Should you let your loved one track your progress?

This is a serious question. I myself, have came across this question recently. 
Should we let others around us: colleague, mates, friends, family, co-workers track our progress in our skills and or abilities? This may have pros and cons:

The Pros:

• They are aware of your desires to improve;
• They get to know you;
• You have that as a subject matter of conversation;
• At least they know you're doing something with your life; 

The Cons:

• It can get annoying, if you don't have any other topics to be always talking about yourself;
• You might spark unwanted conflicts or competitions;

And most importantly

• They won't be impressed, in the view of the fact that it would never be a surprise at all! 

The truth is, I am allowing the person I love to track any developments of my progress. So I'm taking these conclusions from my own personal experience.