I did it.
I just finished the draft of my book 🙌🏼
20/20: 20 Questions to Ask in Your 20’s to Set Yourself up for a Lifetime of Success
That’s a mouthful—ok, it’s just a working title for now. Maybe you’ve got a better idea?
The book is a collection of the 20 questions I think every 20-something should spend time asking and reflecting on. In a world with answers on demand (thanks, Google and Chat GPT) what we need more than ever are people who can think for themselves (and by themselves), reflect deeply on the important questions, and suspend judgement long enough to see beyond the surface.
So, below I’ve included the 20 questions I chose. I’ve also included the entire introduction of the book along with a tiny piece of each chapter to give you a sense for the structure and content.
There are two things I need your help with:
Share! Hit forward and send it on to a friend or maybe to a kid or grandkid and just tell them you’re helping me out with a project and I’d love their thoughts (the good, the bad, and the ugly!)
Hit me with your feedback! I’ve got a link to a Google Form here to keep it super easy. What are 3 questions that just hit the spot and what are 3 questions you could live without?
That’s it! And now to the main event….
INTRODUCTION
“We run this company on questions, not answers.” Eric Schmidt, Former CEO of Google
What if you ran your life like this?
You can… and should. And that’s why we’re here.
What’s the most valuable life skill you can develop?
Relationship building?
Investing?
Public Speaking?
Negotiation?
In 2020, I was asked to speak to a group of high school juniors about “life skills.” I decided to crowdsource my presentation so I asked the students to tell me what life skill they believed would bring them the most value.
Over 250 students told me: taxes.
There’s definitely some great stuff you can do if you understand tax law. Unfortunately, I’m a communications major which means my understanding of taxes is limited to downloading TurboTax or hiring someone else to do it for me.
So I tossed my crowdsourcing idea out and began my own search.
At the time I was reading Gary Keller’s book, The One Thing where he asks this question:
“What’s the one thing you can do such that by doing it everything else will be easier or unnecessary?”
I altered the question slightly and then had my own guiding question:
“What’s the one skill you can learn that will make everything easier or unnecessary?”
Creativity?
Communication?
Collaboration?
I was searching for the first domino—the one thing that if I could always get it right, the next dominos would always fall into place.
And then I came across a quote (wrongly) attributed to Albert Einstein.
“If I had an hour to solve a problem and my life depended on it, I would use the first 55 minutes determining the proper question to ask, for once I know the proper question, I could solve the problem in less than five minutes.”
-anonymous-
Einstein may not have said it, but the idea hit.
Asking the right question.
Inquiry, curiosity, asking. Whatever you want to call it, this is your first domino. Asking well positively impacts everything you do after.
We live in a world where answers are pushed on us all day, every day. Many times the answers appear before the questions ever surfaced. And before you know it, you’ve jumped into action, trying to implement the guidance you pulled from the latest “top 10 tips” article you found online.
There is no advice in this book—this is not a book of answers. You don’t need it.
The majority of your life to this point has been spent being advised, directed, and maybe even ordered.
“You should go to this college…”
“If you want to make a lot of money, you should do something in finance or tech…”
“You shouldn’t be staring at your phone all day…”
“All advice is autobiographical.”
Austin Kleon
Think of a piece of advice you’ve received and who gave it to you. Their advice was the result of their lived experience. They took their experience, reflected on the impact it had on their life, and then crafted a little gem of wisdom to guide their future actions.
Treasures like this are most valuable to the treasure hunter.
This little nugget of advice was mined by and provided value to someone else. Unfortunately, those gems aren’t always valuable in different contexts. What worked for your mom, your uncle, your high school teacher, or your best friend is not necessarily the same advice you need.
“You need to dig your own treasure. Only then, will you treasure your treasure.”
Christopher Munday
That’s why we’re here right now.
As your friend (we’ve made it this far, so now we’re in it together), I’m going to kick start your treasure hunt with a series of questions. No advice, directives, or how-to’s—just questions.
The 20 questions that follow are the shovels and pickaxes that will help you mine your own treasure throughout your 20s. The questions in this book are a starting sampler that will help you:
make better decisions;
live more purposefully;
strengthen your relationships;
and most importantly help you build your own treasure collection.
Here’s three ways to read this book
Cover to cover. It’s a short book - this won’t take long.
Choose your own adventure. Pick a question based on what you need at any given moment.
Closed. Leave it out somewhere you’ll see it often—coffee table, nightstand, car dashboard. Just seeing the cover will remind you that you need to stay curious and ask more questions.
Each chapter is laid out with the following pieces:
What’s in it for you?
A brief explanation of the question’s benefits.
Story
A story to illustrate the question in action.
Keys
Key ideas for how you might approach the question. These aren’t the only way to look at the question, they’re just ideas to get you going.
More Questions
A handful of related questions that might help on your journey.
❓Who do you want to become❓
“The only person you are destined to become is the person you decide to be.”
Ralph Waldo Emerson
What’s in it for you?
Your best life.
Someday you will be old. And I don’t mean 30—although that comes faster than you think. No, I mean like really old. 80, 90, and if science keeps advancing maybe something like 140. When you get to this point, death will feel more present and you’ll begin to reflect on your life.
What do you think is the number one regret of people nearing the end of their life?
"I wish I'd had the courage to live a life true to myself, not the life others expected of me."
I get it. 80 seems like it will never come. But then, remember how far away your 20s felt when you were in elementary school? If your “elementary school self” could see you now, what would they say?
Would they be proud, disappointed, excited, grateful?
Whether it seems distant or not, 80 is coming. So what are you doing now to make sure that “future-you” is proud, grateful, and living the life they chose?
You ask this question to ensure you live your best life.
❓What do you want to get A’s in❓
“Maintaining friendships. Building a great company. Spending time with family. Staying fit. Getting sleep. Pick 3.”
Randi Zuckerberg
What’s in it for you?
A personal report card.
It’s possible to get all A’s when you’re taking a handful of classes. But while you were getting A’s in a few classes, how were your health, social, family, personal growth grades?
This question forces you to confront a reality that our “culture of more” wants to pretend doesn’t exist—life is filled with trade-offs. You will have to make choices.
Build your personal report card and don’t get caught up looking at someone else’s grades.
❓What are you still carrying❓
Letting go gives us freedom, and freedom is the only condition for happiness. If, in our heart, we still cling to anything—anger, anxiety, or possessions—we cannot be free."
Thich Nhat Hanh
What’s in it for you?
Freedom.
For roughly two decades you have been adding things to your “backpack”—experiences, emotions, trauma, beliefs, perceptions, biases, and more.
Have you ever stopped to look in the backpack? Do you know what’s there?
This question forces you to do an inventory of what you’ve collected and then ask, how is this item helping or hindering your journey?
❓What are you doing with what you have❓
“At the end, it’s not about what you have or even what you’ve accomplished. It’s about who you’ve lifted up, who you’ve made better. It’s about what you’ve given back.
Denzel Washington
What’s in it for you?
Fulfilment.
You were born in the most technologically advanced era in the history of the world. Health care has never been better. Economic opportunities abound. Education is easily accessible. Even the fact that you’re reading this book at this moment likely means you enjoy privileges others do not.
But if you need a self-serving reason to share what you have with others, here it is…
“There is a lot of evidence that one of the best anti-anxiety medications available is generosity. The great thing about showing up for other people is that it doesn’t have to cost a whole lot or anything at all, and it ends up being beneficial to the giver.”
Adam Grant
❓What will you do with this feeling❓
“Anything that is mentionable, can be more manageable.”
Fred Rogers
What’s in it for you?
Control.
All emotions serve a purpose. But some emotions, when left entirely unchecked, can take over our lives and leave us helpless.
When you learn to pause, name what you’re feeling, and then decide how you want to use the emotion, you take back control of the situation. Name it to tame it.
❓When are you at your best❓
“We simply don’t take issues of when as seriously as we take questions of what”
Daniel H. Pink
What’s in it for you?
Optimization.
Think about professional marathon runners—they don’t practice running marathons. Instead they have a specific training plan that leads them all the way up to race day when they finally peak.
What if you understood when you were at your peak? This question will get you to stop and consider everything from the time of day, environment you are in, and all of the other components that contribute to your peak state.
❓Whose responsibility is this❓
“The price of greatness is responsibility.”
Winston Churchill
What’s in it for you?
Accountability.
How many times do you hear someone pass the blame? You want to stand out from your peers and colleagues? Be the type of person who raises their hand, accepts responsibility, and gets stuff done.
❓What’s inside your control❓
“The chief task in life is simply this: to identify and separate matters so that I can say clearly to myself which are externals not under my control, and which have to do with the choices I actually control. Where then do I look for good and evil? Not to uncontrollable externals, but within myself to the choices that are my own…”
Epictetus
What’s in it for you?
Impactful resource allocation.
You have a fixed amount of resources to spend at any given time—time, energy, emotion, money. When you ask this question you learn where to spend your resources. Spending resources on something outside of your control doesn’t guarantee you get the outcome you want. Spending resources on things inside your control will always pay off.
❓What’s the true cost of this decision❓
"The price of anything is the amount of life you exchange for it. Make sure you're willing to pay that price before you decide."
Henry David Thoreau
What’s in it for you?
Informed decision making.
The sticker price is never the actual price. When you look beyond the surface you’ll find that every decision comes with hidden costs. When you understand the hidden costs, you make better decisions.
❓How can you experiment with this❓
“All life is an experiment. The more experiments you make the better.”
Ralph Waldo Emerson
What’s in it for you?
Data.
You can find 1,000 studies that will tell you to follow a certain nutrition plan.
You can find 1,000 studies that will tell you to follow the exact opposite nutrition plan.
Which is right?
You will only learn what works for you by collecting data from the most important sample size of all, you! You experiment so you have accurate personal data to refine future actions.
❓What are your biases❓
“The first principle is not to fool yourself – and you are the easiest person to fool.”
Richard Feynman
What’s in it for you?
Self awareness.
Everyone is biased.
But not everyone knows (or accepts) this truth.
Once you understand some of your stronger biases you can intentionally disrupt their power in the moment. People with this type of awareness are rare. This type of self awareness is a superpower.
❓What’s your next best option❓
“When one door of happiness closes, another opens; but often we look so long at the closed door that we do not see the one which has been opened for us.”
Sheryl Sandberg and Adam Grant
What’s in it for you?
Options.
We live in a world where things go wrong. Sometimes it’s your fault and many times, it’s just life. Asking this question is like hitting ‘fast forward’ and skipping over all the complaining and unnecessary moping and recognizing there is always another option.
You’ll save yourself so much time by learning to ask this question when things fall apart.
❓What advice would you give a friend❓
“I always pass on good advice. It is the only thing to do with it. It is never of any use to oneself.”
Oscar Wilde
What’s in it for you?
A better view.
You have all the wisdom in the world when you’re giving advice to a close friend. You’re not blinded by emotion, bias, or other obstacles. You see things clearly.
Yet, when you face the same challenge, everything is “different.” Your situation is harder or worse because you can’t distance yourself. This question is a quick trick you can play on your brain to help you see things as they really are.
❓What are you willing to sacrifice❓
“The important thing is this: to be ready at any moment to sacrifice what you are for what you could become.”
Charles Dickens
What’s in it for you?
Growth.
Your list of wants is endless. That’s the easy list to create. On the opposite side of each want is an endless list of things you must sacrifice first. Everything comes with a cost. You have to figure out what you’re willing to give up in order to have what you want.
❓Why do you want this❓
"If you have a strong 'why,' you can endure almost any 'how.'"
Frederick Nietzsche
What’s in it for you?
Purpose.
Whether you like it or even know it or not, you are being influenced by everyone and everything around you. Before clicking buy, changing jobs, moving homes, or jumping into a relationship, pause and ask ‘why’? There isn’t one right reason for doing something but you need to make sure you understand YOUR ‘why’ because that will give purpose to the action.
❓How much would you bet on it❓
“Wanna bet”? Suddenly, you are not so sure. That challenge puts you on your heels, causing you to back off your declaration and question the belief that you just declared with such assurance.”
Annie Duke
What’s in it for you?
Confidence.
Sometimes.
Most of the time.
Possible.
Probable.
Improbable.
Do you know what these words mean? But, like, really know what they mean? If we met up and used these words, we’d almost certainly have different definitions of what these mean.
But what happens when you’re forced to attach a number to your thinking? Well, now you can express yourself clearly.
I’m 90% sure.
I’m 50% sure.
Now you can start making better decisions.
❓What type of team have you built❓
“You are the average of the five people you spend the most time with.”
Jim Rohn
What’s in it for you?
Growth.
Life is a team sport. You were born into a team who you spend 18 years with before you then begin building each team that follows. Each teammate either makes you better or worse. You get to choose. You ask this question to ensure you’ve built a team that will help you become the person you want to become.
❓What are your non-negotiables❓
“It’s easier to hold your principles 100 percent of the time than it is to hold them 98 percent of the time.”
Clayton M. Christensen
What’s in it for you?
Freedom.
Setting boundaries is like giving yourself the gift of freedom. It's about creating a space for you. When you set limits, it's like drawing a circle around your well-being. You can be yourself, make choices that matter, and have healthy relationships. It's about being you and living life your way.
❓What’s important now❓
“Don’t think about winning the SEC Championship. Don’t think about the national championship. Think about what you needed to do in this drill, on this play, in this moment. That’s the process: Let’s think about what we can do today, the task at hand.”
Nick Saban
What’s in it for you?
Presence.
The value of this question comes from its ability to help you cut through the noise and determine what you need to do right now. It brings clarity and demands you to stay present in the moment.
Have you ever made it to the end of a busy day and thought, “what did I actually accomplish today?” Everyone is busy—or at least that’s become the default so many people live in. But a much smaller percentage of those people are truly working on the most important things.
Focus on what needs to happen in the moment and everything else will take care of itself.
❓Are you your own best friend❓
The greatest thing in the world is to know how to belong to oneself.
Michel de Montaigne
What’s in it for you?
Companionship.
You probably think this question is the least practical and most fluffy of the ones in this book.
I’d argue it’s actually the most important question in here because of this chart:
What do you notice about this chart?
You’re about to spend more time with yourself than anyone else throughout your life. Do you think this is a relationship worth investing in? This question is a “gut-check” moment where you are forced to confront how much you actually like your own company.
—--
Oh snap! You made it all the way through. Thank you!
If you did that and now you’re interested in checking out the complete manuscript draft - hit me up with a comment here or just message me directly (kkaldous@gmail.com) and I’ll share the complete manuscript draft with you. I’d love to share this with as many people as possible!
Don’t forget to share this and give me 30 seconds of feedback!
Keep Asking,
Kyle
Book? For reals? Wow.
You should read The Lord’s Question, if you haven’t. Similar framework.
Hey Kyle, please share your manuscript with me. I'd love to take a closer look! I'm actually working on something myself and infusing story into it as well. I love how you're guiding thinking by leading with questions. I would say for me, establishing a love of learning, followed by learning how to learn well are two of the big dominos. Asking good questions is so foundational to that process as we become more self aware of our strengths and weaknesses.