Why Investing Feels So Uncomfortable – And Why That’s Normal

Published on 2 March 2026 at 10:17

I’ve been involved in investing, on and off, throughout my career both personally and with the firms I’ve worked for and alongside. Over that time, I’ve learned something that isn’t talked about enough:

Investing is meant to feel uncomfortable.

Not constantly. Not overwhelmingly. But at times, discomfort is part of the process.

If it doesn’t feel uncomfortable at all, you’re probably not experiencing real market risk and without risk, there is rarely long-term return.

Let me explain.

FOMO: The Fear of Missing Out

One of the strongest emotions in investing is FOMO, the fear of missing out.

You hear about:

  • Someone who made a fortune on Bitcoin

  • Someone who bought Nvidia early

  • A fund manager launching a new strategy everyone wants access to

It creates a powerful emotional response: “Have I missed something?”

History is full of these moments.

There was the rush to invest in technology funds during the dot-com boom. I remember building fund lists at the time and feeling desperate to include tech funds without really understanding what that meant.

There was the excitement around high-profile launches, such as well-known managers moving into new sectors where they had little experience, relying on past success rather than future certainty.

And each time, the same pattern emerges:

  • Excitement

  • Inflows

  • Headlines

  • Followed by disappointment for many

The crux of FOMO is simple: we chase without fully thinking. We respond emotionally rather than strategically.

Volatility: The Emotional Test of Investing

Volatility, the ups and downs of markets, is probably the hardest aspect of investing.

It’s easy to enjoy investments when they are rising.
It’s much harder when they fall.

But volatility isn’t a flaw in investing it’s a feature.

Take Bitcoin as an example. It has exhibited annualised volatility of over 60% at times. To put that into perspective, global equities have historically experienced volatility closer to 15–20% per annum.

Volatility simply measures how widely prices swing.

The higher the volatility:

  • The greater the potential upside

  • The greater the potential downside

  • The harder it is emotionally to stay invested

Over the years, and I include myself in this, I’ve seen investors sell at the worst possible moments because they simply couldn’t cope with the discomfort. They allowed emotion to take control.

Research in behavioural finance, including the work of Daniel Kahneman, shows that losses hurt roughly twice as much as gains feel good. That imbalance explains why volatility feels so painful, even when it is expected.

Patience: The Most Underrated Investment Skill

If volatility is the test, patience is the skill.

Investing is not about today or tomorrow.
It is about the next 5, 10, 15 years and beyond.

Good investing should feel almost boring:

  • Diversified

  • Structured

  • Aligned to goals

  • Not driven by headlines

Short-term bets, by contrast, are closer to gambling. They may work occasionally, but they bring higher stress, higher volatility, and a greater chance of regret.

The irony is that the more exciting investing feels, the more likely it is that risk is dominating discipline.

Why Discomfort Is Normal

Investing feels uncomfortable because:

  • Markets move unpredictably

  • Headlines amplify fear and greed

  • We compare ourselves to the few big winners

  • Losses feel more intense than gains

But discomfort does not mean something is wrong.

It often means:

  • You are exposed to growth assets

  • You are invested for the long term

  • You are experiencing the “price” of potential returns

Trying to eliminate all discomfort often leads to eliminating growth.

In Summary

Investing can feel uncomfortable and that’s normal.

The key is not to remove discomfort, but to:

  • Understand it

  • Expect it

  • Manage it through structure and planning

Focusing on long-term outcomes, rather than short-term noise, helps reduce stress. Pausing before reacting to headlines is often the simplest and most powerful discipline.

The aim is not to make investing exciting.
It’s to make it effective.

And sometimes, the most reassuring thing to know is this:

If investing feels uncomfortable at times, you’re probably experiencing it properly.

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