Karen M. Winkelman

The LifeCrafting Guide

Intuitive Consultant for Your Personal,
Professional and Creative Life

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~ Siddartha

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by Karen Winkelman Monday, May 20, 2024

Pictures of women in different hats with the words Try a Different HatRecently, I was thinking about the choices I made and the things I did in my life, my career/jobs, and my business.

And my creative expression!


Can’t leave that one out… again.

Anyway, some many of the choices I made did not come from my heart or my intuitive guidance. 

Some choices were made from inaccurate conclusions or habitual reactions.

And, a bunch of them were based on what I thought I needed to do to achieve the result I wanted (succeed, keep the peace, be liked, and so on).

In my life and career, it often showed up as choosing to be supportive of someone or something else over being supportive of my own needs at the time.

End result, others could count on me to show up…

but I couldn’t count on me to show up for myself.

In my metaphysical/spiritual business, these choices were things I thought I needed to do to grow my business... 

Like doing readings at events and other things that drained me.

Or basing my services and offerings on what other people were doing who seemed to be successful.

Yeah, that really doesn’t work.

In my creative expression (especially my writing and my art), I usually chose to do something else instead.

Often a silly “should” got the time slot reserved for my creativity.

Blue background with the words "Your should dos are usually great excuses to not do the things you really love doingShoulds can seem like they are urgent and important, and they are usually a great excuse not to do the things you really love doing.

(My shoulds were usually things like laundry, cleaning, grocery shopping, taking care of the cats, and so on.)

They really didn’t have to be done right then.

But again, an excellent excuse not to show up for yourself.


As all these past choice considerations cycled through me, I felt like I made bad decisions based on what I thought I should do or needed to do…

That started to bring me down.

I slipped into a judgy place.

Although I did not fully beat myself up, it wasn’t supportive.

I felt disappointed that I had let myself down.

And that made me feel sad. A bit depressed even.

Then I heard a soft, clear voice say,

“Those choices are no different than trying on hats.

No more, no less. So let them go.”


That stopped the downward spiral of self-recrimination and presented me with another perspective.

Trying on hats.

It made me smile.

What if it really is that easy?

Your life, career, business, relationship, and creative expression choices are like trying on different hats.

Sometimes, you choose a hat because everyone else has one like it, or because someone told you it looked good on you.

You get it home, and no matter how many times you put it on, it never feels right. But you keep trying to make it work somehow.

Or make yourself wrong for choosing it.

Sometimes, that darn hat is so friggin’ uncomfortable that you can’t wait to take it off.

If you outgrow a hat, it may be time to retire it and pick another.

Sometimes we love a worn, frayed hat so much that we keep wearing it, even though it is falling apart.

We want to hang on to it.

But really, we want to hang on to the comfort and known elements of that old hat rather than test out a new hat.

(Yeah, the unknown can stop our forward momentum because it feels risky.)


And lately, I’ve noticed that some of the hats I chose are more for the person I was 10-20-30 or more years ago… not who I am now.

And even if I loved that hat, it no longer fits me.

Who I am now. Who I am becoming.

Time to choose a new hat or hats that resonate with me now.

collage of Karen in different hats with the quote: "Those choices are no different than trying on hats. No more. No less. So let them go." The past choices that I was ruminating on weren’t real life-or-death decisions (for the most part).  

I suspect the same is true for you.

Choices were really experiments that created experiences for us to learn and grow.

Testing the waters, seeing what worked and what didn’t.

And lessons were learned.

For me, sometimes this was with less grace and ease than I’d have preferred, but learn I did.

This works (Yay, smiley face, feels good). smiley

This doesn’t work (Ugh, frowny face, this kinda sucked). sad

Let’s choose more of the things that work!

Things that feel good. Things that make you smile inside and out.


To do this, I suggest centering yourself first. (Aligned conscious choices make all the difference.)

  • Take a nice deep breath or three.
  • Acknowledge any emotions that pop up, and gently move them to the side, instead of letting them drive.
  • Check in with your intuition and your body, and choose from that space.
  • If you need additional guidance, ask a trusted friend. But be sure their advice resonates with you before you act.

I hope this perspective of trying on hats contributes to you in some way.

Especially around choices you made in the past, so you can move on without those unhelpful judgy voices in your head.

So, what do you think? Is it time to try a different hat somewhere in your life?

You never know what this new hat could do for you.

It might even be fun!


With deep love and appreciation,


PS. Do you have something you'd like to share about choices or trying on different hats?  I'd love to hear it. Share in the comments area below!

Posted by Karen Winkelman on Monday, May 20, 2024 12:00 AM
Categories: Healing, Intuition, Self-Acceptance, Self-Care, Self-Awareness, Empowerment
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