What Comes Next

...2 days to go...

With this year-long project coming to a close, many of you have asked me what comes next.

Honestly, it’s something I’ve struggled with for months.

When I started this year, I assumed it would be temporary. I’d scratch some itch to do good in the world, then head back to Big Tech, satisfied. But relatively early on, I realized I didn’t actually want that. The reasons I left Big Tech in the first place—the sense that it’s ultimately part of the problem, not part of the solution—are still exactly how I feel.

So I spent months considering paths that would let me help more directly. A role in Katie Wilson’s administration? Direct work at a Seattle nonprofit? A position with a national organization like Goodwill (which I got to know during a project at Deloitte) or the Salvation Army?

I’ve come to believe none of those paths are quite right for me, and the reasons why are tied together.

There’s too much I don’t understand about the political process, and too much I don’t understand about nonprofit management. I’d worry about making real mistakes with other people’s lives at stake. Meanwhile, I’ve met so many people this year who have spent decades deeply involved in these organizations—people who understand what actually works and what doesn’t. As I wrote a few weeks ago, this year has given me enormous trust in these organizations and the people powering them.

One way to see this is to look at two very different approaches to big philanthropy.

MacKenzie Scott has given away more than $26 billion across 2,700+ gifts since 2019, almost entirely unrestricted, with minimal reporting requirements and little interference in how organizations use the money. Mark Zuckerberg’s Chan Zuckerberg Initiative takes the opposite approach: grantees submit detailed applications proving alignment with CZI’s priorities, then commit to ongoing reporting, CZI’s preferred ethical-conduct standards, and more. When CZI gave $100 million to Newark’s public schools, it came bundled with a demand to renegotiate teacher contracts around merit pay and weakened tenure.

Five years later, journalist Dale Russakoff’s book The Prize documented how the plan for Newark’s public schools unraveled: test scores barely moved, tens of millions went to consultants, and the reform was designed with little meaningful input from the community it was supposed to serve. It’s a near-perfect illustration of the failure mode of “we know best, and we’ll pay for the right to prove it.”

With the notable exception of MacKenzie Scott, Big Tech leaders tend to assume their success in capitalism means that they know a better way, and they can improve outcomes just by applying that success to other types of ventures like nonprofits, or education.

This year has taught me to be skeptical that big changes from smart outsiders automatically improve outcomes in the nonprofit and government worlds. The population we’re trying to serve is often nothing like a company’s employees or customers, and the skills that make someone effective at running a business don’t automatically transfer.

My own neighborhood offers another good example. For two decades, the Fort Lawton Redevelopment Project has tried to turn a 34-acre former Army Reserve parcel bordering Discovery Park into housing for as many as 500 low-income and homeless individuals. The project has been slowed again and again by organized opposition from groups like Friends of Discovery Park, concerned about tree loss and infrastructure strain. My city councilman tells me it’s finally likely to proceed. But watching this process up close for even a few months has shown me that a founder’s or CEO’s ability to simply direct action, without resistance, isn’t remotely the skill needed here. What’s actually required is the much slower, much harder work of organizing a community.

That’s not a skill my career has given me. And I don’t think I’d be a particularly effective advocate for homeless Seattleites by parachuting into one of these organizations or into government.

This year has shown me that I prefer MacKenzie Scott’s approach.

So Here’s What I’m Doing

For the last few months, I’ve been quietly dipping my toe back into work: independent strategy consulting, mostly helping retailers and consumer products companies figure out how to grow and better serve their customers. It’s work I genuinely love, and it comes with something I haven’t had in years: real flexibility.

I can choose to work with companies I feel good about, and say no to those I don’t. While I expect the bulk of my work to be in the for-profit sector, I can work with nonprofits adding real social value, and cut my rates for them to a price they can afford.

I can say yes to projects, or say no. I’ve kept next month entirely open, because my family and I are heading to Spain for a month of culture, beach time, and Spanish practice for Natalie as she heads into Spanish 2. And the work leaves me time to keep volunteering, continue serving on FareStart’s gala planning committee, and be present for my family.

I plan to direct a meaningful portion of the income from this business toward the organizations I’ve come to care about this year. It won’t be my whole paycheck, the way this year’s project has been—the family’s got to eat—but it will be real.

So if you have a strategy project, for a big retailer or a local nonprofit, please reach out - I’d love to talk. And I can promise you that some of the cost will go toward a cause worth supporting.

Stay tuned for my final post, coming Wednesday.