The Generalist's Edge: Why Not Having One Specialty Is a Specialty in Itself

I'm excited to continue growing Headwind Strategies, and was reminded recently why I started the firm in the first place. A mentor of mine years ago pointed out that I'm a generalist, a rare specialty in and of itself. My career has spanned Congress, the State House, City Hall, and K Street, along with campaigns at every level. Headwind Strategies is the outlet I built to put all of it to work for clients.

The Advice That Reframed My Career

That mentor caught me at a moment of real anxiety and hand-wringing over the direction of my career. At that point I had worked in federal government, on K Street, in state government, and city government, as well as a number of political campaigns. I had held roles and led teams that touched on many different issues. Throughout all of them I worked with brilliant people who knew their issues well, and I always felt insecure being the person in the room who didn't have a niche expertise. I felt I needed to find one and sprint toward it.

In every position I've held I've been the person who solves the problems that don't fall neatly into one bucket or another. They require creative solutions and finding new paths forward, and I often discounted my contributions. Thanks to my mentor, I realized that as an attorney with legislative, administrative, operational, and political experience, I had a vantage point others in the room simply didn't have.

What Happens in the First Hour

When coworkers hit a wall, they knock on my door and ask if I have a minute. An hour later we've got a game plan in place.

Here's what that hour looks like. I probe what the goal is, where things stand now, and where they want to be. I outline the internal decisions within their control and those at the mercy of external stakeholders, a board, a commission, a committee, an elected official, recognizing that the former can greatly affect the outcome of the latter.

For what's within control, I ask three questions: what are the next steps, what can be done concurrently, and what follow-on steps come once the ball is rolling. Then I plot decision points and deadlines on a calendar. It may sound rudimentary, but it's a quick way to crystallize what needs to happen, and by when, to keep a project or a goal on time.

The Track Record

I've helped take a hospital system from announcing a five billion dollar new campus to preparing to accept patients in a brand new facility. I've worked major legislative changes and surgical fixes to solve acute problems. I've helped steer decade-old litigation to resolution within months. I've helped bring together local and state governments, utilities, neighborhood groups, and social services to address long-standing blight in neglected neighborhoods.

These are only a handful of the projects I look back on with pride, knowing my specialty as a generalist is what helped achieve those outcomes.

Why This Matters for Clients

Organizations, general counsels, and founders may not always know where to start when tackling a major problem. With my experience, I provide that initial outlet for their questions, concerns, and anxieties, and I can help them chart an efficient path forward.

A generalist with real experience behind the label brings a wide view to a narrow moment. That's what turns a scattered set of facts into a plan, and a plan into progress.

I'm bringing that same approach to California. The jurisdiction has changed. The skill set has not.