I Can, Therefore I Should? Or Not?


“I think that it’s important for us to recognize the elephant in the room,” my CEO suggested.

Less than a year after I had relocated back to San Francisco with my company, I discussed career planning with my CEO. Our second one-one-one meeting in my two years with his company. We had recently upgraded to a new office, a sign that our West Coast expansion was advancing in ways that our executives had carefully planned. I successfully pitched a transfer back to the Bay Area from Colorado as a calculated move into bigger opportunity for a growing career in advertising technology. My intent was half true.

Sitting across from my CEO, huddled in a room barely large enough to be called a room, I had an acute awareness that I needed to focus on my career in ways I hadn’t previously prioritized. Newly single as the result of life’s unexpected turns, I needed to step into navigating decisions as an individual rather than one half of a pair. My new role had me tied to a revenue number for the first time, instantly putting my work on the radar of our executive team. Within months of moving back to the Bay Area, the boss who recruited me West exited suddenly. My first job in sales quickly evolved to me managing the business of our top tier West Coast partnerships. My responsibilities skyrocketed and yet I felt no more equipped to handle it than I had 10 years earlier in my career.

I had never created a plan to move from point A to point B. I had followed other people’s directions, not my own. I was living the pages of a manual crafted by the people who had the closest exposure to my work.

At my first job, in financial services, my boss noticed, “you are really good with Excel” and asked if I had considered data analysis. I had not. I knew I liked creating spreadsheets, but lacked an understanding of what that meant. I didn’t know what was possible from fostering that particular skill (or any for that matter). I was sent a job description of an open position and applied to a job that was handed to me.

In that position, our entire team relied heavily on one man who could write more advanced code to make our reporting more efficient. He knew SQL. Two years later, when I wanted a move away from financial services, an acquaintance from business school suggested I look at positions at Williams Sonoma, where she had worked since graduation. I found an analytics role that gave me the opportunity to learn SQL myself. I joined a small team of people who had built their career as business consultants. My experience in data analytics set me apart. I took ownership of a few special projects beyond what I was hired to do, at the suggestion of my manager. Those initiatives would later be the foundation for my work at startups.

On the other side of the last recession, after moving back to Colorado, job prospects were limited. I was hired by someone based on our shared experience as Semester at Sea alumni. I was placed as a media buyer at a digital advertising agency. Saying “yes” to the next move suggested to me gave me opportunity while saving me from needing to identify what I wanted in my career.

I was in a position of privilege with opportunities being thrown my way. I’d be ungrateful and insane not to say “yes” to the people putting me in a position of privilege. So I continued on.

Two years later, a former colleague recruited me to a small but fast-growing company. Based on my skills and experience, my new team decided where to put me within the organization, freeing me again from needing to state the actual job I desired. I became a product manager, responsible for a product that required me to be in front of clients. The opportunity to work direct with clients was extended to me on mostly blind faith. Another privilege. That experience with clients became the bridge to my new role in San Francisco. I worked tirelessly at client management, a mission that speaks more to my determination not to let people down than to my interest in working direct with clients.

My determination was recognized. In that room, sitting with my CEO, he asked me “what I wanted to focus on in the coming fiscal year.” No one had asked me what I wanted to do. Worse, I had never thought about where to point my career. I had simplify followed a set of directions outlined for me. Too scared to claim a path and unclear about the platter of options, silence stood between me and my CEO. Eventually my CEO named the elephant. “We are going to need someone to run the Google business for the firm, similar to what we have done with Facebook. It makes sense based on the percent of dollars flow through those two companies. We should approach them similarly.”

“Exactly,” I said with conviction. “That sounds perfect.” And like that, I was outlining a plan with another executive to hire and offload the remainder of my accounts to create focus. I would make two more shifts in the coming three years, each of them suggestions from other people.

At the close of that company’s acquisition to Oracle, I was again faced with the same question of what I wanted to do with my career. As an early stage employee, I was given the space to influence my future role within a new organization. I was no better equipped to answer that question. I had built a career focused on doing the things that other people suggested and being rewarded for stepping into their visions of me. I had not set aside the critical time to reflect. I didn’t have a sense of what gave me energy, what provided the right mix of challenge and flow, or where my strengths gave me a competitive advantage. I had prioritized performance over planning.

I wish I would have met people, early in my career, who told me I could influence what I wanted of my career. That I had more choice than simply saying “yes.” That just because I can do something, doesn’t mean I should. When the choice to shape my own career became more obvious, years later, I did not know how to respond. I hadn’t build the skills.

I co-founded the Inside Out Incubator because I believe that women have the power to shape their lives. That power strengthens when they are given the tools to do that early and often. Our programs introduce those skills and guide women to understanding who they are how their experience translates to identifying what they want. This combination allows you to seek and secure opportunities more likely to bring fulfillment to your life.

Shine On,


Alicia Jabbar