“What you seek is seeking you.”Rumi (1207 – 1273)
Sometime after college, I was exposed to the idea that…
Questions are extremely powerful.
In his book, Tribe of Mentors, Tim Ferriss says that the answers to anything and everything that we want is in other people’s heads and questions are our pickaxes. He attributes his 10x, 100x, and 1000x gains to his development of better questions.
I instantly fell in love with this idea. Not because I immediately recognized how useful that perspective is (although I wish I could say that), but because I was having trouble finding answers to the questions that were burning inside of me.
Why am I always getting the short end of the stick?
How come I’m not being rewarded for doing the right thing?
Is this all there is to life?
Will it ever get easier?
What’s the point of understanding complicated things if no one cares about them?
When will I have sacrificed enough?
How do I make more money?
Why do I keep making bad choices?
The frustration drove me deeper and deeper into nihilism, but this new piece of knowledge was bright enough to help me see the light.
It’s not that life was giving me harsh answers to my questions, it’s that I wasn’t asking the right questions at all. Then I realized…
Improve my questions, improve my life.
It’s not that knowing that asking better questions suddenly made my life better, but knowing that there is something I could do to give me a fighting chance was liberating and empowering.
I just needed to ask better questions.
Little did I know that the best was yet to come, and I was just beginning to understand the power of questions. There was another way to use questions powerfully.
This other idea was clearly articulated to me by Jordan Peterson, but I found it to be true in many other instances of my life.
When we’re asked questions, our minds almost immediately go to work on finding an answer.
This can be extremely uncomfortable if we’re asked the wrong (or right) questions. We can ignore the answers and act as if we don’t know them, but we will. The curse of knowledge is that we will never unknow something, so once we are asked the question we are also given the answer.
The cool part is that it doesn’t matter who asks the questions. We just need to be asked the question in order to start looking for an answer. This means that we can ask ourselves these questions or find someone to ask them to us.
At first, this idea seemed inconsequential but then I realized that I can discover honest and reasonable answers if I take a little bit of time to be asked what I really think I should do.
It can be something as small as “What do I want to eat for dinner?” or something as big as “What do I want my life to mean when everything is said and done?” Our minds will find us an answer if we let it.
This can be done in a way that is ineffective, but the key is to want to answer the question in a way that does not compromise ourselves. Try to be genuinely curious about the answers.
Suddenly, big questions don’t worry me as much and smaller questions are answered with myself in mind. My major life choices aren’t made carelessly or for other people. Learning and practicing this is so freeing.
Despite my question list being presented in no particular order, I do think it’s important to mention that good questions in the wrong order can get bad responses. Sometimes jumping right to the deep work questions can surface some superficial answers. If we take the time to warm people up with easier questions before jumping right into the difficult stuff, we’ll get answers that are more honest and well thought out.
My Question List
Here is a list of every question that I’ve found worthwhile to ask myself. I recommend spending at least 5 minutes thinking about each one (obviously in your own time, there are way too many of them to do it all at once). A lot of these questions aren’t necessarily designed to give me pragmatic answers, but to get me to think differently and break old ways of thinking.
I think everyone should keep a question list, if you decide to make one please share it with me at firstname.lastname@example.org. I would love to see what other people’s pickaxes look like.
Bolded questions are the ones that I would argue have most impacted my life.
“Often, all that stands between you and what you want is a better set of questions.”Tim Ferriss (Tribe of Mentors)
In no particular order:
- What do I want to change and how will I know when I have?
- What would this look like if it were easy?
- What am I avoiding just because I know the answer is painful?
- How can I make my 10-year plans happen in 6 months?
- How am I complicit in creating the conditions I say I don’t want?
- What am I not saying that needs to be said?
- What’s being said that I’m not hearing?
- What are the actions I need to take today?
- What am I unwilling to feel?
- Whose expectations am I trying to fulfill? My own or those of someone else?
- How much would I pay to relive this moment 40 years from now?
- Who do I know that can help me with this?
- Do I need this?
- Is there an action that I can take now to make this better?
- What is something that feels productive to me at the moment, but usually ends up wasting time and energy?
- Am I doing this for Present Me or Future Me?
- What do I enjoy refining?
- What makes me different?
- What is something that I know is stupid that I can stop doing today?
- What are my 7 streams of passive income?
- What skill am I working on?
- If someone could only see my actions and not hear my words, what would they say are my priorities?
- What is the biggest small thing I could do today?
- Is there a way I can automate this?
- What do I have to offer?
- What am I good at?
- What am I preventing myself from feeling?
- What can I work on today that will continue working for me years from now?
- What am I avoiding just because the desired outcome would take longer than I’d like?
- What can I do now that I would be so happy I started doing 3 years from now?
- Have I earned this?
- Are my goals my own, or simply what I think I should want?
- How much of my life had I missed from under planning? Overplanning?
- How could I be kinder to myself?
- How could I better say no to the noise to better say yes to the adventures I crave?
- Assume that more than one path exists to achieve your ideal life. What would some of the alternative routes look like?
- What would make today great?
- What are the three amazing things that happened today?
- How could I have made today even better?
- What two things am I going to try to improve this month?
- Which thoughts have I had over the past week that are worth remembering forever?
- Will this new endeavor either supply me with long-lasting relationships or a new skill set? In other words, will I win even if I lose?
- Imagine each day is only 12 hours long. What would I cut out?
- If I had a gun to my head and could only work for 2 hours today what would I work on?
- Which areas of my life are in maintenance mode? Which areas are in growth mode?
- What’s a tiny problem that irritates me every day?
- Am I being effective or just busy?
- What do I wish I had?
- What are the 1-2 things that if I get them done today, I’ll go to bed content?
- At what point is the flower perfect? (Refer to The Art of Practice)
- Is there a better way? Is there a kinder way?
- If I keep living the way I am, what will my life look like in 20 years? Do I need patience or action?
- What’s stopping me?
- Where do I have healthy momentum right now? Where do I have unhealthy momentum?
- What is the little bit of extra work that has a huge upside?
- Who can I collaborate with to make this easier?
- What part of this situation is under my control?
- What is one repeating problem I can automate or eliminate today?
- Why did I fail?
Like my Must-Read Book List, and many of us, this list is always in a state of becoming.
Every so often I’ll update this list with any new, and worthwhile questions I come across in my journey.