The Five Keys to Overcoming the Air Sandwich

Learn more about the five key ways that you can overcome the air sandwich, including how to build boundaries, stay disciplined, and more.

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When we have the urge to address the air sandwich, we naturally reach for to-do lists, plans, apps, and books, but that often fails because, at best, those tools address top-level issues. The challenges filling the air sandwich rest a level below those issues. For instance, there’s nothing intellectually difficult about planning our day; the challenge lies in following that plan, and there’s no killer app, system, or big idea that’s going to help us do that.

What will help us do that is discipline and boundaries. The core keys to unlocking our best work include:

  • Intention
  • Awareness
  • Boundaries
  • Courage
  • Discipline

These keys are a modern-day synthesis of Aristotelian virtues and habits. I’m using virtue in the same way that Aristotle used it, in the sense that it’s a practiced behavior that we can over- or under-cultivate. Either cultivation extreme leads to diminished thriving; the goal is to find the middle way between these extremes. The millennia-old challenge of applying the right key in the right amount remains just as challenging as it’s always been, but if the air sandwich shows us which doors need to be unlocked, we at least have five keys that can unlock any of those doors.

Let’s take a look at each individual key before we start to see how they can be used to address the air sandwich.


Start with why. Begin with the end in mind. Consider where you want your life to be in three years. These common phrases all point to the same thing using different language: intention.

Most of our conversations about purpose are anchored to intention. The assumption is that if we know our purpose, we’ll be more intentional about how we spend our days and life. If we don’t know our purpose, then our actions can feel random or meaningless. (So the story goes — a lot of purpose-seeking is deeply rooted and nicely camouflaged fear of uncertainty.)

Intention comes up in nearly every conversation I have with clients and students because we’re discussing planning. To make a plan, you have to set a goal. Plans and goals are intentions about the way you will (and won’t) use your time, as well as what is and isn’t important to you. Many of us don’t do our best work because we haven’t set a clear intention to do it, especially when we zoom down to how we’re planning our days.

Under-cultivation of intention is easier to grasp and see in ourselves and others than over-cultivation of intention, at least at first blush. But when we look around and see how stricken with anxiety people are because they’re so focused on achieving certain goals by certain times by certain ways, it’s easy to see how much people’s suffering comes from being attached to the world matching their intention. The world has an annoying way of not doing what we want it to, but as the thirteenth-century Persian poet Rumi said, “Yesterday I was clever, so I wanted to change the world. Today I am wise, so I am changing myself.” (Afzal Iqbal, The Life and Work of Jalal-ud-din Rumi (Selangor, Malaysia: Other Press, 2014))

But for intention to have any grip, it has to be about something. One of the chief reasons we’re using a project as an anchor for changing our work is because it gives us a focal point to be intentional about how we’re specifically using our time, energy, and attention on the project. The project is analogous to focusing on our breath or a specific feeling in meditation.


“Know thyself ” is a cardinal maxim that appears in foundational philosophies from around the world, from Socrates to Lao Tzu to the Buddha to the Bhagavad Gita to the Bible. In each case, calamity comes to those who don’t know who they are.

Setting existential considerations aside, we can still see how important awareness is. For instance, when we’re planning to do our best work, we should base our plans on what kind of energy and how much time we have available to us. Deep, creative, and focused work requires a certain kind of energy. Some of us are especially cantankerous or especially friendly at certain times of the day. And so on.

Awareness is required to know what your best work is and to notice how your emotions and presence shift when you’re doing your best work. A rare few of us seem to know exactly what our best work is, whereas many of us have to pay attention to whispers in our minds and light touches in our hearts to find our way to it. Cultivating the awareness to pay attention to when we’re lit up, wondrous, and in flow, or when we’re stifled, numb, and full of dread, is critical to growth.

Much of this book thus far has been about creating awareness. Seeing the challenges and opportunities of the project world lets us embrace swimming in the ocean of change rather than being crushed by its waves. Seeing what’s filling the air sandwich helps us identify how we might mitigate those challenges. You can neither use nor beat what you can’t see.


Most conversations on boundaries discuss them in the context of social boundaries. Those conversations typically focus on the importance of limiting what behavior you’ll accept from others and how you’ll respond to create space away from them and those behaviors. While that’s important, it’s a very limiting view of boundaries that often leads to people not wanting to discuss boundaries; they see them as being about pushing people out or opening the door for them to be pushed away from other people.

We can take a more expansive view of boundaries, though. There are positive and negative boundaries, with positive boundaries creating space for something and negative boundaries creating space from something. The aforementioned social boundaries are negative boundaries. A positive social boundary would be the space we might create for our kids, partner, or friends. While it’s true that we often have to push something away to create space for something — that is, to create a positive boundary, we often have to simultaneously create a negative boundary — it’s the intention that matters here. Many people’s negative boundaries collapse because they aren’t clear what they’ve made that space for.

If you don’t set up boundaries for your best work and from the things that keep you from doing it, your best work will always be displaced by other things. Setting up and maintaining boundaries can be hard — it’s not just you. But like so many things in life, it’s worth it.


There’s an abundance of smart, compassionate people with ideas worth finishing and ample know-how who can’t get momentum on those ideas for the simple reason that their courage is lacking. Courage is more important than talent when it comes to finishing what matters most, for courageous action can build talent, but fear keeps us stuck in the confines of yesterday.

I’m aware that courage conjures heroic stories such as soldiers in battle, firefighters saving people, or people standing up against machines of injustice. For many people, a courageous action is something that ends up on the news or in books and movies.

While it’s true that those are acts of courage and should be commended, typifying larger-than-life heroic actions as courage can too easily mask the everyday courage we need to thrive; it also gives us an easy out.

Every day that you make a choice to do your best work is a day you practice being courageous. Every day that you initiate or participate in a hard conversation or maintain a boundary is a day you practice being courageous. Every day that you dare to share your best work with someone is a day you practice being courageous. Every day that you lean into a “stuck and not getting anywhere” phase of work rather than run from it is a day you practiced courage.

Of course, it’s also true that every day you punt that hard conversation, avoid your best work, or run from a stuck project is a day you practice cowardice and make it easier to take the
cowardly route the next time. No one wants to be called a coward or wear the mantle; it’s within our power to avoid that fate.

When we properly identify lack of courage as what’s keeping us from doing our best work and thriving, it allows us to ask more powerful and pointed questions about how to go forward. For instance, when we mistakenly believe we have a knowledge gap, we put research on our action list. But when it comes to our best work, there will always be a chasm between the information we’d like to have and the information we can acquire, for both the inputs and outcomes of our best work are uncertain. Our best work changes us and the world in ways that no present information can fully capture.

In a similar vein, if we think we have a competency or talent gap — which we more often articulate as not being good enough — then it’s really easy to spend time in safe learning environments that more often reinforce that we’re not good enough than push us to grow in ways that propel our best work forward. Years and scores of thousands of dollars are spent getting degrees and certificates that fundamentally don’t cultivate people’s courage such that they can thrive in the professional world.

Humor me here. Think about one of your top three most important projects. Ask yourself two questions about the project:

  1. What’s the smartest next step on this project?
  2. What’s the most courageous next step on this project?

Your answers to these questions will likely be wildly different if you’re being honest with yourself, not just in how you feel about them but also in how you would go about taking that next step. The reality is that your smartest next step is probably the most courageous next step. We don’t need more geniuses; we need more courageous people. (Tweet this.)

If you’re doing your best work, you will face a continual stream of chances to back down when fear shows its ugly head — and fear is strongest when it doesn’t show its ugly head and instead lurks, unseen, in the background. Information, know-how, talent, or general readiness will insufficiently arm you to step forward. Courage and the faith it inspires are your only weapons and armor.

Luckily, it’s all you need, and the more you use it, the stronger it gets.


That a disciplined person with much less talent and experience can brute-force their way into success inspires no end of frustration for us creatives. While we’re quarter-working on the ideas and interests that we absolutely can’t let go of, they have advanced their “too narrow,” “too specific,” “too unoriginal” (by our evaluation) work a few steps forward. In response, we go back to not working even harder during the day and eating more ice cream in the evenings.

At a deep level we know our frustration isn’t really about the disciplined folks grinding their way to success but rather our own discipline. We know how much more we’d thrive and be happy if we were disciplined. Yet we often feel constitutionally wired to not be disciplined, so much so that even the word discipline is something that provokes a visceral reaction for many of us. (I suspect that you’re only still reading this section because your curiosity and self-awareness has overruled the grimacing and urge to skip on to something more comfortable.)

Our innate talent, creativity, and drive combined with discipline are what make us forces of nature.

Without discipline, though, we can be miserable, petty, and unfulfilled. Discipline channels our energy into purposeful, constructive action; a lack of discipline diffuses our energy into destructive outlets — and what we destroy the easiest and most often is ourselves.

Habits are discipline made automatic, but they’re made automatic in the beginning and maintained via discipline. Morning routines are an example of discipline made automatic, but effective morning routines don’t happen on their own. You have to set up the boundaries that create them and then stick with those boundaries via discipline.

Zooming up, picking fewer projects to finish also requires discipline. You’re carrying too many projects because you’ve said yes to so many that you’ve effectively said no to making massive progress on any of them.

A major part of our resistance to discipline is that we more often associate discipline with punishment or pain than with freedom or happiness. This association is understandable since, as children, for a lot of us, discipline very often meant punishment or pain. Those experiences aren’t the totality of discipline, though. The reality is that the happiest and most successful of the creatives among us are often the most disciplined. For instance, a near-universal practice among the titans and mentors that bestselling self-help author Tim Ferriss has interviewed is either a meditation practice or an exercise regimen. I’ve seen the same patterns among my high-achieving friends, colleagues, and clients as well. Discipline undergirds those practices and regimens, and most people report that it’s those practices and regimens that prepare them to do their best work.

An additional upshot to discipline is that it limits the decision fatigue that plagues so many of us. A consistent morning routine eliminates scores of choices every day. Habits remove other choices. Time blocking removes more choices about when you’ll do what type of work. Every decision removed from a day frees up mental and creative energy that can fuel your best work.

We’re happiest when we’re doing and finishing our best work, and discipline, rightly applied and cultivated, allows us to do more of our best work. As paradoxical as it sounds, discipline creates freedom and happiness precisely because it’s what sets the foundation for us to do the things that matter most.

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