The Abyss, The Adaptation, & The Arrival
Building The Plane On The way down
The Abyss
There are times in the process of real estate development when it seems impossible to bring together so many loose ends in a manageable timeframe to get a construction project started. So many threads are flailing at once, but it’s your job to wrangle them all and tie them down—securing permissions, financing, and resources. There is an idiom I love that captures this feeling incredibly well: jumping off a cliff and assembling an airplane on the way down.
We are about to get rolling on the construction of our Troy project. The site has been empty for a couple of months as we grabbed those loose ends and tied them down. These are the ones we’ve handled so far: historic district approvals; architectural revisions; contractor selection and scheduling; financing contingencies and lender approvals; legal documentation and title clearance; utility connections and permits; tenant pre-leasing commitments; supply chain delays for key materials; insurance requirements; inspection scheduling and compliance issues; and tax incentives still under review.
One of the biggest challenges in building the plane on the way down is having to learn new skills you weren’t prepared to learn, in order to solve problems you didn’t know you would encounter—the aptly named unknown unknowns. While the solution sounds simple—just learn quickly—knowing you can learn new things doesn’t mean doing so is easy. If you know you can learn quickly, it usually means you’re already good at something, and you know it. It’s the getting good at the new thing part that is the real challenge. But sometimes, talent and grit are all you really need. After all, sometimes four words are enough: “I think I can, I think I can, I think I can…”
On this project, I had to learn about historic preservation tax benefits, commercial leases, construction loan financing, municipal industrial development authority programs, and asbestos remediation. When unknown unknowns become known unknowns, it’s my job to turn them into known knowns. You need to believe in your skills and abilities to overcome challenges you have not previously encountered. Sometimes, confidence is all you need.
I have always been amazed at how some people succeed purely from confidence; they simply talk themselves into incredible situations. Of course, they are lucky enough to be in the right place at the right time, but beyond that, what really sets them apart is their willingness to ask. At the same time, I have met many people who could absolutely pull off incredible things but don’t see themselves as “worthy”; they lack confidence. Opening a business is scary and hard. Buying an investment property, finding a new job—these are all major decisions in life. The question you need to ask yourself is this: when you’ve faced these decisions, did you jump, or were you pushed? That’s the simplest way to gauge your confidence.
The Adaptation
In the beginning, you tell yourself you’re just learning the mechanics—how to read a zoning code without your eyes glazing over, how to negotiate a contract without giving away the entire deal, how to sit across from a lender and sound like you belong there. You collect skills like tools, one by one, each tied to a specific part of the process that needs to be completed at that moment.
But somewhere along the way, almost without noticing, something more subtle happens. The tools stop feeling borrowed. The decisions, once difficult and requiring research, become instinctive. And yet, paradoxically, that sense of “arrival” never quite settles in. Because every new project resets the table—new unknowns emerge, new gaps in your knowledge expose themselves, and once again you have the uneasy realization that you are both experienced and unprepared at the same time.
Even more disorienting is the realization that the outside world often recognizes the shift before you do. People begin to treat you differently. They defer to your judgment. Another deal emerges, another set of constraints, another unfamiliar problem disguised as an opportunity. And so you lean on the only evidence that matters: not that you know everything, but that you have survived not knowing before.
Over time, you begin to understand that confidence is not rooted in mastery of the present, but in a quiet trust in your ability to adapt to whatever comes next. The identity you’ve built is not that of someone who has all the answers—it is of someone who no longer needs them in advance.
The Arrival
Deciding you are worthy is not as simple as it sounds, because worthiness is deeply entangled with risk. To declare yourself ready is to expose yourself to the possibility that you are not. Every deal you pursue, every project you champion, becomes a public experiment in your own capability. This is why so many capable people remain on the sidelines—not because they lack skill, but because they are unwilling to subject themselves to that level of scrutiny without guarantees. A steady paycheck is just one such guarantee.
Worthiness rarely announces itself in clear terms; it shows up as hesitation, as overanalysis, as the need for one more piece of validation before moving forward. You look around the room—at people who seem more established, more certain, more legitimate—and assume they crossed some invisible threshold that you have yet to reach. While that imposter syndrome feeling doesn’t go away, your inexperience does.
But over time, you begin to notice something unsettling: that threshold does not actually exist. The people who move projects forward are not the ones deemed worthy in advance—they are the ones who acted as if they were, long enough for the world to agree. Eventually, I think I can becomes I know I can, but it happens so subtly you only realize it when you have long since passed that point.
Confidence, in that sense, is less a personality trait and more a decision to stop seeking permission from an audience that was never explicitly asked to grant it.
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