Sailing close to the wind

Definitions

taking risks
Engage in a risky behavior or activity, often pushing the boundaries of what is considered safe or acceptable
skirting the edges of legality or morality
Acting in a way that is just within the limits of what is allowed or acceptable, often tiptoeing around rules or ethical standards

Examples of Sailing close to the wind

The sales team is sailing close to the competition by offering discounts and promotions to attract new customers.

When a boat sails too close to the wind, it risks being pushed back in the opposite direction by the wind's force. In business, sailing close to the competition means taking bold and potentially risky moves to gain an edge over competitors. Just as a sailboat that sails too close to the wind risks falling behind, a company that gets too close to its competitors may miss out on opportunities otherwise. However, just as a skilled sailor knows when it's worth the risk to sail close to the wind for the potential benefits, a savvy business understands when it's worth taking calculated risks to gain an edge.
The new marketing campaign is sailing close to the edge, as it targets a niche audience and makes bold claims about the product's benefits.

In this example, "sailing close to the edge" refers to a risky strategy whereby the marketing campaign is targeting a very specific audience with bold claims about the product's benefits. This is akin to a sailboat sailing close to the cliffs, where the danger is heightened but so is the potential reward. The edge here is defined as the boundary between success and failure, and sailing too close to the edge means taking risks that could lead to either outcome. By targeting a niche audience with bold claims, the marketing campaign is sailing close to the edge, as it's not clear whether the audience will find the claims credible or dismiss them as overhyped.
The startup's financial situation is sailing close to the storm, as they've experienced a string of setbacks and are struggling to make ends meet.

Here, "sailing close to the storm" is used to describe a situation where a company is facing a series of challenges and is in danger of being overwhelmed. Just as a sailboat sailing close to a storm could be capsized by the wind and rain, a startup facing a series of setbacks may be at risk of failing. In this context, "storm" is metaphorically used to describe the hurdles that the startup is facing, underscoring the seriousness of the situation. Sailing too close to the storm means being proactive in addressing the challenges rather than simply reacting to them, and in the case of the startup, it could involve seeking out investors or partners, cutting costs, or pivoting the business model.
The speaker's confidence in the project is sailing close to the sky, as they've set incredibly high expectations for the results.

In this instance, "sailing close to the sky" is used to denote extreme optimism or expectations. Just as a sailboat sailing too close to the sky could be hit by turbulence or gusts of wind, a project with incredibly high expectations could face setbacks or fail to meet the lofty goals. This metaphor is particularly fitting when used to describe someone's belief in a project, as it highlights the risks associated with setting excessively high expectations. Sailing close to the sky means taking a risk by aiming for the stars, but it also means acknowledging the possibility of failure and being prepared to navigate the consequences.
The sales department was sailing close to the wind during the holiday season, with inventory levels running low and high demand threatening to outstrip supply.

This idiom is used to describe a situation in which one is taking significant risks in order to gain an advantage. Just as a sailor must navigate close to the wind in order to make progress against the force of the wind, the sales department was carefully balancing the need to satisfy customer demand with the risk of running out of stock. By sailing close to the wind, the sales department was able to meet customer needs, but only just, and were continuously monitoring the situation in order to avoid running aground.
The politician's campaign was sailing close to the wind as he was taking aggressive positions on hotly contested issues, which could easily backfire and damage his chances of winning the election.

This idiom is used to describe a situation where a person or organization is taking risks or making bold moves, often close to the limits of what is socially, politically, or legally acceptable. It comes from the nautical practice of sailing a ship as close as possible to the wind without crossing over it, as this reduces the distance that needs to be covered and helps to reach the destination faster. However, it also increases the risk of capsizing or being pushed back by the wind, much like how taking extreme positions in politics can lead to unintended consequences and negative repercussions.
The entrepreneur's startup was sailing close to the wind as it was operating on a tight budget and had to make a tough call between scaling up the business or cutting back on expenses.

Here, the idiom refers to a situation where a person or organization is operating in a challenging or uncertain environment, where it needs to take calculated risks to succeed. It can be used to describe a variety of situations, including financial, strategic, or competitive risks. By sailing close to the wind, the entrepreneur was willing to take risks, but also recognized the importance of being prudent and not overexposing the business to undue risks.
The athlete's performance was sailing close to the wind as she was pushing herself to the limit, but also risking injury or burnout.

This example highlights the use of the idiom in the context of athletics or performance, where it refers to a situation where a person is performing at the highest level of his or her ability, but also acknowledges the risks and challenges involved. The use of the idiom in this context emphasizes the importance of finding the right balance between pushing oneself to the limit and avoiding excessive risks that could lead to injury, burnout or poor performance in the long run.

Conclusion

The idiom "sailing close to the wind" can be used to describe both taking risks and skirting the edges of legality or morality. It often conveys a sense of pushing boundaries and living on the edge, whether in terms of personal behavior or in a broader context such as business or politics.

Origin of "Sailing close to the wind"

The origin of the idiom "sailing close to the wind" comes from the nautical world. In sailing, "close-hauled" refers to sailing as close to the direction of the wind as possible without the sails luffing or losing power. This maneuver allows a sailboat to travel as directly into the wind as possible, although it requires precision and skill to avoid being pushed off course. "Sailing close to the wind" became a metaphor for taking risks or pushing boundaries, as it requires a delicate balance between daring and caution. Over time, the idiom has evolved to encompass not just the literal act of sailing, but also the broader concept of navigating risky or borderline situations.