Getting Lost on Purpose: Venice Edition

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When was the last time you got lost on purpose?

I’m writing this while sipping on an Aperol spritz while waiting for a “Secret Itineraries” tour of the Doge’s Palace in Venice, Italy. 

It took me about 25 minutes to walk here from my hotel. At first, I tried to carefully follow the blue dots that Google maps was instructing me to follow, but then I decided to get lost on purpose. 

I put away my phone, had a few pointers in mind, and then dove into the pleasure of getting lost in the narrow, winding, cobblestone paths of Venezia!

Getting lost on purpose is an important process, both metaphorically and literally, in life and in leadership. The process of getting lost allows you to discover things that you didn’t even know existed.

It also shows a high level of trust in yourself and in your team. It shows that although you don’t know exactly how to get from point A to point B, you have enough faith in everybody that you will figure it out together while enjoying the process along the way.

Getting lost on purpose is different from wandering aimlessly without any consideration of people’s time, safety, energy, and efforts. In a literal sense, you don’t want to be so ignorant of your surroundings that you’ve walked into the mouth of an active volcano. 

In a metaphorical sense, you don’t want to be brainstorming ideas with your project team on how to help hold each other more accountable without any agreements about when things will be implemented or how you will prevent the team from talking about the same problems for months without any decisions being made.

Here are a few guidelines to keep in mind when getting lost on purpose in order to maintain trust and effectiveness. Without these guidelines, then people may feel chaotic, unsafe and that their time is not being appreciated. 

Have a General Idea Where You Want To Go

In my Venice example, I knew that my destination was the Doge’s Palace. This allowed me to have a sense of purpose in my wandering. In leadership, it is important for the team to agree where are all going. It doesn’t have to be fully formed yet, but it is important that everybody understands the outcome we are trying to achieve.

For example, while we don’t know what it looks like yet, let’s have a conversation about how we can make our client’s astonishment process better and more efficient.

Have a General Sense of Direction How To Get There

In Venice, I knew that I wanted to get to the Doge’s Palace, and I was unfamiliar with the path to get there. What I did know was the general direction of the palace and which side of the Grand Canal the palace was sitting on. I walked up and down the curvy alleyways keeping in mind which side of the Grand Canal I was on. This allowed me to put away the map knowing that I was headed in the right direction without knowing exactly what the next steps would entail.

In leadership, this is where it is crucial to have a psychologically safe and brave space. You must have clear agreements that all ideas are welcome and not to be judged. With everybody on the same page of where you are going, it is also important to have general guidelines. 

For example, while we don’t know exactly how we are going to get there, what DO we know? (eg. Like how I knew which side of the Grand Canal I was on). Maybe you know that the budget of the project is $5000 or which departments need to be included in each conversation. Make sure that everybody knows about these general details.

Have a Timeframe When You Want To Arrive

For me, I had a specific time that my tour started at the Palace. So that already gave me a timeframe where I knew I had to reach my destination. This was very useful because it allowed me to get lost and explore, but not for an indefinite amount of time.

The same is true in leadership and teams. Decide on a deadline when decisions will be made or when executing an idea will take place. Getting lost on purpose is only effective when parties know that not having a plan is not indefinite. 

Have Fun Exploring and Just Go!

With these guidelines in place, just go and have fun! Let ideas rip, try new things, and see what gets discovered!

Some of you true adventure seekers who are allergic to rules and structures (eg Enneagram 7s), may feel that having ANY guidelines defeats the purpose of truly getting lost. 

However, getting lost on purpose is different from getting lost without a purpose.

Only when we have a general idea of where we are going, have a general sense of direction how to get there and a timeframe of when we want to get there, can we truly enjoy the process of getting lost in discovery and exploration.

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