John McCaskill is an entrepreneur, writer, and product manager. He is the Founder and CEO of The Cost, a media company focusing on connecting professionals, helping aspiring professionals, and easing the discomfort and intimidation of career change.
Where did you grow up and what was your childhood like? Did you have any particular experiences/stories that shaped your adult life?
I grew up in a small country town in Oklahoma. I come from a very large family with six sisters and 5 brothers. My father was in the military and always carried himself in a grandeur way. This level of behavior shaped me into what I am today. It taught me to always look at the bigger picture. Becoming offended or angry is still indeed a choice. We have the power to decide whether or not to react a certain way or let things go. Just because an employer sends a rejection letter doesn’t mean I have to feel bad or even question my skills. I can still enjoy the rest of my day understanding that my value in the eyes of others can’t always be controlled. Keep moving regardless of setbacks and disappointments. That’s what my father was.
What is something you wish you would’ve realized earlier in your life?
Thank goodness this doesn’t apply to me too much because from the beginning I knew I wanted to live a life that I wanted and no one else. Many people have many regrets or ponder about what they wish they realized but that wasn’t me. Everything up to this point has been calculated from the beginning. I knew I was different because I didn’t care what someone thought of me. This is not to say I didn’t consider the feelings or thoughts of others, but it seems like many people want you to be something they desire for you and not what you desire for yourself. If a family has a history of picking the military as a career, then ultimately there’s pressure to join the military. For myself, I knew early on that I wanted to become an entrepreneur, and I never looked back despite many trying to talk me out of it.
What are bad recommendations you hear in your profession or area of expertise?
Haha, there are so many. One thing is this constant hustle culture. There’s a belief that if an entrepreneur is not hustling 25/8 (yes I added an extra hour and day) then they’re not going to be successful. An entrepreneur for sure has to be diligent in their work, but not at the cost of losing themselves. The problem with this is that you can’t hustle development. Development takes time and can’t be rushed. Imagine if a baby was rushed inside the womb instead of allowing the 9 months to develop? Premature babies often have complications. Hustling more is not always the formula for success because some things just take time. Many don’t truly understand how long some of the most popular brands have been around. Below take a look at how long many of the companies we’ve come to love have been around. It takes time to build a brand and no amount of hustle can replace that type of brand development.
Berkshire Hathaway – 1839
Target – 1902
Disney – 1923
Samsung – 1928
Sony – 1946
Nike – 1964
Starbucks – 1971
Tell me about one of the darker periods you’ve experienced in life. How you came out of it and what you learned from it?
I’ve been homeless before. As I was pursuing a degree, times became tough as I had to make decisions whether to eat that day or pay a bill. Ultimately I found myself homeless while attending college and would have to shower in the dorms just to stay clean and keep my grades up. What’s interesting is I never felt sorry for myself, but I did take much notice. I came to learn and understand financial responsibility. I purchased many finance books to understand how to get a hold of my finances and never looked back. I practiced saving and budgeting for the next several years of my life and I enjoy it every day. Especially knowing where I came from.
What is one thing that you do that you feel has been the biggest contributor to your success so far?
I don’t think it’s ever one thing that contributes to anyone’s success. There are many factors that help along the way. Many of us wouldn’t want to have a spouse that is an excellent cook, but inconsiderate. Neither would many of us want a spouse that has excellent communication skills, but very rude. We all desire many traits when we are considering a spouse. So by the same measure, I’ll mention a couple of factors. First, I learn a lot. I probably learn something new every week that I didn’t previously know or understand. Second, I’m persistent in accomplishing the goals I desire. If I want to be able to sell better, I work on it consistently until I’m better. Lastly, I always audit myself on my performance and goals. If I didn’t meet them I wouldn’t beat myself up, but understand why I didn’t accomplish them.
Was the time frame realistic? Do I need to learn more? Did I slack? Does the goal naturally take time? Asking yourself these instead of beating yourself up is the better option. These contributing factors are what lead to my successes and many more to come.
What is your morning routine?
I normally wake up and drink water while reading a book. As far as the wake-up time I’ve experimented with over the years. I have woken up as early as 5 am and as late as 10 am. For sure I can get more done waking up at 5 am, but I always asked myself why do I want to get more done? Does getting more done to make me feel more important? Instead of focusing on time, I focus on efficiency. When I’m working I’m working, not checking the phone or social media. These days I wake up anywhere between 7 am – 9 am. I grab a book, drink (water, sometimes coffee), and read for about 30mins to an hour in silence.
What habit or behavior that you have pursued for a few years has most improved your life?
I’m always learning. There are always courses, classes, books, or documentaries in my vicinity. It’s one of the habits that have made me what I am today. I love to learn and more importantly understand a different perspective.
What are your strategies for being productive and using your time most efficiently?
When you’re working, be working. Don’t check social media or any other distractions. The more efficient you are the more likely you don’t have to wake up at 5 am to “get more done.” Second, hang around people that have the same vision and passion as you do. If you love to learn then spend time around others that love to learn, this can significantly change your life when your inner circle is always exchanging meaningful and helpful information with one another. Lastly, make sure you read. Don’t fall into the “I don’t have time”, or “I can’t sit still and read”.
These are normally excuses for people who rather watch Netflix than read something that they need to. We always have time; we just decide to substitute reading with something else. You don’t have to bury yourself in a 30 chapter book every day, but something about reading makes our minds comprehend and analyze information better. I don’t know the exact science (I do, but want to leave room for curiosity), but reading can definitely help you stay sharp. Even if it’s only 20mins a day, read something that will help you improve your life.
What book(s) have influenced your life the most? Why?
The one book that started my entire journey was a book called “More Than a Hobby” by David Green, the Founder, and CEO of Hobby Lobby. Why? While going to college I wasn’t sure what I really wanted to do and at the time I was working at a hobby lobby part-time. I noticed his book while at the store one day so I purchased it and read most of it that night. It was interesting because he was from the same hometown I was from and after reading it I knew immediately that’s what I wanted to do with my life.
This was the first time I heard the word “entrepreneur” and haven’t looked back since. I changed my major to business and bought as many entrepreneur books as my part-time salary could afford. I wanted to become a first-generation entrepreneur in my family.
Do you have any quotes you live by or think of often?
I’m not a big quote guy because it’s difficult to understand an author’s intent or the true meaning behind their statements. We can take a good guess at what they meant and quotes can sound nice, but most of the time we assume what an author’s statement meant when they could have meant something completely different. Instead, I study the behavior and habits of individuals. Habits that I can pick up in my life that progress me. I measure individuals by their behavior and not necessarily what they say. Quotes can sound good but without the author living up to what they’re saying it doesn’t add much value to it.