I’m a serial tinkerer with trading strategies, particularly in index options trading. In most cases, I’ll start with a simple concept and iterate from lessons learned along the way.

Each iteration is done with good intentions as I’m finding holes in the process and trying to fill them as I go along. I’m like a deckhand moving around the boat, patching small leaks with spackle.

This goes on for a while. And it happens slowly. But like compound interest, it grows stealthily… then mightily.

Unfortunately, I too often find myself in a situation where my PnL is going the wrong way and I’m suddenly handcuffed because I’ve created too many patchwork rules that are doing nothing now but causing confusion and slowing me down.

Then, frustration sets in.

Headlines.

We all read them and they mess with our heads. It takes steadfast resolve to listen to the message of price action when everything else we read tries to trick us into doing the wrong thing.

The best way to keep ourselves level-headed when taking risks is to define that risk and trade small. There are few things more powerful than knowing with complete certainty the most I can lose, no matter what the market throws at me.

With this in mind, we're putting on a trade today in a stock that has the potential to be a real highflier if the markets stabilize and head higher following any Washington drama while limiting our risk in case we're early or wrong.

It's been a good run for many of our bullish long trades. As such, it wouldn't surprise me if stocks took a bit of a breather soon.

And considering so many stocks we've been tracking are starting to look pretty extended, I'm going to go fishing in the weak stocks pond to find some opportunities for portfolio diversification in the event that stocks go sideways or dip a little bit in the weeks ahead.

One nice thing is the stock market lift this week has really zapped options premiums across the board. So today's trade offers us a somewhat rare opportunity to get responsibly short with long puts.

[9/7: stop moved to 260. We're already #FreeRiding on this one. So whatever we sell the remaining position for is pure profit!]

Today's trade leans against a significant support level that we believe will hold. But because the stock is at such a delicate level where it could quickly collapse on us if the level doesn't hold, we're going to keep the play simple and cleanly define our risks.

A picture is worth a thousand words, so here's the chart of Caterpillar $CAT that's got our attention:

[9/7: updated stop to 180. We're already #FreeRiding, so whatever we sell for is pure profit!]

It's time for the small caps to make a stand. The time is now. If they don't, it could be 'goodnight' for a long time.

JC posted earlier this week about the Russell 200 index and had this to say:

We’re back to a key level of interest for Small-caps on an absolute basis. And we’re back down to historic levels relative to Large-caps. The chart tells a very powerful story.

I’m a buyer down here.

If the Russell2000 is above last Summer’s lows, I will be long the $IWM ETF. I also think there will be plenty of opportunities this summer in small-cap stocks.

We talked about $IWM internally this morning and I suggested a good, levered way to play this thesis while honoring a nearby risk management level that will get us out of the trade without much pain if we're wrong.

But first, here's the chart of $IWM:

I make quick decisions.

Is that because I’m a trader? Or am I a trader because I make quick decisions?

Over time, I think I’ve come to the conclusion that being a trader has instilled in me a knack and preference for quick decision-making. I wasn’t always like this. 25 years of trading has taught me to work with only 75% of the information I might want, and that is good enough to take action.

The phrase “invest, then investigate,” as Stanley Druckenmiller said, comes to mind.

Outside of trading, this can also affect my day-to-day decision-making. I think it frustrates my wife when I make decisions so quickly. In her mind, she probably thinks I’m being irrational, emotional, or acting on impulse. She, in contrast, is very deliberate. Cautious. Analyzes every detail…

You might have seen some of my tweets about an impressive trader I met earlier this week. I felt the encounter was too good to keep to myself – so here’s the full story…

I had a truly profound experience at the traders meetup I hosted in Denver on Tuesday night, where I met a new trader who completely blew me away.

Despite only having about a year of experience trading real money, this young man in his early 30s had a depth of knowledge and understanding that was truly remarkable. He carried with him a notebook filled with detailed market observations, trading strategies, post-mortems on trades, and more. No detail was left unnoticed, and his passion for trading was evident in everything he said.

What was even more impressive was his humility. He was incredibly smart, but he didn't flaunt his intelligence or try to impress anyone with his knowledge. Instead, he was genuinely curious about trading and had a thirst for knowledge that was inspiring to see.

I imagine it’s not uncommon for people to realize sooner or later that the person they thought they were is not at all who they really are. Perhaps not even close.

Are you being yourself?

Think hard about this. And be careful. Because your conclusion might have important ramifications beyond your day-to-day daydreaming through life. It will also likely have significant impacts on who you are as a trader and how you approach your relationship with risk – even your courtship of success (or lack thereof).

Everyone’s path to personal discovery will have its own speed limit, hills and valleys, and complements of sharp turns and extreme weather conditions.

The visibility isn’t always clear. For me, the wiper-fluid that cleaned my windows and sharpened my vision was my elimination of alcohol from my routine.

This week will be an opportunity for me to practice the art of giving up control. It will also be an incredible opportunity to practice acceptance and patience.

The market is open and I’m typing this piece while traveling 30,000 feet above Midwestern corn fields en route to New York City.

Thankfully, I’ve got internet access on the plane and can keep tabs on the market and my positions. But it’s not perfect. Anyone who’s tried to work with airplane WiFi knows it isn’t always as reliable as we’d like it to be.

I’m headed to NYC to reconnect with the All Star Charts team, celebrate our friend Brian Shannon in honor of his recent book release, and attend the Chartered Market Technician’s 50th Annual Symposium.

All week, I’ll be gathering with some of the smartest market minds, driven traders, and portfolio managers around. I’m hoping to sponge as much great content and smart ideas as I can possibly cram into my cranium.

The challenge for me will be in managing my open positions — particularly my highly active index options trading.

Finally, a setup I love that has earnings out of the way! There's light at the end of the tunnel. And no surprise I find this setup in a strong sector that wants to lead the market higher.

We're going to leverage some cheap options to position for a breakout to 52-week highs in this big cap name.