Everything you were taught about career paths was wrong


Early in my professional life, when I worked in merchandising and brand management for one of the world’s most recognizable global retailers, I was told that leaving would be the biggest mistake of my career. I am so glad that I didn’t listen. Years later, I am still reaping the benefits of sidestepping a “traditional” linear career path.

A nontraditional career path isn’t always the most comfortable approach, but it’s one that can make job candidates more appealing to a smart recruiter or hiring manager. For example, in my experience, intentionally making myself uncomfortable has helped me develop a more holistic skill set. For some, a nontraditional career path can be too challenging to handle. But I have learned that you don’t need to stifle internal anxiety about making big career changes. It’s natural, and an opportunity to learn and grow personally and professionally. The key is to use that discomfort productively and ultimately master the situations that seem overwhelming at first.

There are (at least) five lessons I have learned throughout my career in which taking the “easy” route would have been perfectly acceptable, but by taking the road less traveled I gained much bigger rewards.


Early on, I threw away the notion that big employer brands matter. I turned down an offer at Google to focus on a lesser-known company where the learning opportunities were exponentially higher. Don’t get me wrong. I believe that working at a big company can be very good for professionals—especially at the beginning of their careers. Big brands have the resources to train people well. But if you desire a career with velocity and autonomy, a big company is not where you want to spend the entirety of your career. Many people who have grand career aspirations become dependent on navigating internal politics based on their employer’s logo and become less focused on the actual work. Large companies tend to be complex, bureaucratic organizations. While they might be highly competitive and impress your friends and family, you may be unable to progress your career quickly.

For me, moving on from a well-known brand allowed me to manage a large team at a young age—something that would have taken me years to achieve had I been concerned with working my way up the corporate ladder. This is the type of intangible experience that gives a career velocity.

While working with Gap Inc., I became passionate about marketing but realized I wanted a broader scope. Working for such a large company trained me well for the workforce. But I knew I wanted more, and it showed. So I chose to move to a smaller company that wasn’t as well-known, but where I could challenge myself with roles and responsibilities that would have taken years to achieve elsewhere.


As a woman, it’s vital to force yourself to have uncomfortable conversations with your managers about other priorities in your life, specifically your children and family obligations. You must set expectations—both at work and at home—to achieve enough balance to thrive in each environment. As a younger woman, finding your voice and setting those boundaries with your superiors can be challenging and intimidating. I have witnessed many young women burn out because they pretended that they didn’t have obligations outside of the office and instead poured the majority of their energy into their work. But that’s not reality.

More recently, COVID-19 and the work-from-home culture has made having a family very apparent. You can’t hide the fact that kids are home because they’re bursting into your home office, interrupting Zoom calls, and have homeschool schedules that require your attention. It’s brought about a reckoning. Previously, uncomfortable expectation-setting conversations about family responsibilities were mostly relegated to women, but that is starting to shift. The pandemic has democratized this aspect of work-life balance by making it more ubiquitous and gender-neutral.


The truth is that no one, not even an executive, is good at everything. Some are amazing people managers and fantastic at leading a team. And others are the wicked-smart types, geniuses but genuinely terrible at managing people.

I’ve been lucky. I’ve had the chance to work for, and learn from, the full spectrum of leaders. I spent several years working for a mentor who was a great leader of people and manager of teams. Later I went to work at an organization where my manager wasn’t a particularly great people-leader. Still, they were so smart and creative that I gained a lot of important functional experience.

It’s important to remember that there’s no such thing as a perfect leader, and often we don’t get to choose who we work for. It often comes down to taking the initiative to recognize and learn from the strengths of whoever your leaders are at a given moment and translating both their strengths and weaknesses into skills that you can use in the future.


Looking back, I’ve always taken on tasks and responsibilities that were “below my pay grade” as a way to build trust with my team. I’ll get into the weeds and write email copy, or go to meetings where I’m not expected. Even now, as a CMO, I often do things that not all CMOs would consider to be their direct responsibility.

Doing the unexpected builds trust, affinity, and goodwill with your teams. It also builds credibility because you show your team members that you are a good practitioner, not just a figurehead devising strategy. It also throws ego out the door. My team knows that if they need help with something, all they have to do is ask me, and we’ll tackle it together. I believe this approach creates a healthy culture and establishes your role as a leader. Nobody wants to work for someone who delegates responsibility and is incapable of understanding what the real work looks like and what it takes for teams to be productive.


I am a very risk-averse person who doesn’t like a lot of change in other aspects of my life. But my career is the antithesis of my personality. I have found that when managing the anxiety that accompanies uncomfortable situations and challenging decisions you endure throughout your career, you have to move through it and not let it own you.

For some people, the anxiety that accompanies navigating a career can be an unpleasant nagging, but it can be downright debilitating for others. By acknowledging its presence and moving through the discomfort, you learn how to manage it rather than let it control you. Some people may view it as a weakness. I am proof that you can allow discomfort to exist and turn it into a tool to not only survive but to thrive.

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