So, I need a new roof. The current roof dates to before I bought the house and I've owned my home for 19+ years. It's time. It's just about to move from the world of "want" to the world of "need."

I've requested three estimates from roofers and contractors who work in my area. I've checked their reviews and references and I'm comparing prices and terms.

Even though I'm taking all the necessary steps and I've been saving with this expense in mind, it's still a daunting purchase. There's no way that writing a check with so many zeroes on it will ever be easy for me. It also doesn't help that this expense will come in the midst of expensive dental work (for me and my dog), initial payments on the family vacation, and some other unforeseen expenses (like replacing my STOLEN hammock stand.

But having good money habits means I'll pay these important bills, dial back some discretionary expenses, be extra careful to turn off lights, wear a sweater instead of using the heater and open the windows instead of running the air conditioning. And I have a few side gigs that will cover some costs. I'll get through it just fine — but I recognize the challenge.