Welcome to Ideal-to-Real Updates, a series where we check in with idealists taking action on their good ideas to see what they’ve been up to and what gems of wisdom they’ve learned along the way.

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A little over a year ago we wrote about Alex Linsker, an Oregonian who was undertaking the ginormous task of overhauling the state’s tax system through his initiative, Tax and Conversation.

It’s a big project to lead, but Alex has been taking small steps forward. Since we last spoke, he’s talked with thousands of people—friends, influential people in the state, tax experts, people affected by underfunded state and local services—to learn more and get buy-in for the project.

“Sometimes the work gets tiring but then I talk with someone who is affected by tax and who cares about people, and that inspires me and shows me the way forward,” he says.

Alex taking notes at a City Club of Portland meeting.
(photo courtesy Rachel Loskill, Program & Communications Director, City Club of Portland)

Most of the people he’s met with have been referrals. Others have been chance encounters with everyday Oregonians.

Once, when Alex was biking home from an event, a guy walking on the sidewalk stopped him while he was at a stoplight. He was a farmer and former Marine from Eastern Oregon, and started telling Alex about his son and grandson, and a motorcycle they all rode over the years. He talked about limits and rules, and Alex saw the connection to Tax and Conversation, which on a fundamental level, is about the same thing.

“He leads an agricultural co-op and he sends out two trucks each day: one sells milk to Idaho, and the other gives cream, cheese, and gas to Oregonians who can’t afford it. He wanted the tax system to change so the people around him can buy those things,” Alex says. “Even though he doesn’t speak the same words I do, we realized we share a lot of the same values. We talked about tax, food, medical care, government, courts, schools. I listened, he listened, we learned and agreed.”

The idea is that this farmer’s voice and thousands of others are informing the rewrite of the current policy, which in a nutshell is this: people and companies who have the most money pay less tax.

Alex wants to flip this system by refunding all payroll tax to residents, ending Oregon income and property taxes, and progressively taxing net assets. This will simplify tax law so that people can better understand where their money’s going, and create more jobs, especially for teachers.

Of course, it takes time to build momentum. As the co-founder of The Collective Agency, a democratically-run shared workplace, Alex knows one thing for sure: only move forward if the majority agrees to move forward.

“There was one week last year where I had an idea, and asked people about it. They all said it was terrible. If I think something is good, and everyone else says it’s terrible, then it’s not worth pursuing,” he says. “So there are a lot of checks and balances.”

The project has had its ups and downs and there’s a lot of work ahead—like raising $15 million (!) for a statewide campaign—but for Alex, the sometimes taxing nature of it is anything but an obstacle.

“This project is a mix of statistics and empathy. It’s similar to how I started Collective Agency, but a lot harder,” Alex says. “I’m constantly choosing to work on this. It’s challenging, but I’m meeting amazing people and it’s fun.”

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Want to help? From referring to writing to donating, there are many ways you can support Tax and Conversation.

If you’re looking to start a similar initiative where you live but don’t know how to begin, feel free to get in touch with Alex for tips and advice: Council@TaxAndConversation.com.