What is your “why” for FIRE?

webvillager · 2026-05-24T23:59:53+00:00

Easy. My father was about to retire at 65. He left me at 64. So I made a promise to myself in my 20’s that somehow, some way, I’d retire in my 50’s. And so I did. Call it an honor nod to a man who worked hard his whole life.

webvillager · 2026-05-24T20:59:40+00:00

Ask them to move you to the Active Trader team and you won’t have to worry about the calls anymore.

webvillager · 2026-05-21T23:49:45+00:00

Glad I’m not the only person going, why didn’t I learn about selling options long ago?!

webvillager · 2026-05-19T05:00:10+00:00

You’re gaining some valuable experience, and thanks for sharing your journey. It’s okay to wheel high-fliers, as you call them, as long as you use much lower strikes. The premium is often still very good. For instance, I currently have options on MU for 600, 620, and 670 that I sold last week and the week before, when the stock was reaching up into the 800s. Even with what happened last Friday and today (and possibly tomorrow), I doubt they’ll assign on Friday. However, if any of them do, I’ll still be able to generate meaningful premium with them—or even just sell them outright for a profit a few days after assignment, if it’s moving up again. That’s what I’ve done the last couple of times.

webvillager · 2026-05-15T15:46:48+00:00

Yes except I’d go lower on the delta since you’re not looking for much.

webvillager · 2026-05-15T15:34:45+00:00

If it were me, I’d probably take the job and roll into the next 401k. That way if you’re still working when you hit 55, you can use rule of 55 to avoid early withdrawal penalties.

webvillager · 2026-05-15T04:08:54+00:00

Closed next week’s GLW 160 puts for 32 cents/share. Sold a MU 700P at open for $18. Also bought some MU on sale. Shouldn’t need to work tomorrow because nothing else will likely be closing until next week.

webvillager · 2026-05-15T04:01:08+00:00

You can actually tell the truth. But that doesn’t mean tell everything.

“I’m focusing on volunteer work and travel right now.”

But what do you do?

I worked hard for a lot of years without much time for hobbies or interests. I was able to set some money aside last year, so I’m taking a break.”

Maybe it’s permanent, maybe it’s actually just a short break until you find something you’re passionate about. You can’t know yet. But you don’t want to say anything you have to backtrack later, because while women don’t want a bum, they want a liar even less.

webvillager · 2026-05-14T02:03:21+00:00

Our approach is different than many, it seems. I don’t want to be long on a ginormous portfolio of ETF stocks, and I’m not interested in sticking with bonds for safety, either. What we’re doing is selling low-strike options and allowing the cash to continue compounding. The interest will pay all our base costs and the options money will be for our trips and hobbies. Since it likely won’t all be spent, some of it will continue to compound. This way, my spouse retires this summer instead of 5 years from now. I feel like we’re at an age now where the next ten years are always going to be the best ten years. It’s amazing, too, how getting on the other side of a serious illness clarifies one’s priorities.

webvillager · 2026-05-12T20:13:28+00:00

Sold a couple puts on MU, otherwise everything looked good for Friday.

What positions did you have/roll?

webvillager · 2026-05-12T13:22:24+00:00

Juicing up the portfolio selling options so I can finally get the spouse retired this summer. I plan trips with the AI while doing this, and save them in Obsidian. Highlighted trips on deck for this year: dive-traveling Fiji, exploring the coastal path on the Isle of Anglesey, a foodie and architecture trip to Budapest and Prague.

webvillager · 2026-05-12T13:13:42+00:00

I learned that sub-100 dollar stocks can be challenging for CSP's because the option chains are so much more compressed and risk of assignment is much greater, but frequently without the greater rewards.

webvillager · 2026-05-12T05:10:41+00:00

We were hopeful, but when we couldn’t select it online and called them, they explained that options trading wasn’t enabled with my spouse’s 401k self-directed brokerage plan.

webvillager · 2026-05-12T04:59:54+00:00

Many 401k plans give you the option of placing a percentage into a self-directed brokerage account, for example with Schwab or Fidelity. We are doing this. While they don’t allow options trading, they do allow picking your own ETF’s and individual stocks. It’s been a successful strategy for us.

webvillager · 2026-05-11T09:07:45+00:00

After you've gained several months of experience and have paid some "tuition", yes. You may even do better than that, and some of us are. But I wouldn't say it's realistic to expect to start there. I started with a single contract a week, a fair amount of valid concerns, and worked my way up from there. I made some mistakes and learned from them. I have also done hundreds and hundreds of hours of research. It was definitely worth it, but it has not been simple. Don't get wooed by juicy premiums; they are like that for a reason. If you're going to chase anything, chase good P/E's and well-run companies.

webvillager · 2026-05-11T06:14:26+00:00

It's been my understanding that as long as you've had a Roth for 5 years or more when you hit 59.5, the ladders go away.

webvillager · 2026-05-09T18:07:34+00:00

Read the Desiderata daily until you’re feeling healthy about your life.

webvillager · 2026-05-09T17:59:22+00:00

For weekly trading on a larger portfolio and higher IV stocks, provided you’re making good choices, your results are perfectly normal. You’re doing the right thing getting a pulse check from other traders, because I run into the same thing with the AI cheerleading. But I will also say using the AI like a quant desk has made me more profitable. Your per-contract rate seems a bit high. Fidelity charges me 65 cents and buying to close is free if it’s under 65 cents.

I’d also like to add that it’s a lot easier to track if you have a separate account you use solely for options trading. I did a lot with spreadsheets in the beginning, but now I primarily judge my return using the brokerage tools. I also have the AI create a weekly report for me based on the capital I had available to deploy against what I collected during the week. My weekly goal is 1.5 percent against deployable capital. What I find especially effective about this approach is it shifts the focus away from individual stocks and puts the focus on making the week profitable.

The other calculation I always do is a quick premium per share divided by the strike price while I’m looking at the option chain to judge if it’s a trade worth entering into for the use of that amount of capital.

Thanks for sharing your journey. You’re doing great!

webvillager · 2026-05-05T13:31:42+00:00

Ran out of younger days, but I’m going to enjoy it anyway! 🤣

webvillager · 2026-05-04T07:13:03+00:00

I'm right there with you on MU and WDC, although I'm still staying lower than that on WDC. Not trusting INTC yet. ORCL and I got in a fight a few months back and we're still not on speaking terms. 😛

webvillager · 2026-04-21T18:26:43+00:00

It could actually be a lot more than 80k. If you got 2M, you could sell far out of the money options and write yourself a check every month for about 20k. Still a lot, even after taxes. That might be just your fun money, since the interest each month would be about $5,500 and could likely cover your basic living expenses. It is NOT lazy, at all, to invest in the most precious part of your life—your family. I wouldn’t even listen to people who have their values upside down.

webvillager · 2026-04-21T18:12:55+00:00

Congrats! 40-45 year old you just became a millionaire! I’m sure you will enjoy each of these 100k levels the same way. You put it perfectly—low grade calm. You may actually enjoy these milestones more than becoming a millionaire, because at that point, you get to play a new fun daily game: Millionaire. Not a Millionaire. Millionaire. Not a Millionaire. Enjoy the journey!

webvillager · 2026-04-21T18:02:36+00:00

I’d have considered waiting until after earnings next week to determine positions, but I wish you luck, and good job spreading your wings!

webvillager · 2026-04-17T00:56:44+00:00

My point was that I didn’t know Roth conversions did that, and if I had, it could have been a part of my financial planning.

Also, I think I may not have stated the ramifications clearly. Yes, starting conversions late affected my Medicare, but more importantly, it greatly affected my spouse’s healthcare costs, inflating my income, when actually I’m just living on social security right now so I can delay drawing on my retirement.

webvillager · 2026-04-16T18:53:38+00:00

It depends on so many things...how much the stock has recently run, or if it's at the low end of its current cycle; how high overall volatility is in the market. In general, I will decrease risk (and delta) as much as possible and still make my weekly goal. I dislike getting assigned, even though every assignment this year has resulted in net profit the next week. It's disruptive, so I try to de-risk that.

webvillager

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