In Design Observer, Michael Bierut shares The Mysterious Power of Context, which muses on logo design and fonts, with a larger eye on brand identity. He cites Paul Rand (new to me) in a few sentences which reminds me that some decisions are just not that important in the long run.
In the world of identity design, very few designs mean anything when they’re brand new. A good logo, according to Paul Rand, provides the “pleasure of recognition and the promise of meaning.” The promise, of course, is only fulfilled over time. “It is only by association with a product, a service, a business, or a corporation that a logo takes on any real meaning,” Rand wrote in 1991. “It derives its meaning and usefulness from the quality of that which it symbolizes.”
When should you agonize over design, logo, language, and each of the individually small, cumulatively large decisions which go into communicating what you offer and what you stand for? My short answer would be: every day, but not for very long.
Keep moving forward. If you keep delivering a service or product of value, you can improve how you explain yourself and how you represent yourself to potential new customers. If you’re not providing value… the rest is just lipstick on a pig.