Good design is the enemy of great design.
This isn't to say that good design gets in the way of great design, since the latter is only possible when surrounded by the former. But our hardest struggles as designers emerge when we confront what could be great, rather than what is thoroughly good.
We often don't know what's great until someone else points it out for us. We lack the critical distance to understand the difference in quality, especially when we drown in the minutia of minor color variations and typeface choices.
We choose to lose ourselves in a flow experience, rather than opting for key moments in our work where we gauge our level of effort versus the result. Some great ideas require countless hours of labor to execute, but often we labor to lose ourselves in the act of creation while ignoring the lack of quality in the very idea we're trying to define visually. This is nothing more than chasing ghosts with our client's billable hours and starves away days we could be using to create great work where such output is actually feasible. Then again...
Great design requires great waste. Great design requires a strong stomach and a willingness to discard the entire box of Cracker Jacks (nibbling not allowed!) to get at the prize. No matter how hard we struggle to create the most compelling design directions out of the husks of hundreds of weaker creative solutions, we will always be hobbled by the little children we left behind on crumpled-up paper, document pasteboards, and Time Machine backups littered with gigabytes of discarded comps that we keep for "reference."
We lack a strong sense of design's history, which keeps us from recognizing the circadian rhythms of our daily output. Cogent design relies on patterns that our audience recognize implicitly. How those patterns are mingled and formed with reference to history, in a combination that seems startlingly evident and novel to the eye—that is where great design thrives. And those patterns which seem new to the young design eye are the molecules that flow through our profession's history. Recognizing what may have been a great success (or massive failure) in the past is often the recipe for understanding what may outlive the rubbish heap.
Great design work frequently seeks to transcend the boundaries of design itself. There is nothing wrong with bowing at the altars of the art world, especially when great works of design cross over into the realms of conceptual art or lurk at the margins of perceived norms in our profession. One can create a big career in our industry by taking a outsider's tack, but it is highly unlikely you will bill out at a rate commensurate with your time investment. This is the cost of "personal work" that may lead to plum projects down the path, but is often not personal when you think about the resulting artifacts and their impact on your audiences.
Great design becomes like water over time. The designer's ego must be cast aside in the face of society's desire. Millions of people squeeze their OXO Good Grips vegetable peelers while cleaning cucumbers for their daily salad. Awards and praise showered upon this lovely product vanish in the face of daily, happy use. The designer is invisible. The reward is the use—no more, no less.
Great design is identified in hindsight. The real struggle for our profession is not in identifying what designed artifacts are good, bad, and/or great as we have made them. Our battles for illusory greatness will be won and lost based on how context is created for our creations. What makes a designed solution truly transcend its peers within the marketplace is contingent on so many factors that we can't control—it's almost crazy to embark on creating a design without being aware of the odds against its success. In a sense, great design is a kind of marketing we've created to assuage the level of sacrifice necessary to wade through failure after failure after failure in search of success.
And how you define success—whether by form, function, fit, or fancy—that is what actually makes great design possible.