Can the First Step Stand on Its Own?

Years ago, I got involved with a major economic development project that the Dean Administration wanted Milton to approve.

The vision was impressive.  Twenty buildings.  Two thousand jobs.  A new bridge.  Expanded infrastructure.  A transformed local economy.

I remember touring the company’s headquarters in Toronto and walking away genuinely impressed.  They were world-class.  I had no doubt they could build what they were proposing.

What bothered me wasn’t whether they could pull it off.  It was that Milton was being asked to bet on the vision, and my feeling that we were way out of our league.

Back in Vermont, the vision translated into infrastructure requirements.  Water.  Wastewater. Road improvements.  A future bridge.  Additional fire protection equipment.  Future maintenance obligations.  Most of those investments had to be made by Milton and had to happen before the campus existed.  As I often do, I put on the skeptic’s lens.

The State saw plans for twenty buildings.  I saw a commitment for one.

The State saw future tax revenue.  I saw infrastructure debt.

The State saw opportunity.  I saw risk.

Neither of those perspectives were irrational.  They were simply focused on different sides of the issue.

As the plans became more detailed, I found myself repeatedly asking a question that nobody seemed particularly interested in answering: What happens if only the first building gets built?

If every building was eventually constructed, Milton would benefit enormously.  If they weren’t, the town would still own, and need to pay for, the infrastructure.

For a long time, the State’s answer was essentially: Trust us.  The jobs would come.  The tax revenue would come.  The growth would come.  I wasn’t comfortable making a twenty‑million‑dollar decision based on hope.

Then Art Hogan, Executive Director of the Chittenden County Regional Planning Commission, introduced the concept of a Tax Increment Financing district.  Art believed it solved the problem.  I wasn’t ready to take his word for it.

Experience has taught me that confidence on paper does not necessarily equate to a viable result in the real world.  So, I did what I usually do when the stakes matter.  I checked the work myself.  I studied the TIF structure.  I ran my own numbers.  Then I sat down with someone I trusted completely: John Cushing, Milton’s long-time Town Clerk and Treasurer.

John would be responsible for ultimately making the concept work if we implemented it.  Together we walked through the assumptions.  The revenues.  The debt.  The timing.  When we finished, I realized something important.  For the first time, the project worked even if the optimistic future never fully materialized.  The infrastructure could be supported by the first building. 

The State would forego education tax revenue and therefore have real skin in the game.  The incentives were aligned.  The risk was shared.

Most importantly, the first step stood on its own.  Everything after that became upside.

That was the moment my position changed.  Not because I became more optimistic.  Because the risk structure changed.

I’ve seen versions of this situation many times since.  People become captivated by a vision.  A strategy.  A project.  An acquisition.  A partnership.  The discussion focuses on what success looks like if everything goes right.

Far less attention is paid to what happens if reality falls short of the plan.  One of the most useful questions I’ve learned to ask is: Can the first step stand on its own?

If the answer is yes, the future becomes opportunity.  If the answer is no, the future becomes a requirement.  Those are very different things.

Most people evaluate the dream.  Strategic judgment often begins by evaluating the first step.