Losing Money in the Market? You’re Probably Doing These 10 Things

OIJ (#30) A 10-Step Guide to Breaking the Losing Streak

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Losing money in the stock market is easy… and it SUCKS. It’s practically a rite of passage. We like to call it paying tuition to the market.

But once you’ve burned enough cash to heat a mid-sized Alpine cabin, you start wondering if maybe, just maybe, you’re doing something wrong.

So here’s your guide (or anti-guide) on 10 painfully obvious (yet rarely followed) steps to stop blowing up your brokerage account.

🔇 Step 1 Stop Taking Advice from Dave at the BBQ

Unless your cousin actually is Warren Buffett, politely nod and ignore 99% of the people giving you stock tips.

Most people don’t know what they’re talking about. They confuse conviction with volume, and FOMO with insight. Just because someone made money in the markets 10 years ago doesn’t mean they know what they were doing.

Build your own framework. Filter ruthlessly. Be kind, but trust your brain more than someone else’s bravado.

💵 Step 2 Invest in Stuff That Makes Real Money

Wild concept, I know. But if the company has no revenue, no free cash flow, and its “main product” is vibes and dilution, maybe, just maybe, it’s not a steal.

Look for cash. Not hype. Not hope.

Cold, boring, glorious cash.

🎯 Step 3 Find Your Edge, Not Someone Else’s

Do you know something the market doesn’t? Are you closer to the ground?

No? Then you’re playing poker without seeing the cards.

Get an edge or get out.

📉 Step 4 Stop Checking the Damn Price

Staring at your portfolio five times a day won’t make it go up.

If you did the work, trust it. If you didn’t, no amount of refreshing will help.

🧠 Step 5 Doubt Less, Hold More

Second-guessing every trade kills more returns than bad ideas do. Let your thesis breathe. If you're going to panic, do it in private and don't touch the sell button.

Think hard before you buy. Map out the big picture. But once you're in, give it time, at least 6 months.

If your conviction can’t survive a few red days, it wasn’t conviction to begin with.

📚 Step 6 Study History (No, Not the TikTok Kind)

Every bubble, bust, boom, and bailout leaves clues. Start digging through them and build your internal thermometer.

You don’t need to time the market, but you do need to know when the water’s getting warm.

Read books, not memes. 10-Ks, not just tweets. The stock market may not repeat, but it sure likes to rhyme.

✨ Step 7 Avoid Shiny S**t

If it sounds like a moonshot, it probably ends in moon dust. Amazing opportunities do come, but only once or twice in a 30-year investment career.

You’re not missing out. You’re staying solvent.

If the word “crypto” is followed by “bro,” just run.

💼 Step 8 Treat This Like a Business

Would you buy a local restaurant without reading the menu, checking the cash register, or meeting the owner?

Then stop doing that with stocks.

Own businesses, not lottery tickets.

🪓 Step 9 Scale Like a Lumberjack, Not a Junkie

Never go all-in. Ever.

Build your positions like you're stacking firewood: slowly, deliberately, and in season. Rushing gets you splinters. Patience keeps you warm through winter.

Develop your system, and actually stick to it. Checklists, conviction thresholds, position sizing rules… whatever works.

But make it yours, and treat it like scripture.

🕯️ Step 10 Play the Long Game (Because That’s the Only Game)

If your time horizon is measured in hours, you're not investing, you're donating money to Wall Street bankers (they sure like their fat bonus).

Compounding only works for the patient and the stubborn.

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💬 Bonus Tip: Write down your thesis

If you’re embarrassed reading it out loud a year later… congrats, you’ve grown.

If not… congrats, you probably made a bunch of money.

🙏 Feel free to ❤️ and comment so that more people can discover and enjoy this Substack 😇