Comfortable with Being Uncomfortable

“Internal job opening.” That’s a phrase you often hear at Warby Parker. So much so that it’s a section in our company newsletter. In fact, it’s part of why I felt so strongly about working here—“start-up” meant growth opportunity. However, I never thought I’d transition from our Customer Experience team to our Technology team.

When I started as a Business Analyst, I had only a vague idea of what it entailed. Sure, I knew some buzzwords: “requirements gathering”; “agile”; “velocity”. I knew I’d be part of the software development process. I knew I’d help articulate what the final product would do.

Besides that? This was a new world to me. I didn’t know how I was going to do those things. Only that I should be doing them. My background was primarily in data analysis, and my only exposure to programming was the introductory Java class I needed to graduate from MIT.

Fast forward two years and I’ve worked with my team to build out our core business systems, including an internal prescription processing tool, several transportation integrations, point of sale functionality, and more.

This is what I’ve learned along the way.

Impostor syndrome? Get comfortable with it

When I start a new role, I not only want to show that I’m qualified, but also that I can add value—and most importantly, I’m the correct hire. The problem: I wasn’t quite sure how to do that when I was still learning.

Some days, I was convinced my team would realize I had no clue what I was doing. They’d provide updates during scrum, and I’d nod like I understood. I’d sit in meetings where terms like “third-party integration,” “tech debt,” and “API” would fly around—and it was hard to piece out how they fit together.

The solution: Accept that feeling.

It’s okay.
It’s expected.
It took six months before I felt I could follow the conversations around me.

Give yourself time.
Six months is a good place to start.
This does not mean you should be comfortable feeling lost and then expect an epiphany after six months.

  • Set goals.
  • Check in with yourself periodically (weekly, monthly, etc) to review them.
  • Check in with others—feedback helps you pinpoint the most effective way to spend your energy.
  • Take a moment to acknowledge your own progress—one big moment for me was when I noticed myself starting to use the words that had baffled me in the past.

Here’s a glimpse of the long-term from our CTO: “That feeling never, ever goes away—and only gets stronger. The majority of experts I know feel like the more they know, the more they realize they don’t know much.”


Ask until you get it
Have the courage to admit when a concept or conversation is not making sense. I’ve lost count of how often I’ve said to my team, “I don’t understand. Can you explain it to me again?”

You’re working with people who are so familiar with the system and subjects that they do not even realize they’re using terms (like acronyms) you may not know.

If you get frustrated, below are some aids:

  • Ask for visuals and diagrams—“Can you draw it out for me?” or “Let’s whiteboard this.”
  • Talk it out in person. Personally, I find explanations over chat and email harder to digest. One of the keys to learning rapidly is discovering what medium best suits your learning style.
  • Explain what you do understand to make it clear what gaps need to be filled.

Ask open questions
Consciously think about how questions are framed. Open questions allow people to elaborate while closed questions result in a “yes” or “no.

Some ways to start open questions include: why, what can we do, how can we, when can we.

As an exercise, consciously swap:

  • “are there” with “what are”
  • “can we” with “what can we”
  • “is this” with “what might be”

Ask for advice
Most of the problems you’ll encounter are not unique.
Patterns emerge.

If you’re stuck, help is an e-mail or chat away.
Leverage the people around you.

Before you get too hasty, do some research beforehand. Show the person you value their time by bringing potential solutions to the table. This provides a better framework for the conversation to increase effectiveness.

  • Project timelines are slipping? Talk to someone who is great at managing projects and deliverables. Maybe they use detailed task breakdowns, expertly manage scope, or are flexible when there are perceived blockers.
  • Requirements are getting missed? Ask to shadow a project end to end. Observe how requirements are elicited.
  • Feel overall lost and not sure where to start? Schedule 30 minutes with someone and ask him or her questions. They key is to get the conversation started.

Review and practice what you take in

Listening is not the same as understanding.
In discussions around processes and requirements, I reinforce new information by repeating it back to make sure it still makes sense. If I’m taking notes, I’ll rewrite them more concisely afterwards. In doing this, I’ll sometimes realize there are still pieces that are confusing to me.

Knowing is not the same as doing.
I keep a document with learnings I want to practice. Every few weeks, I’ll review it and agree with what I wrote down. However, none of those notes are helpful unless I take action.

So what are you waiting for?
As employees at Warby Parker would say, “Learn. Grow. Repeat.”

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