I lost money after buying Bitcoin. How do I get my confidence back?

December 2, 2025 — 1.51pm

I’ve had some pretty negative experiences of investing. Some years ago, I put some money into Bitcoin, but got nervous when the price dropped and sold at a loss. I’ve bought an investment property that had unexpectedly high maintenance costs. After that experience, I signed up with a buyer’s agent hoping they’d be able to find a better investment property. However, a friend who is an experienced property investor said that the property recommended by the agent wasn’t a good investment, so now I’m doubtful.

I want to invest, I’m trying to invest. But I seem to keep losing money. How do I rebuild confidence after losing money? And how do I stop losing money?

Investing can seem as easy as picking an asset and diving in. But there’s a lot more to learn.Credit: Simon Letch

There is a misguided notion that investing is largely about buying investments. It’s easy to think: “I am buying investments, therefore I am investing” or “I want to invest, therefore I should buy investments”. There is an over-emphasis on “buying” as the key part of the process.

But isn’t it true? Investing is about buying investments, right? Yes, that is the key action required to invest. However, it’s just one step in a bigger process.

To use an analogy – it looks like swimming is about jumping in the water and moving your arms. But if those were the only things a five-year-old had observed about swimming, and they tried to replicate those actions – what’s the likelihood that they would be able to swim successfully?

Pretty low because there are many other skills required to swim that are not obvious to the naked eye. In the process of learning to swim, you learn to float, how to breathe correctly, how to tread water, and so on. In many ways, there are more “invisible” skills than visible ones.

You’re doing the obvious action (buying investments) without having developed the core skills required to invest successfully.

But someone who doesn’t know that there’s more to swimming than moving their arms will keep jumping in a different pool hoping “this time” it works out … until they’re traumatised enough to stop trying.

But it doesn’t matter if you jump in a lake, a pond or a pool – if you don’t realise there’s more to swimming than moving your arms, you’ll never be able to swim successfully.

To me, it sounds like you haven’t developed those other skills, but you keep jumping in the pool hoping that this time will be different. You’re doing the obvious action (buying investments) without having developed the core skills required to invest successfully.

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There’s more to investing than buying an investment. If you do it right, then buying the investment is the least eventful part of the process. The majority of the work occurs before the buying (to determine what to buy), or afterwards (to manage what you’ve bought). So, if you want to rebuild your confidence (and stop losing money), stop buying investments for a while and start learning:

1. How different asset classes work

How is property different to shares, or bonds different to crypto, as an asset class? What are the pros and cons of each? How do their risks differ? Why do funds often use a combination of these when building portfolios, instead of putting everything into a single asset class?

Through this process, you’ll start to understand where different asset classes might fit into your personal investing strategy, based on your personal goals and risk profile.

You’ll start to see that investing is less about picking one specific investment that does well or doesn’t, and more about designing an overall collection (portfolio) of investments from different asset classes that work together to achieve a particular objective.

You’ll stop asking “what investment should I buy?” and start asking “how do I design a portfolio that will meet my goals?”

2. How different investing strategies work

How does day-trading differ from buy-and-hold investing? Why do some people flip houses and others hold them for decades? Why do some invest to maximise income while others invest to maximise capital growth? Which strategies are better for income v growth?

Through this process, you’ll start to see that it’s not just about the asset – it’s about how the asset is being used to achieve a particular objective. You’ll start to understand that investing isn’t just about buying an asset and hoping it does well; it’s about knowing which investment to buy based on the goals you’re trying to achieve.

You’ll stop asking “will this investment do well?” and start asking “does this investment fit my long-term wealth strategy and goals?”

Good investing isn’t just about buying the right investment – it’s about developing the skills to become a confident investor. If you focus on the latter, the former tends to take care of itself.

Paridhi Jain is founder of SkilledSmart, which helps adults learn to manage, save and invest money through financial education courses and classes.

• Advice given in this article is general in nature and not intended to influence readers’ decisions about investing or financial products. They should always seek their own professional advice that takes into account their own personal circumstances before making any financial decisions.

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