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I’m currently at war. With a word. It’s “should.”

I’m more than familiar with Shoulds holding me back from being happy in my career. For years I worked hard, moved up the corporate ladder and met the success I was after but was ultimately unfulfilled once I got there. All those things that should have made it all worth it, weren’t. That was annoying.

Shoulds can hold us back from making choices that feel right to us. Freeing ourselves from their trap can result in more fulfillment and happiness in our careers.

How are the Shoulds in your life?

Many of my clients can relate to this. The truth is, it’s ingrained in us to push through, to keep our heads down, to expect sacrifice in order to get what we want. Many of us see that hardcore work ethic as a badge of honor. Myself included.

Don't Let This Determine Your Career Happiness

What if there were another way?

The worst part about Shoulds is how we hold tight to them.

They give us an excuse for all the times we’ve chosen work over friends and family, all the times we only slept 4 hours because we HAD to get that project done, for the times we’ve taken tons of shit in order to get a promotion that then wasn’t what we wanted after all.

For the times we sold out in order to get ahead.

Shoulds become a security blanket that we don’t love but we almost need. And when we see someone else holding onto theirs, it gives us comfort in our attachment to our own. “Ah, you too do nothing but work at the expense of your happiness and sanity? Me too. I respect that (read: please respect me.)” Kindreds.

As my Dad always says, 2 wrongs don’t make a right.

The cold hard facts

Should is a bully, a mean girl. She tells you how to dress, what size to be, how to present yourself, what to do with your time, how to act. She’s a dictator. And she’s a nasty B.

As the mean girl, Should pressures you when your head says “You know what, I don’t want that promotion even though I’ll make more money.”

She counters with “You can’t change your mind now! You must not be serious about your career. Sheryl Sandberg would be disappointed.” She lays it on pretty thick.

Yeah, she’s terrible but she’s not 100% wrong- those things she’s pressured you into chasing can pay off.

The job you’ve worked tirelessly for does look good on paper and may really impress at your college reunion. The 1000 calories she suggests you take in each day do allow you to squeeze into your favorite jeans…never mind you’re moody as hell and haven’t had a carb since the late 90’s.

So it depends: do you want to be miserable living by someone else’s rules, or do you want to be the one driving your own decisions?

In my opinion, Should is not a lifelong mate. Eventually we have to face her head on.

It’s time to make new friends

It’s easy to be pressured by how we should live, what our career path should look like, what our post-baby body should look like (by the way, Stars are not just like us. Just sayin.) but it doesn’t mean it’s right for each of us.

We have to carve out our own path and be confident enough in it not to compare those choices with how we should be living.

This is extremely freeing.

It’s time to let go of your relationship with Should. Don’t worry about her. There will always be another person out there who won’t be able to stand up to her and she can focus all her time on that sad fellow.

You’re not alone

We all fall prey to this little devil. It’s wasted energy to think about how you should have responded to the Shoulds all your life. You can only look forward.

Here’s an exercise I do with my 1 on 1 clients to help them get rid of their Shoulds and to highlight what’s truly important:

Step 1:

Get out pen and paper and list everything you should be doing.

For example: going to the gym daily, making dinner, having kids, going after the promotion, making _ $, buying a house, sending birthday cards, etc.

Write down everything your family, friends, society, the media says you should do. List them all, even the most ridiculous. Anything that pressures you even in the littlest way.

Step 2:

Next make another list of everything that matters most to you. Your true priorities: family, stability, kids, your health, going back to school, having _ in savings. Be as specific as you can.

Step 3:

Narrow those priorities down. You can only focus on so much at any given point. Pick 5-6 where you can focus your energy. What actions need to be taken regularly for you to focus on those things? Those are the only Shoulds allowed.

Everything else can be moved to the Should list to be done if you’re suddenly blessed with free time and still want to do them.


What’s left in that second list is what you’re choosing to focus on. These will dictate your decisions and what you say yes to. The only Shoulds that can stay are those that’ll get you closer to your priorities.

Who cares if you get to the gym everyday if you still feel good? Who cares if you have matching furniture? Who cares if you buy cookies for your kid’s last day of school party instead of making them? Who cares!? If it’s not you, then don’t do it!


Eliminate 2-3 Shoulds from your life today.

Embrace the mindset that you are the only person allowed to make a Should demand. You know how you feel, what you have time for and what really matters. This isn’t about making everyone else happy or presenting your life as something it’s not. It’s about being confident and at ease in what’s important to you and protecting those things with all your might.

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Do those things as best you can. Really kill it. That’ll fulfill you more so than half-assing all those Shoulds on your list and resenting your life for having to do so.

What Shoulds are driving your life? Can you eliminate any today? Let us know in the comments below! Together we can ban Should!

If you know others who may like this article, please share, like or tweet it!


 Anne Omland is a career development expert, writer and mentor. She uses her years of experience as a VP for a Fortune 500 company to share all she knows from the “other side” of the table. Her mission is to help ambitious women create corporate careers that are sustainable, mindful and purposeful. Seen as a career stylist, she can help you customize your career to fit your lifestyle perfectly. Click here to inquire about working with Anne.  
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  • Laura Carmody June 18, 2014, 4:52 pm

    I love the way you write!
    Focusing on the “cans” is so much more rewarding than those pesky “shoulds”
    I’ve seen Mean Girls enough times to spot a “should” a mile away!

    • Anne Omland June 19, 2014, 1:04 pm

      Thanks Laura! I love Mean Girls…the movie, not the actual people. But you knew that :)

  • Ana Verzone June 18, 2014, 5:03 pm

    Amen, sistah! Two of the bravest things I did were going against Shoulds. Divorcing my super nice, handsome head-neck surgeon husband and deciding not to complete the doctoral program of the top school in the country that I had been accepted to. That took balls. The cool realization was that if I had honored not doing the shoulds even earlier on, I would have never gotten engaged or applied to the program. I’m still learning;) Thanks for the reminder!

    • Anne Omland June 19, 2014, 1:03 pm

      Awesome, Ana!! I love it. And agreed, it definitely takes balls. You’re awesome. Thanks for your support! x

  • Julia June 18, 2014, 6:15 pm

    Great article! These days, I’m pretty good at not having too many “Shoulds” in my life. Whenever I followed my intuition and left a “Should” behind, my life changed to the better. You got to have nerves, but it’s SO worth it. Will definitely give your exercise a go!

    • Anne Omland June 19, 2014, 1:02 pm

      I love this, Julia! Our intuition usually knows what’s right, it’s our brain (and this case the “shoulds” hanging out in there) that hold us back. Thanks for your comment!

  • victoria m. June 18, 2014, 8:13 pm

    I am not sure where I read a similar argument about shoulds… and I love this because it is SO true… shoulds are really a reminder of what someone else wants from you, not what YOU want for you. Your exercise looks great and will definitively give it a try! Thank you for sharing it.

    • Anne Omland June 19, 2014, 1:00 pm

      Thanks Victoria! I hope it’s helpful to you.

  • Bremda June 18, 2014, 8:28 pm

    Anne, I’m going to do this exercise tomorrow. All my life, should was my biggest enemy! In fact, I stayed in a very lucrative career for much longer than I should have because of should. NO more!

    • Anne Omland June 19, 2014, 1:00 pm

      I can SO relate, Brenda! I did the same. Good luck with it!

  • Stacey June 18, 2014, 8:35 pm

    Avoiding the “sh” word can be such a game-changer for so many people, my clients included and myself. I love the way your remind people to connect back to their core values to help narrow down the “should” list to 5 or 6 important areas to focus on. I will often use the word “choose” to help me take ownership of my decision…I can choose to do the laundry or I can choose not to! Thanks for presenting this topic in a new and fun way!

    • Anne Omland June 19, 2014, 12:59 pm

      Thanks, Stacey! I’m going to implement your idea of using “choose.” Love that!

  • Yvelette June 18, 2014, 8:50 pm

    This is a great post and exercise. I have many shoulds to get rid of. It is a great way to focus on what is important.

    • Anne Omland June 19, 2014, 12:58 pm

      Thanks Yvelette! Glad it’s helpful :)

  • Lily June 19, 2014, 5:56 am

    I like for everything in my business to be enjoyable, at least on some level. So one thing I’ve been doing when looking at my “should” list is ask myself how that project could be made easier. Sort of a “what if?” Once I explore it from that angle, I can more easily cross things off my list, prioritize, or delegate it to someone else.

    • Anne Omland June 19, 2014, 12:57 pm

      I love this. Great tip, Lily. Thanks for sharing!

  • Sabrina Bolin June 19, 2014, 8:03 pm

    Love this article Anne! I used to say “Should is a dirty word, so stop shoulding all over yourself!” I no longer believe it’s all “evil” – but truly it is a signpost in our lives where we’re letting others dictate what is important.

    Your exercise to get back to the core of our values is great. For me, one area of borderline “shouldness” is with my relationship with my body and movement.

    In truth, I am excited about strengthening my body – but it’s a balance between running 2 miles because society says I should and running those 2 miles because it makes me feel alive, free, and healthy!

    Everything is energy, so what I do is simply flip the switch on the energy around it – and that should actually becomes something that helps me rather than keeps me stuck :).

    • Anne Omland June 20, 2014, 12:43 pm

      That is HILARIOUS Sabrina! I love it!

      I agree- the shoulds that get me the most are those around my activity. If I feel lethargic but “should” be running, do I and hope that once I start I’ll get that energy, or do I listen to my body and take a break? It’s hard to decide and is a work in progress.

      Thanks for your support! x

  • Janelle June 20, 2014, 5:21 pm

    Wow you really got my wheels turning here! So many shoulds that shouldn’t be making me feel down or guilty! I especially feel this way with my family, they are all very active in church and I’m the only one who is not. I just don’t feel it is for me yet I feel the should! Thanks for this!

    • Anne Omland June 23, 2014, 6:53 pm

      Thanks Janelle! Let me know how it goes as you sort out your “shoulds.”

  • Susan June 20, 2014, 8:12 pm

    Wow. Should IS a bully ha! I love your system for showing her who’s boss. Can’t wait to try it, thanks Anne!

    • Anne Omland June 23, 2014, 6:52 pm

      Thanks Susan!

  • Leanne Chesser June 22, 2014, 5:55 pm

    I’m totally with you on eliminating shoulds! For me, getting rid of the stuff we think we “should” do is part of becoming our authentic selves.

    • Anne Omland June 23, 2014, 6:51 pm

      Amen to that! Thanks Leanne!

  • Emily King July 10, 2014, 5:33 pm

    Love this Anne! This was something I needed to read and I’m looking forward to trying out the exercise. Love the site and everything you are doing – thanks for all the tips!

    • Anne Omland July 11, 2014, 12:29 pm

      Thanks Em! I appreciate your support! x

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