Leadership & Career Coaching

Trust your direction. Commit to what matters.

For high performers at a crossroads, when the next rung feels hollow or the "impressive" path no longer fits. Together we clarify your True North and shape a way forward you can actually live with, without blowing up your life.

ICF ACC · Certified Integral Coach · Berkeley Haas MBA · 15 years in consulting

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Will Oldfather, leadership and career coach, smiling and seated in a leather chair in a bright office

A “True North” Orientation

Most high performers are living a borrowed definition of success, one that says "keep climbing" or "push through," even when the cost starts to show.

A "True North" orientation brings you back to what's actually true for you: what you want, what you need, and what you're no longer willing to trade away. Not a destination out in the distance. An internal compass you can trust week by week.

You’ll walk away with:

  • A clearer distinction between what’s “impressive” and what’s true

  • Decision criteria you can stand behind, including the tradeoffs you’re consciously choosing

  • Small, intentional experiments that translate clarity into lived change

Will Oldfather in a dark blazer, standing in a modern office with a slight smile

Real-world experience. Coaching with integrity.

I spent 15 years in global consulting. Complex projects, high-stakes teams, the tension between doing what's expected and doing what you know to be true. Being coached myself taught me that people deserve space to tell the truth about what they want, and support to choose a path where they feel fully alive.

Trained in Integral Coaching and credentialed by the ICF (ACC).

About Will

When Coaching Can Help

A few common starting points. If one resonates, we’ll shape the work around what matters and the real context of your life.

Watercolor of a lone figure standing still amid bursting orange confetti and streamers, looking down at a single scrap in their hand

You’re successful on paper, but something feels off.

You’ve checked the boxes. Maybe you’re even thriving (which makes it harder to explain). But inside, something isn’t landing. The work feels flat, the wins barely register, and you can’t shake the question: Is this really it? You want space to figure out what’s true for you, before deciding anything.

Watercolor of a figure on a dark cliff edge, looking across open teal water toward a distant shore with warm lights

You can feel the next chapter… but you can’t see the path.

You have a direction that feels real: maybe a pivot, a different kind of work, something that’s more yours. But it feels hard to reach from where you’re standing. You’re tired of going in circles. You want clarity you can live by, so you can take your next step with confidence.

Watercolor of a figure on a tall stacked pillar, orange fragments blowing away from their chest in the wind

You’ve reached the next level, and it’s harder to stay yourself.

More responsibility. More visibility. More pressure. You still want to perform at a high level, but the pace and the unspoken expectations are starting to pull you away from what you care about most. You want ambition with boundaries, and a way to show up that still feels like you.

Wherever you’re starting, we begin with what’s true right now.

How It Works

What Clients Say

  • "Will brought so much positivity, vulnerability, empathy, wisdom, encouragement and consistency and a really wonderful way of inviting me to consider new perspectives. Will's way of motivating me to consider other angles to so many different situations was very helpful in unlocking a new level of clarity and seeing a positive and fruitful way forward that was aligned to my intentions."

    Engineering Program Manager at Apple

  • “Will is a gifted coach and incredible human. It is so rare in this world to be seen, safely held for growth, and cherished. This is what Will does. Because of Will’s coaching, I uncovered the what and why of my true purpose in life, and discovered an effortless expansion of possibilities and new ways of being. This experience of being coached by Will transformed my life. I am eternally grateful.”

    Fortune 50 executive embracing a new second act

  • "Being coached by Will during my career transition helped me address personal obstacles I was aware of but lost sight of during a stressful and full time of my life. There were many times he was able to key in on an issue that I lost sight of. One that comes to mind was the lack of confidence in my own abilities, which led to a lack of voice. Things got better after I was reminded it's okay to advocate for myself and take a seat at the table."

    Business Operations Manager at a leading enterprise data storage company

If something resonates, let’s start with a 30-minute Discovery Call.

Book a Discovery Call