← All coursesCourse N° 01 / DRI Your Career

Shape your career, or capitalism will.

DRI Your Career.

Figure out what you actually want — and make it happen. Become the Directly Responsible Individual of your own growth.

Starts July 13, 20268 weeks · async45–60 min / weekFrom $449

Enroll now See the curriculum

Illustration of a raccoon hiking with a map

N° 01 / DRI

01The premise

We're all Toronto raccoons now.

Pampered ZIRP-era raccoons are a thing of the past. Illustrations by Joe Groove.

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.

It's time to figure out what you want.

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.

02This course is for you if…

You're the team player. What about you?

✦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.

03What you'll walk away with

A career strategy you can name out loud.

✓Your career strategy toolkitCareer thesis (north star), proximate objectives (next steps), and guiding principles (values-based compass).
✓Your support network mapWho fills which roles (manager, mentor, sponsor, coach) and where the gaps are.
✓Your wants list and next actionsDistinguish “shoulds” from authentic desires and define 3 concrete steps to move forward.
✓A mindset shiftFrom “following the path” to being the DRI of your own growth.
✓Practical frameworks that workEnergy management, feedback as data, values-driven decision making, and permission to explore for 12+ months.
✓Confidence to navigate transitionsTools to actively seek feedback instead of waiting for annual reviews.

04The curriculum

Four modules. Eight weeks.

A mix of introspection, structure, and support — with just the right amount of accountability. Each module includes exercises with a submission deadline and personal feedback from Cate & Jean.

N° 01

Weeks 1–2

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.

N° 02

Weeks 3–4

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.

N° 03

Weeks 5–6

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.

N° 04

Weeks 7–8

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.

Want to see what the course feels like? Preview the Getting Started module for free.

Preview Intro Module

05How it works

Structured enough to keep you on track.

Self-paced and asynchronous, but never alone — a cohort, a pace, and personal feedback on everything you turn in.

/ 01

8 weeks.

4 modules over 8 weeks of self-paced, asynchronous content.

/ 02

45–60 min a week.

Fits around a busy schedule. Mornings, weekends, the gaps between meetings.

/ 03

Audio conversations.

Recorded conversations between Cate & Jean, including personal stories and reflections.

/ 04

Written material.

Module content and frameworks designed for reflection, not just reading.

/ 05

Exercises that think.

Prompts to apply each module to your own situation. Writing generates thinking.

/ 06

Personal feedback.

Jean and Cate read every submission. Real written feedback, not AI, not a rubric.

06Meet your course guides

The coaches.

Cate Huston

Author · Fractional CTO · Coach

Author of The Engineering Leader, fractional CTO at Twill, and engineering leadership coach. Previously in leadership roles at DuckDuckGo and Automattic, and an advisor at Glowforge. She has been all over the world, but now lives in Ireland.

More about Cate at cate.blog →

Jean Hsu

Builder · Coach · Fractional VPE

Builder, writer, coach, and fractional engineering leader at early-stage startups. Previously in leadership roles at Pulse, Medium, and Range, and built out a leadership development company focused on engineers. She lives in Berkeley with her partner and three kids.

More about Jean at jeanhsu.com →

Cate and Jean have been coaching engineers and engineering leaders for years. This course distills their best frameworks into structured exercises you can apply to your own career — with personal feedback on every submission.

07Frequently asked

Common questions.

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?

You get structured frameworks and exercises applied to your own situation, plus written feedback from Cate and Jean on every submission. It's more guided than solo reflection, and more affordable than 1:1 coaching.

Why raccoons?

Cate has been a long-time admirer of adorable raccoons. But they're also the perfect mascot for this moment in tech — resourceful, adaptable, and thriving in adverse conditions. We're all Toronto raccoons now.

Do you offer scholarships?

We offer scholarships on a per-cohort basis. Sign up for cohort notifications and we'll let you know when they're available.

Cohort opens · July 13, 2026

Ready to join us? We'd love to have you.

Take ownership of your career with clarity, confidence, and intention. One-time payment, eight weeks, and Cate & Jean in your corner.

One-time payment

$449$499

Early bird pricing active.

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