Getting Out: The 18-Month Path from Decision to Exit
Somewhere around forty, tech veterans start thinking about getting out. The ones who leave with any dignity give themselves an 18-month runway from the moment they decide. The impulse version — fed up on Tuesday, resigned on Wednesday — mostly turns into regret inside six months.
Leaving isn't a single move. It's four things adjusted in parallel: money, skills, relationships, and your head.
Step 0: Verify You Actually Want Out
Plenty of people say they want out when what they want is a better version of being in — a break, a different team, a different company, a side project, early retirement. None of that is leaving.
Answer honestly:
- If I gave you six months off, what would you do? If the answer is "rest for a while" or "haven't figured it out yet," you don't want out. You're tired.
- Would you take a job at half your current pay — easy, stable, small money? If the answer is "then why bother," you don't want to leave work. You want FIRE.
The only real exit is "there's a specific thing I want to do and this job is incompatible with it." Those people land fine, because the next stop is already clear.
Months 1-6: The Financial Floor
Your cash has to survive at least three years with no real salary.
Run the actual numbers — this FIRE calculator is the one I built for it. The variables that matter:
- investable assets today, excluding the home you live in
- expected monthly spend after you stop, modeled on the life you actually want rather than the one you have now
- a health reserve — major medical, plus both sets of parents
The most common miss: underestimating how much spending inflates in a no-salary year. Off payroll your insurance copay goes up, your social spend changes shape, you might move, and whatever you start has startup costs. Year one usually comes in about 30% over budget.
Your floor = the honest number × 1.3. Below that, keep working.
Months 4-9: Moving the Skills Over
If the plan after leaving involves doing something else — a company, consulting, content, teaching — the preheating has to start while you're still employed.
Why:
- While employed you have a company platform, colleague reach, and a survivable cost of failure
- Start after you leave and your "former colleague network" depreciates fast
Concretely:
- Content or consulting: in your last year on payroll, start publishing in public. A thousand real followers is worth more than a one-time fire sale of your contacts
- Starting a company: have the dinners, scan the space, build the prototype while you still have a paycheck. Don't quit and then go looking for a direction
- Investing: start trading small positions two years before you leave. Don't walk in with zero experience and a large account
Months 7-12: Banking the Relationships
Ninety percent of your network in this industry came from "we worked on something together." That supply freezes the day you leave.
Start actively maintaining it twelve months out:
- List the 30-50 people who have helped you, who you respect, and who you think you'll cross paths with again
- Get a meal or a video call with some slice of them every quarter
- Keep an informal check-in every couple of months with peers still in the trenches
The key: don't maintain with an agenda. People can feel the agenda, and it makes the whole thing worse. Treat it as how you keep a feel for what's happening in the industry.
Months 12-18: The Head Part
The hardest step, and the one almost nobody writes about.
The job gives you more than income:
- a strong sense of being needed — people call on you in standup, @ you in chat, read what you write
- a clean sense of rank and progress — this month's work is done, next quarter's goals are set
- a social identity that explains what you do — "I'm a staff engineer at X"
All three disappear at once. About 70% of people hit an identity crisis somewhere in months three through nine — feeling like you're nothing, no drive to do anything, no idea how to introduce yourself at a dinner.
Prevent it in advance:
- Start partially detaching six months out: fewer optional meetings, stop reaching for work outside your scope, quietly leave a few group chats
- Keep a regular schedule for the first three months after. Don't drift into 3 a.m. nights
- Give yourself a new daily anchor — writing, training, studying, cooking, your kids. Anything, as long as it happens every day.
Five Common Mistakes
- Quitting cold without doing the math, then panic-applying six months later → the gap on your résumé costs more than you think
- Piling into the sell-a-course business in year one → red ocean, and if it doesn't work the previous five years were spent for nothing
- Assuming a side project transfers cleanly → a side project netting ¥50k a month while employed does not necessarily clear ¥30k as your full-time job
- Cutting all ties with your old company → keep a consulting door open. It's your downside insurance
- Over-accommodating your family's rhythm → leaving is your call, but your spouse's, parents', and kids' schedules didn't change. Set expectations early, or "he's home all day doing nothing" becomes a relationship problem
Closing
The best exit isn't an escape, it's a switch — from one bounded structure to another. If the state you're switching into has no boundaries, no structure, and no source of meaning, all you did was trade job anxiety for void anxiety.
Plan eighteen months out. Give yourself a decent transition.