The Overemployed Checklist PDF

The Overemployed Checklist What you need to know...that no one else is telling you. BEFORE YOU START 1. Confirm why you want to be Overemployed ☐ Re-visit life priorities and write down your Ultimate Goal ☐ Assess your bandwidth with the first job (J1), family...

The Overemployed Checklist What you need to know...that no one else is telling you. BEFORE YOU START 1. Confirm why you want to be Overemployed ☐ Re-visit life priorities and write down your Ultimate Goal ☐ Assess your bandwidth with the first job (J1), family obligations, and extracurriculars ☐ Make a list of trade-offs to see if working two jobs is worth it (see blog post) ☐ Get "buy-in" from spouse / significant other; start following the 12 rules 2. Apply for the second job ☐ Get a separate phone, phone number, and email for your interviews and new J2 (burner job) ☐ Decide if J2 should be full-time / contract / or part-time based on your Ultimate Goal ☐ Confirm J2 is permanently remote or hybrid; latter will add additional stress ☐ Assess J2 potential workload during interviews; ask open-ended questions, e.g. what's your culture on asynchronous work and meetings? ☐ OPTIONAL: Reach out to former employees on LinkedIn with similar roles to assess further; and if you can, ask what background check vendor is used by J2 (see blog post) MAKING THE JUMP TO OVEREMPLOYED 1. Accept J2 (or J2 and J3 at the same time) ☐ Negotiation: Ask for a higher base salary, annual bonus, restricted stock units, and sign-on bonus in order of priority. There is one simple rule: you only get what you ask for ☐ Plan to take a couple of weeks off from J1 during J2 onboarding, preferably a month off ☐ RECOMMENDED: Hibernate your LinkedIn account ☐ OPTIONAL: Get a personal VPN to protect your mobile and personal devices 2. Starting J2 ☐ Set up your workstation and audio control (see tech setup) ☐ Buy a mouse jiggler, KVM switch, and monitor ☐ OPTIONAL: Buy monitor arms, laptop vertical holder, mouse and keyboard combo set ☐ OPTIONAL: Use an "alt profile" for your introductions to avoid getting caught (see blog post) ☐ Make accommodations for lunch, dinner, daycare, and school drop offs and pickups (prepare for potentially longer than normal working hours until you get a hang of 2x-ing) ☐ Formulate your exit strategy from J1 and/or J2; my favorite is a severance, or what I've started to refer as my sign-off bonus (see my story) 3. J2 Onboarding ☐ Set W-4 tax withholding by claiming "0" for your dependents, formerly exemptions. This is the most conservative withholding without having extra withholding ☐ Maximize your employer matching across multiple 401Ks (see blog post) ☐ Make benefits selection and health, dental, and vision insurance. Simplicity over hyper- optimization. Plan to have some overlaps due to enrollment period differences (see blog post) ☐ RECOMMENDED: Request record removal from open-source data scrapers like Signal Hire, Rocket Reach, and ZoomInfo ☐ RECOMMENDED: Freeze employment verification data services, e.g. The Work Number, and credit bureaus ☐ OPTIONAL: Reduce your open-source exposure by removing or privatizing your social media VIVA LA VIDA LOCA: THE OVEREMPLOYED LIFESTYLE 1. Taxes ☐ Set aside money to make quarterly estimated payments to IRS and/or state-equivalent (see blog post) ☐ Consult an accountant who is familiar with multiple W-2s and 1099s and RSUs, if required 2. Create a daily routine (Atomic Habits and Essentialism) ☐Cross-check calendars before the start of the workday and at the end of the workday ☐Build-in time for Sleep, Presence, Activity, Creativity, and Eating; you need 8+ hours sleep to be able to prioritize and get into the effortless state, aka flow ☐Continuously retro and assess what can be improved or automated ☐OPTIONAL: Hire a trusted virtual assistant (VA) to help with high effort low return tasks ☐OPTIONAL: Get a live-in nanny or family to help watch over kids and cooking duties ☐RECOMMENDED: Upskilling with Educative.io or through work-provided trainings 3. Take breaks, it's a marathon not a sprint ☐ Plan for the double-paid 1-2 weeks vacation from J1 and J2 twice a year ☐ If unlimited PTO, it's your job to manage up and take your PTO (no one will do it for you) ☐ Seasonally go back to one job if you need to take a break and not jeopardize quality of life ☐ Read our top books, like the OG financial independence book Your Money or Your Life ☐ Investing conservatively, focusing on accumulation, and get financially independent early (see blog post); track your progress with Personal Capital AFTER OVEREMPLOYED ☐ Imagine how you want to be remembered at your own eulogy ☐ Stay mindful and present; relationships are your happiness, not Overemployed or the money ☐ Remember all we have is 4160 weeks in 80 years. How much time do you have left? ☐ Smile and be grateful; we do it every day. Join our community. Live long and prosper 🖖