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“In the future, there will be no female leaders. There will just be leaders.” 
― Sheryl Sandberg

Build a Fulfilling Career in One Easy Step

Build a Fulfilling Career in One Easy Step

Chris Castillo

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In my work as a career clarity coach, I’ve learned one thing for sure: there are a lot of people who want to build fulfilling careers. I hear stories day in and day out from folks feeling frustrated and stuck in their jobs, daydreaming about a career they care about. The challenge, for most of them, is they have no idea how to get there.

It doesn’t have to be as hard as you think, thanks to my number one favorite, easy, foundational tip: If you want to build a fulfilling career, you have to start by defining what success means to you.

While this may sound obvious, it’s a common problem with clients I work with. Most haven’t ever considered what success looks like to them, so when I ask, they stare at me slack-jawed.

If this resonates, you’re in good company.

Here’s the thing: if you haven’t considered your own personal definition of success, then you’re probably building your career based on someone else’s. Maybe you’re building your career off of the “shoulds” you heard from your family growing up, or maybe you’re building it off the path you’ve seen peers take. Either way, if you’re not building your career off what you personally want, you’re probably going to end up frustrated and unfulfilled. As Dave Eggers says, “it’s better to be at the bottom of a ladder you want to climb than in the middle of some ladder you don’t.”

Part of the reason I’m so passionate about this work is because I’ve been at the top of the wrong ladder before. Back before my career coaching days, I worked in corporate advertising. At my “peak,” I worked at an ad agency in San Francisco with Google as my main client. It was the kind of career that’s perfect on paper: working in a fast-paced industry, being paid well, working with a great client—everything your parents can’t wait to tell their friends about. The only problem was the career wasn’t perfect for me.

I got into the world of advertising because it seemed like the logical next step after majoring in business administration with a marketing emphasis in college. This is what happens when you’ve never asked yourself what you actually want: you follow steps mindlessly because they’re easy. Upon graduation, all I had to do was (ironically) Google “marketing jobs” in the Bay Area, and the rest was history.

Several years post-grad, when I had been in the industry for a bit and was getting comfortable, I started to have doubts, seemingly out of nowhere. They started as a small whisper in the back of my head: “Are you sure this is really what you want to be doing? Is this the career you want to do until death do you part?” I ignored it at first, pushed it down, and told myself my career was perfect. Only when the whisper grew into a full blown scream I couldn’t ignore did I realize I was building a career that made others happy, but didn’t make me happy.

What came next was a messy process. I wasn’t in the career I wanted, but even scarier, I had no idea what I did want. I had never asked myself what was fulfilling to me, and I felt totally alone. That’s why I do this work: to teach my clients the steps I took to find career clarity and get un-stuck. I teach clients to separate out the pressure they feel about their career from what they actually want, which is a beautiful (and empowering) thing.

True success (the fulfilling kind) comes from defining what success means to you, and then making sure your life aligns. If you’ve never defined what actually matters to you, you run the risk of building a life based on “shoulds” and pressures imposed by others.

Want to figure out your own definition of success? Start by considering your best-case scenario. If you could do whatever you wanted and money and time were no factor, what kind of thing would you be doing?

Now, while it’s obviously unlikely that money and time won’t be an issue in your real life, (we’ve all got bills to pay), this exercise starts to tell you the TYPE of things that matter to you. Is flexibility a key pillar of your “dream life?” Autonomy? Fulfillment? By looking at your dream “no responsibilities” life, you can identify a few key characteristics of personal success.

For example, one of my clients always defined success by pay-grade, by the level of notoriety they had, or by how “good” their work sounded to others. Once I asked them to do this exercise, they realized success to them was actually about living a deeply fulfilling life where they do creative and purposeful work they’re proud of. It actually had nothing to do with the level of pay or respect they got from others. By identifying the gap between what they thought and actually felt, they were able to identify the source of friction in their career. After that, everything changed.

If you’re feeling stuck in your career, spend some time examining where friction might be coming up for you, consider what actually feels fulfilling to you, and release the pressure from others on what your path “should” look like.

This is where the magic truly happens.


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Chris is the founder of Empowered Achievers, where she helps millennials build professional lives and small businesses that fulfill their true calling. Having worked in advertising with clients like Google, YouTube, and Expedia, she traded in the agency life for the world of talent development and culture. She created Empowered Achievers when she realized her deepest calling was to help others find their calling as well, and transition into a life of fulfillment doing work that they love. She was voted one of the Best Millennial Career Experts by PeopleMaven. Chris has articles in Thrive Global & Kivo Daily, and features on sites like Business News Daily and HelloGiggles.

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