If a stranger had walked up to me on the street when I was 19 or 20 years old and said, “Blaine, these are the only 5 questions you’ll ever need to ask and answer for yourself if you want to lead a fulfilling and meaningful life”, I’m not exactly sure what I would’ve done back then, but the 52 year old me of today hopes that younger version of myself would listen and takes notes. 

5 questions! That’s it, just 5. Not 4, not 7, not 6, but 5 questions to have a fulfilling and meaningful life. Of course, if we’re being serious, 5 is an arbitrary number when it comes to the most important questions about life. The point is that, over time, if we’re awake, alert, and documenting our lives along the way, we’re bound to gather questions that have been asked of us over the years that have more meaning than we initially think. The 8 questions I’m about to share with you in this episode were that for me. These are questions that were given to me from a variety of different sources over the years, but one’s I’ve found myself coming back to over the years and contemplating more deeply. 

Without further ado, let’s get into them. 

Question number 1: 

Who are you spending time with? 

We’ve talked about this one many times on this show, so it shouldn’t come as a surprise. It’s not a complex question by any means, but a vital one to be sure. Who we spend time with is important because, as management and leadership author, Bob Sutton, said, ‘choose wisely who you spend time with because you will become more like them, they won’t become like you.’ (paraphrased) 

There are only 3 options for how the people we spend our time with can affect us and it’s important to take note and really think deeply about everyone we grant access to our lives. The people we spend time with are either making us better, they’re making us worse, or they’re keeping us in the same place. Better, worse, or same, which equals no growth. The first two are easy. We know instinctively if somebody is making us worse. We know instinctively if somebody is making us better. We may not always make the right choices about those people in the moment, but there is a part of us that knows. 

I’m sure we can all think back to our grade school, high school, and college years and come up with a list of people we spent time with that were definitely not helping us be better in the moment. They may not have been bad people, but when we were with them we may not have made the best decisions. Heck, I was probably that person for some of the people who hung out with me back then. I was the one encouraging them to do some of the stupider things we chose to do. Thankfully, we all survived and are better for the lessons, but only if we actually took the time to learn the lesson and make better choices going forward. 

The reality of life as a human being is that we are all big walking balls of energy, and we’re always in the process of transferring and trading that energy with the people in our circles. We’re either absorbing the energy from those around us, regardless of whether it’s good or bad energy, or we’re giving away our own energy to those around us. For those of us who are more introverted, we’re likely giving away our energy more often than not. The extroverts tend to absorb energy from other people, meaning they get more energized being around others, even as they’re giving off their own energy. 

Regardless of how you’re wired, this is one of the most important questions to ask yourself on the regular. Are the people you’re spending time with averaging you toward where you want to be in life, or are they slowly moving you away from it. One of the most insidious forms of this is those who are keeping you the same. They’re not moving you forward, but it doesn’t feel like they’re moving you away from it either. For some reason, by you spending time with this person (or people), you’re simply not changing in any significant way. Be on the lookout for all three versions in the people you spend time with. 

Question number 2: 

This question is a two-part question: Is this in my control? What am I doing about the things that are in my control? 

I love this question! This one question alone has allowed me a great amount of freedom over the years because it forces us to assess how many ‘effs’ we’re giving to things that we have no control over. We say it all the time, we have limited time and attention available to us, and there’s an opportunity cost calculation that has to be done every time we choose to focus on something. As soon as you choose to collapse your choices down to one thing to focus on, you’re deselecting every other option. When you choose to focus on something that is beyond your control, you’re deselecting the option to focus on a variety of things within your control. 

Just look around at what most people are complaining about on social media and you will see this one in action. Most people are complaining about things that are outside of their control, and the action they’re taking by complaining about it online is, in a way, answering the second part of the question: What am I doing about the things I can control. If you’re complaining about things outside of your control, you’re wasting your most precious resources, which are your time and attention. 

Ask this question daily if you really want to see and feel a shift in control over the more important things in your life. When you shift your mindset to focusing on what is in your control, and away from the things outside of your control, your energy flows differently, your mood changes, anxiety goes away, and you can quickly move to tackling things you can actually have some impact on. 

Question number 3: 

Does this actually matter? 

This question flows naturally from the last one. When you can start to shift away from giving attention to things outside of your control, you’re starting to free yourself up to begin asking this next question, which is, ‘does this actually matter?’ 

If you began to look at your day and what you spend the majority of your time doing, you’d undoubtedly find a variety of things you do that simply don’t or shouldn’t be done at all. We can chalk it up to the tyranny of the routine, which is the insidious loop of activities we often let our habits bully us into that keep us in a cycle of doing things simply to do them. The cold reality is that many of the things we do in that tyranny of routine simply don’t matter in the bigger picture. The problem most people face is that they’ve never really taken the time to think about what matters and what doesn’t. If you don’t have some kind of system, even just an informal mental model of what is important to you and what isn’t, not only will your routine take over, you’ll inevitably succumb to what’s called the tyranny of the urgent. 

The tyranny of the urgent is the cacophony of noise and demands coming at you screaming for your attention and energy. The problem is that the vast majority of the urgent things demanding your attention aren’t important, and almost everything that you would call important if you took some time to really assess, aren’t urgent. Ask yourself daily, and with everything that comes across your desk and demands that you take notice, ‘does this actually matter?’ My challenge to you is to really qualify the word ‘matter’ and make the definition as strict as possible. 

The goal is to get to the point where very few things really matter in the grand scheme of things. That doesn’t mean you just stop doing stuff like paying bills, answering emails, and attending to the little things. It simply means that you become much more discerning about what gets your attention and what you delegate, automate, or eliminate. If you want to lead a life of meaning and significance, ask yourself often, ‘does this really matter?’ 

Question number 4: 

Who is this for? 

Another super important question to be asking, at least twice per year, in my opinion. What does this question mean? What is it asking? This question is simply asking for us to get clear on who we’re creating whatever it is that we’re creating for. If you have never thought about, and then written out who your ideal client and customer is, you’ll think anybody offering you money is a client or customer and they simply can’t all be. 

Everyone listening to this has likely experienced accepting an appraisal order, or working with a client in some way that turned into an absolute nightmare. Everybody is not your ideal client or customer, they simply can’t be. Until you get very clear about who your product or service is actually for, and what kind of clients and customers you’re trying to attract, you’ll inevitably end up wasting some of your time and life energy dealing with people and companies that are not for you, and for whom you should not be for either. 

Take some time to write out who, in the most ideal scenario, you’d like to be working with and creating for. I encourage you to know who your market of clients and customers really are. Who is your ideal client avatar? What do they look like, act like, how do they make decisions, what's important to them, what are their fears and worries, their dreams and aspirations, and how do they prefer to be treated? These are all important questions to ask in business because the more clear you get on those questions, the more you'll see those types of clients arriving on your doorstep. What also happens when you get clear on those questions is that you start to really see who you're not for, and who is not for you! 

Question number 5: 

To be or to do? 

Alright friends, last question for this episode, and it comes from Col. John Boyd. Col. Boyd was one of the most important military strategists of the 20th century. He came up with what became known as the OODA loop, which stands for observe, orient, decide, and act. We don’t have the time in this episode to go into the OODA loop and how it applies to life and business, but I always encourage listeners to look into and see if you don’t find it as interesting as I do. 

Nevertheless, this last question from Col. Boyd has been in my list of vital questions for at least 20 years after first reading it. It comes from a story about a speech Col. Boyd was giving to a classroom of fighter pilots and he was essentially asking them what mattered more to them, to be a rockstar and soak up the credit, or to create a lasting impact. He was asking them if they are trying to be an important person or do they want to accomplish important things. 

I’ll end this episode with that speech from Col. Boyd. Here’s what he said to those students in that classroom: “One day you’re going to come to a fork in the road, and you’re going to have to make a decision about which direction you want to go.” He raised his hand and pointed. “If you go that way you can be somebody. You will have to make compromises and you will have to turn your back on your friends. But you will be a member of the club and you will get promoted and you will get good assignments.” Then Boyd raised his other hand and pointed another direction. “Or you can go that way and you can do something — something for your country and for your Air Force and for yourself. If you decide you want to do something, you may not get promoted and you may not get the good assignments and you certainly will not be a favorite of your superiors. But you won’t have to compromise yourself. You will be true to your friends and to yourself. And your work might make a difference. To be somebody or to do something. In life there is often a roll call. That’s when you will have to make a decision. To be or to do? Which way will you go?” 


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