Fender's final approach to retirement.

[fenders53]

(08-09-2021, 01:40 PM)crimsonghost747 Wrote: A little thought on the whole screen time thing.
I know options are a pretty big part of your cash flows. And that might cause some issues.

Now I know that you will find yourself trading during your retirement too. Sometimes you just get bored and let's face it, options can be fun. At least when you get them right. But I would really love to see you in a situation where the other streams of income are enough. This is just so that trading is indeed a fun hobby you do and your monthly income or even your splurging money is not dependent on it at all. Then, and only then, will it truly become a hobby and you can put it down if you feel like it and go fish for two weeks without a worry in the world.

If options/trading are a big part of your monthly income, you will think about those on your 2 week fishing trip. Or at least that happened to me a couple of times during my year off when I made it a mission to survive on investment income alone.

Honestly I think that during retirement you should be able to spend what you want without worrying about the money. I know this is more of a dream than reality to most, but that's how it should be. Same goes to where that money comes from - it should be on autopilot. Doesn't mean you shouldn't trade, but you should trade because you want to trade, not because you want more money.

These are just my own feelings. As you might remember I had a "mini-retirement" and I honestly didn't know if I was ever going to come back to work. But I quickly noticed that I wasn't enjoying it as much as I could have been because I was worrying about finances. So a few more years of work and more predictability into my cash flows and then I'll consider retiring again.

I failed to adequately respond to this.  You really have nailed down many of my concerns.  

Options are indeed a huge part of my port income.  I've traded them for decades but put them through a real three year test.  Fortunately there were a couple hard market dips so I am confident I understand the risk reward.  35% of my port routinely yields $3K/MO.  $4K+ perhaps three times a year.  A sustained down period like fall 2018 and it can be months of sub $2K because you are forced to buy shares in a downtrend and the capital is tied up.  The key of course is to make sure 80% of these companies pay a decent dividend so the income stream is not completely turned off.  SPEC stocks pay huge option premiums so it requires a lot of discipline to only have a few of those open at once.  

You are right I have to work around vacations or I will think about my investments.  It's not too hard to lighten up before I leave, and make sure overly speculative contracts expire near my dates.  Being forced to buy some discounted JNJ shares isn't the same as a high flying SOFI or ENPH contract.  I have sold them often enough to know it's a matter of time before I would get bit.  A majority of the SPACs are still down 50% this year.  The reality is until we have a correction even my DGI blue chip type put sells aren't as safe as they were a few years ago.      

The real challenge is going to re-allocating my portfolio in a timely manner.  Glad I am starting now.  I'm not comfortable buying a huge quantity of SPY or any other ETF right now.  I need to make progress though so I will gradually sell puts on the indexes until I get some shares.  At least I will get some income in the meantime.  Infrastructure package is likely to keep inflation high and the FED can't wait forever to address it.  The markets are going to get rattled at some point.  I'm invested enough while I wait.