody who is highly educated...

I have a niece who is a lawyer and got a job with a city... she had the option to get into a really good pension plan but she thought she was just there for a year or so... well, 5 years later she is still there and cannot get in... a horrible decision.. my sister just did not teach her kids anything... OH, another decision I find bonkers is that she makes minimum payments on her student loans... just does not care how much interest she is paying...

I have heard horror stories from others out there that have advanced degrees or jobs...
Just being well educated or even "smart" doesn't mean one knows how to live life well. It's sad to see folks you'd think should have life figured out screwing things up when they don't have to.
 
Finally watched a short video on selling covered calls. Sort of dumbfounded by how simple it is but I feel like I'm still missing something. Is the worst case scenario that your calls expire worthless (meaning you're out nothing?) but you pick up the call premium which is paid as soon as you execute the trade?

I was always under the impression if you did calls or puts you had to hit your strike price or your options expired worthless and you were out the entire amount paid for the contract.


Seems like it's basically free money to do 5 - 10% over the current price calls one month out. If your shares are called you get the up front premium along with the 5 - 10% gain. If nothing happens or the stock even goes down you still get paid the premium and aren't out any money beyond the drop in value of your shares that would have happened regardless.
The "worst case scenario" with covered call options is that the price of the shares will shoot up astronomically and you will have already agreed on a lower price to sell your shares. In that sense you have a "loss" but only if you weren't happy with the profit you booked even though if you were a prophet you would have known to avoid that covered call option. In my experience, based on my methods, that is rare. I just move on when that happens and invest the proceeds in another optionable stock.
YTD I have had 847 contracts expire (mostly covered calls, but a few cash covered puts) and none of the contracts have been called. Total income of $128K YTD makes it worth the "worst case scenario" if it does happen.
 
Finally watched a short video on selling covered calls. Sort of dumbfounded by how simple it is but I feel like I'm still missing something. Is the worst case scenario that your calls expire worthless (meaning you're out nothing?) but you pick up the call premium which is paid as soon as you execute the trade?

I was always under the impression if you did calls or puts you had to hit your strike price or your options expired worthless and you were out the entire amount paid for the contract.


Seems like it's basically free money to do 5 - 10% over the current price calls one month out. If your shares are called you get the up front premium along with the 5 - 10% gain. If nothing happens or the stock even goes down you still get paid the premium and aren't out any money beyond the drop in value of your shares that would have happened regardless.
I did covered calls once upon a time. It is far from free money, given the capital risk. Am not posting to dissuade anyone but here is what can happen. Obviously the downside risk is much greater than the upside. If a bear market occurs or simply some of your inventory of covered call stocks start to crash, you can only roll out the call options so much, and collect so much on premiums. You may find that the inventory of stocks for which you have covered calls are becoming the worst stocks to own, and that you are having to select lower and lower strike prices for longer and longer expiration periods, even LEAPS. Maybe a partial solution is to pick stocks that seem unlikely to go substantially down, though they will have less appealing premiums. Not sure. But it is not free money, though for a while it may seem so. I use to relay it was the best thing since sliced bread...until it wasn't.
 
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Yes, I wish I could turn back the clock. Money takes care of itself, but you can’t fence time. Even now at 62, I am getting anxious about how many more adventures I have left in my body. Big reason why a bought a new bike. Only so many more climbs in my legs.
This is my view and thoughts as well. I'm hoping for more years and would be fine with less money. I want more time to do all the things that I love to do. Can't buy back time!!
 
… If a bear market occurs or simply some of your inventory of covered call stocks start to crash, you can only roll out the call options so much, and collect so much on premiums. You may find that the inventory of stocks for which you have covered calls are becoming the worst stocks to own, and that you are having to select lower and lower strike prices for longer and longer expiration periods, even LEAPS. Maybe a partial solution is to pick stocks that seem unlikely to go substantially down, though they will have less appealing premiums. Not sure. But it is not free money, though for a while it may seem so. I use to relay it was the best thing since sliced bread...until it wasn't.
I agree especially if you sell put options and end up keeping crappy stocks that just don’t recover. I have lost thousands of dollars on one stock or ETF, which is hard to make up by selling options with only hundred dollar premium each.
Some stocks and ETFs seem unlikely to go substantially down as you say and can even recover fairly quickly. Also stocks/ETFs that I wouldn’t mind holding long term are my option plays these days, e.g., WMT, XLE, BJ, ARM, SMH.
 
I agree especially if you sell put options and end up keeping crappy stocks that just don’t recover. I have lost thousands of dollars on one stock or ETF, which is hard to make up by selling options with only hundred dollar premium each.
Some stocks and ETFs seem unlikely to go substantially down as you say and can even recover fairly quickly. Also stocks/ETFs that I wouldn’t mind holding long term are my option plays these days, e.g., WMT, XLE, BJ, ARM, SMH.
Same thing as selling naked puts, or if prefer cash covered if sounds better. But good luck to all.
 
Agree with all of you. Great idea educating the kids over time. All assets are in a Revocable Living Trust at present but there are no specific directions as to how the assets are handled except that they pass to the beneficiaries. Guess it's time to call the Estate Attorney and talk about clarifying some things.
I would appreciatte a new thread on this topic of passing along the value of some
wealth management to future generations
I'm new and still figuring how to use this forum however quite clear that their are many like minded folk with major experience
I have been thinking about extending what I have I've learned about building and maintaining wealth to my kids, for last couple years
And I have mostly succeeded only in officially disturbing the chill amongst our go lucky family
You guys have highlighted the obvious start early,it takes lots of modeling ,and putting square pegs into round holes are stressful
Seems that Trusts can also get complicated for such goals
I really am thankful for all your time contribution to this valued forum
Sincerely
David /LTSTRYAGIN
 
End of the week status with Month End next week.
  • Div's on track for the month (~$9.6k)
  • Cost basis improved (from April month end) slightly. Almost no changes to positions so far this month.
Note that Cost basis includes monthly "paycheck" distribution/withdrawal. Will decide on investments of remaining div's at month end.

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Actual + Forecasted for 2025 slightly up (~+$3k)

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Flieger
 
A question comes to my mind, and I hope I can ask it here --

How would a 'Dividend Strategy' like this compare to some of the Annuity products ?

I confess to a limited understanding of Annuities. My DW inherited some a few years ago, and we're still trying to figure out what they are.
She also inherited a ton of Merck, which throws off a nice Divi (currently re-investing this). She's got Verizon and T also re-investing.

Would there be Income Taxes on the Dividends ? Are they Qualified Dividends ? Is there an upper limit to the Income you can draw ?
 
A question comes to my mind, and I hope I can ask it here --

How would a 'Dividend Strategy' like this compare to some of the Annuity products ?

I confess to a limited understanding of Annuities. My DW inherited some a few years ago, and we're still trying to figure out what they are.
She also inherited a ton of Merck, which throws off a nice Divi (currently re-investing this). She's got Verizon and T also re-investing.

Would there be Income Taxes on the Dividends ? Are they Qualified Dividends ? Is there an upper limit to the Income you can draw ?
Most domestic equities pay qualified dividends, which along with long-term capital gains, are taxed at lower rates of 0% or 15% for most people depending on their income level. Merck, Verizon and T would be qualified dividends.

A dividend strategy is commonly selecting stocks that pay higher than average dividends. While it is popular among retirees because of the higher income, the total return of dividend stocks are not better than stocks in general.

Annuities are a totally different animal.
 
I did covered calls once upon a time. It is far from free money, given the capital risk. Am not posting to dissuade anyone but here is what can happen. Obviously the downside risk is much greater than the upside. If a bear market occurs or simply some of your inventory of covered call stocks start to crash, you can only roll out the call options so much, and collect so much on premiums. You may find that the inventory of stocks for which you have covered calls are becoming the worst stocks to own, and that you are having to select lower and lower strike prices for longer and longer expiration periods, even LEAPS. Maybe a partial solution is to pick stocks that seem unlikely to go substantially down, though they will have less appealing premiums. Not sure. But it is not free money, though for a while it may seem so. I use to relay it was the best thing since sliced bread...until it wasn't.
Agree it is not a free money and require some work to be done. But there are strategies designed to reduce downside risk you're talking about. One approach could be to limit downside of your option by -10% for example and close it at the moment it crosses that point. Then initiate another call for the same or different stock with more realistic strike price. Some part of premium would be lost on closure fee, but it may be still better in the long term than allow it to get further down.
Overall, it is the same approach for any investment style: do not own a junk which is expected to fall on you.
 
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A question comes to my mind, and I hope I can ask it here --

How would a 'Dividend Strategy' like this compare to some of the Annuity products ?

I confess to a limited understanding of Annuities. My DW inherited some a few years ago, and we're still trying to figure out what they are.
She also inherited a ton of Merck, which throws off a nice Divi (currently re-investing this). She's got Verizon and T also re-investing.

Would there be Income Taxes on the Dividends ? Are they Qualified Dividends ? Is there an upper limit to the Income you can draw ?
I don't have any annuity investments, and have generally been avoiding even looking at them due to the negative attention they generally get. I should probably have a better understanding and response.

A dividend strategy is commonly selecting stocks that pay higher than average dividends. While it is popular among retirees because of the higher income, the total return of dividend stocks are not better than stocks in general.
This is true for the most part. One other aspect is that you are not selling the stock/etf at a loss during down cycles as we are in now. On the other hand, if you get to "greedy" (and I have done a little of that), you have a product that without reinvestment of dividends is at best break even or sometimes worse.

My particular "overall strategy" or plan, as outlined earlier, is to have a mix of Growth, Income and Short Term parts of my Portfolio. At the moment that mix is ~ 20% Growth, 60% Income and 20% Short Term. When I start SS sometime between now and 67 (about 4.5 yrs) I will reduce the Income as my income needs will change accordingly.

I post things like the above just to show one persons approach and how it is working out.

Flieger
 
I would appreciatte a new thread on this topic of passing along the value of some
wealth management to future generations
I'm new and still figuring how to use this forum however quite clear that their are many like minded folk with major experience
I have been thinking about extending what I have I've learned about building and maintaining wealth to my kids, for last couple years
And I have mostly succeeded only in officially disturbing the chill amongst our go lucky family
You guys have highlighted the obvious start early,it takes lots of modeling ,and putting square pegs into round holes are stressful
Seems that Trusts can also get complicated for such goals
I really am thankful for all your time contribution to this valued forum
Sincerely
David /LTSTRYAGIN
Hi LTSTRYAGIN -

I would suggest looking for that topic using the search feature in the upper right side of the leader above:
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If you don't find/see what you are looking for, start your own thread! :) People will be more than happy to provide their thoughts and experiences for sure!

Flieger
 
I explored trusts and they didn’t make sense for our transfer of wealth, but they could for others. It’s a rabbit hole onto itself and requires deeper discussions with legal folks as much as financial folks.
 
I rolled $415,000 in a IRA for a 72t two plus years ago and set it up in treasury bills and bonds for a guaranteed $25,000 yearly income withdrawal. Account has had $50k of withdrawals and currently has a bit over $406,000 in it. Does that count? Note that I still have a fair bit of other money in the S&P500 index. It has done well better than the $415,000, but it is nice to know we have that $25,000 every single year no matter what.
Hi new here. If roughly equal portions VTI as secondary income and a group of CEF’s for income in a TIRA. In 15 years, since the bank crisis, VTI has about tripled in value and CEF income has tripled churning excess to needs money back into selected CEF’s and turning present income needs cash flow faucets off and on depending mostly on present values, read premiums. I am also a buy and hold investor so very little if any trading
 
Most domestic equities pay qualified dividends, which along with long-term capital gains, are taxed at lower rates of 0% or 15% for most people depending on their income level. Merck, Verizon and T would be qualified dividends.

A dividend strategy is commonly selecting stocks that pay higher than average dividends. While it is popular among retirees because of the higher income, the total return of dividend stocks are not better than stocks in general.

Annuities are a totally different animal.
Thanks for clarifying my thoughts on these dividends.
DW's inheritance will probably be passed down to our next generation, as we don't need to tap into it at this time. That's why we're re-investing the Divis.
 
YTD dividends are $63,396. Estimated dividends for 2025 should easily hit $170K. I use Seeking Alpha to analyze my portfolio. There are some numbers in the following image (my traditional IRA only) that do not reflect true annualized estimated income. It appears that the ETFs are grossly under estimated. VYM is my largest holding and I know the VYM dividends are far more than $680 per year. My ROTH IRA is the second largest account and I'm working to make it larger than the traditional IRA using ROTH conversions.
2025-05-26_SeekingAlpha-WLW-IRA-Dividend-Analysis.jpg
 
YTD dividends are $63,396. Estimated dividends for 2025 should easily hit $170K. I use Seeking Alpha to analyze my portfolio. There are some numbers in the following image (my traditional IRA only) that do not reflect true annualized estimated income. It appears that the ETFs are grossly under estimated. VYM is my largest holding and I know the VYM dividends are far more than $680 per year. My ROTH IRA is the second largest account and I'm working to make it larger than the traditional IRA using ROTH conversions.
Some nice holdings there. A little less "risky" than my overall Portfolio (and obviously a larger investment). I hope to move more to this level of risk once I start my SS. Thanks for sharing Waynew!

Flieger
 
We’re at about $120,000 YTD. About half that is boring bond income and the other half CEF based. June and July are big muni interest months so by early July the total will be a little more juiced.
 
We’re at about $120,000 YTD. About half that is boring bond income and the other half CEF based. June and July are big muni interest months so by early July the total will be a little more juiced.

Yep, we are about $134,000 YTD. Likewise June and July are strong months and I will be reinvesting more then. Bad news - wife's Audi just failed!
You guys are rock stars!

Flieger
 
I'm a bit over $200k YTD taxable and tax-exempt investment income.

Looking at making a modest investment in TGT - Target. Currently yielding 4.7%. Stock price has been hammered since 2021-09. Target is my go-to place for misc household goods; no complaints.

A while back I bought some Intel in a relative's brokerage account. Had a high dividend yield and I figured that it was too big to fail. Not much later Intel halted dividend payments - ouch! This is why I'm not a day trader or speculator - would probably lose my shirt. :popcorn:
 
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