4 kinds of career discomfort

(and which one is slowing you down)

career discomfort matters more
than career comfort. yes.

comfort kills faster than a bad boss or a funding freeze. when you're comfortable, you stop scanning for threats. you stop building new capabilities. you optimize for today's game while tomorrow's game shifts underneath you.

discomfort signals change before your logical brain catches up. here's what 12 years of watching startup careers taught me: the people who advance fastest aren't the ones who avoid discomfort. they're the ones who can diagnose it accurately and respond fast.

understanding which discomfort you’re in is critical. treat growth discomfort like direction discomfort and you’ll waste months learning the wrong things. misread change discomfort as performance discomfort and you’ll jump to the wrong company for the wrong reasons.

thankfully, across
1 billion white collar professionals,
100 industries,
25 functions,
and every seniority level,

career discomfort shows up in just 4 forms.
and each one is solvable.

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#1 growth discomfort

i remember my first leadership role. three months in, i realized i was spending more time googling "how to" than i was comfortable admitting. how to give difficult feedback. how to set team priorities. how to create a “vision doc”. the discomfort was real, but so was the learning curve.

this type of discomfort feels like not being good enough. you're in meetings where people reference concepts you don't understand. frameworks you've heard of but never used. tools that everyone assumes you know.

the good news?
you can name what you don't know! you can see others doing what you can't do. and you actually know what you want to solve. here's your action plan for growth discomfort.

first, document what you don't know. make an actual list. not knowing something stops being scary when you name it explicitly.

second, set learning deadlines. give yourself six weeks to understand a topic, not six months.

third, find someone who's been where you're going. ask specific questions about their first 90 days in a similar role.

see, you don't become ready for bigger roles by staying comfortable in smaller ones. you become ready by doing work that scares you a little.

growth discomfort has a timeline. six months, maybe eight, and suddenly you're not googling basic concepts anymore. you're now the one driving the discussions that once intimidated you. the stretch becomes your new normal.

---

#2 direction discomfort

this one's trickier.
this feels like being lost in your own life.

you're making progress,
but toward what?
you're growing but for which future?

every choice feels like a loss because there’s no clear destination. i know the feeling, and it f*cking sucks.

i've watched talented people stay stuck in direction discomfort for years. they analyze every option to death. they wait for perfect clarity before making any move.

perfect clarity doesn't exist in career decisions! you work with incomplete information and make the best choice you can. you build clarity through actions, not planning.

direction discomfort is the most fundamental because it makes every other decision harder. without direction, you can't tell if you're building relevant skills or pursuing meaningful impact.

first, time boxing decisions.
set a deadline for career choices, even arbitrary ones. thirty days to decide between job offers. three months to determine if you'll pursue that industry switch. decision deadlines force action over analysis. it’s the only way you’ll stop over analysing.

next, run experiments,
not job searches. schedule three casual interviews in your target field before updating your resume. shadow someone for a day. take on a side project that exposes you to different work. volunteer in an adjacent area. action creates clarity, not the reverse.

and when you’re doing this,
track your energy, not just your interests. notice which conversations make you lean forward versus check the time ;)

pay attention to what work you do when no one is watching. energy patterns show what you like better than personality tests.

here's what i've learned:
you figure out your career path by engaging with the world and paying attention to what energises you. what makes you get back to that flow state.

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#3 change discomfort

change discomfort is inevitable because change is inevitable.

the industry shifts. your company re-orgs your role evolves. you move to a new city. the familiar becomes unfamiliar. and your nervous system notices. and boy oh boy does it not like that :)

change discomfort is different from the other types because it's often imposed rather than chosen. you didn't ask for the merger or worse that layoff which changed your team. you didn't request the new boss who works completely differently from your old one. but here you are, adapting.

the mistake people make with change discomfort is thinking it should resolve quickly. It doesn't. change discomfort has its own rhythm. you'll have good days where everything feels normal and bad days where nothing makes sense. that's not a bug in your adaptation system. that's a feature.

first,
some days you need to accept, some days you take action. start by acknowledging what you're losing. write it down. the familiar team dynamics. the established routines. the confidence that comes from knowing how things work. feeling bad about the old way makes room for the new way. (yes! this is a lot like therapy)

second,
build stability anchors outside work while your professional life shifts. basically you’re building predictable things outside of work that make you feel grounded, hence the word anchor. build some new routines- learn an instrument, start meditating, workout, early mornings, workouts etc. do whatever floats your boat. cause when everything at work feels unpredictable, predictability elsewhere helps your brain cope.

once that’s done,
creat some anchors in your new environment. setup coffee with three new colleagues. join professional groups related to your new role. find mentors who've navigated similar transitions. because if you feel isolated, that is going 100% amplify change discomfort. find your tribe.

i've been through enough organizational changes to recognize the pattern. month one: everything is new and confusing. month three: you start to see the logic in new systems. month six: you stop missing the old way of doing things. month twelve: you can't imagine working any other way.

change discomfort requires patience more than strategy. you're not broken if change feels hard. you're human.

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#4 performance discomfort

performance discomfort is the weight of expectations. either it’s your own expectations or you’re taking everyone else's.

maybe, you got the promotion. or maybe you landed THE big client. or you're presenting at your first industry conference. now you have to deliver.

performance discomfort usually happens right after success. you've proven you can do something once, and now everyone expects you to do it again. the pressure is real because the stakes are real. you’re thinking, “it took my 200% to do it once, how the fuck can i do it again and again?”

start with separating process from outcomes. you can't control whether you'll another $1M ticket size client, but you can control your prep quality. you can't guarantee your team will hit every quarterly goal, but you can def guarantee you'll track progress weekly and adjust course when needed.

build feedback loops before you need them. schedule monthly check ins with your manager about expectations and performance. ask clients for input weekly, not just at the end. find accountability buddies with peers.

we are doing this for 2 reasons- sure, you’re controlling the input levers but WAY MORE importantly, regular feedback prevents surprises and reduces anxiety. this is what we want to avoid.

performance discomfort responds well to systems thinking. i learnt this from a former boss. he was always calm under crazy pressure, (like $1B pressure). and one day he told me why. “pressure is a prioritisation signal,” he said. “the more pressure you feel, the more important it probably is.”

no pressure? you’re likely not working on anything that matters.

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reading the signals

these four types of discomfort often overlap.

you might feel performance pressure while navigating a change while questioning your direction. that's normal.

let me share the most simple way to remember each type and how to solve it

comfort feels safe.
until it isn't.

discomfort feels risky.
until it saves you.

next time the knot shows up in your
chest, ask: what is this trying to
tell me about what’s next?

this was day #2 of #100DaysOfCareers

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