On Designing Your Life Like a Strategist

Sometime in 2017, I reached a breaking point.

I was 30 years old, had no real savings, a meager amount set aside for retirement, and was more or less overwhelmed by my growing student loan debt. I was in my fifth year of working as a writer and researcher in the nonprofit industry, freelancing on the side, while also attempting to run a business that was very much doomed to fail. I was burnt out, desperate, and stuck.

I knew I needed a big shift, but while I could clearly see the contours of what I wanted my life to look like (more than a few hundred dollars in my bank account, for starters) I had only a vague idea of how to get there. Up until that point, I had never even heard the term UX, and if someone had mentioned it to me earlier I would have guessed, somewhat accurately, that it was one of those cool Millennial jobs that I felt wholly locked out of.

But these were desperate times. I was determined to join the cool club. (Eventually I learned that the tech sector is not nearly as exclusive as I had thought, even if it is very cool.)

I’ll skip the details of what that next year looked like: learning about the various roles in the tech industry, talking to anyone and everyone about how to break into it, ending my flailing business, quitting my job, panicking about quitting my job, teaching myself Photoshop, teaching myself Squarespace, learning CSS, crying over JavaScript, and eventually, enrolling in the UX design course that would officially mark the next chapter of my life. In the broadest of terms, I got real about my priorities, and started making some decisions.

I entered the tech industry eager to learn but impatient to get to the next step. My career up until that point had instilled certain skills that were helpful: I knew how to research, I could distill complicated concepts down to their simplest parts, and I was an effective communicator. Still, the first few months of my UX course saw me frustrated daily: with myself, with the assignments, with my teachers. I wanted to cram as much information as I could into my mind and then be done with it and onto the next. What do you mean my transit app didn’t meet the user problem? I designed it to look just like Google Maps! What do you mean the users didn’t ask for a map? What do you mean I need to spend more time with my research? Why can’t this be easier? Why am I doing this anyway?

And on, and on. Had I not been so desperate for change I might have quit. I hadn’t taken a test since I graduated college in 2009. Learning a new thing was hard. It felt, many times, impossible.

But I had to get through it, because I knew the opportunities waiting for me on the other side were vast. I had three more months to go, but I was learning that white knuckling my way through a career change was not going to work. I needed to slow down, to breathe, and to take it all in.

Eventually — following much more practice and a big dose of humility — I finished the course. By the end of it, I had so much gratitude for my teachers and the assignments, I could cry. They had painstakingly changed me from an insecure person clawing her way into a career change into a focused design thinker embracing a new chapter with grace and confidence.

Soon after, I started my first official UX Strategy job at an agency. Two years later, I came to Vanguard. Throughout that time, I continued to learn so much, things that couldn’t be taught in a UX program. I learned about people, their motivations, their worries, and how much it mattered to get the design right for them. I learned to take critical feedback. I learned how to listen. I learned that not all ideas are good ones. I learned that most people just want to be heard. I learned to iterate, to take in new information, to reprioritize, and to change direction — even if I thought I’d discovered the solution. Even if I’d invested a lot of time on trying to make that solution work.

You sense the metaphor here, surely.

Thinking like a strategist has crept into many parts of my life, for the positive. I’ve learned to be more grounded and a more active listener (taking time to really understand the problem). I’ve learned to think ten steps ahead while understanding current day’s realities (planning an MVP and iteration cycle). I’ve learned to have difficult conversations, to be a better leader, and to be a more patient student. I’ve become more curious and more flexible, understanding that everything is in motion.

We’re creatures that are always evolving. We learn new information, we combine it with what we already know, we reprioritize, we recenter on what’s important. Throughout our lives we’ll change our mind, change our beliefs, and reframe our perspectives. Maybe we decide to take on a new challenge that intimidates us. Maybe we spend time quietly listening and learning, being present in our day-to-day.

Our lives can move in a thousand different directions. We choose the direction that works for us based on what we know in the moment, being flexible enough to understand that later on, as we learn new information and again reprioritize, we will surely pivot. It’s what makes life hopeful, interesting, and ever-changing. We can’t white-knuckle our way through it, we can only work with what we have, when we have it, try something, test it out, learn something new, make a change, and repeat again and again.

It is not lost on me that one goal of this particular life experiment was to become more financially secure, and my day to day now consists of working on my little piece of the larger Vanguard puzzle to help our clients achieve just that. I look forward to everything that is sure to come in my career as a UX Strategist at Vanguard, and to all the lessons this career continues to teach me, for all aspects of my life.

This article is part of the “Chart a Course” series, which features Vanguard crew telling the story of the different career pathways to becoming a UX professional.