Think Outside the Lines Coaching

Create the life you want.

Most people aren’t living their lives — they’re managing them.

Going through the motions. Checking the boxes. Operating on autopilot while the days blur together.

You might be successful by most standards. You might even look like you have it all figured out. But somewhere along the way, achievement stopped feeling meaningful. And now you’re wondering: Is this really it?

If you’re here, the answer is probably no.

This work isn’t about fixing what’s broken. It’s about reconnecting with what matters — and building a life that actually feels like yours.

Not by default. Not by someone else’s definition of success.

By choice.

The Problem Isn’t You

The world teaches us to optimize, produce, and perform. To measure our worth by how much we accomplish. To keep moving, even when we’ve lost sight of where we’re going.

And after years of that, it makes sense if you feel:

Disconnected from yourself

Exhausted by the constant “doing”

Unsure of what you actually want anymore

Stuck between who you’ve been and who you’re becoming

You don’t need to work harder. You don’t need another productivity hack.

You need space to hear yourself again.

What Alignment Actually Means

Alignment isn’t about perfection. It’s not about having everything figured out or living some curated, Instagram-ready life.

It’s about getting honest with yourself.

It’s about making choices that reflect what you actually value — not what you think you should value.

It’s about building a life that feels lighter, clearer, and more intentional.

Not because you’ve abandoned ambition.

But because you’ve reconnected it to meaning.

How I Work

I spent over a decade leading teams at companies like Apple, Activision, and Microsoft. I know what it’s like to be good at something and still feel disconnected from it. I know what it’s like to achieve the things you thought you wanted — and realize they don’t fit anymore.

Today, I help people navigate that tension.

Not by telling you what to do, but by helping you remember who you are — and what you’re capable of when you stop living on autopilot.

My approach combines leadership experience, creative strategy, and a deep belief that you already have more wisdom than you think. You just need the right questions to access it.

The people I work with — I call them resilient dreamers — are thoughtful, capable, and ready for something more intentional. They’re not looking for hype or quick fixes. They’re looking for clarity, self-trust, and a path forward that actually feels aligned.

If that sounds like you, keep reading.

Ways to Work Together

1:1 Coaching

This is 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 and accountability between sessions

Access to tools, frameworks, and guided resources

Investment:

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

$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

A follow-up check-in two weeks later

Investment: $500

Digital Courses

I’m building guided courses for people who want to deepen this work at their own pace.

These aren’t typical online courses. They’re designed to feel like coaching — thoughtful, reflective, and deeply practical — just in a format that lets you move through the material on your own time.

If you prefer self-directed learning, or want ongoing support beyond our work together, these courses may be a great fit.

Upcoming offerings and early access are shared through my newsletter.

What Others Have Said

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

— Jennifer

“Shawn balances professionalism with genuine empathy, creating a supportive environment that fosters real growth.”

— Nive

“His leadership and mentorship were transformative — grounded, thoughtful, and deeply human.”

— Ken

If This Resonates

Coaching works best when you’re open, curious, and willing to be honest with yourself.

If something here feels aligned, I’d love to explore what working together might look like.

Click here to complete the new client form and kickoff the process.