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Charting New Year Resolutions for 2021: How to manage beyond disaster with quick and minimally-thorough planning.

2020 was the textbook definition of annus horribilis. If we have made it thus far, we are thankful while acknowledging the long day’s journey into night. With a new year upon us, and a new dawn on the horizon, many of us begin to think about our resolutions and plans for 2021.

We are beginning a new collective journey and starting to plan what it might look like for 2021. All journeys start with two things:

  • your origin / where you are now
  • your destination / where you intend to go

Every journey is fraught with risk. At the onset of your journey much is known, including your port of origin. Your destination represents your ambition, but it is assumed. With the best of planning and intents you might perish before arriving at your intended destination.

This risk applies to terrestrial, oceanic, and interstellar travel as much as it does to the personal and professional journeys we are attempting to chart at the beginning of the New Year.

At humble ventures, we try to minimize risk by coming up with a quick but minimally thorough high-level plan by using two design thinking exercises.

Sailboat: an assessment of what ‘is’.

The first exercise is called Sailboat and helps individuals and organizations assess their current state and speak truth about what is going on within themselves, their teams, communities or organizations. It helps us practice Mindfulness. This exercise helps establish where you come from, the current state of your being, and the origin of your journey. Without judgement, it helps document what ‘is’.

Sailboat is the humble ventures’ remix of the speedboat exercise. A sailboat moves when the sails catch the wind. It comes to rest and is held in place through the use of anchors.

Sails represent all the positive activities that drive an organization forward. When we facilitate this exercise, we focus the attendees’ attention first on the positive activities, assets, efforts and individuals that help propel them forward. It is usually easy to highlight the positives within an organization — and we like to afford 20–25 minutes in discussing the Sails within an organization. When completing this exercise with a group, it is expected to have duplicate ‘Sails’ across participants. This is a good thing and these ‘duplicates’ should be noted, as they represent a well known quantity within your organization.

After we conclude accentuating the positives within our organization by highlighting the ‘sails’ that exist,, we turn our attention to the anchors that sit below the waterline of the organization. Anchors represent all the forces that create drag and friction on the organization and impede forward progress towards growth and our ultimate destination. A discussion of anchors works best when approached with an attitude of therapy, the objectivity of a scientist and the courage of speaking Truth to power. After a few anchors are established, you may uncover a breakthrough insight when a participant is emboldened to share something that has been weighing on their heart. Anchors can span any number of categories — they will at minimum reflect resourcing, cultural, and preparedness gaps. You may see duplicate Anchors — these duplicates are indicative of how strong an anchor may be.

At the end of this exercise, the humble ventures team usually will categorize the ‘Sails’ and ‘Anchors’, arranged by theme based on what has been uncovered in the workshops. You may encounter the same item as both a Sail AND Anchor- recognition that your strongest individual or organizational assets can also be your biggest liabilities.

Sailboat provides a great snapshot of what’s working and what’s not working. An honest reckoning and self-acknowledgement is authentic and cathartic when done with the right intentions. A critical success factor in this exercise is making sure that the participants represent the most diverse representation of your organization, across all functions and levels of activity and support.

Cover Story: an artifact from the future that captures ambition.

The second exercise is called Cover Story, and helps organizations quantify and express their growth ambition in highlighting the destination that they want to arrive at or live into.

It is from the great minds at Gamestorming and is conceptually similar to the Amazon approach to writing a press-release from the future. This exercise is based on envisioning a future state so great, so impactful that it places the participant on the cover of a magazine. The exercise itself is about building out the cover, and thinking through the proper elements of what constitutes a magazine cover and helps us visualize, then actualize.

First things first, you must decide on the magazine you are going to design. The magazine you choose dictates the audience your story is geared towards.

Secondly, how far in the future does this cover take place? Answers can range from 3 months to 3 years to even longer, however we find most utility in keeping the time frame between 3 — 12 because within this timeframe, you have the highest chance of reaching your destination.

The key elements of the cover are below:

  • Brainstorm: Use this time and this space to track the brainstorm of your team. All ideas are good — capture and collect both the BIG ideas as well as small facts or minutia.
  • Cover: What appears on the cover? What image graces the cover? What is the big concept of the Cover?
  • Headline: What is the declarative statement that best conveys your story? What does the title read? Think tweet-length, then shorten it. Remember the importance of brevity, clarity and Force!
  • Quote: Most magazine covers include a quote on the cover that indicates the success of the story you are trying to convey. What quote best represents an endorsement of your strategy and its success? Who would be the person quoted?
  • Sidebar: many covers of magazines include bulleted sub-headlines that advertise what other content and stories can be found within the contents of the magazine’s pages. What are the sidebar topics that provide additional, supporting details around the cover story that you are telling?
  • Images: What are the images that support the sidebar and the other elements of your story that you highlighted? What pictures will convey thousands of words when added to your cover?

This exercise can take anywhere from 30 minutes to over an hour. We like to run this exercise and capture at least one, if not two magazine covers. At the conclusion of this exercise, we create a higher fidelity version of this cover that looks more like a finished magazine cover.

By spending an hour, you too can come up with a high-level plan for 2021. The brilliance of these exercises lie in their simplicity and what their frameworks force you to think through; they provide a snapshot of your current location and the intended direction of your motion. The gaps between your current state and your future state become clear when you attempt to chart the course between the two. The gaps are jobs-to-be-done for some assortment of humans and need to be addressed with resources and effort.

Like all plans or resolutions, the more you revisit them, the better your chances of success. A bi-monthly revisiting of sailboat and cover story can give you enough snapshots to provide a high fidelity picture of your journey and progress, helping you course correct amongst the rocks and reefs.

If you are in the process of trying to determine your own personal or professional growth or innovation journey, give both of these exercises a try. And if this sounds like something you could see useful to your organization, we’re happy to help you out.

Our plan for 2021 is that we’re trying to stay alive, keep our feet moving, and give thanks for all things. We wish you the best of luck and look forward to seeing you out on the road less travelled.



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Ajit Verghese

Ajit Verghese

future of digital, future of health | Building @humbleventures | Edu: @BabsonGraduate, @Georgetown, @StAlbans_STA