When should a brand change it’s logo, and should Plum Creative bite the bullet?

Updating your logo can be a hazardous undertaking – hit the mark and you give your brand a shot in the arm, but get it wrong and you alienate the very people you want to engage. Case in point – the recent GAP logo snafu. The logo outraged just about everyone to the point that the brand was forced to withdraw the logo (and apologize profusely). On the other hand, VIrgin Atlantic's new logo was perceived as lighter and more contemporary and was generally well received by customers and the design community alike.   So, when it was recently suggested to me that I give Plum Creative a new look, I decided to get some feedback from my peers.

Here’s the back-story. Plum Creative works with top-level talent freelance talent such as art directors, copywriters and illustrators. Depending on our client’s particular project needs, we’ll find the perfect person (or team) for the job and manage the whole thing from beginning to end.  This year I launched Pitch Perfect Presentation (http://www.pitchperfectpresentation.com/) so that I might share my knowledge with freelance talent beyond those represented by Plum Creative. Through seminars, workshops and one-on-one counseling I teach the business, interpersonal and project management skills creative talent need to turn their bright ideas into business (and essentially represent themselves).

So while both businesses have a different target audience – they are 2 sides are the same coin (and my face is on both). So here’s my question: should I re-brand Plum to tie in more closely with Pitch Perfect, or should the two remain totally separate?

I’d love to hear what you think and under what circumstances YOU would make the change.