A Free Six-Week Email Course

The lessons no one teaches you about how work actually works.

32 lessons. 32 questions. Built from years of watching people navigate the hardest transition of their career — and making plenty of wrong turns myself.

You did the things you were supposed to do. Got the degree, got the job, showed up, worked hard. And somewhere around year three or four, a thought started forming that you couldn’t quite shake:

Something about the way this works isn’t working. And you’re not sure if it’s the job, the company, or you.

Here’s what I can tell you after 25 years of building products, leading teams, and teaching: it’s usually not you. It’s the conditions. The same person in two different environments produces completely different results. The capability was always there. The environment either let it show up or it didn’t.

These 32 lessons won’t give you a career plan. They’ll give you something more useful — the questions that help you figure out what’s actually going on, so you can stop drifting and start designing.

What You’ll Get

Six weeks. Five lessons per week.
Each one built to make you rethink something
you thought you’d figured out.

Week 1

The Foundation

Who you are when no one’s watching.

Week 2

The Work

How you show up and what you produce.

Week 3

The People

Relationships, communication, and showing up for others.

Week 4

The Mind

How you think, learn, and handle being wrong.

Week 5

The Path

Purpose, direction, and navigating uncertainty.

Week 6 · Overtime

The Overtime

The foundation gets you in the game. These lessons help you shape the outcome.

A Taste of the Questions

Each lesson ends with one question
you won’t be able to stop thinking about.

What do you think you’re known for versus what do people actually come to you for — and what does that gap reveal about how your reputation is really being built?

Who in your network are you avoiding reaching out to because you “don’t want to bother them” — when they might actually benefit from hearing from you?

What belief are you most confident about because you’ve “done your research” — and how much of that research was actually just finding smart people who already agreed with you?

What do you say is your “deeper purpose” versus what actually gets you out of bed on the days when you don’t feel like doing the work?

What story are you hoping your work tells about you versus what story does your work actually tell — and how might the gap be costing you opportunities?

This Is For You If

✓You’re a few years into your career and something feels off but you can’t name it
✓You’re productive but not sure it’s sustainable — or meaningful
✓You’ve been promoted and the playbook that got you here isn’t working anymore
✓You’re trying to figure out whether to fix what you have or start something new
✓You’re tired of advice that sounds good in a podcast but doesn’t survive contact with your actual Tuesday

Where These Came From

These lessons started as a lecture I gave at the end of every semester while teaching UX and Design Thinking at the University of Houston. The things I wished someone had told me when I was navigating the same transition my students were about to face.

They’re not rules. They’re not a career plan. They’re field notes from someone who’s been building products and leading teams for 25 years, and who keeps seeing the same patterns show up in different people at the same life stage.

The challenges are universal. Everyone faces the same fundamental questions about work, meaning, and direction — they just show up wearing different clothes. The uncertainty and confusion aren’t defects. They’re how the system works. These lessons help you navigate more effectively by naming the patterns you’re already living inside.

— Kelsey Ruger

Start with one question
that changes one conversation.

That’s the unit of change. Not a complete transformation. One shift, this week, that makes the next conversation different. The rest follows.

Free. Six weeks. 32 lessons. Unsubscribe anytime.