Ideas through time: Second Sailings

Leandro Cota Hevia
3 min readApr 10, 2022

Every project has two phases. The first one is governed by passion, and it starts when an idea comes to your mind and you start drafting, planning, playing around with sketches or chords or diagrams, and you simply can’t avoid being dragged forward by the rush of excitement. It is the phase that is involved when you are doing something new, and all you want to do is to put together the pieces, create, and let the world see and get inspired by your invention.

At some point, this phase comes to an end. You no longer feel that push, the thing that was dragging you forward is no longer there, or worse yet, it started going in circles, pushing you a few steps in every direction and leaving you just where you started.

There may be some lucky persons who can finish their projects while they are still in the enthusiasm phase, but most of us run out of excitement before we run out of items to cross off the to-do list. As the obstacles make themselves visible, and the wind is no longer in our favor, the actual effort begins. It is the time for the second phase. It is the time for the second sailing.

On the Phaedo, in the midst of an argument on moral phenomena, Socrates refers to a second sailing as a metaphor for pursuing the destination he was heading to but employing a different means to reach it. The literal meaning of this term refers to the moment when the first attempt to set sail ends up in failure, either because the wind is still or because it is working against us, but the crew does not follow Aeolos’ whims. It takes the oars and remains on course. This sailing is, by definition, more laborious, but it guarantees the arrival at the destination.

The first navigation is near the coast, where there is wind and you just need to unfurl the sails to let it carry you along. It is the enthusiasm phase. But this can only take you so far, and when the wind ceases, it is time for you to decide if you want to go back, or to roll up your sleeves and start paddling. No great journey was ever made just carried by the wind, and no great project can be completed with enthusiasm only.

This also applies to leaders. It is hard to achieve greatness by only sailing along the shore. Think of any remarkable project you have ever taken a part in, and ask yourself if the journey was more like sailing near the beach or a struggle through a hard sea. Think of any great leader you have ever encountered, and consider if they could have become that person by navigating only where the wind took them.

There is nothing worth doing that is not a bit scary, and no one has achieved greatness without wrestling with their own doubts and limitations. In this path, you may break some paddles, get some holes in your ship and cover them as best you can, but as put by Thomas Aquinas, “If the highest aim of a captain were to preserve his ship, he would keep it in port forever”.

The passion and enthusiasm not only come from working on something new, and remembering what it was that got you in the sea is a good way of energizing yourself. Most likely it was not just the wind, but the idea of how things will be once you are on the other side that got you there in the first place.

It could be that you are doing something hard and challenging and this motivates you, or you could be working towards a mission with an impact that you really believe in, something that you deemed that is not only relevant but also necessary, and for which your contribution will make a difference. Regardless of what it is, there is no escape from paddling.

This is the third article on the Leadership ideas enriched by time series. I will be going over different ideas on leadership following the concept that an idea that has been around for a long period of time is worth revisiting.