Letter to My Younger Self: Jessica Taylor, Executive Office, New York

Dear Jessica,

As you read this letter, you’re probably on the road, organizing youth development and community health projects across the US. After graduating from the University of Virginia with a successful softball career in your rearview mirror, the only thing you are ready to commit to is keeping your options open, and giving yourself the freedom to try new things.

You’ll have the unique opportunity to serve in the Peace Corps in Guatemala, an experience that will shape your perspective and give you the confidence to trust yourself when future challenges present themselves. Eventually, you’ll come back state-side and get a job at the New York City Department of Small Business Services, where you will help the city recover from Hurricane Sandy. During that period, you’ll double down on your interest in public service, earning a master’s in Public Affairs from Columbia University.

Soon after, you will make your way to the Office of Corporate Engagement at Goldman Sachs, where you find yourself, eight years later, leading 10,000 Small Businesses – one of the firm’s signature philanthropic initiatives – as a managing director.

As you embark on this journey, I am sharing five pieces of advice to help you along the way:

P.S. As you get ready to welcome your third child and prepare for a move to the suburbs, you’ll look back fondly on your time traveling and volunteering. Your current role is well-suited for this chapter in your life – and still full of adventure.

Show that you can be counted on. Figure out what your managers and team need from you. As a steady and reliable contributor, you’ll end up moving the needle quickly and effectively. 

Cultivate trust. There will be points in your career where you feel like you could be doing more. Instead of always focusing on how to get to the next step, use this time to invest in your relationship with your managers and team members. Goldman Sachs has been around for more than 150 years because of its ability to evolve – that evolution requires change and change leads to opportunities. Allow yourself the time and the grace to be present but the confidence to leap at opportunity.

Let your work speak for itself. As a corollary to staying the course, focus on creating the best work product you can and showing up for your team, clients, and stakeholders. Eventually – because of the quality of your work and your ability to remain steadfast – you will be recognized for your output. 

Hone your judgement. Throughout your career, you will benefit from managers and others giving you room to run and trusting in your ability to make decisions. As you become a leader, try to instill that same trust in your team – set the parameters, and empower those around you to advance your collective strategy. 

Lean into your information gaps. It is always better to ask questions than to pretend you know the answer. Being honest about what you don’t know will help you gain the knowledge that you need to add value. When you become a manager, you’ll be reassured when your team asks questions because it shows they are engaged and eager to learn.