Billy Hyland

About Me

You’ve accomplished a lot. You’ve built experience, a career, maybe even a life that looks pretty successful from the outside.

And yet, something may be telling you there’s more.

Maybe you’re thinking about a change. Maybe you’ve reached a point where what worked before doesn’t feel quite right anymore. Or maybe you simply find yourself asking, What’s next?

That’s where I come in.

I work with accomplished professionals and leaders who want to think differently about what comes next—and intentionally design it.

My approach is built around a simple idea: better questions can open possibilities that better answers sometimes can’t.

Through my work with Level Positive and The What If Shift, I help people challenge the assumptions that may be keeping them stuck, explore possibilities they haven’t considered, and turn those possibilities into meaningful action.

I’m not here to tell you what your next chapter should look like. You already bring years of experience, instincts, strengths, and perspective to the conversation.

My role is to help you ask better questions about what you want to do with all of it.

Because you’re not starting over.

You’re starting from experience.

Coaching with me

Results & Goals

My goal is to help you move from wondering what’s next to actively exploring and creating it.

Together, we may work to challenge assumptions that are limiting what you see, identify possibilities you haven’t considered, make more intentional decisions, and turn ideas into meaningful action.

You may come away seeing your situation differently, asking better questions, and feeling more equipped to take the next step—not because I gave you the answer, but because you discovered what’s possible for yourself.

The goal isn’t to have everything figured out. It’s to start moving toward something that feels worth creating.

How I like to coach

I coach through conversation, curiosity, and questions.

I’ll listen closely, challenge you when it’s useful, help you notice assumptions you may not realize you’re making, and ask questions designed to open possibilities rather than prescribe answers.

You can expect our conversations to be thoughtful, practical, candid, and human. There may be reflection, there may be homework, and there will almost certainly be a few “What if…?” questions along the way.

I believe you bring far more experience and wisdom to the conversation than you may realize. My job isn’t to hand you a blueprint for your life. It’s to help you see more of what could be possible—and decide what you want to do next.

Offerings

Coaching

I offer one-on-one coaching for accomplished professionals and leaders who are thinking about what’s next and want to explore it with greater intention.

Sessions are conversational, thought-provoking, and tailored to what you’re navigating. We’ll challenge assumptions, explore possibilities, and identify meaningful actions you can take next.

Start with a complimentary 30-minute discovery conversation to see if working together feels like the right fit. Individual coaching sessions and ongoing coaching engagements are available.

Courses

The What If Shift is a self-guided course designed to help you think differently about change and intentionally explore what comes next.

Through six modules, you’ll learn how to face what’s changing, choose a powerful What If question, see new possibilities, create supportive habits, build resilience and accountability, and begin living your What If.

The course includes guided exercises and practical tools you can use at your own pace.

Digital Products

In addition to coaching, I offer resources through The What If Shift designed to help people ask better questions and explore what’s possible next.

Resources include The What If Shift book, practical guides and exercises, and other tools for reflection and intentional change. I also offer workshops and presentations for organizations and groups focused on better questions, better decisions, and navigating what comes next.

Experience, Certifications & Training

Certifications and Degrees

• Certified High Performance Coach (CHPC)

Training and development

• Certified High Performance Coach (CHPC)

Professional and life experience

I bring decades of experience as a creative leader, writer, strategist, and team leader, helping people and organizations navigate complex challenges, make decisions, communicate ideas, and see possibilities others may miss.

Alongside my professional career, I’m the founder of Level Positive and creator of The What If Shift, an approach built around the belief that better questions can change what we see—and what we choose to do next.

I’m also an author, speaker, and workshop facilitator, working with professionals, entrepreneurs, and organizations on intentional change, decision-making, and designing what comes next.

Most importantly, I don’t approach this work only from theory. I know what it’s like to reach points in life and career where what worked before may no longer be enough—and to ask yourself, “What now?”

Fee description

I offer a complimentary 30-minute discovery conversation to explore what you’re navigating and determine whether working together is a good fit. Individual coaching and ongoing coaching engagements are available based on your goals and needs. We’ll discuss the best approach and associated fees during our discovery conversation.