What crypto and property investors sometimes have in common

Saturday, 20 June 2026

Investors resist selling losing assets to avoid admitting mistakes and ending their hopeful narratives.

Holding an underperforming asset is a continuous, active decision carrying high opportunity costs.

Overcome this sunk-cost bias by asking if you would buy the asset today with fresh capital.

Katie Wesney is a qualified financial adviser and national coaching lead at Enable Me.

OPINION: Here’s something I’ve noticed about the perception of ‘loss’. People will tolerate a remarkable amount of financial pain: the weekly top-up, the opportunity cost, the quiet dread of checking their app, as long as selling remains off the table.

Because selling means it happened. Holding means it might still un-happen.

I’ve been sitting with two clients this year who are, on paper, in very different situations. One owns property. One owns crypto. What they share is more interesting than what separates them.

Both, in different ways, are paying to keep a particular story alive. The one where it works out. The one where they weren’t ‘wrong’.

The property investor

The first client bought an Auckland rental at the end of 2021, near the peak, although very few people were calling it that at the time. A lot of people were calling it ‘the new normal’.

She paid $1.8 million. It’s worth roughly $1.3 million now. The property is cashflow negative at current interest rates, so she’s topping it up every week, and has been for a while.

She’s not selling. She’s waiting for the property value to come back.

Many property markets have recovered over long periods, but that’s not guaranteed, and even when values do recover, the journey matters. Years of cashflow top-ups, financing expenses and missed opportunities, have a cost too.

Not every asset recovers on your timeline. And some don’t recover at all. The question isn’t whether the market is cyclical. The question is whether this particular investment is the best use of your capital from this point forward.

I asked her one thing: if you didn’t already own this property, would you buy it today? Would you go to the bank now, borrow $1.3 million, and buy this house, at this yield, with this cashflow drag?

She laughed.

Absolutely not.

That gap between what you’d do with fresh eyes and what you’re actually doing is where the sunk cost fallacy lives.

The digital currency investor

The second client bought when it felt like everyone was buying.

While he’s been holding onto it, the value has halved. He checks the price often enough that I’d call it a habit, maybe an anxious one.

He won’t sell because selling, he says, would lock in the loss.

This framing comes up constantly and it’s worth dismantling.

The loss isn’t locked in by the decision to sell. The market value has already changed. Selling doesn’t create the loss; it simply recognises today’s value.

What he means, what most people mean when they say this, is that selling would make it official. Undeniable.

Instead, he waits. And every day he waits is a day he’s actively choosing to hold this position with capital that could be doing something else.

Holding isn’t passive. It’s a decision you’re making over and over, usually without realising it.

Why smart people do this

Loss aversion is real. We tend to feel losses more sharply than equivalent gains.

But I think there’s something else going on, something that doesn’t get named as often: the internal story we tell ourselves.

Selling a bad investment doesn’t just formalise a financial loss. It ends a particular version of the future. The one where it worked out. The one where the timing was fine. The one where you were right.

Holding keeps that version alive. It costs money, but it preserves something that feels more important in the moment: the possibility that the mistake hasn’t really happened yet.

That’s an expensive story to maintain.

The question I use

When a client is stuck in this pattern, I don’t ask whether they should sell. That question has too much ego attached to it.

I ask: if this capital were sitting in your bank account today, would you put it into this investment at its current price and terms?

If the answer is no, and it usually is, then we talk about what’s keeping them there. Because often it’s no longer about investment fundamentals. Those tend to get buried once ego and hope take over.

What happened

My property client is still holding. But she’s running the real numbers now: the cumulative top-up cost, the equity tied up in the property, what that same capital could do against her mortgage or elsewhere. She hasn’t decided yet, but she’s asking different questions than she was three months ago.

Asking the right questions can be more important, than simply believing you have the right answers. That’s the difference between passively holding and consciously investing.

My crypto client sold half. He paid down debt with it. He told me the week after felt awful, then it didn’t.

The weight of a bad position isn’t just financial. You carry it. It shows up in other decisions, other conversations, other moments of doubt.

The purchase price isn’t the answer

Markets don’t care what you paid. Property doesn’t care what you paid. Crypto doesn’t care what you paid.

Your purchase price matters to you, far more than it matters to the market.

The useful question isn’t whether this investment will eventually get you back to where you started. The question is whether you’d choose it again today.

Because the money you have now deserves better than being held hostage by the money you’ve already lost.

Disclaimer: The information in this article is of a general nature and is not intended to be personalised financial advice. It does not take into account your individual circumstances or financial goals.