Clear sailing is a common English idiom used to describe a situation that is free of obstacles or challenges.  This can be especially relevant after said obstacles or challenges have been overcome.

In this case the challenges (or as optimists say – the opportunities) are identified, plans to overcome them are created and then executed.  Once completed, with a sigh of relieve a state of clear sailing is declared. 

Historic Reference

Travel by sailing ship was a common practice in the 19th century and earlier, it was not until the early 20th century that self powered ships (steam, gas or otherwise) became common.  

Sailing ships were very much at the mercy of the weather.  Motive power was derived from the wind and if there was no wind then their was no power.  

Additionally of course the level of sea turbulence (a factor dictated by weather) also determined the ease of a journey by sailing vessel.  Rough weather led to rough unpleasant trips, even dangerous ones. 

Planning to avoid rough sailing, or if it was encountered overcoming it, led to clear sailing and ultimately today’s idiom which is based on the conceptually meaning but does not necessarily apply to sailing alone. 

Setting yourself up for clear sailing

The concept of clear sailing can help with planning.  The primary goal of any plan, first and foremost (a little redundant emphasis) is for execution to proceed smoothly (i.e., smooth sailing).

Keeping this objective top of mind during planning can make it more likely for risks to occur to you as you draft the activities, schedule and resources.  Remembering the trip will not be clear sailing if things go wrong, focus tasks that contain on low risk, high probability of success. 

And then, sit back and enjoy clear sailing.