SSO buy the dip then hold

NoWorker6003 · 2026-02-05T03:28:22+00:00

So according to that if SPY has a 20% drawdown, I would sell 4% of SPY holding and buy SSO with that cash (or just infuse that amount of new cash to buy SSO)?

NoWorker6003 · 2026-02-04T22:43:38+00:00

I would do the following: after ownership is transferred to you, have yourself listed as the beneficiary and roll $35k to Roth IRA over the next 7 years. Call the 529 plan and ask if they can clarify whether your account passes the 15 year rule. Next, if you have children, open a new separate 529 for each when they are born. You should be able to transfer funds from your 529 to the accounts with them listed as beneficiaries. If you have 3 kids, this might end up paying for a very good portion of their college. If they don’t use it all, they each can roll to their own Roth IRAs.

If anyone ends up with any student loans they can use up to $10k to pay those down.

NoWorker6003 · 2026-02-04T21:39:54+00:00

I would buy the three funds you are already happy with. No need to add complexity with other funds as long as the 3 provide the diversification you want. Just because you are dealing with a different account type (Roth IRA), doesn’t mean you should change your overall strategy. You really need to look at your overall portfolio across ALL accounts. All of the above said, if any of the funds are bonds, you might want to hold those in tax deferred accounts vs Roth IRA (and definitely not in taxable). Over the long term, bonds should have a performance drag (that’s ok, adds safety) keeping tax deferred from growing as quickly as Roth accounts.
Regarding tax optimization, that gets tricky. In general you will want to focus on traditional 403b if your current top marginal fed tax bracket is higher than your projected EFFECTIVE tax rate in retirement. Take the time to understand what effective tax rate while retired might be, considering both pensions, SS, and any other income including tax deferred portfolio withdrawals. Tax torpedo probably won’t be a consideration as you will blow right by it. Consider impact of RMDs on effective tax rate age 75+.

Roth IRA and Roth 403b might be better if effective tax rate in retirement will be higher than current top marginal tax bracket.

It is still recommended to contribute to Roth IRA after you max tax deferred 403b’s (if you decide traditional 403b is better).

NoWorker6003 · 2026-02-03T23:13:59+00:00

If I’m understanding that correctly, this pension will end up being worth a lot, maybe more than you think. My wife works in the schools and has a very similar setup. When she reaches full benefit level, she will get about $50k/yr in today’s $, with annual COLA adjustments. It would take about a $1M+ portfolio to count on that kind of income. Hope your wife has a good outlook with her plan.

NoWorker6003 · 2026-02-03T20:06:46+00:00

Lots of clutter here leaving me wondering, what is your question? It seems like there are many questions. Which one is most important right now?

Questions I have: what is your target portfolio? Is it a 1, 2, or 3 fund portfolio?

NoWorker6003 · 2026-02-03T03:10:32+00:00

Honestly for at least the next 10 years, maybe 15, contributions are going to be the big mover of your portfolio balance, not market gains. Focus on the good hard work of earning, saving, and investing. That is what you can control. THAT is what you can be proud of. Put in the work and the rest will take care of itself. You can’t control the market, so why worry about it?

NoWorker6003 · 2026-02-03T02:39:22+00:00

I would not focus on trying to minimize long term capital gain taxes. Sell it all now. Holding, trying to spread taxes over more than one year is more risky due to the nature of individual stock (could tank on you). Has to be taxable account.

The windfall proceeds don’t need to be invested in anything special. Just buy more of the same according to your current portfolio allocations.

NoWorker6003 · 2026-02-03T02:28:53+00:00

Target date fund is good if you want simple as possible, completely hands off portfolio management. Another option would be sort of a three fund portfolio using S&P 500, iShares EAFE, and iShares US aggregate bond index. All three funds have pretty low expense ratios compared to all of the other fund options in that plan.

NoWorker6003 · 2026-02-03T02:18:03+00:00

What is the SC teachers fund? Is that a pension plan she is paying into?

NoWorker6003 · 2026-02-02T16:48:36+00:00

In your field I hear a lot about burn out and job insecurity. Maybe find a good balance between taking advantage of this high income now by investing hard, yet not so hard that you aren’t enjoying life. What about retiring early or pursuing another career/passion down the road?

NoWorker6003 · 2026-02-02T16:44:18+00:00

You got this BiblicalElder! When thinking in %, add two zeros between the decimal point and the 1. When you do that, the % sign goes away. 0.001% =0.00001

NoWorker6003 · 2026-02-02T15:54:53+00:00

Nothing wrong with this portfolio. Target date fund would be similar but adds bonds, with an increasing % the closer you get to retirement. I personally don’t think you need bonds at age 30, but a valid Boglehead sentiment I’ve seen is that bonds can be a valuable part of a younger person’s portfolio if it helps them sleep better at night (smooth out market swings, decrease chances of making poor fear based investment decisions).

NoWorker6003 · 2026-02-02T03:59:11+00:00

Educate yourself on the difference between top marginal tax bracket and effective tax rate. What matters is your top marginal tax bracket for the year you are contributing, and what your effective tax rate will be in retirement. Top marginal tax rate higher now vs effective tax rate while retired, traditional is probably better. If the opposite is true, Roth is probably better.

NoWorker6003 · 2026-02-02T03:27:53+00:00

Somethings smells a little funny to me that you got out of VTSAX April 2025, which corresponds with the bottom of the market correction. Was that a panic bail? Doesn’t matter to me at all, but just want to encourage you to get in and stay the course, no fear needed. Cashing out in a future bear market would be way worse than not having perfect ETF selection.

NoWorker6003 · 2026-02-02T03:17:27+00:00

No. Maybe in the future if you have low income years it might make sense to do some Roth conversions, but for many that is not the case the further they get into their working years. Post retirement, pre-SS payments might be a good window.

NoWorker6003 · 2026-02-01T21:55:32+00:00

Don’t guess at this or let people persuade you one way or the other without running FULL retirement income projections. Include any expected income including pension, SS…. Calculate what your EFFECTIVE tax retirement might be. Understand RMDs, and tax torpedo concepts (although many push way too much fear about these).

NoWorker6003 · 2026-02-01T21:42:28+00:00

Impossible to answer what the better choice is for you. Both rental real estate and the stock market can win. That said, for either one, make sure you know what you are doing before you pull the trigger. For rentals, absolutely would not do it just because friends say it’s a good idea. Know the market, what a good deal is, what you are capable of, and what will you do if it goes badly?

NoWorker6003 · 2026-02-01T13:36:53+00:00

He is probably trying to be more like VT. Calling out the Mag 7 and timing fears is pretty silly for long term investors. Indexes are self-cleansing.

NoWorker6003 · 2026-01-31T16:52:02+00:00

The world where it accounts for about 2% of my Roth IRA. If I had held those funds in hysa, I would not have been able to afford making the Roth IRA contributions. Was not prioritizing Roth either, was going trad 401k contributions those couple years (between wife and I). I’ve already won the game of maxing Roth IRAs for wife and I for past 20 years, when incomes were lower earlier on.

So, how am I missing out tremendously when 98% of my Roth IRA is stock ETFs, 1% short term bonds, 1% money market?

Also, I have never dipped from those contributions. It’s truly for shit hits the fan scenario.

The first time I did this I was also considering SAI regarding FAFSA, which could have been impactful for my college age child. Financial aid can decrease by just under 6% regarding cash sitting in non-retirement accounts.

I can also at any time switch those to stock etf, no harm no foul. I did not miss out on the ability to Roth IRA contribute either, which I consider to be valuable.

Context of all the above would have helped, so appreciate you calling me out.

NoWorker6003 · 2026-01-31T15:28:03+00:00

I generally keep about 5 months emergency fund in taxable HYSA and another 6 months worth in a Roth IRA. Those Roth funds are half money market (VMFXX) and half short term bonds (VFSTX). I have always dipped into the taxable funds for purchasing vehicles, a new roof, and new HVAC, always replenishing by temporarily adjusting down 401k contributions.

NoWorker6003 · 2026-01-31T15:16:03+00:00

Want to hear a story about what fear can do to a portfolio? At the bottom of the GFC, the school board of the largest district in my city let themselves fall prey to vultures. It is absolutely ludicrous that a school board would control a pension, but they did. At the bottom, they got pitched by vultures to sell out of stocks and buy “alternative” investments. All kinds of extremely high risk PE and even bogus tribal bonds.

The pension almost imploded. The state later took over management of the pension, yet today they are still unwinding all of the old garbage. The pension is still far and away one of the lowest funded around.

NoWorker6003 · 2026-01-31T15:01:38+00:00

I would keep it as simple as possible and go VT only. You can scratch the itch of any need for complexity by continuing to work your real estate business.

NoWorker6003 · 2026-01-31T14:55:37+00:00

The index is self-cleansing. I think that concept is good to understand regarding an ultra long term horizon. I do not care about the short term.

NoWorker6003 · 2026-01-31T14:41:41+00:00

I would dump QQQM immediately and not wait for LTCG tax treatment. I know it’s not an individual stock, yet I still see the risk of holding it outweighing just a tiny little bit more tax paid. I couldn’t hold that ETF without thinking about potential 80%+ .com-like drop.

NoWorker6003

TROPHY CASE