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Inspiring Conversations with Angela Di Filippo of Angela Di Coaching

Today we’d like to introduce you to Angela Di Filippo.

Hi Angela, so excited to have you on the platform. So before we get into questions about your work-life, maybe you can bring our readers up to speed on your story and how you got to where you are today?
My name is Angela Di Filippo, and I am a leadership coach and a creative. I was born on the East Coast and have lived in Washington state for the past 12 years. As a child, I always knew I wanted to help people, but figuring out how to best do that took me a while. With jobs in everything from retail to early childhood education to marketing to social work, I found my answer in coaching.

I now train and coach leaders, particularly those who work in non-profit and community support spaces. My goal is not just to empower people to take action and reach their full potential in their lives, but also to help them clear out the noise in their lives so they can see and understand themselves, their goals, and their community more clearly.

I also am an expressionist painter and writer, and in both my creative pursuits and my coaching, I have centered my process in collaboration. As a painter, my works are the collaboration between my direct actions (like the paint color I have chosen or where I’m starting on the canvas) and natural forces (like gravity). This gives space for natural growth and the opportunity to balance chaos and order, which allows my pieces to achieve a level of authenticity that is impossible to replicate. My coaching is the same way – I get to honor people’s strengths and shadows and work with them so they can find what they want to grow into.

We all face challenges, but looking back would you describe it as a relatively smooth road?
Most people have had blessings in some areas and challenges in others, and I’m no different. One of the largest struggles I’ve faced in my life was my diagnosis with Type 1 Diabetes, which I received at 14 years old. While I was relieved to have a name for what I was going through, it was still a shock. Going from being a healthy teenager to having to worry about devices, doing math calculations every time I ate, and shots at all times of the day because I was born with a genetic marker that made my body not produce insulin was an unexpected and severe shift. It didn’t feel fair in a visceral way. Especially because, at that young age, I had a very hard time accepting that we do not always control how our bodies respond to themselves.

I don’t blame my young self for the anger, sadness, or isolation I felt, especially during those first few years, and I also wish I could go back and help her work through some of that mess so she could have been braver. Diabetes is expensive, and there are so many limitations that I felt I had to put on myself and my future to ensure my survival. It also meant that I doubted myself in many areas of my life, because, ultimately, if one part of me was born broken, how could I assume other parts weren’t?

I learned over time how to challenge that story and found my way (otherwise, I wouldn’t be sharing this story with you here!). I now occasionally mentor young people who were recently diagnosed, and am a strong advocate for holistic health approaches and honoring people’s lived experience. The struggle helped me learn resilience, understanding, and hope, and I’m proud to say that while I will always be aware of the reality of the world I live in and what that means for managing my disease, I have already done more than my 14-year-old self thought possible.

Appreciate you sharing that. What should we know about Angela Di Coaching?
Angela Di Coaching is my life, leadership, and strategic coaching business. It is also (most of) my name. I have worked predominantly with leaders across a variety of spaces. My first coachee, after getting my Master’s and still building hours towards my credential, was a local city council candidate. She had started in grassroots community advocacy and later used her elected role to ensure evidence-based polices that supported safety, access, and equity were passed in our city.

From that time, I’ve continued to coach those focused on creating a positive change in their communities (including business leaders, entrepreneurs, and political candidates), as well as on creating a positive change in themselves. I often work with leaders who are in new, formalized power positions, as well as leaders who are making transitions, such as growing their business, investing in new projects, or altering their role so they can lead in different ways.

This means that what really sets me apart is my ability to work in uncertainty without judgment. Not knowing is uncomfortable for most, if not all of us, and working through those foggy spaces is easier when you have a partner, and when there’s the understanding that those spaces are a necessary and natural part of change. One time, a leader shared that they were excited for me to coach them because they’d heard from a different leader that, after coaching sessions, they always felt refreshed and like they could actually take action on their issue. It’s one of the best compliments I’ve received as a coach.

I want people to know that coaching is not about telling someone what they need or how to do something. You have the secret to your best life inside of you – it’s one of those beautiful and inspiring parts of being human. And there’s also so much noise in our lives; so many things pulling us this way and that. Coaching is really just about clearing the noise, giving a space to center on what is actually important by asking questions so a person can delve in just that little bit deeper and access the understanding they need to find action. Coaching is for everyone – not just because everyone is a leader in their own life – but also because we all have goals, we all have potential, and we all deserve the opportunity to tap into our inner resources and achieve our dreams.

Can you talk to us about how you think about risk?
Risk is the only way we grow, and the most important risks are often not the grand gestures that we often think of when it comes to risk. I mean, I always think of some extreme activities – like bungee jumping, skydiving, or swimming with sharks – when I think of risk takers. And that’s not me (well, I would try skydiving, but no sharks).

Despite what comes to mind, most risks are found in smaller actions, although the impacts are often just as significant. We all take risks every day and in so many different ways. After all, it’s a risk to be vulnerable, to acknowledge where we want to grow, that we care about others, even that we want more. Existence, in many ways, is risky, and there’s a kind of power that can present itself when we are emboldened to think of risk as part of being present and engaged with life.

My greatest risk was when I was 23. I was still in North Carolina, where I had grown up, and I was ready to leave. I was working in Early Childhood Education at the time and started searching for where I wanted to go, assuming I could work in that field anywhere in the country. The day after I started searching, my best friend from college called me – she was in New York with her then boyfriend, now husband. They were moving to Seattle, where he grew up. They offered me a room in the house they were living in, and I said yes.

I knew what it would mean to move so far away, and with no plan or job or anything but a car. And it still felt right. It’s one of the few times in my life where I have made a decision with zero forethought, and I have never regretted it because I used the opportunity to grow the way I was meant to. And I think that is truly the heart of taking risks – we have to trust ourselves, keep hold of hope, and use the opportunity to become our truest selves.

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