How far should you look ahead?
I'm a consultant. So an easy answer would be,"It depends."
My real answer is more nuanced: only look ahead far enough to see some significant issue and a plausible way to resolve it. If you want to get better, practice looking ahead in the context of your work and its established rhythms and natural cycles.
If your organization doesn't value planning and you want to look ahead, start by taking small steps. The reason to look ahead is to check for some pre-work or preparation that is likely to save time or money.
If you are a tech lead, try looking ahead in the context of release planning. See what architecture risks you spot (or new design requirements) as new features are scoped. Take notes on what you are concerned about. Spend some time speculating on what you should be doing architecturally to support the next release. Have a conversation with a trusted colleague about your concerns. Identify concrete follow-on activities specifically targeted at addressing your biggest concerns.
If you are an agile developer, you may not want to look further ahead than the current sprint. If you aren't already doing so, try some iteration modeling for a couple of hours at the beginning of an iteration. Grab a handful of related story cards for a new feature and sketch out some design ideas. Draw sequence diagrams on a white board. Jot down class or component responsibilities on CRC cards. Noodle around. Give yourself the luxury of exploring with your co-workers how things might work. Don't expect a final design, just a plausible one that will be fleshed out and revised as you implement those stories.
If your organization tends to look too far ahead, take actions to personally shift your focus away from endless planning. Winston Churchill said, "It is always wise to look ahead, but difficult to look further than you can see." Looking too far ahead is also a big waste of time. Remedy this time suck by limiting the scope of what you plan for. Find opportunities to build and measure things. Learn to perform small experiments, make small decisions, communicate your results and move things along.
Colleagues and co-workers I'd classify as over-eager forward-looking designers typically build up comfortable infrastructure they think will be needed as a matter of course before they settle in to the programming task at hand. A good indicator that they've gone overboard is how others react to their work. One unhappy forward-looking architect remarked recently, "Not many people appreciate what I am trying to accomplish."
You may not be aware that you look too far ahead. One indicator: you view most programming tasks as an opportunity to build or try out a cool new framework or create your own special DSL. (If you are part of an infrastructure team, then, fine, that is your job. Don't embellish your creations. And make sure others can actually use your stuff.) If you are an application developer, nudge yourself towards refactoring and finding abstractions through concrete scenarios. Hold yourself back from writing speculative code. I look to my colleague, Joe Yoder, as someone who takes a balanced approach when creating infrastructure or suggesting novel architectures. Joe likes to build flexible, adaptable systems, in particular Adaptive Object-Model architectures. He has years of experience doing this. He's enthusiastic when opportunities come up to build these kinds of systems, but knows that this architecture style isn't a good fit for every rapidly changing system. And he doesn't build every part of such a system this way; only the parts that require extensive, ongoing customizations.
How far do you look ahead? Do you think you've found a good balance?