Meet Brennan Hilleary

We caught up with the brilliant and insightful Brennan Hilleary a few weeks ago and have shared our conversation below.

Brennan, we’re so excited for our community to get to know you and learn from your journey and the wisdom you’ve acquired over time. Let’s kick things off with a discussion on self-confidence and self-esteem. How did you develop yours?

I developed my confidence and self-esteem by learning to honor my own needs and boundaries first. For many years, I struggled deeply with people-pleasing, overcommitting myself, and placing my worth in external achievements—leading to burnout and loss of identity. It wasn’t until I faced the truth that self-worth and confidence come from within that things shifted. By focusing on aligning my life with my core values, prioritizing personal fulfillment over external validation, and setting firm, clear boundaries, I gradually rebuilt my self-esteem from the inside out. Real confidence, I’ve learned, comes from living in alignment with who you truly are—not who others expect you to be.

Thanks for sharing that. So, before we get any further into our conversation, can you tell our readers a bit about yourself and what you’re working on?

I’m a speaker, coach, Marine Corps veteran, and founder of Build Your Power LLC. My work focuses on helping high-achieving professionals break free from burnout and reconnect deeply with what truly fulfills them.

My passion for this work is deeply personal. Growing up between two drastically different households, I constantly adapted myself to meet conflicting expectations, eventually losing sight of who I really was. At 15, I faced a rare tumor that led to years of medical procedures and a difficult battle with addiction, as I struggled emotionally to cope with the trauma I’d experienced.

Though I eventually overcame the physical health challenges, I continued chasing external validation—achieving success on the outside, while quietly suffering burnout on the inside. After hitting rock bottom, losing my career, relationships, and sense of identity, I realized that burnout wasn’t just about working too much. It was about living out of alignment with my true values and self. This realization was life-changing: fulfillment doesn’t come from external achievements alone—it comes from building a life that reflects who you truly are.

That insight inspired me to create Build Your Power. Today, through my workshops, keynote presentations, and my podcast, Circumstantially Successful, I guide others in creating clear boundaries, prioritizing genuine fulfillment, and regaining control over their time and energy—without sacrificing their professional success.

I’m especially excited about the launch of my self-paced online course, From Overcommitted to In Control. It’s specifically designed for busy professionals who are ready to stop feeling overwhelmed and exhausted, and instead regain clarity, confidence, and genuine balance in their lives. Readers of this will get $147 off the original course price. You can learn more and enroll here: https://brennan-hilleary.mykajabi.com/from-overcommitted-to-in-control

I also invite you to join my newsletter, Build With Brennan, where I share weekly insights and practical strategies to help high-achievers prevent burnout and stay aligned with what matters most. You can subscribe here: https://brennan-hilleary.mykajabi.com/newsletter-sign-up

For more about my work, please visit my website at www.build-your-power.com or tune in to my podcast, Circumstantially Successful, on all major platforms.

I’m grateful to be on this journey with you. Let’s build a life that energizes you.

If you had to pick three qualities that are most important to develop, which three would you say matter most?

Looking back, these three skills made the biggest difference in my journey:

1. Building Faith in Myself:
This meant consistently taking action that matched what I valued most, even when it felt uncomfortable or scary. Every small action helped me trust myself more, and gave me the courage to honestly face the things holding me back.

Advice:
Take one small step each day that aligns with who you want to become—this builds real self-belief faster than anything else.

2. Prioritizing What’s Important:
We can’t perfectly balance every part of our life, but we can always decide what’s most important right now based on the season we’re in. When you’re clear on what matters, it’s much easier to say no to things that drain you and yes to things that fulfill you.

Advice:
Check in with yourself often: identify clearly what matters most in your current life season, then focus your energy and attention there first.

3. Emotional Regulation:
For a long time, I procrastinated or avoided hard things because I didn’t want to face the uncomfortable emotions waiting on the other side. Learning practical ways to manage my emotions and regulate my nervous system allowed me to finally let go of old patterns and create habits that genuinely supported who I wanted to be.

Advice:
Practice simple strategies like breathwork, meditation, or journaling regularly. Instead of avoiding discomfort, lean into it. Your emotions get easier to manage when you learn to face them head-on.

Tell us what your ideal client would be like?

My ideal clients generally fall into three main categories, each sharing the common thread of operating in high-pressure environments and deeply caring about preventing burnout and improving well-being:

1. Keynote Audiences:
These are high-achieving leaders and professionals who feel quietly exhausted or stuck, even if they’re still performing at a high level. They include:

Business owners, founders, senior executives, HR leaders, and professionals in fast-paced fields like healthcare, law, or real estate.

People who genuinely love their work, but feel disconnected and are noticing early signs of burnout. They’re looking for honest conversations about sustainability rather than surface-level motivation

2. 1-on-1 Coaching Clients:
These individuals are self-aware, high-performing leaders or entrepreneurs who’ve built impressive careers or businesses but feel increasingly exhausted, unfulfilled, and stuck. They’re:

Business owners, senior managers, entrepreneurs, or real estate professionals who have normalized burnout as part of success. They love what they do but feel like work is consuming their life, their personal areas of life are suffering in some capacity, they are aware that the way they’re operating isn’t sustainable, and they are trying to make changes.

3. Team Workshop Clients:
Organizations that deeply value their teams’ well-being and proactively seek to prevent burnout. They include:

Purpose-driven companies, real estate firms, healthcare organizations, addiction recovery centers, behavioral health centers, and and any businesses with strong missions and demanding work environments.

Teams or groups ranging from small leadership teams to larger company-wide audiences that want practical tools to recognize early burnout signs, manage stress effectively, and proactively cultivate a healthier, more engaged workforce.

Characteristics of Ideal Organizations Across All Three Avatars:

High-performance cultures, but also a genuine commitment to employee well-being.

Leaders who recognize burnout isn’t just about individual stress, but organizational culture.

Organizations that value proactive, practical solutions rather than reactive or surface-level approaches.

Bottom Line:
My ideal clients are people and organizations committed to both high performance and sustainable success—who want deeper, meaningful conversations and practical solutions around burnout prevention, alignment, and employee well-being.

Contact Info:

Image Credits

https://www.instagram.com/benevolent_photographer/

James Carter

Suggest a Story: BoldJourney is built on recommendations from the community; it’s how we uncover hidden gems,
so if you or someone you know deserves recognition please let us know here.
Highlighter Series
What do the first 90 minutes of your day look like?

Coffee? Workouts? Hitting the snooze button 14 times? Everyone has their morning ritual and we

Highlighter Series
What have been the defining wounds of your life—and how have you healed them?

Our deepest wounds often shape us as much as our greatest joys. The pain we

Highlighter Series
Are you doing what you were born to do—or what you were told to do?

Culture, economic circumstances, family traditions, local customs and more can often influence us more than