Banish Your “Should” List

We live in a time where it seems like everything we do is a culmination of other people’s agendas, a time when we’re unconsciously following someone else’s idea of what we should be doing with our lives, our businesses, our relationships—you name it. Is this by accident? As children, we’re conditioned to look to everyone else for the answers. If we’re “good little children” and do as we’re told, we’ll succeed in life. Our teachers and parents told us what to read, how to act, and outlined what choices to make to achieve the fabled “American dream.” And while some of this can be seen as necessary, it also places many intended and unintended expectations on us that can leave one feeling overwhelmed, exhausted, bored, and sometimes apathetic.

And while the wisdom and lessons learned from our forebears are an invaluable well of knowledge and insights, we’re rarely given the space to check in with ourselves and examine what pieces of that wisdom resonate. Instead, we come up with an ever-expanding list of things to do.

Recently, while coaching a client, she kept repeating the word “should” repeatedly as she described what was holding her back in her business. I should be doing this. I know I need to be doing that. I should be doing this so that I can… She was left paralyzed by her list. As a doer by nature, her inaction had turned into anxiety, guilt, disappointment, and shame from living out of integrity herself.

How many things on her should-list resonated with her and would empower her to move closer to her goals? She had a massive list of things to do that she was either procrastinating on or didn’t want to do.

Interestingly, the word “should” is almost always used to describe a demand, naturally creating resistance. How many times have you heard an idea and got so excited that it never had the chance to get on a list? Now think of a time when someone told you this is what you should be doing. A different receptivity, in most cases.

What can you do if this is something holding you back? Here’s a framework that allows you to take a step back, slow down, and take stock of your should-list. This exercise aims to help you gain clarity around what on your list is what you want to keep versus what you can say not to to move forward in your business (life, too!).

Getting Started

Before you get started, let's not make this exercise another should, but something you could do to gain clarity. Please note that each step in this framework builds on the last. You’ll need space to write. Digital mediums are the easiest to work with, but pen to paper is ideal. Either way, each subsequent step will take you back to the start of your list.

The Framework

So, what’s on your should-list?

_{Step One:} Write down your list of shoulds.
What should you be doing?
These can be anything, but try to think of the things you’re constantly thinking about, regardless of whether you’re doing it. This step can bring on a sense of catharsis, but you're not done. Keep going. Take as much time as you need at this initial step. Sit with it. To give you a rough idea, this phase in the framework yielded 100 shoulds, and it took my client a week.

_{Step Two:} Write down where each "should" originated.
Don't hold back here, be honest and sit with these questions. This can be one of the hardest steps, and it doesn't have to be done all at once. I took over a week to reflect, meditate, and breathe into some of these before I could get a sense of where they came from. Also, it's OK if it doesn't have an origin, not everything can be traced to a specific memory, and that's OK.

Ask yourself these questions to get you started:
When was the first time I thought this?
Who told me this?
Where did it come from?If no one told me this, what sparked this directive or narrative in me?

_{Step Three:} Going back to the beginning, and answer the following:
How does this "should" make me feel today?
What will happen if I don’t do this?
Conversely, what will happen if I do it?
How will I feel?

_{Step Four:} Finally, read through each should on your list from steps one to three.
Ask yourself, do I want to do this? Does this resonate with me and my goals?
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I’ve found the best way to do this (at least the first round) is through speed. Read through the list, ask yourself the question, and immediately write down what comes to mind: yes or no. Don't think further or judge the answer; just go with the first answer that pops into your head.

If you're having difficulty beginning this exercise, visit the basics. Consider things like: I should brush my teeth. I should wash my clothes. I found that once I started, no matter how slow or basic or silly I was feeling, I eventually got into a rhythm, and then everything started to come freely.  

Try not to judge, overthink, or criticize as you write. The idea here is just to let them out and get them down on paper. If you find yourself saying anything like, “this is stupid, or this is silly," bring yourself back to the task at hand and move on to the next. Again, we're trying not to judge what comes up.

Some things to note about this exercise:

• ‍This is not a quick exercise (my client had over 100 in the end). It can get really deep. So I recommend you get comfortable with being uncomfortable with what may come up.
• You’ll get what you give. Putting in the work will yield the best results.
• If you end up with a list that isn’t any shorter, consider what’s holding you back from taking action. How can you turn this list of shoulds into a list of accomplishments or a list of "coulds"?
• Avoid this trap! Remember my client who had over 100 to explore? When she got through step one, she felt a release, a catharsis from getting them out. This will likely happen, but don't let this fool you; you have just begun the work. Put in all the work.

Once you’ve completed this exercise, it's time to start thinking through what steps you can take and what little wins you can achieve to build excitement and momentum for yourself.

Hopefully this can help you stop shoulding all over yourself and start doing things from a place of choice.