11 Questions with a 40 Year Old

On February 14, 2020 I turn 40. I wasn’t sure what to write as a blog post for this momentous occasion, but I knew I wanted to do something to celebrate such an achievement. 


I came into the office this evening (February 12) to finish up some tasks to then take the day off work tomorrow. After getting through some emails, I needed to move on to some prepping for the next day. I plan on interviewing my dad for the new podcast we are trying to get going. With that I needed some questions specific to him, a business owner who hasn’t owned a business for a while. 


I recently bought (but not read yet) a book by Timothy Ferriss called Tribe of Mentors. In the book he has 11 different questions he asks 100-plus “experts”. So I thought, “why not use those for my interview with Dad?”. After digging into them, they seemed a little off for my 77-year-old father, but for a guy just turning 40, these are perfect. In fact, Tim wrote the book to help him cope with moving into this next stage of his life – life after 40.


Here are those 11 questions, and my answers: 


1. What is the book (or books) you’ve given most as a gift, and why? Or what are one to three books that have greatly influenced your life?


The True Measure of a Man was a book I read a few times and have given as a gift to many friends in the last 10 years. The book speaks to how easy it is to get caught up in worldly and societal views of achievement and success. It reveals how men often sit in depressed states when they don’t live up to those false measuring posts. It then focuses on how to find value and identity outside of that singular view. I highly recommend this book to everyone. 


2. What purchase of $100 or less has most positively impacted your life in the last six months (or in recent memory)? My readers love specifics like brand and model, where you found it, etc.


It has been well over six months – probably five years, but my wife bought a waterproof bluetooth speaker on Facebook marketplace. It was a very sketchy post. He had something like 30 of them for $25 bucks each. Stolen goods or not, we were in the market for one so she got it. It’s called the Jam Splash, and I use that thing every day of my life. I listen to podcasts and books in the morning while I get ready. I take it on trips with me. I don’t even know if I know how to take a shower anymore without it. 


3. How has a failure, or apparent failure, set you up for later success? Do you have a “favorite failure” of yours?


My first day of classes at Western as a freshman I dropped a class and changed my major. I was pre-med and had honors Biology and honors Chemistry with a total load of 21 -hours. I called my mom and dad from the phone located in the lobby of Thompson Complex and told them I thought it was too much and didn’t really want to keep down that path. I was pretty torn up about it as I thought I had to do pre-med because you know…money. My parents were understanding and told me they would fully support whatever I did. I dropped the chemistry class and jumped into the 100 level computer science later that week, and 4 years later graduated with a degree in Computer Science. 


4. If you could have a gigantic billboard anywhere with anything on it — metaphorically speaking, getting a message out to millions or billions — what would it say and why? It could be a few words or a paragraph. (If helpful, it can be someone else’s quote: Are there any quotes you think of often or live your life by?)


“Be Kind. Always.”


Life is better for you and everyone around you if you are simply kind. We could all use more grace and kindness given to us, so why not give it to others? 


5. What is one of the best or most worthwhile investments you’ve ever made? (Could be an investment of money, time, energy, etc.)


After we were married and before we had kids I purchased a third vehicle, a Jeep Wrangler. It was less than $8,000 with over 100k miles on it, but it was solid. I really enjoyed that vehicle. After a year or so, we had our first child and I sold it and my wife’s car to get her something newer and safer for Piper. I don’t regret selling it, but I do want to buy another one soon. Maybe this summer because you know…midlife crisis. 


6. What is an unusual habit or an absurd thing that you love?


I collect sneakers. Nike Air Jordans, specifically. I have large feet so they don’t often come out in my size, but if they do, and I think they are dope, I buy them. I also don’t wear them. I think that is absurd. My reasoning is they are not cheap, so why would I get them dirty? They also seem to go up in value – another reason not to get them scuffed up. At the time of typing this post, I have 27 pairs of unworn size 16 Jordans in boxes. I picture one day having a spot in my office or “man cave” where they are displayed in all their glory. I also picture my kids selling them ridiculously cheap once I kick the bucket. Be on the lookout for that fire sale! 


Side note: the AJ 3 Black Cements are my favorite. Those are works of art.


7. In the last five years, what new belief, behavior, or habit has most improved your life?


Listening to books while walking. I love to walk up on campus at WKU at night. Yeah I know, not creepy at all, right? Two laps around the outside of the campus is four miles, which is a good, solid number of miles to be called exercise. I feel like I am kind of working out while accomplishing a goal of “reading” more books. 


8. What advice would you give to a smart, driven college student about to enter the “real world”? What advice should they ignore?


Always, always, ALWAYS put the most you can into the company 401k. And if they are matching a certain amount, you’d better be putting at least that in there to get that free money. No 401k? Then you need to start a Roth. Compound interest is AMAZING. What you do at ages 22-32 will absolutely blow your mind at 65. I am telling you – don’t decide you will start it in three years; start it now!


9. What are bad recommendations you hear in your profession or area of expertise?


I have heard some clients say “We tried that and it didn’t work for us”. Many times what that means is they tried one iteration of something for two weeks with a budget of $50 to a landing page with no contact information. That isn’t a legit test of most digital advertising efforts. That is like saying “I did 10 sit ups and I don’t see a 6 pack yet” while holding a twinkie. 


10. In the last five years, what have you become better at saying no to (distractions, invitations, etc.)? What new realizations and/or approaches helped? Any other tips?


I am trying to be better about not letting work distractions interfere with my weekdays from 6 a.m. to 8:30 a.m. and from 5 p.m. to 9 p.m. Those are the times when some combination of my family is awake and we have time together. It is hard not to grab that phone and start checking the overnight emails or answering someone who shot you something at 6 p.m. In the macro I am getting better, but from a micro level it could still use work. 


11. When you feel overwhelmed or unfocused, or have lost your focus temporarily, what do you do? (If helpful: What questions do you ask yourself?)


I take a break and try to get away from distractions. Many times I have to work at a time when everyone else is asleep or just not around. I am able to get more done between 9 p.m. and 12 a.m. than most days from 9 a.m to 5 p.m. 


There you have it – 11 questions answered, my gift to you on my 40th birthday. I challenge some of you to do the same and put it out to the world. I know I would be interested in what you have to say and I bet others would too.


By Chad Webb

Chad Webb (who is 40) is one of CrowdSouth’s Partners and brings years (not quite 40) of experience managing multi-million dollar website projects to your business. He loves hoodies, puffy vests, jeans and flip flops.

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