A long time ago in a galaxy far, far away, I had a boss and (for purposes of this article) his name was Fred. 

Fred was a powerful man in every way you can imagine. He was wealthy, cunning, and handsome. I was his Executive Assistant and those attributes (for 19 year old me) were also extremely intimidating. Often communication was difficult and forced me to become comfortable with the “hard conversations”. 

That skill set is the single most valuable that I’ve developed as a professional, and maybe even as a person. 

However, there are things one can do - steps one can take - conversations one can have - that make the “hard conversations” unnecessary, and that’s ideal. 

The ability to say no is one of the hardest things for me… always has been. The art of turning down opportunities, invitations, dates, I suck at. And I’m even worse at saying no when asked for a favor. 

In business, some of my worst decisions were made simply because I didn’t say no to the wrong opportunity. 

In one case in particular I was asked to contract with a group of professionals similar to myself, but arguably more successful at the time. They were all of course older, seemingly wiser, and I respected them. Honestly I was just excited and honored to be considered part of the team. 

After “rock staring” for this group through several projects, I started feeling more like their secretary and less like a partner. Like it was somehow forgotten that I was also a business owner, and successful in my industry. Like it was somehow forgotten that my weigh in on decisions was equally valuable. 

It came down to one of the “hard conversations” that I had become so good at over the years, and that was a success (as open communication often is). 

But the relationship ended anyways because the damage had been done in the very beginning when I simply didn’t say no as more secretarial tasks were being piled on me. When I simply didn’t speak up and remind the rest of the team that my ambitions were the same as theirs, and that it was never my ambition to work for them but with them. 

Had I simply said no earlier in the relationship the “hard conversation” that severed our partnership would have been unnecessary. 


Taking a glimpse at my personal life on this same topic - - I don’t care to dive too deep. However I will tell you that very similar circumstances as I’ve described above are true for a number of my personal relationships as well. 

I advise my friends, loved ones, readers, to learn to say no earlier in life than I did. Become comfortable with the idea that you cannot please everyone in every circumstance. And if you get into a situation where you could please someone else at the expense of your own happiness in any capacity… turn around and walk away. Communicate openly and honestly from the very beginning about what you want (even if what you have to say will not make the others involved happy) and you will not have to become so comfortable with the hard conversations that come later.