When I entered the workforce in 1998, Netscape was how you found things online, CDs were how you owned music, and a Blockbuster membership was a reasonable and valued household expense. All of it felt like the permanent infrastructure of modern life. None of it survived the next decade. For most of the 28 years since, neither did my initial career plans — and for a long time, I thought that was the problem.
I moved between sectors — large national nonprofits, national advocacy organizations, regional economic development, independent consulting. I earned an M.Ed. in my twenty-first year of professional work, not at the beginning of it. I facilitated organizational change through a fundraising budget. I built leadership programs inside a chamber of commerce.
From the outside, I understand how it looked.
Yet, what I’ve come to understand — slowly, honestly, with some resistance of my own — is that it was never as scattered as it appeared. Every organization I worked within, I was studying the same set of problems from a different vantage point: how people change, how organizations resist change, and what it actually takes to build something that lasts beyond the training event.
I wasn’t wandering.
I was researching.
“Every organization I worked within, I was studying the same set of problems from a different vantage point.”
For instance:
At Habitat for Humanity International, I worked inside a $1B+ global organization navigating the gap between transactional systems and relational ones. The nominal function was fundraising. The actual work was organizational change — getting a large, matrixed institution to shift how it thought about constituent relationships, and what that shift required from the people inside it.
At the Sierra Club, I built a technology-enabled personalization framework grounded in donor psychology and behavioral segmentation — a real solution to a real problem. And then I watched it not happen, because the organization wasn’t ready for what the solution required of it. The project didn’t survive. I did. And what I extracted from that failure was more valuable than anything an easy win would have taught me: a good idea and a solid plan are not sufficient. Change asks something of the people living inside the system you’re trying to change. When organizations aren’t ready to reckon with that, good ideas stall. Understanding why they stall — that became one of the most important things I know.
At the Lewis County Chamber of Commerce, I designed and ran a nine-month cohort-based leadership development program. Three cohorts. Thirty-three participants. A complete curriculum redesign in year three. And for the first time, I had the language and the methodology to measure what I’d always been trying to do: not whether people completed the program, but whether they actually changed how they led. Kirkpatrick Level 3. Observable behavior change, documented through quarterly impact assessments.
The thread was always the same. The contexts were just different laboratories.
Here’s what that research has produced — five things I now know about learning and organizational change that I couldn’t have arrived at without doing the work across all of those contexts:
1. Learning is really about change.
We talk about learning as if it’s an event — a course completed, a skill acquired, a box checked. But real learning isn’t accumulation. It’s transformation. It requires a person to do something differently than they did before, which means giving something up: a habit, an assumption, a way of seeing themselves. That’s not a training problem. That’s a change problem. And until L&D treats it like one, the gap between what people learn and what they actually do will stay exactly where it is.
2. Resistance is data.
When people push back on a development program, a new process, a change initiative — most organizations treat that as a problem to manage. I’ve learned to treat it as the most useful signal in the room. Resistance tells you what the change is asking people to give up. It tells you where the design is missing something. It tells you whose identity is bound up in the way things currently work. An organization that learns to read its own resistance becomes smarter faster than one that keeps trying to push through it.
3. Learning has to be practiced in the wild, not in a conference room.
The conference room is controlled. The actual workplace is not. Real learning happens when someone takes what they encountered in a session and tries to use it under pressure, with real stakes, in front of people they actually work with. Which means the design question isn’t just “what will we cover” — it’s “what will they do with it between now and the next time we meet, and how will we know?” Programs that don’t answer that question are building for completion, not for change.
4. Psychological safety isn’t a nice-to-have. It’s the mechanism.
Learning requires risk. It asks people to try something they might not do well, to surface a gap they’d rather keep hidden, to be wrong in front of others. People do not take those risks in environments where being wrong has a cost. Which means the emotional climate of a learning experience isn’t separate from the content — it is the content. Get that wrong and everything else is performance.
5. Learning has to connect to a problem the learner actually has right now.
This one is widely stated and almost universally ignored in program design. We build curricula around what organizations think people should need and deliver it on a schedule that works for the calendar. What actually drives engagement — and transfer — is a learner who can draw a direct line between what they’re working on in a session and a real problem sitting on their desk. Not eventually. Now. The organizations that build that connection into the design see different outcomes than the ones that don’t.
I’m not offering these as original discoveries. Versions of all five appear in the research — Kirkpatrick, Kegan, Edmondson, Knowles, and so many others. What I’m offering is what it looks like when you’ve watched them play out across real organizations, in real programs, with real people who had real jobs to get back to.
That’s what 28 years of moving through different organizational contexts actually gives you. Not a tidy career trajectory. Not a credential stack. A body of evidence about what works, what doesn’t, and why.
