When I look back at my twenties, I realise I had the wrong end of the stick.
I believed that if I didn’t get things right early — really right — I’d miss my shot. I saw life as having a narrow window, where momentum mattered more than learning, where mistakes carried too much weight, and where one wrong move could quietly put me behind for good. So, I carried pressure everywhere. Pressure to be certain. Pressure to move fast. Pressure not to screw it up.
At the time, I thought that type of pressure is what I needed. That it would force clarity and accelerate progress.
But it didn’t. It made me tighter. Less flexible in my thinking. Less willing to back myself. More cautious than I needed to be at that age.
What I understand now — and what I wish I’d understood earlier at 20, is you can fail repeatedly for the next ten years and still be young. Wrong jobs. Bad ideas. Poor decisions. None of that ends you. Failure at that age isn’t fatal — it’s formative. It’s how judgement is built, how resilience is earned, and how you learn where your real strengths actually are.
Your twenties are meant to expose you. To responsibility. To pressure. To consequences. To people. And ultimately, to yourself.
Every role that doesn’t fit, every terrible idea, every uncomfortable lesson is doing exactly what it’s supposed to do — provided you’re paying attention.
In saying that, this isn’t an excuse to drift through the decade unfocused, half-committed, and distracted. That’s not growth — that’s avoidance. Failing forward still requires intent, effort, and discipline.
If you’re going to fail, fail while working hard. Fail while building skills. Fail while taking responsibility for your choices. Change direction if you need to — but don’t check out and call it “finding myself”.
When you look at it that way, the irony becomes obvious.
Your twenties are the safest decade of your life to take risk, yet they’re the decade most people waste time playing it safe. If you mess something up at 25, you recover. You reset. The cost is low. Just some battle scars to show for it. If you don’t back yourself for ten straight years, the cost doesn’t disappear — it just shows up later in regret, stagnation, and lost opportunity.
That’s why the instruction is simple.
Pick a direction. Commit to it. Take responsibility. Then move.
Start the thing that might fail. Put your hand up before you feel ready. Take the role that stretches you. Ask the question. Change towns if you need to. Do it deliberately, not casually, and don’t wait for certainty to arrive first.
Because the goal isn’t to win your twenties. The goal is to reach your thirties with enough experience, judgement, and self-belief to know how to win the decades that follow.
And what you will come to see is that people who look lucky later in life aren’t lucky at all. They’re the ones who earned some battle scars early on, while others just sat it out.
Battle scars are cool. And your twenties are the cheapest, safest place you’ll ever have to earn them.
Until next time,
Cheers, Ben
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Disclaimer: The information contained in this article is general in nature and for education purposes only. It is not financial advice. No one should act on the information without appropriate specific advice for your particular circumstances. Ben Law is a former financial advisor but is no longer licensed and cannot and will not give you specific or personal advice in this article. The Financial Bloke Group Pty Ltd accepts no responsibility for any loss or damage occasioned by any person acting or refraining from action as a result of reliance on the information in this article.