A list I collected a couple summers ago, inspired by Josh Kauffman's list and another list I'm unable to track down at the moment. Clearly incomplete, too specific in some areas and too sparse in others, and some questions are probably leading. Not sure whether there is value here since I've never really used it since compiling it, but the idea of a list to make sure there aren't gaps seems useful.

Pick up a journal, set aside a few hours, and spend time answering questions in an area you haven't considered in a while. Make it fun: treat yourself to a nice lunch or go somewhere special while you answer questions. Thinking, especially about large topics, is hard work.

Global Heuristics

Keep in mind that in any given area of your life, you are unlikely to be at the optimum; for instance, unless you think you are already traveling too much, you should be traveling more. If you had to change a little bit, which direction should it be in?

Pay attention to opportunity costs. Even if something is desirable, you might be giving up something even better. Trade offs have to be made and optimizing locally may not produce global optima. At the same time, question your assumptions about trade-offs. Is there any way to acheive all goal simultaneously?

Pay attention to fungible goods, considering alternate ways to achieve the same goals in a cheaper way. For instance, rather than justifying an extra bedroom by saying your mother could stay in it when she visits, consider cheaper and nearly as good solutions like paying for her hotel room or giving her your room. Remember that money is not the only way to measure costs. Economize between money, time, attention, good will, energy, and other goods.

Avoid framing choices as "whether or not" (as in "I'm trying to decide whether or not to break up with my boyfriend"). Empirically, framing a situation this narrowly tends towards poor decisions (see Decisive by Chip Heath and Dan Heath). Thinking of just one more option can cast light on what's important to you and what's feasible in general.

Work

1. Career
   • Which career path am I pursuing?
   • What resources do I have to inform me of new opportunities? Promotions?
   • What am I looking for in a job? How do I prioritize salary, time off, interesting work, meaningful work, influence, access to resources, etc?
   • Am I developing skills that will help me progress in my current career? Open up other careers?
2. On the job
   • Is my work environment productive, with sufficient tools, resources, and support?
   • Would I benefit from a personal assistant?
   • Are there any tasks I can outsource?
   • Do I appropriately balance work and other pursuits?
   • Should I take more or less time off?
   • Should my work day be longer or shorter?
   • Do I respond to emails quickly and reliably? Am I distracted by my inbox? Do I make it clear to others when I won't be able to respond?
   • Do I get along well with my coworkers? Clients? Managers? Staff?

Relationships

1. Friends and acquaintances
   • Do I have a circle of friends who appreciate me for who I am?
   • Do I tell others how much I appreciate them?
   • Am I current with personal calls, letters, and emails?
   • Is there anyone I am avoiding or would feel uncomfortable running into on the street or at a part?
   • Am I able to let go of relationships that are no longer beneficial?
   • Have I communicated or attempted to communicate with everyone whom I have hurt, injured or seriously upset, even if it wasn't fully my fault?
   • Do I gossip or talk poorly about others?
   • Do I quickly correct miscommunications and misunderstandings when they occur?
   • Do I take any comments others make to me "personally"?
   • Do I take action or make requests rather than complain?
2. Family
   • Should I be in contact more or less frequently with my parents? Siblings? Grandparents? Cousins?
   • Significant Other(s)
     1. Am I aware of my needs and wants and communicate them clearly?
     2. Am I on good terms with past lovers or spouses?
   • Children
3. Pets

Home

1. Location
   • Am I living in the right place? Would another neighborhood, city, state, or country give me greater access to family, opportunities, culture, experiences?
   • Am I commuting a long distance? Can I live closer to places I frequently visit?
   • Do I need a smaller or larger living space?
2. Cleanliness and organization
   • Are my personal files, papers, and receipts neatly filed?
   • Is my home clean? Vacuumed, closets and drawers organized, desks and tables clear, furniture and windows clean?
   • Do my appliances and equipment work well (refridgerator, oven, lawn mower, air conditioner, water heater, television etc.)
   • Are my plants and animals healthy? Being fed and watered regularly, with adequate attention?
   • Is my bed/bedroom arranged for the best sleep possible (quality bed, adequate darkness, air, temp)?
   • Is there any housework I can outsource?
3. Aesthetics
   • Do I enjoy being in my home?
   • Is there a generous amount of quality lighting?
   • Is my home appropriately decorated and personalized?
4. Transportation
   • Are there different forms of transport available (car, public transport, bicycling, carpool)?
   • If I use a car, do I know how much common trips cost in fuel and anticipated maintenance?
   • Does my car need cleaning, repairs, or replacement?

Body

1. Sleep
   • Should I sleep more or less at night?
   • Should I have take greater or fewer naps?
   • Is my sleep restful?
   • Should I shift my sleep schedule earlier or later?
2. Energy and stress
   • Am I managing my energy well each day?
   • How do I manage daily stress?
   • Do I have good posture and poise?
   • Is my mind clear and focused?
   • Am I confident, relaxed, and productive?
   • Am I consistently early or on time? Am I frequently rushed?
3. Diet
   • What is the quality of my current diet?
   • Are there foods I eat too regularly?
   • Should I have more or less variety in what I eat?
   • Should I eat out more or less often?
   • Should I track what I am eating?
   • What foods should I always have on hand?
   • Should I eat more or less sugar?
   • Should I drink more or less soda? Tea and coffee? Alcohol?
4. Activity
   • Am I active? Do I walk frequently?
   • Should I exercise more or less?
   • Am I following a specific exercise program?
   • Do I avoid sitting or being sedentary for long periods?
5. Supplements
   • What supplements am I taking? Are they accomplishing their intended effect?
   • Am I taking fish oil or vitamin D?
   • Should I use more or less caffeine?
6. Medical
   • Have I had a complete physical exam within the past three years?
   • Do I know my and my family's medical histories?
   • Am I taking appropriate medication regularly?
   • Am I satisfied with my weight?
   • Is my blood pressure at a healthy level?
   • Is my cholesterol at a healthy level?
7. Vision
   • Have I had a complete eye examination within the past two years?
   • Do I have eye strain in any situation?
   • Should I buy new glasses? Switch to or from contacts? Consider Lasik?
   • Should I wear sunglasses while outside or driving?
8. Dental
   • Have I been to the dentist recently?
   • Do I brush and floss regularly?
   • Are my teeth and gums healthy?
   • Should I whiten or straighten my teeth?
9. Appearance
   • Are my nails are healthy and well maintained?
   • Do I have dry skin or lips?