The word “should” is a heavy word.  Think about the very definition:

should  [SHo͝od, SHəd]:  used to indicate obligation, duty, or correctness, typically when criticizing someone’s actions.

When I hear this word from others, I can feel myself pushing back and starting to tune them out.  I even try really hard to not roll my eyes and sigh.  However, when I say this word to myself, something completely different happens. I actually take those words to heart and I actually find myself feeling badly about myself.  I find myself fixating on all of the things I should have done – regardless of the amount of work and the quality of work I actually did accomplish.  I beat myself up a bit each time that word surfaces.  You know:  Self-Criticism.

As entrepreneurs, I believe we have something within us that always begs for more.  More time, more calls made, more work completed, more sales made and so on.  I also believe that as entrepreneurs we are extra hard on ourselves.   This effects everything:  our day to day to work, how we communicate with others (and ourselves), if we allow it to – if we choose to push forward. Ultimately, how much we “should” all  over ourselves.

There is one particular event in my entrepreneurial life that continues to rear up.  It is a part of my business that was shut down (not by choice, but more so by circumstance) and regardless of what I did I was not able to keep it open.  I used to think of it as a “failure” and made it worse by thinking “I should have tried this”, “I should have done that”, and the ultimate zinger “If I was thinking I should have done it differently”.   Talk about self-criticism!

The experience of this “failure” was so embarrassing and so crippling to me that I wasn’t sure I could recover.  Even after 11 years in business (at the time), I didn’t know how or if I could recover.  There is a belief I have deep in my gut that I absolutely know to be true.  When we put everything we have into an idea, a product or in my case an expansion of a business and it doesn’t go as we planned, we take it so very personally.  We feel it as an injury.  I felt it as physically crippling, hard to breath and painful.  It affected so much more than just the ego.  It almost defines who I was.

It’s now been a few years and I find myself recovered and wiser. From that experience I have re-framed what my should’s look like.  For a very long time, I banished should’s from my conversations.  Instead of shoulding all over myself, I was careful to use the word could. It works well and it’s a powerful and positive word. Instead of doubt (should) I’m finding more power (could) in my thoughts and how I frame my business growth.

Framing how I think about growth in this business is so empowering – “I could do that expansion again, and this time I could do things a bit differently”.  I don’t know if my business expansion will happen in the same way it once did, but I do know that should is still a bad word to me.  I know that should brings feelings of guilt, lack, pain and so much more.   I decided long ago to assign that past lesson the word “should“. My next big idea will be assigned a new word and I will not should all over myself.  I don’t know what the vaccine is against the should’s but I do know that the antidote is time and moving on to the next big thing.

Tiffny Hagan is the founder and owner of Virtual Office Advantage.  Our desire is to thoughtfully offer those business services you need to grow your organization with a virtual assistant by your side.  To see all of the services we offer and find out more, I invite you to visit  We’d love to have you share with others what you are reading and let us know if there is a topic you’d like us to help with.  Also be sure to “like” us on Facebook at