19 Self-Reflection Questions that will Totally Realign Your Life
I'm a big believer in the occasional self-audit: Checking in with yourself every so often to make sure that your actions and habits align with the life you want. These questions help do just that.
Welcome back, folks, to another episode of Reid writing about whatever the hell he wants to because there’s only fifty-four of you (subscribers) and I have nobody to answer to!
If only our national media wrote so freely… but, I digress.
This article should be fun for me and for you. I can’t take any credit for the questions - I’m pulling them off an Instagram post from Tyler Wright (@DefiningWealth). I don’t really know who he is or what he’s known for, but at some point I must have followed him and just recently I came across these questions that he posted.
They were really beneficial for me, and helped me kind of “re-center” and bring my most important priorities back to the forefront.
Below are two things:
The list of just the questions. I would encourage you to copy these down and answer them for yourself. I promise you that if nothing else, it’ll remind you of what’s most important in your own life.
The questions with my answers, for those of you who really want a peek inside my brain.
Just the Questions
If you had to give someone a brief 30-second explanation of who you are, what would you say?
If you had to give someone a brief 30-second explanation of who you want to become, what would you say?
What do you want your legacy in life to be?
What matters most to you in life? Does your schedule line up with this?
What do you enjoy doing?
Describe your ideal 48 hours. Pretend you have no job, no responsibilities, and $10,000 to spend. Where would you go? What would you do? Who is there? When do you wake up and sleep?
What is your purpose in life?
At the below ages, write down what you will regret NOT having done by each age: 25, 35, 45, 55.
Where do you want to live and for how long?
Do you plan to get married and/or have kids? Why?
How do you think people feel when they see you walk into the room?
List the TOP 10 things you must do or see before you die and write down a year you plan to do them.
What negative habits/thoughts/people/responsibilities are holding you back from reaching your definition of a dream life?
When was the last time you were REALLY happy? Why was it so long ago? How can you FEEL that level of happiness today and every day?
What are your gifts and how could you use them to contribute to society?
What do you admire most about yourself? Why?
What do you imagine the future “you” to be like 15-20 years down the road? Could you be more like that today?
What things make you motivated, inspired, and/or excited?
Write your own eulogy from the perspective of the person you love the most on this planet, 2 ways: 1) What they would write if you died today. 2) How you would hope they will write it if you die 40 years from now. (Pro tip: model your life after the second eulogy).
My Answers
If you had to give someone a brief 30-second explanation of who you are, what would you say?
I think that in our generation of job-hoppers, I’m permanently in meet-up/mixer/interview mode, and I have a pretty quick and refined “elevator pitch” about who I am, but it really only covers what I do, professionally. Lame.
Sitting down to write this now, I’d tell people something like that I’m a friendly, ambitious, patient person who always tries to see the good in people first. I love being Hannah’s husband and Cannoli’s dad, and I’d do anything for them, my family, and my friends. I’m a dreamer with big ideas on any given day, and I love challenging myself both physically and intellectually. I’m constantly learning and asking questions, and I’m relentlessly curious about the world and my place in it.
Those are the main things, I guess!
If you had to give someone a brief 30-second explanation of who you want to become, what would you say?
I want to become an impactful person for my family and be a provider for everything they want in life. I want to be this person in a very involved way, where I don’t have to sacrifice time away from them to achieve this, since time is the most valuable resource we have. It’s also really important for me to create something important that makes a positive impact on more than just my family. I want to build something and be proud of it, knowing that it’s helping other people. That would be incredibly validating for me. Something else important to me is I want to become a very fit person later in life so that I can live my life to the fullest for as long as I possibly can, and set a lifetime example for health for my future kids to follow.
What do you want your legacy in life to be?
God, these questions are getting harder and harder… This is simple and cliché, but I want my legacy to be as an incredible husband, father, friend, and builder/creator/entrepreneur. Besides my family, I want to leave behind something that I built that outlives me. On a personal level, I want everyone who knows me to think of me as a person who was always respectful, patient, and friendly. I also want my legacy to be as someone who took action - not just a talker. I want people to think of me as an example for, “he didn’t have any advantages over me… that’s what my life can be if I just do it, and work at it.”
What matters most to you in life? Does your schedule line up with this?
I’m shooting from the hip on most of these - each answer would be pages and pages long if I went really, really introspective… so, what first pops into my mind for this answer is Hannah and Cannoli. I think for the most part my schedule lines up with this… albeit, I could do a better job crafting my life in a way with less work travel to other states. I’m grateful that almost every single day that I’m home, my days start and end with walks with both of them. Hannah and I are each other’s best friends, and I hope we always stay that way - there is no one I’d rather spend time with, truly.
What do you enjoy doing?
This answer could be a mile long, too…
Generic, but it’s the first thing that comes to mind - I obviously very much enjoy spending time with Hannah and my dog. Specifically, I love going for walks with both of them and leaving our phones at home, and just talking with my wife while Cannoli sniffs to her heart’s content.
Outside of quality time with them the things I really enjoy that come to mind: Practicing Jiu Jitsu, trail running and hikes around Colorado with my type II fun friends, planning and executing difficult ultramarathons with aforementioned friends, working on bringing businesses to life (always building), using both my hands and my brain to create stuff, learning more about my parents, a great meal after a hard day’s work, and watching my dog swim (Cannoli deserves two mentions).
Describe your ideal 48 hours. Pretend you have no job, no responsibilities, and $10,000 to spend. Where would you go? What would you do? Who is there? When do you wake up and sleep?
I could go into all sorts of minutiae here too and give you an hour-by-hour breakdown, but I’ll spare you the details. Both days would start the same - walking my dog, just the two of us. Next I need some fitness at the beginning of the day. One day I think I’d do a trail run with friends, on the second day I think I would do some paddle boarding with my wife. After that is coffee, just her and I. From there, it gets fuzzy… One day would involve an all-day summer barbecue in some sort of lake setting. Beers, cornhole, sand volleyball, a rope swing, the whole nine. Everyone I love would be there. Fuck it, maybe we’d even roast a pig. The night would end with all of us swapping stories around a fire.
The second 24 hours daytime activity would probably be the winter version of the above scenario. I’d ski all day with my closest friends, without an agenda, stopping for lodge Irish coffees and beers. We’d call it a day at about 4:00 p.m. and meet a much bigger crew for Après at some cozy ski-town bar. The night in this scenario would end much like the first day, around a fire, with the addition of soaking in a hot-tub mixed in there somewhere. Damn, what a phenomenal 48 hours that would be!
What is your purpose in life?
Fuck these questions. I’ve never had to be so introspective on a damn Thursday afternoon! Haha. I think my purpose in life has a couple different fingers. I want to be able to provide my wife with a life so blissful and fulfilling that she doesn’t regret for one minute choosing me as her life partner. She and I will have a few kids and I think a huge part of my purpose will be, and I’m being intentional with my words here, not just ‘giving’ them a better life than I had, but teaching them to be better people than me, in every aspect. Better people, better husbands and wives, better parents, better athletes, better friends, etc.
Those two things encompass about 95% of my purpose in this life, but the icing on the cake that makes me feel purposeful is when I’m building something that I hope can positively affect society at large - how large is to be determined. It’s super important to me to make an impact on a macro-level in addition to the micro-level (my family).
At the below ages, write down what you will regret NOT having done by each age: 25, 35, 45, 55.
25 is dead and gone.
It would be easy to say “not having kids,” by 35, but realistically it wouldn’t be the end of the world if that didn’t happen until 36 or 37. I think what I would regret NOT having done by 35 would be leaving the W2 workforce to dive into an entrepreneurial endeavor full-time.
By 45, I would definitely regret not having kids haha. I think I would have regrets at this age too if I had NOT built a large successful business and NOT kept myself in shape. I think I’d also regret not having made a lifestyle adjustment that allows me to spend more time with my parents as they get older in age, and allowing them to spend quality time with their grandkids.
By 55… That’s a ways ahead. I think I’d regret not being 100% financially independent by then. That doesn’t mean I’d be done working, I think I’ll always be working on something stimulating for me. I think I’d regret NOT having adjusted my lifestyle again at this age to a point where I can be super involved in my kids lives - never missing anything, coaching, mentoring, fun family vacations, you name it. That would be my number one priority at this age.
Where do you want to live and for how long?
Right now at this time, I want to live in Colorado forever. Tough to nail down a specific town, but this state fucking rocks. So much to do on any given day, and just an energy that’s hard to describe, exuding from both the mountains in the west and the city of Denver. The energy coming from the mountains reminds me to be still, enjoy what’s around me, and take no time or this place for granted. The energy coming from Denver is exciting, brought about by all of the innovation and young professionals that are always building and creating there. This is the first place in my life that I’ve lived nearby a big city, and it fuels my imagination.
Do you plan to get married and/or have kids? Why?
No, I never plan to get married… again. That one has obviously already happened and it’s been amazing. Kids are something I think about often and would definitely love to have. I hope one day they can read this blog and ponder over the way I was looking at the world in 2024. I think there’s a lot of value in that. I spend a lot of time digging into incredibly successful people’s lives and seeing what they were doing when they were thirty.
How do you think people feel when they see you walk into the room?
I think this depends on the room. Into my jiu jitsu gym? A lot of people don’t like that so much since I’m a big dude with a wrestling background and some decent jiu jitsu, haha. Into a room full of friends? I’d hope that they’re excited to see me, knowing that I love to have a good time, have great discussions, and listen to them. Into a room full of strangers, I’d like to think I make a good impression right off the bat. I greet everyone with a smile - everyone. I got this from my dad I think - he says “hello” to literally every single person he walks by, anywhere. I think being a big guy, too, I tend to just put out friendly vibes. At least I hope so!
List the TOP 10 things you must do or see before you die and write down a year you plan to do them.
This is obviously incredibly subject to change… but as of today (in no specific order):
Have kids - 2027?
Cross Country RV Trip - 2035
Build a lake cabin for/with my parents - 2032
Hunt and harvest a bull elk - 2040
Visit Normandy with, at minimum, my dad and uncle - 2025
Skydive - 2025
Work for myself full-time - 2025
Hike a 14er with my parents - 2025
Coach my future kids - ~2030-2048?
Epic Type II adventures with my friends - every year from now ‘til I kick the bucket.
What negative habits/thoughts/people/responsibilities are holding you back from reaching your definition of a dream life?
The immediate first thing that popped into my brain was my job. That’s tough though. It’s a double-edged sword. It’s also what is currently funding the majority of my life’s endeavors and investments. A necessary evil - for now. This question triggers a sort-of “Russian doll,” paradox too. It starts with the job holding me back (doll #1). The job funds the real estate investments. Then, I’m sort of trapped by the real estate investments because every month I have to pay two mortgages and my rent (doll #2). Right now I rely on the income from primarily the job to pay for those three big expenses. So in that way, real estate is equal parts freeing and restrictive… hope that makes sense.
When was the last time you were REALLY happy? Why was it so long ago? How can you FEEL that level of happiness today and every day?
I think honestly that the last time I was really happy was, fortunately, not that long ago - roughly a month ago at our friend’s parent’s lake house in Hope, Idaho. It was just so incredibly blissful. Zero agenda every day we were there, no pressure to do… anything. The only way to feel that level of happiness today and every day, that I can see, is to get to a place where I can have the financial means to support that level of unencumbered blissfulness, which is what I’m grinding my ass off for right now.
What are your gifts and how could you use them to contribute to society?
Well this will be a narcissistic answer… I think that my gifts are all intangible. I think of a gift as some quality that I possess that most others do not. I think I’m gifted in my ability to endure. I think I can grind for harder and longer than most people, if I see the the purpose as worth doing. I also think I’m more patient than most. I’m never the first one to lose my cool or composure, if ever, in a stressful situation. I’m very, very solution-oriented… sometimes to a fault. I’ve learned that some situations you can’t fix. I also think I’m very clear-minded. I'm not immune to biases, but I do think I’m capable of making very fair judgments based on all the inputs available to me. I’d say those are some of my greatest gifts. I think all three are critical in building a business - that’s what I plan to contribute to society.
What do you admire most about yourself? Why?
I would say the above three things, to be honest. Those are the big ones. I know the intent of this question is probably some words-of-affirmation “self-love” confidence boost, but there’s no way to answer it without being incredibly vain, lol.
What do you imagine the future “you” to be like 15-20 years down the road? Could you be more like that today?
Ahh good question… I think downstream constantly. My wife reminds me all the time to be more present. I will for a little while, but so often my thought stream wanders to, “how will today’s action’s impact tomorrow?”
In 15-20 years I’ll be 45-50 years old. That future me will be an awesome dad and husband. My kids and wife will love me as much as they ever have, and be grateful for the life I’ve helped build for them. I’ll have accomplished some incredible things and improved lives well beyond my own family. I’ll be equal parts satisfied and eager to learn. I’ll be the example of health at my age, admired by my peers for my level of fitness. Those are how I picture my life down the road. As far as being more like that today… Yes, I’m definitely trying to set the conditions right now for that future state to manifest into reality.
What things make you motivated, inspired, and/or excited?
I know the “right” answer to say here is that my wife inspires me, my family motivates me, etc. I do draw some motivation and excitement from my wife’s energy, no question about it. But, if I’m answering this question honestly, what motivates me the most is seeing people my age or younger accomplishing incredible things. I know, “Comparison is the thief of joy [Theodore Roosevelt].” But I think that if you can handle it and harness other’s success to motivate you, then it’s not a bad thing.
To me, it’s only “the thief of joy” when you let it be, i.e, keeping up with the Joneses and feeling bad about your own situation. I don’t feel bad about my own situation. I know that, relative to most of my peers, I’m more or less “crushing it.” I just know there is still untapped potential on the table for me, because I know other people with less capability accomplishing greater things than I am. That’s not a slight, all the credit to them - it’s just a reminder for me that I have more to do.
Write your own eulogy from the perspective of the person you love the most on this planet, 2 ways: 1) What they would write if you died today. 2) How you would hope they will write it if you die 40 years from now. (Pro tip: model your life after the second eulogy).
I’m not going to answer this one. Feels like another self-affirming “confidence booster” type of question. I’m not going to type out, “My husband Reid was an amazing man…” I know how Hannah feels about me, and I think I know what she could say about me if I died today. We’ve spent nearly seven phenomenal years together and she’s known me for twelve. That’s a lot of context.
And, forty years from now I’d just be guessing. I know that’s the point and that I’m supposed to try and predict what I hope she’ll say forty years from now, but it doesn’t feel right to map it out and forecast it. You can read my above answers and guess what I want to do with my life, but as far as my hypothetical eulogy goes, I’ll leave that to her when my time comes.
Another one bites the dust, folks.
I’m actively trying to suppress the urge in me to write in a way that caters to you guys. I want this blog to be as authentic as possible (or at least as authentic as someone can reasonably be on the internet where everything stays forever). I want this blog to be written so authentically by me that my future kids can read it and hear their dad’s voice. The least article, on resumes, was originally intended to be a catchy LinkedIn article. Fuck all that disingenuous internet bullshit.
Back to more writing from the heart!
Thanks as always for reading this gibberish that I take the time to write.
-Reid