First Person Coaching
OLIVER GILLESPIE · LEADERSHIP COACH
Lead your own life.
Not the one you were handed.
The one you choose.
Let’s jump on a call
About me
"Oliver has a distinct ability to look through me as if I were made of glass. He saw me for who I was, helped me identify emotions I had concealed for years, and supported me through them. 10/10 recommend."— Elizabeth, CEO
"Oliver embodies hard work, ownership, and commitment to change. His passion and personal journey drive his unrelenting, tenacious approach to personal coaching and transforming lives."— Benjamin, Agency Owner
Why I'm here
I’m not someone who has it all figured out. I’m someone who stopped pretending he did.I used to manage startups. Seven years looking like I had it all together, until it crumbled.Not the businesses. Me.I had tightened my grip on everything and everyone I thought I could control, with no idea how to lead the one person I actually needed to.Then I got into a room where I couldn’t hide. Someone showed me what wasn’t working. They stood with me while I chose, and ran with me while I changed. That’s what I build for people now.I’ll give you what I needed — someone willing to get messy, name what’s really happening, and stand for who you’re capable of being, especially when it’s hard to hear.
What a call is like
I’m not here to help you inch forward. I’m here so you will choose to be unrecognizable.Awareness, with action. The moment something becomes clear, we move on it. You commit to something new and live it out within 24 hours.I don’t give answers. I keep asking until the solution is actually yours. Because real transformation is never something happening to you — it’s something you choose.Do that enough, and you’re leading. Your choices, your standards, your life. That’s personal leadership. That’s the work. And I’m in the fire with you, every step of the way.
FAQs
Do you offer payment plans? At booking, you can choose from several pay-over-time options. Your plan, including terms and any interest, is between you and the provider you choose.Is this faith-based? I’m a Christian. I believe you were created on purpose, to know love and live free, period. If you don’t bring up faith, neither will I. It’ll only show up in how seriously I take you and your journey.Is this therapy? No. I'm not a licensed therapist, and this isn't a substitute for therapy if you're dealing with something clinical. This is coaching — forward-facing work on you and how you show up. If I think you'd be better served by a therapist, I'll tell you.