Chris Castillo

It’s often so easy to get wrapped up in “doing mode,” responding to every fire that comes up. I’ve found that the more often I check in with myself about why I am doing this work in the first place, I’m able to keep better perspective and focus on working intentionally opposed to just doggy-paddling.


Chris is the founder of Empowered Achievers, a career coaching and development company focused on helping driven professional women craft careers that they love. Originally coming from the corporate advertising industry where she worked on clients like Google, YouTube, & Expedia, she traded in the agency life for the world of talent development & culture. She transformed her own career into something she loved, and is passionate about getting rid of the “Sunday Scaries” for each one of her clients, too.

Chris works with individuals and companies alike, through both her custom
coaching program as well as corporate trainings. She is a thought-leader, with articles in Thrive Global and features on sites such as Business News Daily and HelloGiggles.

Where did the idea for your company come from?

Empowered Achievers is really at its core about helping high-achieving women take back their power and ownership of their careers. The reason I started the business is because it’s exactly what I personally needed back in late 2014 as I started my transition from Media into the world of Professional Development.

I had been working as a Media Supervisor at an ad agency in San Francisco, and was having doubts about my career. I didn’t feel fulfilled by it, and so I made the transition from media into the world of Talent Development & Culture. I moved onto the TD&C team at my same agency, and fell in love. That said, the transition wasn’t necessarily smooth for me, and I felt very confused while I was trying to figure out my next step. Empowered Achievers was created as an exact response to that: to help other women like me who are successful in their careers, and yet still want more, to learn how to develop their roles.

What does your typical day look like and how do you make it productive?

Typically my days are spent connecting with clients and creating content. I often wake up and do a few brief exercises to make sure I’m focused on the right thing each day, such as using my planner to lay out how I will be spending my time. Then I get started with a big cup of coffee!

I make sure it is productive by laying out what I want to cover, as well as making sure I go into the day thinking proactively about what I want to do versus reactively answering concerns and questions.

How do you bring ideas to life?

Normally when I have an idea in the back of my head I like to take some time to write it out. I do really well with outlines to get all of my thoughts on paper, and then make list of what I need to do first to get started. Getting caught-up in inaction when you’re feeling overwhelmed is typical, which is why I like to just think about the first step.

What’s one trend that excites you?

In the world of talent development, one trend that is particularly exciting to me is how companies are starting to respond to the job seekers market. With the large amount of Millennials in the workforce these days, people are realizing that career fulfillment is more important to employees now than ever. Companies are starting to be more flexible helping employees to get to their long-term goals. With so many young people eager to start their own business or work somewhere that allows them to work remotely, it is really forcing companies to open their minds and consider other ways that they can provide great experiences for their teams.

What is one habit of yours that makes you more productive as an entrepreneur?

I think my tenacity has been incredibly helpful. Because I am so determined, when I know in my gut that something is right or it is what I want to pursue, I make sure that it happens. Even when stumbling blocks pop up, which they inevitably do for all business owners, I am able to keep the big picture in mind and keep moving forward.

What advice would you give your younger self?

You get to define what success is to you. I think I spent a lot of my life creating something that was successful to other people’s standards, and when I realized that it wasn’t feeling fulfilling to me, I was shocked. I realized that my judgement is the thing that really matters at the end of the day. It’s great to make others happy, but if you’re not happy with yourself, you’ll be left feeling empty (even as you reach big goals). This lesson was huge for me and ultimately has driven the business I’ve created.

Tell us something that’s true that almost nobody agrees with you on.

Something that I often say that seems to go against the grain is that millennials aren’t flakes. I think there is this belief that because millennials are more open to job-hopping, it means that they have no loyalty and don’t care about their jobs. I couldn’t disagree more! While there are so many articles about us being lazy and non-committal, I would actually argue that our drive for career fulfillment is our way of commitment. We are willing to actually take the risk and leave a company so that we can find something we love. We care just as much as other generations, we’re just not willing to have the kind of career that we just clock into each day and feel apathetic towards. To me, that signifies some seriously career-driven folks.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

Take time to ask myself why. It’s often so easy to get wrapped up in “doing mode,” responding to every fire that comes up. I’ve found that the more often I check in with myself about why I am doing this work in the first place, I’m able to keep better perspective and focus on working intentionally opposed to just doggy-paddling.

What is one strategy that has helped you grow your business?

Outsource the stuff that is not your sweet spot! This was one of the biggest transformational lessons of my business. I, as most entrepreneurs, felt like I had to do everything at the beginning, from being my own PR person to setting up my branding, from doing my copywriting to creating content. Plus I had to actually have the calls with my clients! I quickly realized that I was spending a lot of time and energy on stuff that I wasn’t great at, and it was taking away from the stuff that is my skill. As such, I started outsourcing. I hired people to do things for me that was their skill, like a PR specialist for example. She is incredibly skilled at what she does, and I’m not! If I had tried to set up all of the great publicity she has gotten for me, it would take me so much longer and I wouldn’t even do a fraction of the great work. Ultimately, it saved me money in the long run, although I know it can feel scary to bite the bullet and make that commitment in the first place. It helped me to scale incredibly.

What is one failure you had as an entrepreneur, and how did you overcome it?

When I started my business, I was so set on selling the way that I thought I was supposed to. I felt gross to me and it didn’t feel an alignment with who I am or how I like to show up. Once I realized that just because a process works for other people it doesn’t have to work for me, it was huge! I gave myself permission to try something new. I was able to work with people who gave me the skills to talk about my business in my way, not someone else’s.

What is one business idea that you’re willing to give away to our readers?

One concept that I’ve been thinking about for years that I wish was a business, is a service to help grieving family members deal with the paperwork after a loss. Personally, when we lost my mom I felt like there was so much paperwork and red tape we had to deal with, and yet all we wanted to do was grieve. Since then, I’ve wished that there was a service, whether it be tied into hospice or something else, that actually comes in and helps you to do all those little things that you don’t want to deal with… like changing your Costco membership over into someone else’s name or moving your credit cards. Having to be on the phone line with a customer care specialist and explaining that someone has died is kind of like salt in the wound. If someone could create the service, I would be eternally grateful.

What is the best $100 you recently spent? What and why?

I bought new running shoes recently for my first half-marathon, and the purchase was so great! Running has become a huge form of stress-management and structure on days when I’m feeling overwhelmed.

What is one piece of software or a web service that helps you be productive? How do you use it?

I use the Google suite for just about everything. Google Docs, Slides, Sheets…all of it. I’m a huge fan because it allows me to work from anywhere, and is very collaborative.

What is the one book that you recommend our community should read and why?

Mindset: the New Psychology of Success, by Dr. Carol Dweck. This book taught me so much, and was one of my first reads in the talent development space. It opened me up to the concept of mindset and how much of an impact it has on our lives. It changed my life, and I always give it out as a gift now.

What is your favorite quote?

I’ve gotta give it to Biggie on this one: “Only make moves when your heart’s in it, and live the phrase ‘sky’s the limit.”

Key learnings:

  • To have a successful career, you must ensure you’re defining success for yourself. Chris had a great career that didn’t truly meet her needs, and this realization was the spark for Empowered Achievers.
  • There’s many ways to sell or promote your business; you don’t have to accept the status quo practice if it doesn’t feel authentic to you.
  • Focus on value-creating activities. It’s easy to fall into habits of staying busy during the day, but by knowing what’s important to achieve each day you’ll be much more productive.
  • Stress management is important. Have a practice that keeps you focused on de-stressed during the work week.