Why Good Design Decisions Feel Risky

Every designer has been there: you present a solution you believe in, but the voice in your head is asking whether it's actually good enough. The gap between projecting confidence and feeling it is a well-known career hurdle, one that’s amplified when you’re making decisions from a mix of experience, instinct, data, and taste—and trying to convince stakeholders whose mix looks different from yours.

You cannot fully control the project or the people involved, but you can control your own internal narrative. The exercises below are designed to help you do that. They are best done in a small group with peers, as hearing how others have handled self-doubt tends to be both revealing and validating. Keep an open mind and move through them in order.

Start With Your Earliest Doubts

Examining early-life confidence struggles can reframe how you see your current narrative. Looking back with some distance encourages a kinder, more generous perspective on the work you need to do on yourself—and makes that work easier to start. When shared in a group, it also breeds empathy and mutual support.

Exercise: The Early Scary Things

Think of a time in your life when you lacked confidence in a particular skill, activity, or discipline. What specific steps did you take to achieve that confidence?

  • Write down a few examples on your own (2–5 minutes).
  • Share your experience and the path you took with your group (5 minutes).

Examples from a workshop:

  • “My biggest fear as a kid was that I wouldn’t be able to read out loud without stuttering. I practiced to myself in my room for hours, yet had zero confidence. So I made an effort to read with my parents and grandparents as often as possible, asking them to correct my mistakes. I needed help a lot at first, but eventually I could read on my own without mistakes—and even landed in an advanced reading group.”
  • “As a child, I lacked confidence in swimming and overcame it by telling my mom. She signed me up for swim classes and gave me goggles. From there, I couldn't avoid participating since I was almost the oldest kid in class. I still lack confidence in it, but now I know how to better manage it.”

The Two Routes to Confidence: Data and Experience

Ultimately, confidence grows in one of two ways: gathering more data or building more experience. Most of the time, you need both—and plenty of repetition.

Data

A designer’s task is to demystify complex problems and make the solution appear effortless. If that feels hard, you may be working without enough information to actually begin. Confidence in this case comes from research, validation, and advice. Talking to peers, to those who have solved similar problems, or to people who are living the problem firsthand will get you to more meaningful conclusions. This stage is about filling your mind with every variable you can find related to the issue. Even after you leave your desk, the brain keeps connecting the dots, which gradually makes the “right” solution more and more obvious.

Experience

The less popular truth is that some confidence simply requires time. Building experience means doing the scary thing repeatedly until it stops being scary. That path is rarely linear—it twists like a spirograph. Designers revisit similar problem types throughout their careers, and each repetition lets them apply past learnings in slightly new ways. Through those repeated cycles, you accumulate tangible, emotional connections to the outcomes of your decisions, and that emotional history becomes your strongest anchor of confidence—both for your successes and for your failures.

Exercise: Name Your Current Gap

  • Write about the area in your life or work right now where you'd like to feel more confident. Pick a specific design project, hobby, or anything else that triggers doubt (5 minutes).
  • Share your "current scary thing" with your group and discuss what would help. Do you mainly need more data, or more courage to dive into experience? Often, it's some of both.

Examples from the workshop:

  1. “Right now I lack confidence in giving unwanted feedback to my direct reports. It terrifies me, but I know keeping the feedback to myself isn’t doing them any favors. This is clearly an experience problem. It will take courage, but I need to keep practicing and trust it becomes more natural over time.”
  2. “I'm currently struggling with confidence in my design craft and in my decisions. For craft, I read articles, study other product executions, and ask for feedback from product teams or design friends. For decisions, I rely on research and stakeholders' input.”

The confidence conundrum is more manageable once you name it. By identifying whether you lack information or practical reps, and giving yourself the empathy that comes from revisiting past wins, the “do I got this?” whisper gets progressively quieter.