Embracing Stretch Assignments: Lessons from the Waterfront to Paid Parking, Part 1

By: Heather Wright, AICP

I’ve always loved stretch assignments—the kind of challenges that push you beyond your comfort zone and expand your expertise. I’ll never forget my first. The island city I worked for had received an unexpected windfall from Washington State Ferries, and the city council decided to reinvest those funds into revitalizing their underutilized and outdated waterfront park. The planning director needed someone to lead the public outreach effort, and I eagerly stepped up.

Before I knew it, I was organizing community meetings, partnering with local groups, and leading walking tours to gather input on how the park should be used. Soon, I was drafting an RFQ, selecting a consultant, and presenting design alternatives to the public for a vote. Along the way, I even added the word "pétanque" to my vocabulary—an unexpected perk of the process! The day I toured the finished park, with its now-iconic stormwater feature flowing through the heart of the space, was one of immense pride.

That was ten years ago. Since then, I’ve transitioned from planner to director and moved to a new city. Three years into my current role, I took on one of my most complex and controversial stretch assignments yet: implementing paid parking.
When I was asked to lead the initiative midway through the public process, I was stepping into a debate that had been ongoing for over 20 years. Up to that point, my experience with parking had been mostly technical—calculating how many spaces were required for various uses, their sizes, and types. I could tell you that commercial spaces typically need three spots per 1,000 square feet and that single-family homes require one or two spaces plus 0.4 visitor spots. But the deeper policy question - whether parking should be free, how pricing impacts business districts, or what influences public perception—hadn’t been part of my planning world.

This article marks the beginning of a series where I’ll share insights on implementing paid parking—what works, what doesn’t, and what can set a program up for success. As parking reform gains momentum and more communities lower or even eliminate parking requirements, I suspect this topic will land on many planners’ desks. My hope is that this series helps others feel more prepared for the challenge.
Tip #1: Hire a Professional

As planners, we wear many hats. Our work extends beyond land use to include stormwater, geological hazards, wetlands, shoreline functions, housing, climate change—the list goes on. But we can’t be experts in everything. Just as we rely on specialists for traffic studies or environmental reports, we should give ourselves permission to seek professional expertise in parking management.
In our city, this was the fourth time we had revisited paid parking, but it was the first time we hired dedicated parking consultants. Bringing in experts not only elevated the conversation but also allowed us to learn from their experience while staying engaged in the process. I applied this same mindset when leading a recent fee study—sometimes, the best decision is recognizing when to call in reinforcements.
The professional knew all the things I didn’t know! While the mechanics of implementing paid parking could likely be mapped out without an expert (signage, enforcement, finding a parking vendor, etc), they provided invaluable insights on which systems work best and how people respond to them. Their expertise helped us go beyond logistics, ensuring we made informed decisions while responding to community and business concerns and needs.

Lastly, it’s good to have an expert in the room when presenting a parking proposal at a community meeting. Parking is a controversial issue. Businesses think it will kill business, and experts say it will help business by leading to turn over and creating available spaces. When having these difficult conversations with the community, and the electeds, it is nice to have research-backed insights on parking patterns, turnover rates, and economic impacts.

Next month’s topic -the focus will be on the importance of a committee - stay tuned!