Like many eager young professional women, I picked up a copy of Sheryl Sandberg’s “Lean In” when it came out and read it cover to cover. Though there were parts of the book I found laughably unrealistic (most of us don’t have the ability to ask the Secretary of the Treasury for favors), I was struck when Sandberg said the best way to describe her career was “a jungle gym scramble.” She went on to say: “I could never have connected the dots from where I started to where I am today.” I realized this was exactly how I had been approaching my career.
Here’s the thing: the proverbial corporate ladder has never interested me. I’ve always been focused on chasing skills regardless of the industry. When presented with the opportunity to try something different, the possibility of learning new things has been my north star when deciding my career trajectory.
Step 1: Leaning out of a miserable job
A little about me, for context: after I graduated with a finance degree, I spent my first year out of college in investment banking. It had the allure of a glamorous life flying around the country to pitch exclusive deals to CEOs and a paycheck that would cover anything I desired. In reality, I was working 16-hour days in my cubicle doing work that was either thrown away or completely unnecessary, like rearranging company logos for hours on end. (If you are curious to learn more about what investment banking is really like, I recommend this book.) After missing too many birthday dinners and canceling on vacations last-minute for work, I quit my job after one year. It was the best decision I ever made.
Step 2: Feeling proud of where I worked
For my next job, I decided I would only apply to companies whose products I actually used. My reasoning was that I would have an informed opinion, be able to immediately empathize with customers, and see my work valued by its consumers. I had been using Indeed for my job search, liked the website, and ended up landing a job there after cold applying to an opening. Even though I had never been to Austin before, after a series of interviews I gladly accepted the position when the offer came and got ready to leave New York City.
I started out at Indeed on the international strategy team, where I leveraged some of the skills I’d learned in investment banking: financial analysis and building persuasive presentations. My new job at Indeed was to do in-depth analyses of the market in different countries and recommend where the company should expand. In addition to having a great team and interesting work, I saw first hand the positive impact Indeed had in my community. While wearing my Indeed t-shirt, I often had people approach me to tell me they found their job on Indeed or that an employer had contacted them through the site. This made me proud of where I worked, in a way that I never did in investment banking.
Step 3: Making an internal move to gain skills I wanted
A year into my role, Indeed created a corporate development team. The team’s mandate was to analyze the human resources (HR) tech market, buy companies that we thought were a good fit and invest in other companies who had potential. I saw an opportunity to learn new skills I wanted: negotiation, figuring out how acquisitions could fit into Indeed’s existing teams and working directly with the senior leadership of the company.
The team needed someone to help with financial valuations and building investment cases, which were skills I had, so I approached the newly hired director of corporate development and told him why I thought I would be a good fit. A year and a half into my time at Indeed, after a round of internal interviews, I joined a new team.
Not long after I started my new role, we invested in a start-up that built skills assessments to help employers with hiring. I developed a close relationship with the founders and when we acquired the company a few years later, we wanted a team that combined the original employees with Indeed employees. I saw an opportunity to switch roles and gain more skills again. By now, I had been at Indeed for four years and was curious to learn more about building digital products.
Step 4: I have no five-year plan, but I want to be a “maker”
When I was given the opportunity to join this new team I was excited but uncertain — I still had a lot to learn from my current team. So I went to a mentor to talk about it. As a way to help me think about it, he asked, “Where do you want to be in five years?” I couldn’t answer because I had no idea. My mentor explained to me that product managers are like mini-CEOs, driving the future of their product and team. They create compelling visions and goals and inspire and motivate their team members and other stakeholders to achieve them.
This opportunity felt like a chance to finally become a “maker” — to own something and dictate the future of it. My other jobs within the company had a ton of autonomy, but felt more like consulting — I would create a strategy for something, but I wouldn’t actually be responsible for it, or see it through to the end. This was a brand new set of skills that, while daunting, I was excited to dive into.
Why a jungle gym is better than a ladder
Though I had four very different jobs in less than six years, and never chased clear-cut promotions, my career did advance. By gaining experience in various areas, I was able to bring in viewpoints that others couldn’t. For example, when I joined my current team, I realized they were accustomed to starting from scratch when we needed to make something or fix a problem. But my background taught me that it was more efficient to analyze what competitors had done to learn from those who had already addressed a similar issue. This allowed us to move faster and built up a mindset of competitive analysis on my team.
With regard to building your career, I invite you to the jungle gym — worry less about what industry you’re in and any ladders you might see. When presented with the opportunity to try something new, especially if it’s something that you know will be challenging, say yes. You won’t be sorry for it.