Many What By When’s coaching and consulting ideas can be used in circumstances as different as corporate strategy to recreational planning.
One of our favorite brainstorming strategies is called the Wishing Well – we use it often, all the way from executive coaching to new business planning, and even with my 8-year-old niece to plan her visits. The Wishing Well emerged on a vacation to Iceland with a small group of friends. Relationship dynamics can be challenging while traveling and expectations are high. Time off is precious, and everyone wants to make the most of it.
There were things I didn’t want to miss - Northern Lights, I’m looking at you! I also cared about what my friends wanted—what caught their attention, sparked an interest or drew curiosity. With a variety of personalities – from shy to extremely extroverted – I knew we would need a tool to meet everyone’s needs. A few simple questions arose:
What’s the easiest way to learn what everyone wants? Ask them.
What’s the easiest way to capture it? Write it down.
What’s the easiest way to decide when to do it? Make a timeline.
The What
When we landed in Iceland, I dropped two papers on the table and colored pens. On one, I wrote the items we already schemed about together like the Blue Lagoon, tasting fermented shark, and the Hallgrímskirkja Cathedral. Then, I lured everyone into throwing their wishes into the well in no set order. The concept was that everyone shared their interests, and no one went unheard.
“The wishing well took the pressure off ‘seeing everything’ and aimed the energy of a day at the activities that felt most fitting. I don’t think we’d have seen the Opera House without it. I tend to keep my thoughts inside, but the process made it natural to throw it on the page. To my surprise, the whole group was into it,” said one of the travelers.
No matter how absurd, all wishes are included. The geothermal hot spring, tasting minke meat, and even visiting the penis museum all made the list.
“It’s a bit like a color kaleidoscope where everyone’s brain goes down on the page, it’s a little blurry, but it’s all together in one picture. It's not just one person's vision. We're doing a kind of brain meld,” said another traveler.
The When
With everyone’s wishes collected, we were ready to think about what we could fit where on the timeline. This is where the second page, The When Page comes in. We sifted the ideas in a realistic way by time, logistics and cost. When starting from scratch, plane tickets and accommodation are first up. Since we were already there, we investigated things that required prearrangements like event tickets or restaurant reservations. Then we added everyone’s must-do items which still left gaps which I love to leave blank inviting spontaneity.
In our case, it turned out our Airbnb hostess had a friend putting on a live Icelandic Saga at a local high school, another friend with a remote Northern-light-proximity restaurant, and a final friend with a car. This spontaneous adventure did not end in seeing the Northern lights, but we did try the most unappetizing thing I’ve ever tasted—fermented shark. We froze our butts off trying to glimpse magic in the sky and rescued one traveler from absconding for a seasonal job with a sketchy hotelier.
The Reward
At the end of the trip, all the travelers agreed the Wishing Well created a structure that allowed everyone to enjoy the vacation, both meeting their own expectations and being pushed to do new things – with much less relational stress than prior trips.
The Wishing Well process helped with consensus, but it’s also about clarity. Some people were looking for alone time more than together time.
“We melded our brains in a way that brought similar colors together and formed an overlap of what we all wanted in common—and just as important—what we wanted to do on our own,” one of the travelers mused.
For others, easing the relationship dynamics was the biggest benefit.
“I appreciate how it brings out folks' expectations, particularly for two types of people—those with no expectations and those with high expectations,” said one of the group members.
Those with no expectations either haven't thought about their expectations beforehand or don't feel comfortable making requests of others. Their initial wishes might sound like, "just being together,” which isn't quite participating in the exercise or the vacation. The wishing well helps them take on more agency and have a stake in their experience.
On the other end, the Wishing Well also helps rein in those with high expectations, which usually manifests as requesting more wishes than the rest of the group. The Wishing Well is egalitarian at its core, so it's a helpful and non-confrontational tool to rein in a family member who is used to having their way.”
What By When – Every project has a What. Let’s find yours.
This travel idea came from an epiphany I had at work about how to get ideas on the page and agreeing to a plan with timing. It’s the same inspiration that eventually led to the name of our company, What by When.
The Wishing Well is the simplest form of a very powerful process; getting clear on what you want to do and pragmatic about when to do it. What by When has used this method with individuals, non-profits, small businesses and corporations to bring ideas into the world. Though this process began a decade ago, its execution and purpose are the same. When writing your own Wishing Well, just remember, any conceivable idea is welcomed because there is no commitment to actualize any of them at this stage.
It's focus is to discover YOUR What.
