Which Is Harder: Buying a Stock or Selling One?

If you’re new to investing, your first major hurdle is learning how to buy. You figure out how markets work, open a brokerage account, and overcome the nerves of making that first trade. It takes research, a bit of know-how, and a leap of faith.

But what most new investors don’t expect is the second hurdle - knowing when (and how) to sell.

Why selling feels so personal
Imagine going shopping. While browsing clothes on a rack, there’s no emotional attachment. You evaluate, decide, and move on. But once you’ve bought something and brought it home, it’s yours. Even if it doesn’t fit or suit you anymore, it sits in your wardrobe - untouched, but hard to let go.

Investments can feel the same way.

Once you buy a stock, it’s no longer just a ticker symbol. It becomes your stock. You check the price, watch the news, celebrate when it goes up - and feel anxious when it dips.

Selling can feel like admitting you made a mistake, even if a stock has changed fundamentally and no longer fits your strategy.

The "cobweb portfolio"
This is why many of my coaching clients come to me with what I call a “cobweb portfolio” - investments they bought years ago but haven’t touched since. These portfolios are filled with old decisions, unreviewed positions, and missed opportunities.

They often say things like:
“I bought this years ago… I don’t really know what it’s doing now.”
“I’m waiting for it to bounce back before I sell.”
“I don’t want to lock in the loss.”

Here’s a common pattern I see in cobweb portfolios:
Quick to take (small) profits
Slow to take (big) losses

But successful investing requires both logic and discipline.

“Buying is logical. Selling is emotional.” ~ Dinah Poehlmann

Buying is often based on research, strategy, or sometimes even a recommendation. It feels proactive. It makes sense.

Selling, on the other hand, brings in all kinds of emotions - regret, hope, fear, attachment. And that’s what makes selling so challenging for many investors, especially beginners.

How to take back control of your portfolio
If you're a new investor, or someone feeling stuck with an old portfolio, here are five steps to move forward with clarity and confidence:

1. Get clarity on your finances
Understand your current cash flow, savings, and financial goals. Know how much you can truly afford to invest.

2. Know your risk profile
Everyone has a different comfort level with risk. Understanding your own helps you choose investments you can stick with through ups and downs.

3. Define your investment strategy
Are you investing for long-term growth? Passive income? Financial freedom? Be clear on your goal before buying any new stock.

4. Buy intentionally
Don’t follow the hype. Choose investments that align with your values, goals, and understanding. You should feel confident in why each stock is in your portfolio.

5. Set selling rules in advance
This is an important one. Emotions cloud judgment. Decide your exit strategy in advance, that means when to take profits, when to cut losses, and when to let winners run. Make selling part of your buying decision.

Keep investing simple
You don’t need to be a finance expert or love spreadsheets to succeed at investing.

You just need:
The right mindset
A clear strategy
And a willingness to keep learning

Have you ever held on to an investment for too long because it was hard to let go? I'd love to hear your story or investing experience.

P.S. I’m linking an old Masterclass called “Invest with Confidence”, which I hosted a few years ago. You'll learn 3 costly mistakes that new investors make and how to build your retirement fund right!

It's free to access - enjoy and share it with your loved ones!