When Do You Know Enough Is Enough?

A good friend of mine is in turmoil. He has an adult daughter struggling with serious drug addiction. What's worse, she has a six-year-old child with a drug-enabling boyfriend she was living with. This woman recently suffered a drug overdose while pregnant with a second child and was in a coma for nearly a full week. The baby died in utero.

The details only get worse from here. I'll spare you the rest.

My friend has been doing everything he can to help his daughter and grandchild get back to safety and on a good path. He's engaged professionals for support. He's paid for therapy. He's completely overhauled his work schedule and other commitments to be available whenever she needs support. He's gone above and beyond. And one of the main efforts was removing this deadbeat, drug-addled, abusive boyfriend from her life.

Everything had been going well enough.

Until it didn't.

She's back with the boyfriend. Putting herself and her child in harm's way once again.

My friend and his family are faced with a choice—is it time to write her off and move on with their lives, cutting off all support and contact until she can prove she's capable of making smart life choices?

Apples and oranges. I don't mean to minimize what he, she, and their family are going through. But my friend's saga reminds me of situations I've been in with trading strategies.

After I've done everything I possibly can to make a strategy work, at what point do I cut bait, turn the page, move on to something else?

When do I know enough is enough?

I wish the answer was as simple as: the strategy is losing money, so end it.

But sometimes it isn't that simple. A strategy might just be temporarily out of sync with the market. And pulling the plug just before it comes around and does exactly what I envisioned would be painful.

Giving up just before the reward. Ouch.

But continuing to pour resources—time, capital, emotional energy—into something that may never work? That's its own kind of devastation.

This is the impossible calculus we face. In life. In trading. In relationships.

How much is enough effort? When does persistence become stubbornness? When does faith in a plan become denial about reality?

I don't have a clean answer for my friend. How could I? The stakes are a human life, a child's welfare, a family's peace of mind. The variables are infinite and most of them are outside his control.

But in trading, I've learned a few things about this question.

First, I need to separate what I can control from what I cannot. I can control my position sizing, my risk management, my adherence to rules. I cannot control whether the market validates my thesis on my preferred timeline.

Second, I need to distinguish between a strategy that's fundamentally broken versus one that's simply experiencing unfavorable conditions. A broken strategy has a flaw in its logic or execution. An out-of-sync strategy might be perfectly sound but mismatched to current market conditions.

Third, I need to be honest about sunk costs. The money and time I've already invested in a strategy doesn't obligate me to continue. That capital is gone whether I persist or pivot. The only question that matters is: given what I know now, is this the best use of my resources going forward?

Fourth, I need to set clear boundaries before I'm in the thick of it. What are my hard stops? Not just price stops, but time stops. Drawdown stops. Psychological stops. If I don't define these in advance, I'll keep moving the goalposts and convince myself that just a little more time, just a little more capital, will turn things around.

But even with all these guidelines, there's still that gnawing uncertainty. What if I quit one day too soon? What if the very next trade would have been the one that validated everything?

This is where I have to trust the process more than the outcome. If I've followed my rules, managed my risk appropriately, given the strategy a fair chance under reasonable conditions, and it's still not working—then I've done everything I can do.

Continuing past that point isn't persistence. It's hope disguised as strategy.

My friend is facing a version of this question that's infinitely more complex and painful than anything I deal with in trading. There are no stop-losses in family relationships. No clear exit signals. No way to backtest what the right decision looks like.

But maybe the question is the same: Have I done everything within my control? Have I given this a fair chance under reasonable conditions? And if the answer is yes, then maybe it's okay to step back. Not forever. Not without the possibility of reassessment. But for now.

Sometimes the hardest trades to close are the ones we're most emotionally invested in. The ones where we've already put in so much work that walking away feels like admitting defeat.

But there's no shame in recognizing when you've done all you can do.

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Sean McLaughlin | Chief Options Strategist, All Star Charts