translate your life goals to careers
how do we make that dream a reality?
you sat with your notebook yesterday
and wrote out your five year future.
the city.
the house.
the kind of work.
the energy of your mornings
and the quiet of your evenings.
if you haven’t done it yet, stop reading.
come back tomorrow. click here to complete that first.
this piece only makes sense
if that vision exists, not in your head, but on paper.
career frameworks share one big delusion.
people plan their careers in isolation.
they start with “what role do I want next?” or “how do i get into X company?”. people treat career moves like shopping for the next item on a menu. but you don’t live in a menu. you live a life. and careers are one part of it.
what happens when you do that?
you choose a goal that sounds impressive. what your parents would approve of. what would make a good linkedin update. but you don't know what a day in your life should feel like. so you optimize for proxies. title progression. salary benchmarks. team size. funding rounds.
that causes a lot of problems.
you take the promotion because it's there. you chase the salary because it's higher. you switch companies because your friends left the company. three years later, you're successful and miserable. you achieved someone else's definition of winning.
that’s why we began with a visualization.
that visualization you wrote is full of clues about what you actually want. not what sounds good in interviews. not what impresses your college friends. what you want a regular fucking day to feel like. because your career decisions need to align with the life you’re designing. not the other way around. if you wrote that you live in a beach facing home with two kids, you’re implicitly deciding on a certain type of income, city, job intensity, and even team size. If you visualized working with ten other sharp operators, you're signalling a specific kind of culture and ownership style.
pull out what you wrote.
actually pull it out.
this article is useless without it.
let's decode it.
we're breaking your life into three pillars.
work,
wealth and
your inner circle.
these are the
3 core pillars of life.
yes, building this clarity isn’t easy.
but nothing that comes easy is worth doing anyway. to make things easy and actionable i’ve broken this down into 3 parts.
today, we will decode
your five year life into a wholistic map for work, money, & personal life.
tomorrow, we will map
the milestones that must be true at year 1, 2, 3, 4, 5.
day after we will action on
a 12 month execution plan that’s tactical like a product roadmap.
sounds hard? don’t worry.
follow me and just WRITE as we go. you just have to commit to writing things down, clearly. thinking alone is a loophole your brain will exploit.
work (the part you keep lying about)
first, forget the title.
the temptation is to jump straight to job titles.
don't.
you've been doing that your whole career, and here you are. look at what you wrote about your actual workday.
here's what to hunt for: the pace. did you describe back to back meetings with quick decisions? or long stretches of focused work?
look for feeling of the kind of problems you're solving. did they feel like technical puzzles that require deep expertise? or did they feel like business challenges that need strategic thinking? or maybe it felt like people problems that demand emotional intelligence? in your visualization how did you feel about the work?
the scope of impact.
some people wrote about features used by millions. others wrote about transforming how their specific team operates. neither is better. but confusing them guarantees frustration.
team dynamics matter more than size.
did you describe collaborative problem solving or solo deep work? leading through hierarchy or influencing without authority? building something new or optimizing something established?
write it down.
not what title you think matches.
the actual work patterns:
"deep technical work with one major problem per quarter" or "fast context switching between customer needs and product decisions" "building new business lines from zero to scale" "optimizing existing systems for 10x performance"
1st pillar: money (the math you're avoiding)
time for some math.
your visualization has expensive taste.
let's find out how expensive ;)
start with the obvious.
housing. you wrote about a place. maybe it has a garden. maybe it's walking distance to good coffee. maybe it has a room where you can close the door. find three real listings today that match what you described. average the price. add 20% because everything costs more than you think.
now monthly costs.
your visualization included lifestyle markers:
the car (or lack of one)
the vacations (how many, how far)
the kids' activities (swimming, coding, etc)
the meals (cooking at home vs eating out)
the emis for the emergency fund that lets you sleep
don't forget the invisible costs.
supporting aging parents.
your partner's career transition.
the medical procedure insurance won't cover.
life happens in expensive ways.
now the composition.
is this mostly base salary?
equity that might be worth something?
bonus tied to company performance?
side income from consulting?
don’t worry about getting it perfect.
focus on the big expenses. the small ones won’t matter.
we just need a finance anchor for tomorow.
2nd pillar: personal
(the part that makes or breaks everything)
this is where most career plans falls apart.
you optimize for work and money,
then wonder why you feel empty.
relationships define boundaries.
in your visualization, who did you eat dinner with? how often? who called when they needed help? who did you help without being asked?
being single gives you maximum flexibility
and total accountability. every decision is yours. every consequence too.
partnership means negotiation.
your visualization included someone else's dreams too. where do they work? what do they need? when do their priorities override yours?
kids rewrite all rules.
school pickup at 4:30 is non negotiable. sick days triple. energy depletes faster. purpose clarifies completely. if your visualization included children, what ages? that determines everything from housing needs to work flexibility.
parents age in ways that reshape
your geography. can you take that international role when mom needs weekly doctors visits? will you move back to cleveland? these aren't theoretical questions.
now the health stuff.
your visualization includes clues.
morning run
(or home gym)
weekend hikes
(needs geo access)
managing chronic condition
(flexible schedule & good insurance)
write what you actually need,
not what sounds virtuous:
"30 mins of movement daily, nothing fancy"
"training seriously for triathlon, 10+ hrs wkly"
"yoga practice that needs leaving work by 6"
"physical job that keeps me active"
the spiritual side, broadly defined.
did you describe:
weekly religious services
that anchor your schedule
meditation practice that needs quiet mornings
creative pursuits that require dedicated space
community involvement that takes weekend time
therapy that happens every tuesday at 2pm
these aren't optional add ons.
they're 100% your load bearing structures for mental health.
the decoding process
now the actual work. get a fresh sheet of paper or use your laptop.
three columns:
work, money, personal.
under each, write exactly what your visualization requires. not what seems reasonable. what you actually described.
work examples:
"building products in climate tech"
"team of 8 to 12, mix of senior and junior"
"direct p&l ownership, no approvals"
"problems change quarterly, not daily"
"remote first but quarterly in person"
money examples:
"total comp: XXX by year 5" "base: XX, equity: XX" "supports: XX mortgage, XX childcare, XX savings" "one time: XX down payment by year 4" "flexibility: could take XX% pay cut for right opportunity"
personal examples:
"married, two kids by year 3" "run 20 kms weekly, one race yearly" "parents live nearby, help with childcare" "core friend group meets monthly" "10% income to causes i care about"
be specific.
vague goals create vague careers.
now look at what you wrote.
circle the conflicts. the startup equity path won't fund the house timeline.
the executive role won't allow
the 5pm family dinner.
the technical specialist track won't
provide the team leadership you crave.
these tensions are real. you can:
extend timelines
(house in year 7, not year 5)
adjust requirements
(3 bedroom, not 4)
sequence priorities
(corporate job first, mission driven later)
redesign entirely
(move somewhere cheaper, change the whole equation)
but you can't pretend they don't exist.
some of you just realized you've been optimizing for a life you don't actually want. the promotion you're chasing leads to a calendar you'll hate. the city you're in doesn't match the life you described. the industry you're in doesn't pay for the dreams you have.good. now you know.
tomorrow, we map the moves.
the specific career stages between here and there.
but today, you clarify the destination. the actual life.
one more thing.
that feeling when you realize the math doesn't work? that's not failure. that's the first honest moment in your career planning. most people spend decades avoiding this math, then wonder why they feel stuck.
tomorrow, we will map the milestones
that must be true at year 1, 2, 3, 4, 5.