The entire point of the question is to NOT find yourself having to carry around 99¢ in change. Going out the door with that much defeats the purpose.
Social Engineering:
If something rings up where I’ll get back over 95¢ in change, I make a big deal about patting my pockets and looking for coins. Then I apologize about not having any – implying that it sucks for the cashier to have to count out all the coins needed to make change. More than half the time, the cashier smiles and gives me back a whole dollar.
Check the Environment:
Look for the “Have a penny, take a penny” collection near the cash register. They’re almost always present at gas stations and independent retailers.
Pocket change:
I don’t mind getting back three quarters. What I despise are the pennies and nickels and dimes needed for more than 75¢ return change. So, I’d probably carry around 1 dime, 1 nickel and 3 pennies. If you find yourself wishing you had 4 pennies because 3 isn’t enough, try the Social Engineering bit.
Plastic:
Using credit and debit cards actually increases the cost of goods. There’s always a small surcharge that the retailer must pay for everything purchased with a bank card. That ends up built into the cost of the goods you’re buying. For small mom & pop stores, I try not to use plastic… and they usually have the penny dishes. But at a place like Wal-Mart, I’ll use my debit card. There’s always some cost for convenience.
End of the Day:
If you’re stuck with a lot of change at the end of every day, then make the most of it. When I get home, I put all my change in a huge pickle jar. It fills up pretty fast. And when I cash it out, I usually collect over $200.