October 1, 2025 | Issue 129

Till Drawdown Do Us Part: Marrying Your Positions

Nikolay Stoykov
Managing Partner at Alaric Securities
Two gold wedding rings casting shadows on a background of stock market candlestick charts, symbolizing marrying your positions in trading.

Marrying your positions is often used as a warning in trading – don’t get too attached, don’t let emotions dictate decisions. Yet the reality is that successful long-term investing does require a form of marriage. The problem is that many traders and investors misunderstand what that truly means, both in markets and in life.

Over my 25 years in trading and investment management, people often ask me:

“What’s the single most important thing in trading?”

Most expect the answer to be discipline, expertise, or risk management. And while those matters, every successful trader has them – those qualities alone don’t separate the winners from the ones who eventually burn out.

As Warren Buffett famously put it:

“The difference is a willingness to marry your positions.”

But before you commit “till drawdown do us part,” you’d better know what it really means to date a stock and when it’s finally ready for marriage.

What Does It Mean to Marry Your Stocks

In life, most couples date for two to five years before getting married. Statistics show that couples who marry in less than a year are about 50% more likely to divorce compared to those who wait.

The same principle applies in trading: if you don’t “date” your stocks long enough before committing long-term, you dramatically increase your chances of a painful breakup.

Two Common Mistakes When Dating Your Positions

Error 1: Paper Expertise

Albert Einstein once said:

“In theory, there is no difference between theory and practice. In practice, there is.”

In trading, nothing could be truer.

In your first year, you should stick to short-term trades. Why? Because no amount of academic preparation—whether it’s a PhD, MBA, or CFA can prepare you for the emotional rollercoaster of live markets.

Even seasoned traders who take time off need a few months of “warm-up” before they’re ready to commit again.

Error 2: Overreliance on Patterns

Scanners, filters, and chart patterns are useful tools, but they’re no substitute for real experience and company knowledge.

Just because a chart looks familiar doesn’t mean it will behave the same way. That’s like assuming your cousin’s lookalike has the same personality. Without context, patterns can easily mislead.

When Is a Company Mature Enough to “Marry”

Here’s an overlooked truth – operational history matters.

Most countries set the legal marriage age at 18, with rare exceptions at 16. Yet in the markets, investors often commit to companies that are barely five years old. That’s not investing, it’s gambling.

A business model needs time to prove itself. Ideally, a company should show at least two complete business cycles (15–20 years) before you can reasonably expect sustainable profitability. Personally, I don’t feel comfortable committing long-term until I see that track record.

Think about it – the average age for marriage worldwide is around 28–30. Would you really want to “marry” a stock that’s still in its teenage years?

Date Before You Marry

Trading and investing are difficult because they require making forward-looking decisions in an uncertain world.

But you can stack the odds in your favor by:

  • Focusing on established companies with at least 15–20 years of operational history

  • Actively following and “dating” a company for 1–2 years before making a long-term allocation.

Only after this period of observation and testing should you “marry” your position.

Final Thoughts

Success in trading isn’t just about discipline, expertise, or risk management. Those are simply the minimum requirements.

The real difference-maker? Knowing when a stock deserves your long-term commitment and having the patience to wait before making a decision.

That’s how you avoid heartbreak and build lasting wealth in the markets.

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Disclaimer

The articles, podcasts, and newsletters from Alaric Securities OOD are classified as marketing communications. The views expressed are solely those of the individual authors affiliated with Alaric Securities OOD and do not necessarily reflect the views of the company, its subsidiaries, or affiliates. This content is provided for informational purposes only. It does not constitute investment advice, a recommendation, or a solicitation to buy or sell any security, digital asset (such as cryptocurrency), or other financial instrument. Third-party content is included solely for informational purposes and does not reflect the views of Alaric Securities OOD. All investments involve risk, including the possible loss of principal. Past performance is not indicative of future results. References to third-party companies, logos, or trademarks are used under fair use/fair dealing principles for analysis and commentary.