Breaking momentum through career stepping

I just started a Chief of Staff role at one of my favorite consumer brands, Cocokind. It took nearly 10 months of recruiting during an unprecedented year, but I am so excited for the chance to join such an incredible team. And after spending the past 4.5 years in finance, I’m ready to take a leap of faith and move over to the operating world.

Career momentum is a funny thing. It can be challenging to change course one you set yourself down a certain path - especially in finance where your next step is secured 1-2 years in advance. From the time I accepted my investment banking internship junior year, the path forward has been clearly laid out: banking internship, two years in banking, two years in private equity, and two years in business school. Post-grad, it’s easy to relish in the security of your future being relatively certain for at least six years.

Breaking momentum

What’s much harder is breaking momentum and deciding to do something different. There are many people who are truly fulfilled by this path, though I wasn't one. I decided one year into my growth equity job that I would leave for something new at the end of my two year commitment. During the second year I wrestled with so many questions. Did I have skills applicable to other industries outside finance? Was it foolish to give up this prestigious job and security on a whim? Would I be judged by my peers? 

On paper my job was great, but I didn’t feel energized by it day-to-day. I tried to pinpoint exactly why. Of all my responsibilities, I most enjoyed meeting with new entrepreneurs. Their excitement and energy for building their companies was contagious. The building process is what investors miss out on - it’s their job to identify potential and capitalize on the success. But the challenge of building is what excited me most and since it was impossible to optimize for that in my current role, I decided that I wanted to join a high-growth startup.

Job search advice that worked

Once I figured this out, I thought the next step would be easier. It wasn’t. Recruiting is way more challenging when it’s less structured and the positions are less defined. I leveraged my network to talk to people in as many different roles as possible across various size companies - Propel was an amazing resource for this and I was blown away with everyone’s willingness to connect. 

Finally after dozens of conversations, I felt ready to go into my search with narrowed criteria. I was less obsessed with title and more focused on three key areas: 1) a generalist role to gain exposure beyond finance, 2) a 15-30 person team to maximize cross-functional opportunities, and 3) an exciting mission-driven company.

The best advice I was given was to make a list of companies that I found to be interesting and find a way to get a warm intro to the team. Mention the list during conversations and send it as follow up to see if that person has any connections. Though more time and energy intensive, the most interesting opportunities came from conversations, not LinkedIn job postings. And often, new opportunities would materialize from any dead ends later on. 

Intuition applies to new jobs, too

Interviewing is always stressful, especially when you fall in love with the idea of a company. However, throughout my career I’ve found that the feeling and intuition you have when you are going through an interview process is usually indicative of how well you'll perform at that company. While interviewing at Cocokind, I had the same visceral reaction that I had experienced while meeting with entrepreneurs (e.g. pulse racing, palms sweating, high-energy buzz). The conversation was fluid and two-sided, and most importantly I felt a real connection with each person that I spoke with. Judge an interview by how energized or drained you feel afterwards, not just by how well you think you did in the interviewer’s eyes. 

Throughout this process I have had to continuously remind myself that there is no perfect job. Each career move should optimize for the parts you enjoy and for skills that you want to expand on. By dismissing the idea of perfection, you open yourself to what I’ll call “interim” jobs - those that aren’t necessarily long-term positions, but will get you one step closer to your dream job. A career is built off of several little steps, not one big jump. Embracing this philosophy relieved some of the pressure I felt to make the “right” decision.  

As I step into this new role, I want to remember how uncomfortable the uncertainty I felt over the past year was, but also the growth that came from it. I’m excited for change and the challenge that comes with it. And while this was the end goal for now, it’ll ultimately be the stepping stone for bigger things to come.