Why I run the options wheel (and how it broke my last spreadsheet)

I got into options partly out of curiosity and partly because I wanted a more active role in my investing. I have two halves that don’t fully agree. One of them just wants to VTI and chill, buy the index and never look at it again. The other one wants to be doing something, constantly.

The wheel is what finally satisfied both.

Gun shy, for good reason

For a long time options scared me off, and honestly for the right reasons. If you spend any time on r/wallstreetbets you see the loss screenshots: accounts down 90% overnight, the calls that went to zero, the person who bet the mortgage on weekly options. That stuff made me gun shy. It looked less like investing and more like a casino with a worse dress code.

So I wanted in on the activity, but not like that. I wanted a way to be active without handing my portfolio to a coin flip.

The wheel gave me both halves

That’s how I found the wheel, and it fit me almost perfectly. It satisfied both of my competing desires at once: I wanted to manage risk, and I wanted to be more active. The wheel let me do both.

The appeal was concrete:

I could pick high-quality stocks I actually wanted to own. Selling a cash-secured put means committing to buy something, so it forces you to only sell puts on companies you’d be happy holding.
I could control my entry. Instead of buying at whatever the price is today, I set the strike where I’d be glad to own the shares, and get paid to wait for it.
I could harvest premium the whole way. Whether or not I got assigned, I was collecting income for showing up.

It gave me what I wanted. Risk I could reason about, a job to do every week, and premium landing in the account along the way.

Then the tracking fell apart

Here’s where it got frustrating. The strategy worked. Keeping track of it by hand did not.

The wheel isn’t a series of independent trades. A put, its assignment, and the covered calls you sell afterward are all one position, one story. To know what that position is actually earning, you have to link those legs together and roll every premium you collect into a running cost basis. Do that across a few tickers, with rolls, and a spreadsheet turns into a second job.

Worse, my brokerage statement was quietly lying to me. It showed a cost basis that ignored all the premium I’d collected getting into a position, which meant it was understating what I’d really made. I was more profitable than the statement said, and I couldn’t easily prove it.

Seeing what the wheel actually earns

That gap, between a strategy I loved and a spreadsheet that couldn’t keep up, is exactly why the options wheel tracker exists in Telemetry. Every put and call links into cycles, premium rolls into a real adjusted cost basis, and each cycle’s profit gets measured against the collateral it ties up, so I can finally see what my broker won’t show me.

If you want the mechanics of the strategy itself, I wrote those up separately in the options wheel, explained. But the short version of my own story is this: the wheel gave both halves of me what they wanted. I just needed a way to see the real numbers behind it.