DRIing Your Career - Cate Huston (Talk Outline)

Cate Huston (leads client engineering at DuckDuckGo; author of Engineering Leader; coach; advisor at Twill) on owning your career — golden nugget: “no one cares more about your career than you — take ownership.” Framing metaphor: tech workers were pampered Instagram raccoons (Melanie on a trike, Piper who paints, Tamer with a crypto scam); in this market we’re now Toronto raccoons — thriving in adverse conditions by being strategic, determined, and resilient (“neuron density of a cat, brain the size of a dog”).

1. Own It (be the DRI)

• Poll: many have had a good manager (who gave feedback, support, opportunities) — treasure them, write them a note. But you can’t rely on always having one (busy/distracted/inexperienced), and your career transcends any single manager.
• Expect more from your career and less from your current job — the thing to optimize is the overall arc, not the current job. Sometimes jobs you dislike develop your skills; sometimes jobs you enjoy don’t develop you — making the trade-off explicit improves decisions.
• Professional-development plans made at review time and forgotten are useless — define your proximate objectives, next achievable goals, and the career/life you want.

2. Proximate Objectives & Planting Opportunities

• A good proximate objective: challenges you but feels possible, you learn something, you want to do it, and it’s within your control. “Get promoted” fails — it’s something someone else gives you (“promotions are a level of capitalism, and capitalism is a con”); “a good goal is one where even if you fail, you learn.”
• Opportunities are like flowers — sometimes given, but if you want them later you must plant now (want to give talks → submit CFPs; want to manage → take on onboarding/docs; want staff → go toward hard problems). Her book (2023 offer, out last year) grew from years of writing/talks building a profile (“being a person who could write a book was also really hard”).
• Be discerning about given opportunities (a rose vs. an unwanted tulip vs. a dandelion “for someone else”) — when opportunity feels scarce we accept everything, so learn to create your own, doing things you actually enjoy. When someone asks you for something, it’s a great time to negotiate — she reframed “token woman” speaking invites as “negotiation practice.”
• A job title is a few words; the work is 40+ hours/week. Don’t cling to a title at the expense of the work you value (a staff engineer on her team “fixes a terrible problem while also shipping” — not everyone wants that). People who fought hard for titles hold them tightly — valid, but don’t sacrifice the work and growth. Account for your life-moment (up for a challenge? need stability? need rest?), write down constraints, and discuss them with your manager (“the worst they’ll say is ‘not possible,’ and often much more is possible than you think”).

3. Strategy, Dreams & the Raccoon Crew

• Career dreams = far-out someday/maybe (concrete or directional); proximate objectives = the next steps; strategy = how you connect them (identify gaps, generate ideas). You don’t need a 5-year plan — just enough direction to make the next decision. You may be in execution mode or an exploratory phase (she’s resting/exploring after her book).
• Write down the plan: the what (specific enough to know you’ve achieved it, broad enough that reaching it expands your capability), the why (your underlying motivation, to look at when discouraged), the resources, and who will support you.
• Build a support system (“raccoon crew”) — you can’t get all needs from one person (true in romance too): manager, skip-level (broader reach/info for opportunities), peers (context, feedback, moving things along), mentors/sponsors (advocate when you’re not in the room), coaches (invested in you without org/social baggage), and the work BFF (data says life is better with one). “Don’t be alone in Toronto.”

4. Becoming Coachable

• Feedback is just information — sometimes usable to improve, sometimes it tells you about the giver, sometimes it goes in the trash. Growth feels hard (”drowning rats / boiling frogs” — both capture “can I do this / sustain this?”). Even good managers aren’t good for everyone all the time (their own constraints), so few people get exactly what they need when they need it.
• The sweet spot is out of your comfort zone with help — find the right help. Distinguish mentoring / managing / coaching (they’re not interchangeable; Marcus Buckingham’s First, Break All the Rules: develop strengths, fix only a controlling weakness). Mentoring that teaches you to “swim in a pool” is useless if you’re “drowning in the ocean.”
• Coachability = receptiveness × actionability. Highly receptive people work through feedback, are self-aware, fit it into (and adjust) their mental model, and believe they can learn from anyone; highly actionable people experiment/iterate and respond to implicit as well as explicit feedback. Be in different quadrants with different people (high-trust up-right, low-trust down-left) — healthy and understandable.
• Five-step plan to be more coachable: (1) build self-awareness (when someone annoys you, what did they trigger/teach?); (2) get a broad perspective (tech isn’t that special — learn from other industries); (3) shed defensiveness (get curious); (4) admit when you screwed up (start with what could go better so people can add to it); (5) ask for advice (a “magic trick” — people prefer giving advice to feedback).
• Know when to bin feedback: she ignores unsolicited criticism from men on the internet for her mental health; but years of feedback about her “annoying voice/accent” eventually yielded a real truth — her pacing is too fast (still working on it). Bad feedback ignores broader context (misses misogyny), negates your input (a boss who won’t say what he wants then complains you didn’t guess), or undermines rather than helps you succeed (Netflix’s No Rules Rules direct feedback works because it’s meant to help you succeed — you can take much harder feedback that way). Feedback meant to tear you down tells you about the giver — bin it, or learn to work around/avoid them. Untangling old feedback trauma is a gift to your resilience.

5. Knowing When to Quit

• She’s become the ”quit your job coach” — but there’s a big difference between quitting because you can’t get what you want and quitting from power knowing what you want and going toward it. Think about quitting annually (she’s at her 5-year anniversary because the org changed and she got better at constructively reconsidering).
• Signals to pay attention to:
  • Learning — the saddest resume is “5 years of experience = 1 year, five times.” If you’re not learning (esp. when you should be), change it (maybe by leaving, maybe not).
  • Coping mechanisms — learning political dances or blame-proof documentation is energy that won’t help (and may harm) you in a better environment.
  • Morally conflicted about hiring — if you think others deserve better, maybe you do too.
  • Confidence — when you feel yourself getting smaller not bigger, it’s corrosive (how abusive environments keep people).
  • Physical — “your job won’t love you back”; take care of yourself.
  • Market reality — in a hot (“Toronto”) market, some frustrations are industry-wide, so interview regularly to know how hard it’d be to find another job and whether it’d actually be better (“if you find out you’re not underleveled/underpaid, use that to be less annoyed — ‘I have a good deal under capitalism’”).
• Takeaways: get clear on what you want (question what capitalism tells you); understand your terrain/constraints; have a strategy (deliberate learning + iterating on proximate objectives, not a 5-year plan); build your raccoon crew; invest in your own learning/development and your relationship with feedback.

6. Q&A

• “Morally conflicted about hiring”? It can mean unfair hiring practices, or just: would you recommend this org to a friend? If no, ask why.
• Work vs. title when the title pays more? The million-dollar question — money and title aren’t the same either; decide how much you care about money on what time frame (her partner contracts between jobs — most money ever, but not a great long-term career move, so fine for a year, not forever). Also, orgs have real constraints (no headcount to promote).
• How to encourage feedback? Ask for advice; and going up the org chart, mine implicit feedback (nobody has full context on your job — she has 9 reports and a boss who by design doesn’t know her details).
• Keeping patience while waiting for the right opportunity? Be clear about what you’re getting now — “if it’s just a paycheck to buy time, that’s fine, and being clear helps you be less frustrated.”
• Low confidence + unsupportive manager — where’s the motivation? Fix confidence first — collect small wins (in corrosive grad school she started a weekly blog to “be in the world” and got engagement her advisor never gave).

People & References Cited

• Cate Huston — speaker; DuckDuckGo; author of Engineering Leader.
• Marcus Buckingham (First, Break All the Rules), Netflix / No Rules Rules (feedback culture), Lara Hogan (“ask for advice” magic trick, referenced).
• Concepts: DRI of your career, proximate objectives, planting/picking opportunities, career dreams vs. strategy, raccoon crew (skip-level/peers/mentors/sponsors/coaches/work-BFF), coachability (receptiveness × actionability), binning feedback, quit signals, interview regularly.

Video: https://www.youtube.com/watch?v=wyKigbA_XaY — Transcript via yt-transcript.sh; outline generated from the transcript.