I have 2 clients for whom I mainly do maintenance updates. In one case, I just designed their site last year and they are already open to making some tweaks to update the look. However, the other one is still using the original design I did for them… 10 YEARS AGO.

So far, I’ve just been giving the latter client some advance notice when I’m going to raise my rates and nudging them with “If you want me to redesign your site, now’s the time to do it before my rates go up!” but they aren’t biting. At the time the design wasn’t bad, however now it really looks dated. Even though it would be nice to have another live site in my portfolio, I don’t dare link to it because by today’s standards it looks really terrible.

I’m pretty sure this client isn’t going to go for anything sounding remotely like a sales pitch, so I’m looking for ways to approach the subject. Any ideas?