They say doing well in real estate investing (REI) takes getting comfortable with being uncomfortable (and by “they,” I mean Tarek …)

That – I’m good at. I’ve put myself in many uncomfortable, potentially embarrassing, at times dangerous situations for the thrill of it. I like learning new things. Even if those new things are learned while splitting open my pants on a marathon training run or being the target of mortar rounds in a combat zone.

I also tend to jump into things quickly, which can be helpful in investing as well. Hesitation can be a real killer. It can make you lose out on a deal, an awesome partnership, or a lower interest rate (that one hits right in the feels, doesn’t it, America?) It can also make you lose the chance to watch the prime minister of Italy dance with his mistress at the G8 Summit in Georgia when you were awaiting your security approval for a new job and had free time and your parents told you not to spend your money driving to Georgia to hang with a friend working the summit. Ahem. Not that I’m still bitter or anything.

So, missed opportunities in my past combined with general fear of missing out have pushed me to be more impulsive than most. Or, in the recent words of someone delivering my results of a personality test: I’m “all gas and no brakes.” Hmm. That seems…positive.

But I do have brakes and they’re called: analysis paralysis. The paralysis kicks in at random. I can say yes without thought to multiple decisions than BAM! I’m found standing like a deer in headlights in the moisturizer aisle of the grocery store unable to choose a night cream.

Because I’m both full of FOMO and an overanalyzer, REI can be a real challenge. Like when I try to sell a piece of property.

If no one bites, I question my initial decision to buy it.

If people bite too quickly, I question my decision to sell it.

Sigh.

And yet, somehow, I’m still really interested in the real estate world. I think a big part of it is that I just like looking at pretty things! I get excited to see the décor of a house. The lines of the architecture. The paint colors. I like picturing the chandeliers I’d put in the closets, above the bathtubs, in the garage… (did I mention I overdo things? No brakes.)

That houses-are-pretty thing was a big part of why I was excited for my first fixer upper.

The house was a blank canvas, so my mind immediately ran wild with décor ideas. First thing was first though: I needed to find a wall to knock down, obviously. If you’ve ever seen any show on HGTV, you know that is just a requirement.

I talked my ideas over with my contractor. He had done work with some of my family members years ago so I figured he must be trustworthy, or they wouldn’t have kept working with him. To my delight, he gave me answers to everything I wanted to do and an estimated budget I was thrilled with. He said he could start as soon as the house closed.

Lesson #1: If a general contractor can get started immediately – they probably aren’t a good general contractor.

I would later discover that really quality GCs were kept so busy in that area that they had waiting lists. If someone said they could start at any time – run. But I didn’t know that yet. I just thought I lucked out because this GC had recently moved back into that town, so I figured he just hadn’t lined jobs up yet and I was reaping the benefits of his availability.

Lesson #2: If a contractor moves around a lot, they might be running from something. Tread cautiously.

Right away, I knew this guy didn’t operate with what you might call “professionalism.” He didn’t have his own contract to sign. I ended up writing out his estimate for me as he rattled off prices for all the things we were planning to do. But I told myself it was to be expected. His passion was construction, not paperwork. So what if he handwrites everything and talks about something called a fax machine to get a signature to me? Whatevs! I needed his house building expertise, not his computer skills.

I started looking into financing options for how I was going to pay for the rehab of this house and the bank told me they required a licensed GC. So, I texted my guy. “You have a license, right?” “Yes.” Excellent.

He tells me he has a “crew” of guys, and they’ll get started right away. The first thing we tackled was the roof. And he did show up quickly with several other men, scurrying around the roof. He told me he “hated to do it,” but he needed to ask for money up front to get them started. I knew this guy did not manage his own money well, so I figured that was just a concession I’d have to make to work with him. I certainly didn’t want to wait to find a different GC (no brakes). Sure! I’ll spot you this time, but we’ll need to make sure ample progress gets made each time I pay you, sound good? “Oh of course!”

You can probably guess what Lesson #3 was: Never give a contractor money up front.

Sadly, that lesson didn’t fully sink in for a couple more payments but more on that later. He did get the roof done quickly and it looked great. But then his “crew” left and the system began to break down.