Calculate your exact runway

Monthly essential expenses × desired buffer months. This is the number that governs everything. Be conservative — most people underestimate monthly spend by 20–30% until they actually track it.

Check your vesting schedule

RSUs, stock options, pension contributions, profit-sharing — when do they vest? A single cliff date 6 weeks away could be worth months of salary. Know the dates before you pick a last day.

Check your bonus cycle timing

Annual bonuses, quarterly targets, commission payouts — what's the cutoff for eligibility, and when does it pay out? Leaving two weeks before payout could be a costly mistake. Leaving two weeks after might be fine.

Understand your PTO payout policy

Some states require unused PTO to be paid out on departure; others don't. Know your state's law and your company's policy. If you have 3 weeks of unused PTO, that could be a significant payout worth timing around.

Research health insurance options

COBRA, ACA marketplace, spouse/partner plan, or Medicaid. Get the actual costs for each option now — not the week before you leave. For U.S. professionals, this is often the biggest surprise cost of a job exit.

Review your 401(k) / retirement accounts

Understand employer vesting of matching contributions (some vest over 3–5 years). Know your rollover options for when you leave: roll to an IRA, roll to new employer's plan, or leave in place temporarily. Don't cash out — the tax penalty is severe.

Accelerate savings toward your target runway

If you're 2 months short of your target cushion, you have 5–6 months to close the gap while still employed. Cut discretionary spend, redirect windfalls, defer purchases. This is the highest-leverage financial action you can take right now.

Re-read your employment contract and offer letter

Look specifically for: required notice period, non-compete clause, non-solicitation clause, IP assignment (who owns work you created), and any clawback provisions on signing bonuses or relocation packages. These have real consequences if violated.

Understand your non-compete obligations

Non-competes are unenforceable in California and several other states, and increasingly restricted elsewhere following FTC rulemaking. But you need to know yours specifically — what it covers, its geographic scope, and its duration — before you accept a competing offer.

Check for signing bonus or relocation clawbacks

Many offers include repayment clauses: leave within 12–24 months, and you owe back some or all of a signing bonus. Calculate exactly what you'd owe and when — it affects your timing.

Review moonlighting or outside work restrictions

If you plan to start freelancing or consulting while still employed, check whether your contract prohibits it — especially for work that competes with or relates to your employer's business. Violations can create grounds for termination without severance.

Research your market rate in your target role and geography

Levels.fyi, LinkedIn Salary, Glassdoor, and industry-specific surveys are your tools. Know the range for your experience level before you're in a negotiation. The candidate who knows the market wins more negotiations than the one who doesn't.

Talk to 3–5 people in your target role or field

Informational interviews serve two purposes: intelligence-gathering and relationship-building. What do they wish they'd known before making this move? What does the hiring process actually look like? What do strong candidates look like?

Identify your top 15–20 target companies

Not a broad wish list — specific companies you'd genuinely want to work for, with a real rationale for each. This list drives your network activation in the next phase.

Write your transition narrative — one clear paragraph

Bridge (where you're coming from) + Proof (what you've done toward the new direction) + Forward momentum (why this specific direction). Practice saying it out loud until it sounds confident, not rehearsed.

Rebuild your résumé for the target role, not the role you're leaving

New professional summary at the top. Role descriptions reframed around transferable outcomes. Skills section updated with current tools. Work history trimmed to 15–20 years maximum. Graduation dates removed if they'll age you.

Update LinkedIn — headline, About, and experience

Headline should describe what you do and who you help, not your job title. About section as a narrative, not a job description. Reframe experience descriptions to emphasize outcomes. Add any recent certifications, projects, or publications.

Request 2–3 LinkedIn recommendations now

Ask colleagues or former managers who know your work well and can speak to skills relevant to your next move. Give them a brief note about the direction you're heading so they can frame it usefully. Do this now — recommendations take time, and people are busy.

Start a portfolio or work samples document

Collect examples of your best work — reports, projects, campaigns, code, decks, outcomes you drove — in a format you can share. This is your proof file. Redact any confidential information. Some of your best work will be locked inside company systems after you leave.

List the skill gaps between your current profile and your target role

Be specific: "familiarity with SQL" is a gap. "No experience with product roadmap tools" is a gap. List them, then prioritize by how much they'll be tested in interviews versus how much you'll need on the job.

Start closing the highest-priority skill gaps now

A course, a side project, a stretch assignment within your current role, a volunteer engagement. Not everything — focus on the two or three gaps that would most visibly strengthen your candidacy.

Build at least one piece of tangible proof of concept

A project, a case study, a published piece, a freelance engagement, a volunteer role. Something that says "I am already doing this" rather than "I want to do this." One concrete proof point does more work than five certifications.

If going independent: validate demand with real conversations

"Would you pay for this?" is a different question than "Do you think people would pay for this?" Have 5–10 real conversations with potential clients or employers. Let their responses calibrate your confidence more than your own intuition.

Contact 20–30 people in your network personally

Individual messages, not a mass email. "I'm making a transition toward [X] and wanted to reconnect. If you hear of anything relevant or anyone I should talk to, I'd appreciate the introduction." Specific enough to be actionable, warm enough to feel human.

Request internal referrals at your target companies

A referral from inside a company routes your application to a person, not a queue. For each target company on your list, check whether anyone in your network has a connection there — and ask for an introduction, not just a name.

Alert your professional references

Give your references a heads-up that you're in a search, tell them the type of role you're targeting, and share a few bullet points about what you'd like them to emphasize. Don't surprise them with a call — give them the context to do a good job.

Engage with relevant professional communities

Industry associations, Slack communities, LinkedIn groups, alumni networks. Being present and contributing in these spaces increases the surface area for opportunities — especially ones that never appear on job boards.

If going independent: have conversations with at least 3 potential clients

Not about landing them yet — about understanding whether there's fit. What are they struggling with? Is this the kind of work you want to do? Do they have budget? These conversations calibrate your service offering before you need the income.

Set up a job search tracking system

A simple spreadsheet works: company, role, contact, application date, status, next step, notes. Searching without a tracking system is flying blind. You will lose track of where you are with 8+ companies in motion.

Set up job alerts on LinkedIn, Indeed, and relevant industry boards

Automated alerts for your target role + geography save the time of manual searching and surface opportunities quickly. Apply within 48–72 hours of a posting appearing — early applications have materially higher response rates.

Set up a personal email for job search correspondence

Your work email will be inaccessible after departure. All job search communication should go to a personal address that you own and will keep regardless of employer. firstname.lastname@gmail.com is fine. Creative addresses are not.

Prepare answers to the most predictable interview questions

"Tell me about yourself." "Why are you leaving?" "Why this company?" "Tell me about a time you failed." "Where do you see yourself in five years?" These are not trick questions — they're almost guaranteed. Prepare them once, well, in advance.

Define your salary floor, target, and stretch number

Your floor is the minimum you can sustainably accept — based on your actual expenses and financial goals, not on what sounds reasonable. Your target is market rate for your experience and role. Your stretch is the top of market. Know all three before you enter a negotiation.

Know your full current package to a precise number

Base + bonus + equity value + benefits (healthcare premium, retirement match, PTO value). This is your total compensation baseline. Negotiating only on base salary often undersells your total package needs and expectations.

Decide what non-salary items matter to you

Title, remote/hybrid flexibility, start date, equity structure, professional development budget, PTO days. Knowing your priorities before an offer arrives means you can negotiate from intention rather than improvisation.

Decide on your notice period and last day before you give notice

Know your contractual requirement, your financial need, and how much transition time is genuinely appropriate. Two weeks is standard in the US; four weeks is more common at senior levels. Don't offer more than you need to — it rarely benefits you and often extends awkward limbo.

Write a transition document for your key responsibilities

Status of active projects. Recurring processes you own. Key contacts and context. Where to find important files. Passwords or system access that needs transferring. Do this even if no one asks — it's a professional courtesy that protects your reputation and often differentiates how you're remembered.

Identify and complete or hand off everything in flight

Projects that are 80% done. Commitments made to clients or partners. Deadlines you agreed to hit. Completing what you started is part of leaving well. Handing off cleanly is the alternative. Abandoning things is the option that follows you.

Brief your manager on any issues that need post-departure attention

Unresolved risks, clients who need extra attention, team dynamics that are fragile. Your manager will remember how you handled the transition. This is not sycophancy — it's professional responsibility.

Have individual conversations with key colleagues before you announce

The people who matter most — mentors, close collaborators, sponsors — should hear it from you directly, not in a group email. "I wanted to tell you before the announcement — I'm moving on. Working with you has been [specific, genuine thing]. I'd love to stay in touch."

Connect on LinkedIn with everyone you want to stay in touch with

During your final weeks you have natural context for reaching out. After you leave, a cold connection request is odd. Send the requests now, while the context is fresh.

Ask for any remaining recommendations or references now

It's easier to ask while you're still present than six months after you've left and people have moved on. Specific requests are better: "Could you write a LinkedIn recommendation that speaks to my work on [X]?" gives the person a useful frame.

Clarify what your employer will say when used as a reference

Ask HR: what is the official policy on employment verification? Will they confirm dates and title only, or will managers speak to performance? If the departure was amicable, ask your manager directly what they'd say. No surprises later.

Use remaining FSA / HSA funds before they expire

Flexible Spending Account funds are typically "use it or lose it" — check your plan's rules on what happens at departure. HSA funds are yours to keep. Stock up on eligible medical/dental/vision expenses before your last day if you have an FSA balance.

Schedule any outstanding medical, dental, or vision appointments

Annual physical, dental cleaning, eye exam, prescription renewals — anything you've been putting off. Your employer coverage ends on departure. Get everything done while it's covered and costs are known.

Understand your exact benefits end date

Health coverage typically ends either on your last day or end of the month you leave — it varies by plan. Dental and vision may differ. Know the exact date so there's no gap in coverage.

Update your mailing address for final W-2 and tax documents

Your W-2 will arrive in January–February for the tax year in which you departed. Make sure HR has a personal address on file — not a work address that no longer exists. While you're at it, confirm the correct personal email is in their system too.

Move any personal subscriptions off your work email or card

Netflix, Spotify, personal software tools, professional subscriptions, cloud storage — anything linked to your work email or expensed to a work card needs to be migrated. You will lose access to that email the day you leave.

Forward any personal emails that arrived at your work address

In the weeks before your last day, start notifying contacts to use your personal email. On your last day, do a final sweep of your work inbox for anything personal. You may have up to 30 days of read-only access depending on company policy — verify.

Return company equipment in good condition

Laptop, phone, badges, access cards, parking passes. Unreturned equipment can be deducted from final pay in some states. Get a receipt or written confirmation that items were returned.

Complete the exit interview honestly and professionally

Exit interviews are optional in most companies. If you choose to give one, be honest but measured — this is not the moment to relitigate every grievance. What would have made you stay? What worked? What's broken? Useful feedback is given with the intention of helping, not venting.

Confirm what you're owed and when it arrives

Final paycheck date, PTO payout amount, any outstanding expense reimbursements, equity exercise windows. Get written confirmation of each, especially equity timelines — some expire faster than you'd expect after departure.

Say genuine goodbyes — in person where possible

A brief, sincere thank-you to the people who made the job worth doing. These relationships are assets that outlast the job. How you leave is part of the story people tell about you.

Send a brief, warm farewell email

To the broader team. Positive tone, brief, genuine. Include your personal email and LinkedIn URL. No scores to settle, no cryptic subtext. People will look back on this message — make it one you'd be comfortable with.

Delete personal files from company devices (carefully)

Personal photos, non-work documents, browser history, personal bookmarks. Don't take company files in either direction. Leave devices clean and the data on them belonging clearly to the company.

File for unemployment insurance (if laid off)

File the day you leave, not the day you remember to. The waiting week starts from your filing date, not your last day of work. Find your state's UI portal via the Department of Labor website.

Activate your health insurance replacement

Elect COBRA within your 60-day window, enroll in the ACA marketplace (you have 60 days from loss of coverage), or join your spouse's plan. Don't leave this to the last minute — coverage gaps are expensive to resolve retroactively.

Confirm your 401(k) rollover plan

Roll to an IRA (most flexibility), roll to your new employer's plan (if joining one soon), or leave in place (acceptable for a period, but check the plan's rules for terminated employees). Never cash out.

Set your daily structure for week one

Block time for: job search / business development, admin catch-up, exercise, and decompression. Without structure, the days blur and momentum stalls. Week one sets the psychological tone — make it purposeful, not chaotic.

If going independent: set up your business entity and bank account

LLC filing, EIN application, business bank account. These take a week or two to process and you need them before you invoice your first client. Start day one.

Give yourself one real day off before the search begins

Not a day of reading career advice or scrolling LinkedIn. A genuinely different kind of day. The transition is disorienting, even when it's chosen. A brief reset before the next sprint matters — and costs very little.