DRI Your Career
An 8-week course to take ownership of your career
with clarity, confidence, and intention
Course starts January 15, 2026
There's a strange corner of Instagram where raccoons live like royalty — trikes, hand-fed snacks, custom hoodies, plush beds. Meanwhile in Toronto, raccoons live in a different reality: scrappy, scavenging, constantly outsmarting raccoon-proof garbage bins. For the past decade, tech workers were more like Instagram raccoons — pampered, courted, offered lavish perks. That era's over. We're all Toronto raccoons now. It's time to learn how to thrive in adverse conditions and become more strategic, more determined, more resilient.
Pampered ZIRP-era raccoons are a thing of the past. It's time to figure out what you want.
Illustrations by Joe Groove.
It's a strange time to think about career development — tech layoffs, daily horrific news headlines, uncertainty everywhere. The impulse is to stay put, keep your head down, and be grateful. But under that is a quieter question: What do I actually want?
This course creates space to explore that question. Whether you want to double down on your current role, take a step back, or move in a completely new direction, DRI Your Career helps you become the Directly Responsible Individual of your own growth — getting clear on your values, your goals, and how to make work work for you.
Meet your course guides
DRI Your Career is led by Cate Huston and Jean Hsu, engineering leaders with deep experience coaching people through career transitions and inflection points.
Cate Huston
Cate is an Engineering Director at DuckDuckGo, advisor at Glowforge and Twill, and author of The Engineering Leader. She has been all over the world, but now lives in Ireland.
More about Cate at cate.blog→
Jean Hsu
Jean is a builder, writer, coach, and engineering leader at early-stage startups. She lives in Berkeley with her partner and three kids.
More about Jean at jeanhsu.com→Early Bird Pricing - Save $50!
Regular price $399 starting January 1, 2026
This course is for you if…
- ✦You're experienced, capable, and have built a solid career. But lately, when someone asks where you're headed next, you don't have a good answer.
- ✦You're mid to senior level in tech (IC or manager) and have always been the “team player,” doing what's needed. But now you're wondering — what do I want?
- ✦You want to feel more intentional about your career path, instead of waiting for your manager to drive the conversation.
- ✦You've spent so much time processing workplace drama and urgent fire drills that you don't have energy left for what actually matters to you.
- ✦You're trying to make work work for you — not the other way around.
- ✦The traditional career ladder doesn't motivate you, and you want something more aligned with your values.
- ✦You feel stuck between “shoulds” and wants, and are ready to explore what's truly yours.
What you'll walk away with
- ✓Your career strategy toolkit — Career thesis (north star), proximate objectives (next steps), and guiding principles (values-based compass)
- ✓Your support network map — who fills which roles (manager, mentor, sponsor, coach) and where the gaps are
- ✓Your wants list and next actions — Distinguish “shoulds” from authentic desires and define 3 concrete steps to move forward
- ✓A mindset shift — from “following the path” to being the DRI (directly responsible individual) of your own growth
- ✓Practical frameworks that work — energy management, feedback as data, values-driven decision making, and permission to explore for 12+ months
- ✓Confidence to navigate transitions — whether that's doubling down on your current role or heading in a totally new direction, with tools to actively seek feedback instead of waiting for annual reviews
How it works
8-week course
4 modules over 8 weeks of self-paced, asynchronous content
Recorded audio content
Conversations between Cate and Jean, including personal stories and reflections you can listen to anytime
Reading material
Module content and frameworks to deepen your understanding
Exercises + reflection prompts
Exercises to help you apply what you've learned in each module to your personal situation
Module submissions
Submit exercises for each module to get personal feedback from us
Personal feedback from us
Jean and Cate review every submission and provide written feedback and coaching
Course Start
January 15, 2026
We designed this course to be a mix of introspection, structure, and support — with just the right amount of accountability. Plan to spend 30-60 minutes per week engaging with the content and working through exercises at your own pace.
Each module includes exercises with a submission deadline. We personally review and provide feedback on all submissions by that date — giving you direct access to Cate and Jean as experienced engineering leaders and coaches.
Modules
Shape Your Career, or Capitalism Will
Reclaim agency over your career decisions. Understand what employers “rent” vs “buy,” distinguish “shoulds” from authentic wants, and see your career in the context of your whole life.
Explore Your Wants and Make Something Happen
Master energy management over time management. Clarify your core values, create guiding principles as your career compass, and identify your proximate objectives — the next most informative steps.
Own Your Growth
Reframe feedback from dreaded criticism to useful data. Learn to seek and process four types of feedback, build cheap and consistent feedback loops, and accelerate your growth.
Synthesis and Clarity
Connect insights from all modules. Write your career thesis (your north star in 1-2 sentences), define 2-3 focus areas for the next 3-6 months, and map your support network.
Being the DRI doesn't mean doing it alone
No single person — not even the best manager — can meet all your career needs. In Module 4, you'll map your support network and identify where the gaps are.
Part of being the DRI of your career is knowing what support you need and actively asking for it — even when that means managing up or seeking help outside your organization.
What people are saying
“Cate and Jean are the ultimate dynamic duo. With clarity, humor, and intense wisdom earned in the trenches, they will shine a light on your reality and help you find new ways to relate to it. I've turned to them for many of my own most important career decisions, and I'm so excited more people will get to tap into their deep well of playful insight through this course.”
“Working with Cate has been the single best investment of my professional life: not only am I a more effective leader, I'm now firmly steering my own career.”
“Jean is empathetic and truly listens. Her insights and thoughtful feedback helped me navigate my overwhelm when starting a new job after a break. Her support has been like having a trusted companion who genuinely cares and helps the path forward feel less lonely.”
Frequently Asked Questions
How much time will this take each week?
Plan to spend a minimum of 45 minutes per week engaging with the content and working through exercises at your own pace. The course is designed to fit into busy schedules while still creating meaningful space for reflection and action.
What if I fall behind?
While we have submission deadlines for exercises to create accountability, the content is entirely self-paced and asynchronous. We encourage you to stay on track, but if you need extra time, you'll still have access to all materials and can catch up.
Is this course only for people who want to change jobs?
Not at all. This course is for anyone who wants more clarity and intention in their career — whether that means doubling down on your current role, exploring a pivot, or something in between.
Is this course just for engineers?
We designed it with engineers in mind, and our personal stories will reference our engineering careers — but the frameworks are generally applicable. This course would also be particularly valuable for product managers, designers, data engineers, and other tech roles where you're looking to take ownership of your career trajectory.
How is this different from career coaching?
This course combines structured curriculum with personalized feedback. You get frameworks and exercises that work (developed from our years as engineering leaders and coaches), plus written feedback from Jean and Cate on your submissions. It's more guided than solo reflection, but much more affordable and flexible than 1:1 coaching.
Why raccoons?
Cate has been a long-time admirer of adorable raccoons. When I asked her "Why raccoons?", she said, "They're just the best animals."
Ready to join us? We'd love to have you.
Take ownership of your career with clarity, confidence, and intention.
Early Bird Pricing - Save $50!
Regular price $399 starting January 1, 2026