142 questions to ask yourself monthly to move your life forward

“An unexamined life is not worth living.” — Socrates

INSTRUCTIONS: Block off one to two hours; grab a journal or notepad, and pen and highlighter; turn off the data on your phone and set it on airplane mode; sit alone on your couch/bed; read and reflect on each question below; jot down your answers in point form (or in long form if you feel inspired); highlight any actionable notes or ideas; schedule those notes/ideas into your calendar as to-do items; repeat this process the following week. You may not get through all the questions in a single sitting, but try to get through all of them at least once each month.

Questions compiled and curated by David Tal | Twitter + Linkedin + Instagram + Snapchat @DavidTalWrites

A personal note from David Tal can be found at the end of this list.

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Improving my personal environment

  • Is my living space cluttered and messy or simple and neat? What time can I set aside this week to clean some of it up?
  • If I have a car, is it clean or just another place to keep my clutter and garbage? What time can I set aside this week to clean it up?
  • Does my environment facilitate the emotions I consistently want to experience? Does it drain or improve my energy? How can I redesign it to emphasize the emotions or energy I wish to feel?
  • Do I keep stuff (like clothes) I no longer use? What can I donate or throw out this week?
  • Are there physical things/items in my life that I have become dependant on in an unhealthy way? What actions can I take to minimize its influence on me?

Protecting my time

  • How much of my time do I feel in complete control of? What can I do to control more of it?
  • Is my time being wasted on things or activities I don’t intrinsically enjoy (daily/weekly)? If so, can I find a way to cut them out? How can I use my time smarter?
  • Are the activities I spend my time doing moving me toward my ideal future? How so?
  • Am I spending most of my time furthering my own agenda or someone else’s? How can I emphasize the former?
  • Do I feel like I’m able to focus on my work/tasks? If not, what adjustments can I make to remove distractions from my life/environment?
  • What activities could I outsource or automate that take up my time?
  • How many things or people did I say ‘no’ to today? This week? Can I say ‘no’ more often to strategically make more time for myself and focus on my goals?
  • What routines/schedules I create for myself and follow each day to reduce the time I spend on making unimportant decisions? (Example: Eating the same breakfast every morning, so I don’t waste time thinking about what to make. Or wearing the same clothes everyday, a la Steve Jobs.)
  • Should I take some time off? How would I use that time off?

Financial health

  • Do I have unnecessary debt? If yes, what is my total debt?
  • Do I know how many dollars I spend each month? Can I better track how I spend my money?
  • What unnecessary expenses can I cut back on this month?
  • How much money, in personal income, am I generating each month?
  • Am I making as much money as I’d like to be? If not, set an income goal for next month that is 2-5% higher than my expected income this month. Make a plan to hit this goal.
  • What’s holding me back from creating more value in other people’s lives (value that can one day be traded for sales or a raise)?
  • Have I taken any time this month to educate myself about personal finances and investment options? How can I spend more time doing so?
  • Am I creating multiple sources of income for myself?
  • Do I have a plan for my retirement? What have I done this month to prepare for it? And more can I do next month?

The hustle

  • Am I standing still more than I’m taking action? What question or course of action am I struggling with and what information do I need to make a decision about it?
  • Did I find myself reacting to life more than I was actively shaping my life this week? If so, what can I do to go back on the offensive and make the world revolve around my plans?
  • How can I get more done this week?
  • Am I working hard enough? How can I improve?
  • Am I working fast enough? How can I improve?
  • Am I working smart enough? How can I improve?
  • What’s coming up that I need to prepare for?
  • Am I building a solid team around me to help me achieve my goals?
  • Have I taken on any new responsibilities to fill my schedule this week/month?
  • Have I researched or experimented with a new business idea this month?

Employment

  • Do I feel inspired and motivated by my work?
  • Do I feel useful at work? Do I feel like I’m making a real contribution?
  • Similarly, am I providing enough value in my current role to that point that I am building a positive reputation with management and among my co-workers? If not, what can I do this month to stand out and get noticed by management and peers, in a positive way, at the office?
  • Am I continuing to learn and feel challenged in my current place of employment? If not, what is holding me back from looking for a new employer?
  • Is there opportunities to advance to a higher role and salary with my employer? Specifically, what will it take to reach that next level?
  • How are my relationships with my co-workers? How can I improve upon them this month?

Minding my physical health

  • Do I eat with the end in mind? Can I portion out my meals better?
  • Am I conscious of and in-control of the foods I put in my body? How can I more strategically buy my food?
  • Does the food I eat worsen or improve the other areas of my life? How can I emphasize the latter?
  • Am I healthier now than I was three months ago? What can I start doing this month to make a positive difference in my health over the next three months?
  • Does my body reflect my highest ideals? Is my body as strong, fit or flexible as I want it to be? How can I increase the time I spend to improving these traits this week?
  • Am I becoming more educated about how to better maintain and improve my body’s performance? What health and fitness education resources can I get access to and follow?
  • Do I have any addictions that are negatively impacting my physical health? If so, what can I start doing each week to moderate this addiction?
  • Do I sleep well? Do I sleep enough? What research articles can I read or actions can I take this month to start improving my sleep?

Mental health matters

  • What aspects of my life (myself, other people, activities or environment) are causing me stress every day?
  • What aspects of my life (myself, other people, activities or environment) are causing me stress weekly?
  • What aspects of my life (myself, other people, activities or environment) are causing me stress monthly?
  • What can I do this week to minimize one or more of these stress triggers?
  • What can I do to track my progress in reducing these stress triggers?
  • Do I have any obsessions that are negatively impacting my mental health? If so, what can I start doing each week to moderate this obsession?
  • Are there any memories that are limiting my ability to engage with the world and with others in the present and future? What steps can I take this month to remove or dull the emotions wrapped up around these memories?
  • Do I have any mental disabilities? Am I actively working to manage them through drugs or therapy? How can I be more consistent with these treatments? Are they working? And if not, what other options are available for me to try?

Perspective

  • Did I expose myself to other points of view this week? How can I expose myself to more viewpoints regardless of whether I agree with them?
  • Did my specific perspective or belief system limit my ability to better connect or interact with others this week? Am I comfortable with this? If not, what small change can I make to my thinking this week to allow me to change my behaviour towards others?
  • Did my specific perspective or belief system limit my ability to take an action or participate in an activity? Am I comfortable with this? If not, what small change can I make to my thinking this week to allow me to change my behaviour?
  • Have I considered the experience or perspective of someone belonging to a different minority or wealth class? How can I improve how I treat others unlike myself?
  • Have I travelled to another state/province or country where I was exposed to an entirely different way of life? If not, how much time and money can I set aside this month to plan my next trip?
  • What weekly problems or stresses am I thankful for?

Intelligence

  • How much time am I creating for myself each week to read fiction or nonfiction books that challenge me? How can I set aside more reading time?
  • How much time am I creating for myself each week to read journalism that informs me and challenges my viewpoints? How can I set aside more reading time?
  • What insightful documentary did I watch this month?
  • What seminars or workshops am I attending this month?
  • What am I planning to learn about or research this month of my own interest? Why do I want to learn about this?
  • What am I planning to become more skilled at this month? How will I apply this skill?
  • What foods and supplements can I eat (or avoid) this month to boost my brainpower?

Self Love

  • What compliment did I give myself this week?
  • What compliment(s) did I receive from others this week that I didn’t cut short rudely, downplay with modesty or reject out of embarrassment?
  • What negative thoughts did I ignore or strike down this week?
  • Were there moments this week when I allowed people’s opinions of me affect me more than they should?
  • What food did I allow myself to indulge upon this week?
  • What activity did I allow myself to enjoy freely this week?
  • What moments in my week did I allow myself to be fully in the moment?

Spiritual energy

  • Do I have a sense of purpose in life?
  • Am I happy? If not, why not? What small changes or habits can I add to my schedule to improve my happiness this month?
  • Have I reflected on meaningful quotes this week? See this: https://goo.gl/4Vnrej
  • Am I setting aside a few hours a week to unplug, pray or meditate?
  • Am I setting aside one to four uninterrupted hours a week to reflect on my life and goals?
  • If I die tomorrow, would I be content with how I have lived my life? With what I have achieved? With how I treated others? With how I treated myself?

Personal Growth

  • What is my ideal vision of the person I want my my friends and my co-workers to see me as? What can I do this month to turn into that person?
  • Have I allowed my ego/pride to get in the way of doing something that is in my benefit? What can I do to overcome the roadblocks my ego is placing in front of me?
  • What mistake have I openly admitted to and taken responsibility for this month?
  • What did I or can I remove/minimize from my life this week?
  • What did I or can I do this week that terrifies me?
  • Have I given a presentation or taken the lead in an important group meeting this month? If not, what can I do this month to push myself into the spotlight?
  • How can I start saying ‘thank you’ more than I say ‘sorry’ this week?
  • Did I make one big ‘ask’ this week of someone who can help me meet my goals?
  • What side projects or hobbies am I working on? If none, what can I take on?
  • Did I complain about something this week? If so, what action did I take to resolve the matter instead of allowing the negative emotions to fester?
  • Am I blaming others for difficulties I could have avoided with simple foresight and planning?
  • For the things I find difficult to accomplish in my life, how would those things look like if they were easy? Then work backwards to make that a reality.
  • What habits do I want to get rid of? What actions can I take this week to gradually ween myself off said habit?
  • What habits do I want to add to my life? What actions can I take this week to train myself to commit this habit to my daily lifestyle?
  • What can I do this month to seek out more constructive criticism about myself or my projects?
  • Does my hygiene and dress reflect the person I want others to see me as, or at least the person I would like to be or become?

Networking

  • Am I making an effort to talk with strangers and network each week to grow my connections? If not, what events or places can I attend this month to begin getting into the habit of networking?
  • What specific types/profiles of people am I looking to meet?
  • For this year, have I created a schedule of key conferences and events, both in my city and in locations I will need to travel to, where I can meet and network with the specific type of people I’m looking to connect with? Have I set aside the time and vacation days needed to stick to this schedule?
  • Am I building relationships with people who inspire and challenge me to grow? If not, who do I want to associate with and where can I meet these people?

Relationship maintenance

  • Are my relationships with other people the most meaningful and enjoyable part of my life? If not, why is this the case?
  • Do I spend enough time nurturing the relationships that really matter? If not, how can I devote more time to them starting next week?
  • Am I present (not distracted) when I’m spending time with those I care about? Especially my significant other? If not, what can I do to reduce my stress or improve my attention starting next week?
  • Am I authentic and honest in my relationships? If not, what is it about myself that I fear that I can’t be honest about with others? How can I resolve those fears?
  • Are those I’m close with pushing me forward or holding me back? How can I surround myself with more go-getters who will encourage me to grow and succeed?
  • Do I maintain toxic relationships that no longer serve me? If so, how can i remove myself from these relationships quickly or gradually starting next week?
  • Am I helping people who don’t deserve or appreciate my help? If I am, how can I limit my exposure to this person/people?

Family

  • Did I support my parents this month financially? How can I support them more?
  • Did I support my family with my time? How can I be more involved with them this month?
  • Do I have siblings? Have I touched base with them this week? What more can I do to support their goals this month?
  • Have I touched base with my extended family over the last three months? If not, how can I be more consistent with connecting with my family?
  • Do I have kids? If so:
  • Am I presenting myself as a good example for who I want my kids to grow up to become?
  • What can I do to become a better example for my children?
  • What can I do this month to teach them how to become more independent? How to become more curious? How to become self-motivated? How to overcome failure?

Giving

  • Have I given money or time to any type of charity this month or directly helped someone who is less fortunate? Can I begin to give more?
  • How have I supported my community this month? Can I begin to do more? How?
  • Do I give without expecting anything in return?
  • Am I doing something kind for someone else daily? How can I become more mindful of opportunities to help others?
  • Do I compliment someone meaningfully on a daily basis? How can I become more mindful of opportunities to compliment others?
  • How can I give more value to those who matter to me?

Balance with the Natural Environment

  • Do I need to eat as much meat as I do? Can I try being a vegan or vegetarian for at least one day a week?
  • Can I recycle more? How can I limit the amount of waste I produce?
  • How can I buy more locally made food, products and services?
  • Do I live in a green home? How I limit my utility bill/usage?
  • Do I live in a city vs a suburb? If the latter, can I move to a more densely populated area? Or can I invest in getting my home off the energy grid by making it energy independent (i.e. solar)?
  • Can I use public transportation and/or car sharing services more often?

Visualize my life

  • Where I’ll be in three years? What can I do to help myself get there in one?
  • What does my ideal work day look like (start to finish; be detailed)? What small step can I take this month to achieve this ideal day more regularly?
  • What does my ideal rest/vacation day look like (start to finish; be detailed)? What small step can I take this month to achieve this ideal day more regularly?
  • What does ‘happiness’ mean to me?
  • What is my perfect self?
  • How will my children remember me?

Key metrics to track my life progress

  • Do I have a detailed list of goals that I want to accomplish this year? Have I looked at it (and, if needed, updated it) this month?
  • Do I have a general list of goals that I want to accomplish over the next three years? Have I looked at it (and, if needed, updated it) this month?
  • What are the important personal, professional, or spiritual metrics I should be tracking this month to achieve my goals?
  • What are the important personal, professional, or spiritual metrics I should be tracking this year to achieve my goals?
  • How am I tracking these metrics (paper and pen, calendar, Excel spreadsheet)? And at what intervals?
  • Am I making progress in achieving my metrics?
  • If no, what is holding me back from achieving my metrics? How can I overcome this roadblock?
  • What are the top three things I want to accomplish today?

Note from David Tal

I know what you’re thinking. This list is excessive. But to be fair, I am obsessive.

Sometimes life keeps you so busy that you never think to stand still and look inward. That’s why once I stepped onto the whole self-improvement train (in part thanks to the advice articles found in the Medium community), I decided to go all in.

At first, this list was only about 20 questions long. But through those initial questions, through that process of self-reflection, new insights about my personal and professional life flooded in. I grew so much in such a short period of time that I was motivated to add more questions and add more structure. I wanted to create a reference tool that forced me to reflect on my life regularly, with the end goal of taking action to improve every aspect of my life.

Hopefully, these questions help to move your life forward as they did mine.

Questions compiled and curated by David Tal | Twitter + Linkedin + Instagram + Snapchat @DavidTalWrites

*About 10–15% of the questions listed above were inspired from some of the questions referenced in these great sources: one, two, three, four, five.

**Yes, I know, depending on how you count, there are much more than 142 questions. For simplicity, I limited my count to the number of bullet points within this list.