Think Outside the Lines Coaching

Create the life you want.

You already know how to succeed.

You’ve done it.

Now, it's time to align that success with who you are actually becoming.

I'm Shawn.

I help high-performers who feel capable, successful on paper, and still somehow disconnected from the life they're actually living.

After spending over a decade navigating high-pressure startups and leadership roles at Apple, Activision, and Microsoft, I know firsthand what that feels like.

From the outside, I had it figured out. Internally, I knew something was off.

I understood ambition and performance, but I also learned what it means to move fast without moving forward.

I stepped away from that world to build something more aligned—not because I knew exactly what was next, but because I could no longer ignore the disconnect.

That gap between external success and internal alignment is the exact space I work in now.

What We Navigate

Through 1:1 coaching, we work together to tackle:

CAREER TRANSITIONS

When what you're good at and what you want start to diverge.

IDENTITY SHIFTS

When titles and roles no longer fit who you're becoming.

THE MESSY MIDDLE

Leaving what looks good for what feels true.

BUILDING SELF TRUST

Finding your footing when there's no script to follow.

AUTOPILOT TO INTENTION

Moving from performance to presence.

My Approach

I combine executive leadership experience with a deep belief that you already have the wisdom you need—you just need the right questions to access it.

My approach is calm, grounded, and fiercely anti-performative.

What you WON’T get:

Five-step frameworks, life hacks, or pressure to hustle harder. I don't believe you need fixing.

What you WILL get:

Clarity when everything feels foggy, a steady presence in the uncertainty, and the space to hear yourself without judgment.

The people I work with aren't looking for hype.

They're looking for clarity, self-trust, and a path forward that actually feels aligned.

  • “Shawn is an exceptional leader who balances professionalism with genuine empathy, creating a supportive environment. His mentorship left a lasting impact on my career, and I highly recommend him for his strength in leading with clarity and compassion.”

    -Nive

  • “Shawn leads with quiet strength. His mentorship has been instrumental and his leadership has left a lasting impact.”

    -Jennifer

  • “Shawn navigates diverse teams and personalities with emotional intelligence and respect, fostering a space where people go the extra mile. His mentorship on leadership and accountability was transformative."

    -Ken

How I Can Support You

1:1 Coaching

A focused coaching relationship designed to help you move from autopilot to intention.

Together, we'll explore what's feeling heavy, what's pulling you forward, and what small, aligned shifts can help life feel lighter and more like yours.

What's included:

Weekly 1:1 sessions (60 minutes, via Zoom)

Personalized alignment work and reflections

Ongoing support between sessions

Access to tools and guided resources

Investment:

$1,000/month (4 sessions + email support)

Best Value:

$2,500 for a 3-month commitment

Momentum Strategy Session

A single, focused session for when you need clarity—now.

We'll cut through the noise, identify what's really holding you back, and map out a clear, actionable path forward.

What's included:

90-minute deep-dive session

A practical action plan

Follow-up check-in two weeks later

Investment: $500

Coming Spring 2026:

Create the Life You Want // Digital Course

Most online courses just give you more boxes to check.

This one is designed to help you step off autopilot entirely.

For those who want to deepen this work at their own pace, I am launching a self-guided experience that mirrors the depth of my 1:1 coaching.

This isn't a typical digital course filled with rigid frameworks.

It is thoughtful, reflective, and deeply practical—giving you the tools to close the gap between external success and internal alignment, on your own time.

  • “Shawn is one of the most strategic and forward-thinking leaders I’ve encountered. He excels in managing complex projects, mentoring teams, and aligning initiatives with business goals. His leadership consistently delivers high-performing teams and exceptional results.”

    -Rob

  • “Shawn’s exceptional leadership is inspiring. He consistently fosters a positive, productive work environment, mentors team members, and drives strategic initiatives with empathy and vision. He is a remarkable leader dedicated to team and organizational success.”

    -Ida

  • “Shawn exemplifies strong leadership, fostering team success with empathy, organization, and a passion for growth. His commitment to improving team dynamics and mentorship has been invaluable."

    -Barry