I feel that the stakes get higher but that you have more experience to tackle them. I see this a lot as a business owner. I've been an entrepreneur all my life, but a lot of my fellow business owners are new to it. They have derailed their old careers, cashed in investments (or credit cards) and are working really hard at something they believe will be fulfilling and rewarding in the long term. In reality it is entirely possible that they will wind up ten years later with a failed business, no savings, damaged credit, and struggling to find the safe harbor of a paycheck. Retirement may or may not be an option.

Of course this isn't limited to people who want to own a business. You're just as much at risk for this sort of setback if you get laid off (especially when your age and experience means that employers are more willing to hire dumb twenty-somethings who will work at a quarter of your wages) if you become seriously ill, or weather a divorce.

And it isn't even that these setbacks don't affect people of any age... it's just that when you're older you feel like you have more to lose and you're running out of time to even the score.

I'll give you an example. I'm thirty, and my husband is 45. Last month we had to spend $5K to fix the transmission in our van, and $2K to fix the furnace. Then this month we discovered that we'd amassed a $6K in taxes we hadn't foreseen.

Most of our disposable income goes into investing in our business and property, so we didn't have a lot of ready cash. This one-two-three punch wiped out our emergency fund and then the balance had to go onto credit cards (luckily at o%).

It was stressful for me, but it gave my husband a week of anxiety nightmares. It felt like we'd lost two years of progress. Even though on the balance sheet we are in a much better position, with better equipment and vehicles and fewer large expenses looming on the horizon, we had only just gotten to the point where we had wiggle room. Now, no wiggle room until this debt goes away.

But I'm thirty. I feel like a two year set-back isn't much in the face of the thirty-plus years i have left to work. I have the confidence I can do this. My husband, on the other hand, is 45, with a chronic illness. To him, setbacks threaten his very survival. Every year brings him closer to possibly greater medical bills and the possibility of not being able to work. Every year the spectre of a pathetic retirement fund looms larger. The certainty that you can fix everything gets shaken.

So like one of the other commenters said; if you do things right, things get easier. If you screw up things get harder. It's not that you're doing anything wrong, though, necessarily, only that your assessment of certain risks gets higher and higher. Hopefully your confidence rises apace, but not always.