“[W]henever you find yourself on the side of the majority; it is time to pause and reflect.” — Mark Twain
If I have learned nothing else, I have learned this. Questions matter. Ones asked to others, but more importantly, the introspective ones that cut to your core and tell you something about who you really are. They can be the lighthouse safely guiding you in the fog to land.
If you are anything like me, you have spent a shit load of time believing the limitations that others set for your life. The “gotta’s” on the path.
You gotta go to college.
You gotta get that job.
You gotta live in this city if you want to make it.
Although this advice is well meaning, it is, for the most part, false. Given by those who probably never took real risks in their life, and so they want you to take the safe route as well. The problem with the safe route is it is usually in contradiction to the life you want. Nothing truly innovative or purposeful comes safely. It takes risks. But most importantly, it takes curiosity to examine the status quo to see if it has any real weight.
Inevitably, better questions lead to better answers, so to hone my skill of asking better questions, I created an inventory to fall back on. Below is a list of my favorites. I tried to attribute each prompt or quote to the source, but in some cases, I couldn’t remember, so I’m sorry for my ignorance. Let me know if you have an idea of the original source and I will add it.
43 Prompts that Will Change Your Life For The Better
1.Make a map of your failures indicating the rough date they occurred. Write beside each one what you learned. (Alain de Botton)
It is normal to forget how far you have come in life. It is even more normal to fear failure. This prompt forces you to remember when you failed in the past, and what you learned from those failures. My failures have always taught me more than my wins. I bet the same is true for you.
2. What might I do to accomplish my 5-year goal in 6-months, if a gun was up against my head? (Tim Ferriss)
This is a question I revisit weekly. If you are running a business or trying to accomplish any personal goal, it is easy to get side tracked by the minutiae. However, when you condense the timeline, you become hyper focused on what matters most.
3. Who was the first person that told me about my career/job? Have I a similar discussions since?
When I first asked myself this question, I was contemplating leaving my first job in consulting. I wanted to understand the narrative arc of my career to make sure I was on a path that was true to my values and goals. So, I thought deeply about why I had ended up there.
After pages of journaling, I determined the first time I learned about management consulting was in my first year at University, when I was I choosing my major. An esteemed alumnus who was a Partner at a top firm in Chicago was giving a speech about consulting. I remember talking to him for an hour about his job. He made a ton of money and got to travel.
Excellent, I thought. And I never looked back.
Make sure you are the reason for being on the path. Not someone else.
4. Where in my life can I trade a short-term, incremental gain for a potential longer-term game-changing upside?
I learned this from George Lucas
Back in the early 1970s, Lucas was a young director with just two films on his résumé and a curious idea for an epic space opera. When 20th Century Fox decided to pick up Star Wars, Lucas came back with a deal: He was willing to accept a $350,000 pay cut as director in order to keep the film’s merchandise rights, along with the rights to any sequels.
Not anticipating how popular the film would be, Fox accepted. Lucas is now worth more than $5 billion, having made one of the most profitable bets in history. In the 38 years since Episode IV: A New Hope, Star Wars has grossed $28 billion in revenue. And less than a sixth of this has come from ticket sales.
5. What is my third most unique strength?
Often I find myself contemplating my BIGGEST strength, only to be left disappointed when the only thing I can come up with is hard-working.
However, when I look two layers deeper, I discovered that after (1)hard-working and (2) ambitious came (3) empathetic. A strength I had never thought critically about, but one that sparked a whole new trajectory in my professional life.
6. What would make what I am doing right now easiest? (Tim Ferriss)
This question broke me out of a slump when I was struggling with starting my first business. I was so worried about doing everything perfect and the “right way.” I was making it harder than it had to be.
I eventually asked myself this question as a last resort, and it resulted in me changing my entire business model. Over the next 3-months, I increased my monthly sales from $1.5k to $8.5k.
There is enormous power in simplicity.
7. What do I spend a silly amount of money on? How might I scratch my itch? (Tim Ferriss)
This is the prompt that got me to pursue the path I am on now. Reading, writing, and sharing what I learn with an audience that is engaged. It is a dream come true, but it was only made possible when I started thinking against the grain.
8. What is the worst possible scenario if I take “x” action? What can I do to limit the downside? (Stoics)
I use this all the time when I have a big decision to make, but I fear the downside. When I quit my job to start my blog, the “worst case” scenario was that I would run out of funds and have to find a new job. Not that bad. AND I could prevent it by picking up odd jobs along the way.
What you fear most, may not look as scary when examined closely.
9. What would I do if I had $10 million but still had to work 40 hours a week? (Financial Samurai)
Cliché, I know. But there is a lot of truth in cliché’s, in particular this one. The goal of life is not to relax on beach, sipping mojitos all day. The purpose is to find something you love that also adds value to the world. When you do that it will not only bring you fulfillment but it will also help those around you.
10. Will I choose make this a dead time or an alive time? (Ryan Holiday)
When Ryan was considering leaving American Apparel to become a full-time author, he told Robert Greene, who then gave him this prompt. If you have to wait to pursue something big, don’t just sit there with you hands down your pants. Be alive. Learn things. Meet people. Make it an alive time.
11. If today were your last day on earth, what would you write?
Whenever I start contemplating whether I should be writing a piece or not, I always ask myself this question. Because honestly, if you are writing something that you are not proud of, you shouldn’t be writing.
12. If I could only work 2 hours per day on income producing activities, what would I focus on? (Tim Ferriss)
The ultimate productivity prompt, by the king himself. By asking yourself this question you will be able to eliminate the nonessential things and leave only what matters most.
13. What is something that doesn’t make sense? (Cal Fussman)
I learned from one of the most trusted macroeconomic advisors in the world. Whenever he finds himself or others saying that something doesn’t make sense. He takes note because it is usually the exact thing that will make a huge difference in the markets.
14. What is the least crowded channel into what I want to accomplish? (Noah Kagan)
The most crowded channel is the hardest place to get noticed. Of course, we all know that, but how often do we listen to it.
When you are searching for a job, do you take the time to build a network in the industry you are interested in or do you only spruce up your resume and sending out to 100 job openings?
Figure out the least common channel and own it.
15. What if the only way to add to my life was to subtract from it? What would be the first 1–2 things that I would remove?
As a below average minimalist, I revisit this question often to make sure that I am not just adding to my life as a way to get more out of it. I have realized that the fewer things that I own; the happier I become.
16. What are the unifying characteristics of the top 3 people I most want to emulate?
Whenever you are trying to determine your motivations for who you want to be, it helps to examine the people you most want to be like. Maybe they all share similar core values or world views. I did this exercise when I was in a job I hated, and realized that all the people I looked up to were writers. Hence, me writing now.
17. What is something I would miss if I no longer had it?
I have incorporated this prompt into my daily gratitude practice. Realize how much you already have by thinking about how much you would miss it if it no longer were around.
Running water? Your dog? Your loved ones?
Life is precious. Appreciate it before it is too late.
18. What is one relationship that I have let slip? What is the reason?
When you ask yourself this question, do not feel guilty if a relationship that needed to fade has slipped, but realize why it slipped. Sometimes an important one has slipped that you need to revitalize.
19. Do I enjoy what I am going to do today? If not, how long has the answer been no? (Steve Jobs)
The ultimate measure of a fulfilled life, to me, is doing work that you love that adds value to the world. If you consistently dread going to work, it is time to ask what the opportunity cost of staying is. Your mental health? The other opportunities you are giving up? Work is important, so find something you enjoy.
20. When was the last time I laughed at work?
When I first thought of this prompt, I actually could not remember ever laughing at work. We all need to be a little less serious when it comes to our jobs. Which leads to the next question…
21. When was the last time I participated in guilt-free play? (Charlie Hoehn)
Charlie has written an entire book on how play can drastically reduce your anxiety. When I was at my stressed and anxious, I was spending zero time participating in guilt-free fun with friends.
Get out there and enjoy life while you can!
22. If I had no fear today, what would I do? (Eleanor Roosevelt)
This question got me to put out my first Medium post. It got me to ask my beautiful fiancé to marry me. It got me to quit my job to pursue my dream of helping people with anxiety and stress.
The more I did this. The more confidence I built in my ability to control the outcomes of my life, which in turn lowered my stress and increased my excitement.
23. Who would be most upset if I quit/moved/tried this?
I contemplated this prompt when I dealt with an existential crisis regarding leaving my job in consulting. I realized that the person I thought would be most upset did not have any right to be controlling my decisions. From that day on, I make sure that the people influencing my decisions are “in the ring with me,” as Brené Brown says.
24. What is your biggest win in the last seven days?
As ambitious people, we tend to overlook the good in our life at the expense of our happiness. I have made it a habit of trying to ask myself this question every week and celebrating all of the small wins along the way.
If you can’t appreciate the small wins, the big ones will feel empty.
25. If I was making my life into a movie, what scene would I make sure to add and what scene would I make sure to remove? (Donald Miller)
The scene I would add: My battle with depression and anxiety
The scene I would remove: Sophomore year of high school. God, I did nothing.
The scenes that always come to mind when thinking about what I would want in the movie of my life are always the scenes where I struggled the most.
The most compelling scenes of life are usually experienced through struggles and challenges; not from comfort and security.
26. What is my most perceived weakness? How can I turn it into a strength? (Arnold Schwarzenegger)
For the longest time, I thought that my anxiety was a huge weakness. But I have since realized that it is my superpower. It helps me understand others who are suffering and it alerts me when something is in misalignment in my life.
27. If I had to instill one piece of advice in your own child’s mind, what advice would I give?
This is a question that will help you figure out what is most important to know in life. Is it the US Presidents? Is it how to format a resume? I doubt it.
28. What is one closely held belief I have? When is the last time someone challenged it? (Marc Andreessen)
Candidly, this is something I need to do way more of, but it changed my entire view of going to get an MBA.
I had a long-held belief that I needed to get an MBA to be successful in business. However, when I had one of my closest friends be a devil’s advocate, I realized that I could obtain the same end goal without getting an MBA.
29. What blogs/books/articles do I read on the normal Saturday morning before any else wakes up? (Ramit Sethi)
I use this question whenever someone is stuck with an idea for a business that they could start. If you are reading something in your free time, it probably means you know more about it than 60–80% of your target market. Dive deeper into the challenges of that market and provide a solution.
30. What is something that I believe that none of my friends do?
This is a great prompt for discovering whether your five chimps are the ones you should be spending time around. Do not kid yourself. If someone is not making you stronger, they are making you weaker.
31. Why do I want to be rich? What are the specific traits or things you will be able to do? Is there a way to have those now?
Many people spend their whole lives working so that they can retire and live a peaceful life by a beach. The reality is that that is possible right now if you know where to look. Most closely held beliefs are false when examined under the lens of introspection.
32. What are the 20% of things in my life that cause 80% of my anxiety? (Pareto’s Law)
For me this was work. I hated my job and it wrecked havoc on my mental fitness. Once I eliminated it from my life, I saw a significant decrease in my anxiety and stress.
Who or what is creating 80% of your stress right now? Eliminate them or it if you want to get better.
33. Who is someone that I have not talked to in awhile that I am grateful for?
In the fast-paced world that we live in, it is common to lose sight on those that helped you get to where you are. Spend a second thinking about someone from you past that you haven’t talked to in awhile that helped you in some way become who you are today.
34. When I had the opportunity, did I choose courage over comfort?
A great gut check on whether you are living from a place of fear or creation.
35. Why am I doing what I am doing? Why? Why? Why? Why?
When in doubt just answer the five why’s.
36. What has become more important to me in the last year and what has become less important?
More: My relationships
Less: My “career capital.”
37. Would my 15-year-old self be proud of who I am today?
I try to flip the common question (what would you tell your younger self) on its head, and instead, ask if the younger me would be proud of who I have become.
Because I can change his vision of me, but I can’t change my direction for him.
38. What dream did I have to give up to get where I am?
For me: Being ultra wealthy.
To get to what we want out of life, it is necessary to drop dreams along the way that no longer fulfill the direction for our life. I no longer hope to be ultra wealthy.
I wish for freedom, love, and beauty to fill up my days.
39. What’s the top lesson your father taught you? (Cal Fussman)
My father taught me that it was okay to march to the beat of my drum.
This is a great question to ask a podcast guest or in a job interview. It cuts straight to the heart of the person you are talking to. Cal used this line to get ~30 minutes with Mikhail Gorbachev.
40. What are some of the choices I have made that made me who I am t0day?
Think about the big decisions you have made over the last 1–2 years. Were they conscious decisions rooted in intentionality and purpose? Or were they made to keep the status quo?
41. When did I learn a lesson the hard way?
I use this as writing prompts when I am stuck in a self-imposed writer’s block. They always produce authentic content.
42. What is something that I lost that I will never get back? (Tara Brach)
Most tension and stressed are caused by our wanting for something to be different or to go back to the way it was before. However, by realizing that life will never be the way it was, accepting who you are now, and moving forward in the present you will find deep understanding of yourself.
43. When did I last perform a random act of kindness?
I believe that the more you give, the more you will receive. If you are ever feeling down and depressed, ask yourself this question. If your answer is longer than three days, get out there and help someone else.
It can be a simple as buying coffee for the guy in line behind you.
Are you ready to wake up, get more focused, and find more happiness in your life?
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