In an ideal world, each of the obstacles in the air sandwich would have one and only one key that solved it. In that same ideal world, we’d only have one obstacle at a time in front of us. In this world, though, we often have multiple dominant obstacles applied to different projects, and we must use multiple keys to work through them. At the same time, you’ll rarely be in a situation where the lack of one key will prevent you from getting some headway when working through a project.

What follows is a rough guide for what go-to keys to start with when addressing different obstacles. It’s not that you won’t use others, but these keys tend to be the most effective at getting some leverage to roll the boulders out of your path.

Align Competing Priorities

Competing priorities are often the result of us not acknowledging our priorities and not seeing how our goals and plans end up at odds. Knowing that, the keys to align competing priorities are pretty straightforward:

  • Awareness. Get clear about what matters to you, claim those priorities, and acknowledge that, try as you might, your reach will always exceed your grasp.
  • Discipline. Keep first things first, even when it’s easy to buckle.
  • Boundaries. Establish structures and expectations that limit the influence of other people’s priorities.

When we think of clearing our own head trash, it’s normal to get a case of the “yeah, buts.” It’s often easier to rebut those yeahbuts by considering what you’d say to a friend grappling with the same head trash you’re dealing with.

Take Out Your Head Trash

While it’s true that head trash is most powerful when you can’t see it for what it is, seeing it doesn’t mean it just goes away. Just because something isn’t true doesn’t mean that it doesn’t work on you. These keys will help you clear out the head trash:

  • Awareness. Be aware of when self-defeating beliefs and patterns are present, and discern what’s real and what’s simply absorbed bullshit.
  • Courage. Have the backbone to challenge those beliefs, design experiments that mitigate the patterns, and accept the reality that your choices and responses have been cocreating whatever you’re experiencing.
  • Discipline. Stick with challenging beliefs, experimenting, and taking responsibility to change; courage without discipline leads to fits and starts rather than deep change.

Remove the No from No Realistic Plan

Before we dive into the keys that will help create realistic plans, remember that plans only create clarity, not certainty. Many people make plans and feel unsatisfied because they know what they need to do but aren’t sure that it will lead to success. Or they create a realistic plan and are scared they won’t be able to muster their resources to do what needs to be done, so then they try to walk backward toward the project so they don’t have to see what’s ahead.

In the next chapter we’ll see that we don’t do ideas — we do projects. But sometimes you’ve already made a plan, in which case you’ll need the following keys:

  • Awareness. Be aware of where you’ll fall down, where you’ll shine, and where you’re likely to bail on the project. We’ll address this in chapter 7.
  • Discipline. Stick with the plan when bright, shiny objects (BSOs) inevitably appear. I use “bright, shiny objects” as a shorthand for random and seemingly unlimited distractions we can spot and pounce on.
  • Intention. Have a clear, unmixed, and as-specific-as-useful goal or destination. As the novelist and philosopher Lewis Carroll said, “If you don’t know where you are going, any road will get you there.” We love to canvas all the roads in lieu of walking down one.

Overcome Too Few Resources

It’s very unlikely that you’ll be in the position where you have all the resources you would like to have to do your best work. The more success you create, the more your best work will scale up to match your new capabilities. Learning to be resourceful regardless of how many resources you have is a lifelong skill, and these keys will show you how to use whatever you have to the fullest:

  • Awareness. Focus on who and what you do have more than what you don’t have. Ask yourself, “How can I do this project without X?” and “What do I have that I’m not using to complete this project?”
  • Discipline. Efficiency requires discipline, and many of us aren’t using what we have efficiently. How might you better use the resources you already have?
  • Courage. Be courageous enough to commit more fully to fewer projects. We often don’t focus our resources on fewer goals and projects because we’re not sure that we’ll be successful with those projects and thus want to hedge our bets. The result is that we invest too little into projects to make them successful and we’re perennially scattered. How would you use your resources if you weren’t hedging bets?

Get Your Team to Work With and For You

An aligned team makes the difference between rowing in circles and having the wind at your back. Given that people have their own plans and can’t read others’ minds, it’s up to you to get them working with and for you. Here are the keys that will help with that:

  • Awareness. Be aware of what you really want, need, and dream to do and be; and be able to communicate this clearly to others. Doing so is harder than most people think it is.
  • Boundaries. Establish expectations, structures, and space to support your goals. Turn someday, someone, and sometime into a specific day, person, and time.
  • Courage. Be brave enough to take up space, ask for help, and stop being the martyr so people will like you.

Which Keys Do You Need to Practice More?

Your upbringing, education, experiences, choices, and preferences heavily influence which keys you cultivate and which could use some more practice. You may undercultivate or overcultivate a particular key in some areas over others. For instance, in a lot of areas, discipline is easy for me, but I’ve always struggled to build a running habit or avoid potatoes. Similarly, I have no problem mustering the courage for public speaking, sales, or sharing my work in public, but I’ll only sing and play guitar in front of people I really trust to see me when I’m that vulnerable despite getting enough feedback that I’m good enough to not be embarrassed.

In my experience, though, most people know which keys they’ve cultivated and which they need to practice more. Remember, the keys are just habits and practices that we get better at the more we use them; they’re not innate talents we’re born with (or without). Telling yourself that you can’t draw boundaries, for instance, is choosing not to practice doing so.

The more you practice the keys, the easier it will be to start finishing your best work and thrive. The keys are both the obstacle and the way to your best work, depending on what you choose to practice. And, speaking of choosing to practice, it’s time to practice the five keys and choose an idea that matters to you.

Originally published at


  • Charlie Gilkey

    Author, Speaker, Business Strategist, Coach

    Charlie Gilkey helps people start finish the stuff that matters. He's the founder of Productive Flourishing, author of the forthcoming Start Finishing and The Small Business Lifecycle, and host of the Productive Flourishing podcast. Prior to starting Productive Flourishing, Charlie was a Joint Force Military Logistics Coordinator while simultaneously pursuing a PhD in Philosophy. He lives with his wife, Angela, in Portland, Oregon.