Overcoming “Should”

Overcoming “Should”


It’s a word I know well. I hear it in conversations with my clients and I know it as a constant personal companion.  

  • I say it when I don’t want to disappoint people.

  • I say it when it feels easier to “‘go along”’ than “‘go against”’ what everyone else seems to think.

  • I say it when there is a conflict between what I know is best for me and what I am hearing “makes sense” externally.

Should has always been there, but it’s having a particular moment right now in this time of deep uncertainty. It lives silently in the back of our minds, quietly gnawing on our focus, draining our energy and eroding our trust in ourselves. Here is a sampling of what I’ve heard just this week alone:.

  • I should get back to studying for the CFP on the weekends.

  • I shouldn’t be so tired at night.

  • I shouldn’t be so annoyed with my kids/spouse.

  • I shouldn’t feel so overwhelmed. People have it a lot worse.

  • I should take this role even though I don’t want it. I might not get another chance.

Should often shows up in coaching conversations disguised as a decision that clients are grappling with.

Here’s how the conversation usually goes:

Me: “What’s the focus of our session today?”

Client: “I need to make a decision and I don’t know what to do…”

It doesn’t take long to understand that they aren’t actually trying to decide something so much as convince themselves of something. What they really mean to say is:

Client: “I actually am really clear about what’s right for me, but it feels uncomfortable/career-limiting/disappointing to others. Help me convince myself about what I should do rather than what I know is right.”

Should ignores our inner wisdom, that part of ourselves that knows what is right, not just for ourselves but for others, too. Too often we turn toward what is expected, logical and practical, ignoring the quieter inner knowing that is harder to put into words. We override want for should, making dishonest decisions that will shape the future. And when we find ourselves in that future, we wake up and wonder, “How did I get here?”

Should denies our humanity – our tiredness, our confusion, our worry, our insecurities. Should insists that we have more than enough time, energy and willpower to do more. And yet, now more than ever, it is our honesty that will create a new reality. Will that be a reality based on what we know to be true or one based on our fear-based should’s? What is the should knocking at your door right now? Can you lay it down, maybe just for this week, and give yourself permission to be human in all of its glorious imperfections?  

As the poet Mary Oliver says, “You only have to let the soft animal of your body love what it loves.” 

Starla Sireno is an Executive Coach in NYC. She partners with leaders to more effectively navigate the complexities of their roles, increase their influence at all levels, and hone their interpersonal communication skills in order to become more impactful both internally and in client-facing roles. Inquire how you can work with Starla or her team.

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