Disclaimer: These prompts are not mine. I did not invent them. I have included the source of where I initially heard them. If that is not the source, it is my fault, not the authors.
1.Make a map of my failures indicating the rough date they occurred.Write beside each one what I learned.
2. What might I do to accomplish my 5-year goal in 6-months, if a gun were against my head? (Tim Ferriss)
3. Who was the first person that told me about the career/job I am currently in? Have I had any similar discussions since?
When I first asked myself this question, I was contemplating leaving my first job at a top consultancy. I thought deeply about why I had ended up there.
Where had all of this started?
I determined the first time I had heard about management consulting was from an esteemed alumni of my fraternity. 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 looked two layers deeper, I discovered that after (1)hard-working and (2) ambitious came (3) empathetic. A strength I had never thought critical about. But it sparked a whole new trajectory in my professional life
6. What would make what I am doing right now easiest?
I used this prompt to break 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 only to sell one item. Over the next 3-months, I increased my monthly sales from $1.5k to $8.5k.
7. What do I spend a silly amount of money own? How might I scratch my own itch? (Tim Ferriss)
This is the very prompt that got me to pursue the path I am on now. I am following my own itch to overcome anxiety and live a life of beauty. And I am sharing any nuggets I have with the world.
Who knows if anyone will listen. I am more concerned with improving my mental fitness, as Brad Feld calls it. If people read and like, that is just gravy for me.
8. What is the worst possible scenario if I take “x” action? What can I do to limit the downside? (Stoicism)
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 something I could prevent by picking up odd jobs along the way.
9. What would I do if I had $10 million but still had to work 40 hours a week? (Financial Samurai)
We were all probably asked a version of this question when we were ten years old. But I think it is an insightful question into what drives us.
10. Will I make this a dead time or an alive time? (Ryan Holiday)
After discovering that my second “dream job,” was anything but a dream, I knew I had to get out. However, I needed to stay for at least a couple of months before I could reasonably leave. This question restructured my thinking towards getting value out of my remaining time at the job versus only complaining about it.
11. How might I build my non-work life around what I do in a way that lets me frame it as a source of greater meaning, joy, connection, and engagement or something that gives me freedom to do other things that provide those feelings? (Jonathan Fields)
Use this if you can’t leave your job, and need to find meaning elsewhere.
12. If I could only work 2 hours per day on income producing activities, what would I focus on? (Tim Ferriss)
This is always a great prompt to get you more focused on the pieces of your life and business that actually matter.
13. What is something that doesn’t make sense?
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. Who are my top 7–10 digital mentors I most want to be like?
Whenever I start to feel overwhelmed with the sheer amount of information thrown at me, I pick 7–10 people that I most want to emulate. I subscribe to whatever content they produce and ignore EVERYTHING else.
This helps me stay focused on output while controlling the input.
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?
19. Do I enjoy what I am going to do today? If not, how long has the question been no? (Steve Jobs)
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 was my 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 my own child’s mind, what advice would I give?
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 a regular 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 I would 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?
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 are you doing what you are doing right now? 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 with those closest to me
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 best lesson my father ever taught me? (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?
42. What is something that I lost that I will never get back?
I use these two as writing prompts when I am stuck in a self-imposed writer’s block. They always produce authentic content.
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.
Bonus: A quote, not a prompt that always helps me clarify my thinking
“[W]henever you find yourself on the side of the majority; it is time to pause and reflect.” — Mark Twain
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