THE ONE THING I'VE STOPPED DOING

So much of being a developer is the mindset. You tell yourself you can do something. Someone tells you you can’t. You have a crisis of confidence. And then you get on with it.

Or, in our case, you build it!

While I’m a social creature - I love talking to people - I have not always been confident. In fact, let’s be honest. If we talked on Twitter two weeks ago, you probably saw me pulling my hair out trying to launch the latest newsletter. At every step of the way, there is doubt.

I was reading through one of my favorite books a few years ago when I came upon this passage that nearly cracked open my brain and gave me some insights into, well, myself. (And possibly you!)

“The writer Andrei Donderi argues that the world is divided between Askers and Guessers. Askers feel no shame when making requests and are willing to be told no without being hurt. They’ll invite themselves over as a guest for a week. They’ll ask for money, to borrow the car, a boat, or a girlfriend (<- I laughed out loud at this!) They have no compunction about asking and do not take offense when they are refused.

Guessers hate asking for favors and feel guilty when saying no to other people’s requests. In Guess culture, Donderi writes, you avoid putting a request into words unless you’re sure the answer will be yes. In Guess culture, you never say no to someone else directly. You make excuses. Every request, made or received, is fraught with emotional and social peril.”

Askers and Guessers.

The distinction blew my mind and gave me a way to think about all of the anxiety I carried with me when I started every project. Property development is one long and sustained collaboration where, at every turn, you’re in danger of being told no. No, I won’t lend you money. No, I won’t sell you my land. No, you cannot change the zoning over here or over there.

No, over and over again.

My crazy-making habit, though, and perhaps yours, was to own the anxiety of “no” before the word had ever been uttered.

That’s really what a Guesser is to me: Someone who says someone else’s no. They say it to themselves, and rejection in hand, carry on with the gloomy (mis)understanding that the “no” was inevitable. They had imagined it. And so, of course, it must be so.

Quick story:

When my partner and I wanted to build Wakpada, our timing was off.

The much celebrated “Minneapolis 2040” plan had passed (the one that upzoned major corridors to allow for dense development and removed single-family zoning throughout the city). BUT the underlying building codes were not yet written. You knew what your height requirement was, but that was about it. When we went to the city to get approvals, our city planner realized that we couldn’t actually use the 2040 plan and the revised zoning it allowed. We wanted to build Wakada on the site where two duplexes and a gas station stood. But because you can’t have two different uses for one site, we needed to rezone everything!

In order to get the land rezoned, you have to get support for the application from nearby residents.

You see where I’m going with this, don’t you?

We needed 14 signatures out of the 22 properties nearby. The Guesser in me? There’s no way this is going to happen. It’s the middle of November. During Covid!

We masked up, knocked on doors, then retreated to a safe distance, six to ten feet away, before we asked for their support. One guy chased me off his porch!

It wasn’t working. So we regrouped, strategized, and headed back out again. We told folks that we could just build on the gas station site, but if we did that, it would be a smaller project and have very limited parking, if any, because we wouldn’t have enough buildable space. But, we explained, if they allowed us to apply for the rezone and we got approval to build on the gas station AND the two duplexes, we could build a bigger building that would include ten times as much parking.

Jeff and I must have gone out together and separately twenty times over the course of 30 days. Asking. More asking. Always coming up short.

I finally knocked on my last door late in November. It was cold out, the skies threatening snow. This lady answered the door, and her face was the very definition of no. Mouth set into a skeptical frown. Arms crossed against her chest. Not only was she my last door, but she was our last chance. We had not been able to contact 7 of the owners, so this was do or die. I remember standing out there as the cold from the concrete crawled up into my sneakers.
We talked…and talked.

She told me about the neighborhood. Her son. I told her about the project we were hoping to build. How we needed to get her permission to apply for the rezone.

She stepped closer and closer every few moments, craning her left ear up toward my head to catch the words. I’d keep on talking, and then, without fail, every five minutes or so she’d look up at me, squinting, and remind me that I was standing too close.

“Back up, young man!” she’d say.

I’d back up.

She’d scoot closer because she couldn’t hear.

I’ll tell you, to this day, I’m not sure if she was gaslighting me because, by the end of our conversation, she had maneuvered me off her front porch, down her sidewalk, and out past the gate that led to her front yard.

I finally held my clipboard out one last time, and she leaned in real close, peered up from underneath her bushy eyebrows, and said:

“What was it you needed again?”

She was smiling. Maybe smirking. Some kind of grin that communicated that she was half my size and twice my smarts.

I reminded her of the building. The zoning. The parking. In my head, I was already walking, defeated, back to my car.

“Oh, that,” she said. “How long have we been talking?”

“Two hours,” I said.

She shook her head and then winked.

“Young man, you could have just asked,” she said.

She took my pen and signed. Turned on her heels and tottered back into her house.

I’m telling you, I think about that lady all the time. Did I go back to my office and immediately become an Asker? No. Only Superman changes that fast.

But I did start practicing.

Even when I know the answer is no, I ask anyhow because while other people may tell me no, I’m not going to say it for them.

I don’t beat around the bush (that took practice as well!).

I ask. And then listen. And I try to be gracious either way.

So let me ask you something. I’m taking an informal poll. Are you an Asker or a Guesser?