A woman with shoulder-length dark wavy hair, wearing a dark button-up shirt with a collar, crossing her arms and looking at the camera in a neutral room.

Life Architecture for People Managing Everything

I help executives design infrastructure for their actual lives — through writing that reframes the chaos, coaching that builds clarity, and custom systems that turn overwhelm into execution.

I'm a writer and advisor with 20 years of experience leading Operations and Transformation at the VP level.

I specialize in helping capable people stop drowning in their own complexity.

No generic frameworks.

No productivity theater.

Just practical wisdom, strategic systems, and the belief that if you can’t find some humor in the chaos, you’ll drown in it.

How I Work

I help executives through strategic coaching, custom infrastructure design, and content that reframes how you think about complexity.

  • Coaching and custom infrastructure for executives managing full-life complexity.

    For capable leaders who are excellent at their jobs but overloaded everywhere else. This work combines executive coaching with systems design to help you build infrastructure that actually fits your life — not an idealized version of it.

  • Operational infrastructure for growing and complex organizations.

    For founders and leadership teams navigating growth, change, or ambiguity. I design practical systems — from information architecture to operating rhythms — that help organizations scale without breaking their people or processes.

    Learn more

  • Ideas about managing chaos you didn’t create.

    I write Stepping In It, a newsletter about navigating complexity — blended families, workplace dysfunction, family logistics — when you’re the person everyone relies on. Essays every Tuesday — often wry, often right.

    Read on Substack

  • Stepwise: Life Architecture for People Managing Everything (launching March 2026). Concrete steps to help with managing complexity, building systems, and staying sane when you're everyone's default problem-solver.

    [Coming Soon]

Let's Talk!

Ready to get started?

But not sure where to begin?

Book a free 30-minute clarity call. We’ll talk about what’s breaking in your current approach and whether we’re a good fit to work together.

Schedule Clarity Call

Have something specific in mind?

Tell me what you’re working on and I’ll get back to you within 48 hours. Use this form or email: admin@karendoak.com