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Conversations with the Inspiring Chris Castillo

Today we’d like to introduce you to Chris Castillo.

Chris, can you briefly walk us through your story – how you started and how you got to where you are today.
Originally, I come from the world of corporate advertising. At my “peak” in the industry, I was working at an agency in San Francisco with Google as my main client, churning out award-winning campaigns. We got to do some pretty great work, and I worked with some of the smartest people I’ve ever met. It checked all of my boxes.

Unfortunately, though, it didn’t tick the box that I didn’t even know I had. I liked my role, I was good at it, and yet, I still had this sneaking suspicion that maybe it wasn’t the work that I wanted to do until retirement. I tried to push the doubts about career fulfillment down repeatedly, but as with all “one step forward, one step back” stories, at some point, I couldn’t deny it anymore. I had fallen into my role, and while I was good at it, I just didn’t love it.

The perfect storm seemed to come together. I was slowly realizing that life is short, both through my questions about my career fulfillment, as well as losing my mom to a hard-fought battle with cancer. That woman taught me a lot of lessons, but her parting lesson that “life is short, so you’d better do what you love” was by far the most impactful. So, I took her lesson, and I refused to feel like I was wasting my life away anymore.

In my determination to find what I did love, I started exploring. And over the next couple of years, everything changed for me.

I took my lifelong love of encouraging people and turned it into a successful employee training career. I stayed at the same ad agency I loved and moved into Talent Development and Culture, soaking up every learning experience I could. I became the energized motivator that I was always meant to be. All the while, I re-ignited my passion for work every day.

I loved employee development because it allowed me to teach others the skills to do their best at work, whether that be delivering effective feedback during a performance review, or serving as an inspiring manager.

From the lessons I learned in the realm of professional development, Empowered Achievers was born. I took my background in soft-skill training, along with a handful of certifications, and turned it into a business. I started teaching people the tools I had created in order to transition from media into talent development & culture. The process of analysis that allowed me to make better decisions in search of long-term fulfillment.

By sharing my process, I was able to expedite the learning curve of others. They no longer had to search for career satisfaction by trying on a bunch of different roles and hoping for the best. Instead, they could start by learning who they are, what they’re motivated by, and how to build a little more of that into their role each day.

It was a long journey for me to get to where I am today, and I’m driven by the desire to make it a little bit shorter for those around me. To limit their time in the indecision and “career confusion” that I experienced.

Most importantly, though, the reason I still wake up every morning ready to go is that I know that life is short. Women deserve fulfillment each day, and my goal is to guide them to clarity on what that might look like for them. I empower my clients to take charge of their life and career because I know they’re capable. I want them to see possibilities everywhere they turn.

Great, so let’s dig a little deeper into the story – has it been an easy path overall and if not, what were the challenges you’ve had to overcome?
Of course, not! Starting a business is one of the quickest paths of growth, in my opinion, because it makes you confront your inner fears like nothing else I’ve experienced.

There have been plenty of struggles over these last 2.5 years at EA, from mentally talking myself into making that leap (because MAN is that scary) to shifts and evolutions in the company. One of the biggest challenges was figuring out how to start, how to position me, and how to get my message across without feeling slimy. I still feel bad for some of the people I met in my early days – I was such a pushy saleswoman!

In terms of advice, I think the most important thing to remember is that roadblocks happen… expect them. As the quote says, “A bird sitting on a tree is never afraid of the branch breaking because her trust is not on the branch but on its own wings.” Remember that you can handle anything coming your way.

What should we know about Empowered Achievers? What do you guys do best? What sets you apart from the competition?
I’m a career coach, who works with millennial women to build more fulfilling careers they love.

What that really means: I work with women to figure out what they want in their career (as opposed to what they think they OUGHT to be doing). I help them get clarity on their path and empower them to take up the driver’s seat, so to speak.

I work with two kinds of clients: 9-5ers (who are in corporate and looking to transition into a more fulfilling role), and side hustlers (looking to start their first service-based business out of passion).

I’m most proud of the shifts I’ve seen in my clients. Of course, their external measures of success are exciting (seeing them sign their first client, seeing them secure that dream job), but my favorite thing to watch is who they become in the process. I’m all about taking ownership because I think that’s the only way to intentionally build a career. Seeing my clients take ownership and start asking for what they want is huge, and it keeps me going every day.

I think a big part of my brand and what sets me apart is the human-ness of it. I’ve been in the exact place that all of my clients are, so my empathy for the situation (without letting them spiral into a “poor me” conversation) is huge.

What do you feel are the biggest barriers today to female leadership, in your industry or generally?
Systemically there are a ton of issues, such as expectations on women, childcare options, etc.

Another issue that is sometimes overlooked is burnout. SO many woman struggle with self-imposed pressure to feel like they have to say “yes” to everything and commit themselves 100%… as a result, we end up seeing a lot of women who are exhausted to the degree of quitting. It’s not ideal for their long-term advancement.

Contact Info:


Image Credit:
most of the photos are by Karen Mitchell, Samantha Neill

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