Previously I’ve written about the easiest $100 I ever made, but today is time to talk about the day I made the most difficult $100.

Actually, it was such a grueling job that it spanned 2 almost full days of work. When I was 16, I got a job making $7.25 as a farmer. I would bike to work at 6am and immediately start picking whatever the vegetable of the day was. Sometimes it would be corn (ever have fresh corn on the cob? The sweetest thing I’ve ever tasted), sometimes it would be strawberries (pick 3, eat 1), and other times it would be sugar snap peas.

But in August, it becomes planting season, which means a lot of weeding in the hot and humid field. And when things haven’t grown yet, it’s not really a field. Just a big brown area many acres long and wide. And I’d stand there weeding around the pumpkins for a few hours, making my way up the line. When I got to the end, I’d move one row over and work my way back.

Obviously this wasn’t the most interesting work, but the time managed to tick by just a little bit faster because I was working with a few friends from school. At noon, we’d go back in for a two hour break when the sun was hot and grab some cold water and usually some bread and jam. At 2pm, we were out the door and back to weeding.

It was brutally hot, 100+ degrees at times, and in New England, it was pretty humid, too. I would come home and shower and the dirt and mud would come off, but I was left with a mighty fine farmer’s tan that summer.

The reason I hated this work was because it involved no thought whatsoever. Every minute was the same as the last one and the same as the next one and there wasn’t much to look forward to. Why? Because the next day was going to be exactly the same. The only thing to look forward to was that I’d be picking an actual vegetable and would be able to grab a healthy bite to eat every few minutes!

Readers, what was the hardest $100 you ever made? Any horror stories from your teenage years?

When I had a chance to get an iPhone 3G S about a year and a half ago, it was a no-brainer to me. I wanted the new phone with the coolest features, even if it came at the cost of a little lifestyle inflation. The cost would be offset and then some, so I was getting the iPhone for free.

Then, it came time to upgrade to the iPhone 4. Again, it made a lot of sense. It was a significant upgrade, and more importantly, it didn’t cost me a dime. Actually, I made money, even though it was a lot of hassle.

Now, the iPhone 4S has been released, and guess what? I’m not getting it this time.

There’s a little pressure because everyone likes the latest gadgets and there are certainly some nice features that I’d like to have. But the desire just isn’t there for me. I don’t think it’s a wise purchase and burning through an upgrade on our family plan for it doesn’t seem like the best decision.

Sure, I could probably sell my iPhone 4 for $350 and buy the iPhone 4S for $200, but that would mean using an upgrade, something that we’re saving up for. If something were to happen to one of our phones, we’d be on the hook because I think cell phone insurance is a scam. Phones are getting more expensive to replace, so having an upgrade is a priority at the moment.

Add in the fact that while the improvements to the phone are nice, they aren’t groundbreaking. The screen is just as clear (something I valued during the last upgrade), it’s the same size, and the camera has been working well for me so I don’t see an immediate need to get something better just for the sake of getting something better.

For me, the value just isn’t there. I’ve been very frugal with my iPhone, and right now, my iPhone is perfect for me. Since there’s no burning desire to get something new, I guess I’ll wait for the iPhone 5 and evaluate whether its features are worth it.