Reviewing all of your life areas and carefully crafting your annual goals can be a terrific exercise in going after your dreams, and it can also turn into a bit of a self-flagellation when we catch ourselves bemoaning where we are, longing to be somewhere different, and comparing ourselves to others both real and imagined.

From believing we “should” have sorted out our career by now to imagining we “should” already be married to the love of our life and making fat, healthy babies with them, for some of us, dreaming and annual goal setting can quickly turn into “shoulding” all over ourselves.

(I wonder if you can relate? I mean, I know I’m certainly not immune to this kind of thinking…)

So what’s to do about it? How can we challenge those self-critical thoughts that tell us we “should” be somewhere other than where we are?

I have two tools – two questions, really – that I want to share with you that might help you stop “shoulding” all over yourself.

Tool #1 for challenging the “shoulds”: Pressure test “should” v.s. want.

As my clients well know, “should” is basically a four-letter word in my therapy office.

Should essentially means we’re using an external marker, an outside expectation, versus being present to our own authentic desires.

When my clients use the phrase “I should be [fill in the blank]”, I’ll interrupt them and ask an important question, “Okay, you think you should be that. But is that what you actually want to be?”

So when you catch yourself shoulding on yourself, please stop and pressure test it by asking this same question: is it a should you imagine you’re expected to do, or is it a true, deep longing, an actual WANT of yours?

And pay particular attention to whether the “want” of that thing shows up as a thought in your head or a feeling in your body — maybe in your chest or belly. If it’s a head-centered thought of wanting, it’s more likely still a “should.” If it’s a sensation that’s coming from your body (anywhere below your head!), then it’s most likely an actual want of yours.

And if it is an actual want of yours, a deep longing, or even a jealousy that’s being triggered, that’s actually really good information for you!

I’ve written about this before but I honestly don’t think jealousy is such a bad thing. All feelings have information for us and I personally think jealousy tries to steer us (albeit clumsily) towards our soul’s deep longings.

So pressure test any shoulds that show up for you by asking yourself the question: “Is this something I think I should do, or is it something I actually want to do?”

If it’s not a true want, I invite you to drop it. Why waste your life energy wishing for or working towards something you don’t actually want in the first place?

But what if it is something you truly do want and you’re stuck comparing yourself against the progress of others imagining you “should” be further along, what then? Well, then there’s another question I want you to ask yourself.

Tool #2 for challenging the “shoulds”: Are we playing on a lifelong level playing field?

If in setting your goals for the new year or any time across the rest of the year, you catch yourself comparing yourself to others and wanting what they have and imagining you should be further along like those you see around you, you simply have to remind yourself of this:

You truly have no idea what anyone else’s internal experience is like, what their background is, or what their story is. It may be completely, utterly unrealistic to compare yourself to that person.

Almost all of us occasionally tend to compare ourselves to the people we see around us — colleagues, Facebook friends, old college classmates, LinkedIn connections — and we frequently judge ourselves as falling short in our career, our love lives, our bank accounts, our general level of competent adulting, etc..  

But the reality always is that we simply don’t know what other people’s whole life experiences are.

That gorgeous, smiley, yoga teacher who just became your neighbor and whose life you compare yourself to? You don’t know her story.

She may have had a healthy functional childhood, doesn’t struggle with her mental health, can count on a huge financial safety net and extensive social safety net, and may have had the advantage of adequate if not excellent teaching and mentoring from her functional parents, family friends, etc..

If this wasn’t your story or, moreover, if you have a background with any trauma, neglect, addiction, social anxiety, etc., you have to remind yourself that it’s simply not fair to compare yourself to someone who possibly didn’t have to spend so much emotional and mental energy recovering from her childhood simply to make it to a baseline level in life where she could even focus on certain goals.

And while this is a bit of a conflated example, my point here is that when you catch yourself comparing your life to those around you, you have to remember that you don’t know what their story is and that it’s utterly unrealistic to compare yourself to someone who probably didn’t have the same deck of cards you were dealt.

That’s why it’s critical to ask yourself this second question if you find yourself “shoulding” on yourself: “Can I be absolutely, 100% sure that this person that I’m comparing myself to has the exact same life-long playing field as me?”

And since you basically never know what another person’s lifelong experience has looked like, since you rarely know proof-positive if you and another person are working with an even playing field, I really invite you to drop the comparison and instead reflect on how far you’ve been able to come given your own particular circumstances and remind yourself that for all you’ve been through, you’re actually doing quite well. 

The only comparison that’s fruitful to make is, I believe, comparing ourselves today to ourselves a year ago, or five years ago, etc.. Compare yourself to you in the past – that’s the only comparison truly worth making because it’s the only fair comparison to make. 

So how to accept where you’re at while still giving yourself permission to strive?

Look, I think setting goals and working towards self-improvement and overall life progress is wonderful. I mean, I’m such a fan about it I wrote an annual planning and goal execution workbook about it!

I would never tell you not to not to set goals and dream big. But when your goal setting and your dreaming turns into “shoulding” all over the life you have and resisting your actual reality, that can create a whole lot of mental pain.

So first of all, always catch yourself when you begin to “should” on yourself using the two tools above. But then if you still find yourself unhappy with where you’re at, ACCEPT that. Actually accept that you’re not happy with where you’re at.

I’m not asking you to fall in love with your life if there are some areas that simply feel unsatisfying to you. I’m just asking you to at least accept it. Accept that you don’t like where you’re at and then move on. Either by creating a plan for going after the thing it is you want instead, or by shifting your focus to another matter in your life.

Resisting your actual reality can cause a whole lot of emotional pain. There can actually be a lot of relief simply in acknowledging and accepting that we don’t like where we’re at. 

From there, we free ourselves us to get curious about what we’d like instead, to clarify our authentic dreams and desires, and then to be curious about how we can make that happen. 

So bottom line: Challenge your “shoulding” of yourself using the two tools above, practice accepting your actual reality, and if you don’t like a part of it, by all means, dream of something different and work towards it. And if it still is not possible, if what you want isn’t going to happen for you, then, honey, you have to grieve that and then work with your new reality.

Now I’d love to hear from you in the comments below: What’s one way you stop yourself from “shoulding” on yourself? What’s worked well for you that might be helpful to anyone else reading this blog? Leave a message in the comments below and I’ll be sure to respond.

If you would like additional support right now and you live in California or Florida, please feel free to reach out to me directly to explore therapy together.

Or if you live outside of these states, please consider enrolling in the waitlist for the Relational Trauma Recovery School – or my signature online course, Hard Families, Good Boundaries, designed to support you in healing your adverse early beginnings and create a beautiful adulthood for yourself, no matter where you started out in life.

And until next time, please take very good care of yourself. You’re so worth it.

Warmly, Annie