What Would Make 2025 an Awesome Year?
An Idea for Consideration
During a recent thought partnership session with my good friend Gerard, we discussed our plans for the upcoming year. After patiently listening to some of my rather uninspired ideas, Gerard interrupted me with a question: “What if you started with, ‘What would make 2025 an awesome year?’”
That simple prompt opened up an entirely new way of thinking about my plan—much less incremental thinking and much more boldness about what is possible. The process led to insights that may be relevant as you consider your plans for the coming year.
The first step in answering “What would make an awesome year?” was to do an unstructured brainstorm. I then used ChatGPT to generate even more ideas and dropped them all into a survey that forced me to rank them.
When I looked at the ranked ideas, I noticed that many of those near the top of the list were escapist. For example, I tried to sell Erin on the idea of moving to London for three years to escape the chaos of D.C. and pursue a PhD. Unsurprisingly, she wasn’t convinced, and that idea didn’t last long.
I realized that my thinking was clouded by the election results and the uncertainty in front of us, which mirrors the mindset of many executives I’ve spoken with recently. Some were overly pessimistic, and others were mulling radical changes, but a common pattern was that it was hard for them—and for me—to pin down exactly how our shifting moods were shaping our “logical” thoughts.
With that insight, I edited the list and did a second round of ranking. The second thing I noticed was that the “awesome” framing had pushed me beyond rational business goals. By not restricting my brainstorming to incremental improvements or current obligations, I freed myself to imagine projects that would be genuinely fun.
On one hand, that could be seen as a flaw in the process since advancing professionally is a nontrivial part of success. But when scrutinizing the list further, I realized that fun isn’t professionally frivolous. Instead, it drives the creative energy I need to do meaningful work, which may lead to that work having a more significant impact than if I started with a business rationale.
While doing that planning, I happened to be reading Rick Rubin’s The Creative Act, which offers a poetic exploration of what it means to be an artist. My instinct to start with fun relates to Rubin’s point about maintaining a pure intention during the creative process. “Fear of criticism. Attachment to a commercial result. Competing with past work. Time and resource constraints. The aspiration of wanting to change the world. And any story beyond ‘I want to make the best thing I can make, whatever it is’ are all undermining forces in the quest for greatness.”
While his insight was especially relevant for artists, I suspect it applies to any work that we want to be great.
On the third edit and ranking, I reflected on why certain projects felt more attractive than others. The insight was that forming a project with a specific outcome and deadline in mind made it too much like a chore, which would sap the joy from the experience. For example, a potential goal was to host more gatherings in the coming year. In the first round, that manifested as ideas for a specific series of events. By the third round, the idea was simply, “Put dates on the calendar as a placeholder, but figure it out as I go.”
Ultimately, this was about using the planning process to reflect on what matters most to me now and what conditions lead to the most impact. For me, the process crystallized the idea that I’m at my best when I’m doing professional work in a playful way and doing play in a professional way. For you, the insights would likely be different and based on your personality.
Either way, I wouldn’t have arrived at those insights without approaching planning through the “awesome” lens.
Tool: Annual Planning Workbook
A couple of weeks ago, a friend asked for the tools I use for annual planning and that my wife and I use for our yearly strategy retreat. As an example of taking a professional approach to play, I used the downtime of Thanksgiving week to create a workbook of the tools.
If you’re interested, check it out here.