The 24 Questions

This is adapted mostly from Tim Ferriss’s 17 questions

Annotated (Copy/paste version below)

1. What would I actually do/have/be if I had unlimited wealth? What’s my real target monthly Income?  Money should only be the goal while it’s actually not enough.  It will never feel like enough, but imagining you had unlimited money, what would be next, and how much do you need to before you can pursue what’s next?
2. What are the worst things that could happen? Could I get back here?  The Stoic practice of deliberately living with much less than you have for a time is intended to teach you that necessities are not what they seem.  So much frenzied work is done out of fear.  Dancing with that fear reduces it power, and focuses your work on a more important mission than loss prevention.
3. If I could only work 2 hours per week on my business, what would I focus it on?  And the flip-side, what would I eliminate?  Should I eliminate it now?
4. What if I let my help make decisions up to $100? $500? $1,000?  Which areas are you unnecessarily micromanaging? Or, if you don’t have help, start there.
5. What do I wish I had been building 10 years ago?  And how can I go about contributing to it now?  The “urgent” things I’m concerned about now are likely crowding out the “important” things that will be a stable structure in the long run.
6. Which gnats are distracting me from my big wins?  Have the courage to eliminate a profitable pet projects that prevent you from investing resources into more profitable ones.
7. What if I created my own real-world MBA?  What areas do I need to beef-up in, in order to be stronger or at least more confident?  If I were teaching someone else about my industry, what would I say, and am I following that advice?
8. What if I could only subtract to solve problems?  However you take it, it’s an interesting contemplation.
9. What might I put in place to allow me to go off the grid for 4 to 8 weeks, with no phone or email?  What’s the longest time you could go right now?  Try it.  What would you need to do to increase that length by any tiny amount?
10. Could it be that everything is fine and complete as is?  Tweaking just to tweak is fine, but that’s a hobby.  Are you sure this is the hobby you want to spend your time on?
11. What would this look like if it were easy?  Don’t even start on a product that will have a mental or emotional threshold that will make you hate it.  Better to have a worse product, that you actually produce, than a great product that you hate is in your inventory.  Automate and eliminate until it’s easy.
12. How can I throw money at this problem? How can I “waste” money to improve the quality of my life?  Money is there to solve problems.  Some problems can only be solved by more money.  Some problems cost more in stress than they do in money.  Can you be sustainably poorer and happier?
13. What would my successor do?  If someone else bought me out today, they wouldn’t care about what I care about.  They’d ruthlessly cut my favorite projects to make it more profitable.  It would hurt, but some of it would be right.  Can I take over my own company and do the same?
14. If I had to double my price tomorrow, what could I do to make it worth that much? Then how could I automate that?  Then probably raise your price.
15. What if I did the opposite for 48 hours?  What would really go wrong? Probably not as much as I think.  What would go surprisingly right?  Probably more than I think.  I would discover all kinds of things.
16. What would make the other tasks easier to do?  Don’t start with the hardest task.  Don’t start with the easiest task.  Start with the task that eliminates or reduces the other tasks.  “I wouldn’t even have to worry about [X] if I had [Y].”  Work on Y.
17. What is stressing me out right now?  List it all.  Even the tiny stuff.  When the flow stops,
    1. gently go back and see which ones can be eliminated easily, or even ignored entirely with little or no consequence (don’t forget to consider emotional and mental consequences)
    2. Then go back and determine which ones are worth eliminating, even if they are difficult to handle
    3. Then see which ones cannot be eliminated at all, and determine what reasonable effort can be made to reduce their impact
18. If this is the only thing I do today, will I be satisfied with myself?  Act in a way you’ll be proud of.
19. What are the top 3 activities I do to postpone work (and/or to avoid rejection and failure)?  Instead of butchering them out of existence cold-turkey, consider replacing them with more enjoyable procrastinations.  Or if you enjoy them, consider purposely increasing the time you put into them.  They may be perfectly healthy activities, when done with a clear conscience. The goal is to make conscious decisions about your time, not to become a 100% efficient android.
    1. 3 times daily ask, “Am I inventing things to do to avoid the mission-critical items?”  And how will I feel when I accomplish those items?
20. Which one, mission-critical task do I most want to accomplish today?  You’re supposed to focus on that, but when there is no urgent, mission-critical task, I often set one anyway, knowing that my creative, procrastinating mind will probably be more productive if it has something to avoid.
21. Am I hurrying or pausing?  Hurry is a sign of fear or lack of presence.  It’s almost always a sign you’re not having fun.  Is this a task you would normally enjoy, but hate because it’s on a deadline?  Aim for more slow and steady rather than hurrying and pausing.
22. Am I multi-tasking?  If so, you’re probably wasting time, effort, and quality. Prioritize and focus.
23. What would Pareto say? This is the 80/20 principle.  Endless options here.  Nearly any cause-effect paradigm of life can be considered this way – which 20% of X are creating the 80% of Y?
    1. Which few marketing expenditures are creating the vast majority of returns?
    2. Which few products are creating the vast majority of sales?
    3. Which few employees are doing the vast majority of the work?
    4. Which few relationships/activities/habits/etc. are creating the vast majority of positive change each time?
    5. This works in the negative as well.  Anything you can’t eliminate, try to automate, even if only partially.
       1. Which few tasks are creating the vast majority of work?
       2. Which few products are requiring the vast majority of customer service?
       3. Which few line items are creating the vast majority of expenditures?
24. What would Parkinson say?  “Work expands so as to fill the time available for its completion.”  This task probably takes a long time because you give it that long.  If it was due sooner, it would be done sooner, and probably even better, or just slightly worse.
    1. Set for yourself impossibly short deadlines.  Even if you don’t hit them, you’ll probably learn a lot.  “If this thing were automated, I could have been done sooner!” or “I left that whole section out and it didn’t really matter.”
    2. Evaluate on a macro and micro level.  From retirement age down to tying your shoes, almost any task can be evaluated this way.  The focus here is reducing time, so do not use it on purposeful leisure time or any task you take joy in doing, not just completing.

Un-annotated, Copy/Paste, short-hand version:

1. What would I actually do/have/be if I had unlimited wealth? What’s my real target monthly Income?
2. What are the worst things that could happen? Could I get back here?
3. If I could only work 2 hours per week on my business, what would I focus it on?
4. What if I let my help make decisions up to $100? $500? $1,000?
5. What do I wish I had been building 10 years ago?
6. Which gnats are distracting me from my big wins?
7. What if I created my own real-world MBA?
8. What if I could only subtract to solve problems?
9. What might I put in place to allow me to go off the grid for 4 to 8 weeks, with no phone or email?
10. Could it be that everything is fine and complete as is?
11. What would this look like if it were easy?
12. How can I throw money at this problem? How can I “waste” money to improve the quality of my life?
13. What would my successor do?
14. If I had to double my price tomorrow, what could I do to make it worth that much?
15. What if I did the opposite for 48 hours?
16. What would make the other tasks easier to do?
17. What is stressing me out right now?
18. If this is the only thing I do today, will I be satisfied with myself?
19. What are the top 3 activities I do to postpone work (and/or to avoid rejection and failure)?
20. Which one, mission-critical task do I most want to accomplish today?
21. Am I hurrying or pausing?
22. Am I multi-tasking?
23. What would Pareto say?
24. What would Parkinson say?