Posted by It might be nice to think that, if you’re being cautious, you’re being smart. But there’s a version of caution that looks like wisdom and is actually just fear. You gather information, run more numbers, wait for more certainty, and somewhere along the way, the decision gets made for you. In real estate and investment, that’s rarely a good outcome.
Most people don’t make bad decisions because they’re reckless. They make them because they’re paralysed, or because they’re letting the wrong things drive the call.
So, this week I want to talk about how to change that.
The cost of not deciding
In property and investment there’s usually a measurable price to indecision. The deal you didn’t move on. The opportunity you waited out until someone else took it. The asset you held too long because selling felt like admitting defeat.
I’ve experienced that myself: an albatross that hung around my neck for 12 years in Dublin. A tenant had pulled out of a deal worth a 600K profit on a unit, which then sat empty for 12 years until we exited at a financial loss.
The problem with doing nothing is that it feels safe. It doesn’t feel like a decision, but it is. Often it’s an expensive one.
There’s also a compounding effect. Every decision you avoid gets harder the longer you leave it. The mental load accumulates, your confidence takes a hit, and the next decision gets harder too. Indecision is rarely a one-off. If you’re not careful, it becomes a pattern.
Why we make bad decisions
No-one ever sets out to make a poor decision. They don’t happen because of bad information. They’re made because of what’s happening in your head at the time. There are a few common culprits:
Confirmation bias: You’ve already decided what you want to do, so you hunt down the evidence to support it. The due diligence becomes a formality. This is particularly dangerous in property, where it’s easy to fall in love with a deal before you’ve stress-tested it.
Loss aversion: The pain of losing something feels roughly twice as powerful as the pleasure of gaining something equivalent. This is why people hold underperforming assets far too long, and why they hesitate to take profits when they should.
Decision fatigue: The more decisions you make, the worse you get at making them. If you’re making big calls at the end of a long week, after a series of smaller ones, your judgment is already compromised.
Emotional state: Stress, anxiety, overconfidence… it all bleeds into your decision-making without you realising. The investor who’s just had a big win is a different decision-maker to the one who’s just taken a loss, even if the opportunity in front of them is identical.
Understanding these tendencies doesn’t make you immune to them, but it does give you a fighting chance. I’ve written more about the emotional side of things here, if you wanted a bit of a deeper dive.
How to start trusting your own judgment
It’s sometimes the case that people who are actually very capable lose confidence in their own judgment. Maybe they’ve taken a few bad hits, or just one really bad one. Whichever it is, they decide to outsource decisions to advisors, partners, or the market. It’s not because those sources are always right, but because it feels safer to have someone else to blame if it goes wrong.
The problem is that this is a habit, and it compounds just like indecision does. The less you trust yourself, the less practice you get at deciding, and the less you trust yourself.
There’s also something to be said about accountability here: you have to own your stuff, even if it’s gone wrong. When you dodge accountability, it feels like you’re protecting yourself in the moment, but actually, you’re paying a steep price over time. Your progress will stall and you miss crucial opportunities for growth.
Start making changes
Avoiding decisions is a habit you can break. Review your track record honestly: not to beat yourself up, but to actually look at the decisions you’ve made. Which ones worked? Which ones didn’t? Do you understand why things went well (or didn’t)? You’ll often find your instincts were right more often than you gave yourself credit for.
Get clear on your criteria before you look at an opportunity. If you know in advance what a good deal looks like (the numbers it needs to hit, the risk profile you’re comfortable with), you take a lot of the emotion out of it. You’re not deciding whether you like a deal, you’re checking whether the numbers stack up.
Separate the decision from the outcome. A good decision can lead to a bad outcome, and a bad decision can get lucky. What you can control is the quality of your process and due diligence: how you gathered information and how you stress-tested the downside.
Put a time limit on it. Decisions expand to fill the time available. Get clear on what information you actually need, give yourself a realistic deadline, and commit to it. Most of the additional information gathered after a certain point doesn’t change the decision, it just delays it.
The decision you keep avoiding
Is there a decision you’ve been sitting on for longer than you should? You’ve thought about it, probably talked about it, maybe even made a list of pros and cons. But you haven’t moved.
Ask yourself honestly whether there’s genuinely more information you need, or whether you’re just waiting until you feel ready. That feeling rarely, if ever, arrives on its own. Readiness is usually a byproduct of making the decision, not a prerequisite for it.
Making good decisions doesn’t mean you’ll never be wrong. But if you make clear decisions with the information available, learn quickly when something isn’t working, and adjust, you’re building a skill that will improve through practice, rather than waiting for certainty that never comes.
You already know more than you think you do. The question is whether you’re going to trust it.
If you’re ready to make better decisions and start converting your knowledge into real results, my Accelerator program can help. Find out more here.