How to? Convincing yourself it's not a lot of money as you move up

[People_Mover]

I remember in 2003, the first time I deposited 100.00. I lost it and I was sad, so I redeposited and lost again. I found twoplustwo, read some books, well a lot of books and redeposited another 100.00, telling myself it would be the last 100.00 I ever deposited. I grinded low stakes, bonus whored and won a 5.00 rebuy for 1800.00 to build a roll and continued to study the game. As I moved up stakes from .10/.25NL to .25/.50 to .50/1, a losing session would become less painful and "part of the game" I'd withdraw a few times to purchase some nice things that poker bought. In 2006, I had my first $1000.00 losing day and I was sad again and it brought memories back of the first 100.00 losing day I had. Still grinded though and moved up to 1/2NL and 2/4NL and took some random shots at 3/6 and 5/10NL nowadays.

The question though: Back then 25.00 was a lot of money to put on the table at one time. Then 100.00 was a lot of money to bring to one table. Then 200.00 seemed like a lot. I've been playing (smallish) winning poker at 2/4 for a few months now and 1/2NL is sort of a jokish money and 400.00 is money that I kind of care about. When I take a shot at 5/10, 1000.00 is a LOT of money (even though I'm rolled for it). How do you get into the right mindset that X amount of $$$ is not a lot anymore even if X $$$ isnt 1/20th of your bankroll?

I struggle with moving up past 2/4NL because 600.00 is a lot of money or 1000.00 is a lot of money even though of course there's risk/reward factor for moving up that maybe I'm struggling with. Any comments are appreciated.