Jon Sterling is an entrepreneur, author, and coach. He is a Managing Partner at, a real estate company that provides services for people buying properties in countries that are not their home countries. Sterling is also an occasional investor, avid traveler, and big-time real estate nerd.

Where did you grow up and what was your childhood like? Did you have any particular experiences/stories that shaped your adult life?

I am originally from the Midwestern United States where the general scene is being surrounded by people who are friendly, polite, and hard-working. I was taught from a young age that if you want anything in life, you have to work for it. I also learned that being polite and friendly is a great way to go through life, especially when confronted with difficult situations.

What is something you wish you would’ve realized earlier in your life?

Although I thought I academically understood it during my 20s and early 30s, I didn’t embrace the idea that there is more to life than “work.” For too much of my adult life, I made the mistake of prioritizing my career and career achievements over almost everything else. In hindsight, I should have prioritized some life balance and put more effort into things that aren’t related to work. We only get one chance at this thing we call life and it’s crazy to think that we spend most of our waking hours chasing money.

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

The belief that a college education is mandatory for success in life is one belief that just won’t die. That may have been more true a few decades ago than it is today, but the state of higher education in the US right now is out of control. The financial cost of higher education is part of the problem (especially when you have to go into heavy debt to get it) and the types of entry-level jobs available to recent college graduates are not very good for most majors. MANY of the successful people I know either didn’t attend college or barely made it through college with mediocre grades. I am a big believer in lifelong learning, but I don’t believe college is the only path (or the best path) for those who wish to be competitive in today’s world. Being buried in debt from the first day out of college is a heavy burden and keeps many people from taking risks and exploring their true potential.

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?

A few years ago, I was involved with a group of people who were engaged in some financial misbehavior at our company. I saw what they were doing and made my concerns known to the top executives at our company, but nothing changed from what I could see. It was extremely stressful for me because I felt powerless to fix what was an obvious problem and I still had to work with the bad actors every day. I made the decision to leave that group and they were eventually removed from the company, but I was long gone by the time everything was resolved. Even though it all worked out in the end, it felt like a lot of wasted time and effort on my part. The way I got through it was by staying true to my values and keeping myself focused on the things I could control. I couldn’t control the bad guys, but I could control where I invested my time and attention.

What is one thing that you do that you feel has been the biggest contributor to your success so far?

Reading as much as I can on as many subjects as possible has probably been the biggest contributor to my success. I read all sorts of books, articles, and blog posts on a wide variety of topics. The best part of this for me is that I am able to borrow ideas and make connections across disciplines that are totally unrelated, which helps me find creative solutions in my business. Having a broad spectrum of knowledge is also useful when speaking with people from all walks of life. Being able to have intelligent conversations with just about anyone is a byproduct of reading all the time, and has helped me build my business

What is your morning routine?

I don’t use an alarm clock to wake-up (unless it’s necessary to join a Zoom call or catch a plane). Prioritizing sleep has made a profound impact on my life. A normal day includes waking up between 6 am and 8 am, having some coffee while I scroll through my various feeds and respond to time-sensitive emails, doing some sort of workout, then eating and showering. The business-building part of my day starts after lunch, where I block time for outbound sales activities and content creation. I used to do all my outbound sales and content creation activities in the morning, but I have found that the hours in the early afternoon work best for that now.

What habit or behavior that you have pursued for a few years has most improved your life?

Keeping tight reigns on my diet has a profound impact on my health and well-being. The most interesting discovery with keeping a healthy diet is that most people in my world (especially those living in the US) have a completely warped view of what they consider “healthy” when it comes to food choices. Of course, those same people are from the most heavily medicated country on Earth, and they are part of the first generation in their country’s history to have a shorter life expectancy than their parents. But many of them want to tell me how I’m going to die early because I eat differently than they do and get my information from doctors outside the US. The US healthcare system is terrifying to me and I do everything in my power to avoid interacting with it. It’s not the best healthcare system in the world (not even close), it’s just the most expensive.

What are your strategies for being productive and using your time most efficiently?

I was lucky to have some great mentors early in my career who taught me how to prioritize my time. In simple terms, I use the 80/20 principle when deciding how to spend my time to be the most productive. It is clear to me that about 20% of my activities will give me about 80% of the results I want. It is easy for me to filter out things that are not going to contribute to my results, and I delegate or simply ignore those things. Learning how to say NO is the most powerful tool I have to keep myself productive.

What book(s) have influenced your life the most? Why?

Not Fade Away by Peter Barton is a great book. It’s about a successful guy in his 40s with a young family who gets cancer and eventually dies. You’d think it would be depressing, but the way he approaches his situation and life during that time is very insightful. The big lesson for me is that we are ALWAYS in control of how we respond to situations even when those situations are not ideal.

Do you have any quotes you live by or think of often?

“Stress does not exist without your participation.” This quote is one that I share all the time (partly to remind myself that it’s true). Stress is not a thing out there in the world waiting for you to grab it–it’s a choice. You can choose to respond to external events by feeling stressed, or you can choose to respond with a different emotion, like curiosity or excitement. It takes some practice, but it works like magic when you embrace it and make it a part of your life.