I remember this pretty well.  I had about $140K saved up and kept talking to my wife about finding a rental property.

In all those conversations, one person ends up playing the other’s devil’s advocate, and there’s always a good reason to wait.

So one day, quietly, I got started.  I was lucky to find a great agent quickly—he was both an agent and a property manager, and was patient enough to hunt around with me.

My first offer was a real test—I half hoped that it’d be declined—telling myself that “nothing’s gonna happen anyways” was the only way to be OK with the biggest purchase of my life at that point.

And just as I’d hoped, it was declined.

So did the next one.

And the next

Before long, my need to win kicked that fear to the curb.  I found a house listed for $360K that checked all my boxes: 4 beds, good schools, decent floor plan, no carpets.

My agent didn’t think it was that good of a deal, but I made an offer anyways, and won.

After we closed, I took my wife, who’s been in the dark this whole time, to the house “for a showing”.  As we looked around, she kept asking when the agent was going to show up, and when I finally broke the news, the joy, surprise, and disbelief on her face that merged into an Eureka of “wow, this is doable” was something I’ll never forget.

And that was my biggest lesson in all of this–getting started is always hard, but once you’ve pedaled that bike for the first few yards, paid up for your first few shares, or took the keys to your first investment house, you’ll never look back.