> ## Content Index > Fetch the complete content index at: https://www.tom-shaw.uk/llms.txt > Use this file to discover other available public pages before exploring further. # Lessons From The Cheshire Cat - URL: https://www.tom-shaw.uk/the-cheshire-cat-had-it-all-figured/ - Published: 2025-07-21T16:00:28.000Z - Updated: 2025-07-21T16:00:28.000Z - Description: 7 lines from the feline feature of Alice's Adventures In Wonderland that can help illuminate the world we live in today. - Author: Tom Shaw - Tags: Reflections, #substack, #substack-type-newsletter, #substack-access-everyone, #Import 2026-10-24 12:50 *Alice’s Adventures in Wonderland,* a whimsical fairytale dotted with [equally fantastical (and often times satirical) poetry](https://www.youtube.com/watch?v=lp3aXa3WRc8&ref=tom-shaw.uk), is noted for bucking the trend of children’s literature of the mid-1800s. At the time of its publication, most material aimed at children was didactic, telling children that they must follow certain societal conventions and be unquestioningly obedient to figures of authority. We seemed to have returned to this state of affairs today, including with children, albeit [in its own techni-coloured flavour](https://odysee.com/@jermwarfare:2/Debbie-DeGroff:0?ref=tom-shaw.uk). History doesn’t repeat, but it does rhyme. This is why it’s still a good idea to read Lewis Carroll’s magnum opus in our current times, and gleam lessons from Alice calling out the zany cast of characters in Wonderland for demanding obedience to clearly absurd rules, changing the definitions of words to suit their own agendas, corruption of the courts and engaging in meaningless discussion when there are far more pressing matters at hand - and the list goes on. I find one of the more illuminating and interesting characters living in Wonderland to be the Cheshire Cat, who appears throughout Alice’s Adventure to guide her through the craziness she finds in Wonderland. This is often done through him posing philosophical and amusing ideas to Alice which, while often frustrating her, forces Alice keep her mind open and to lead from her own heart and intuition in navigating this unfamiliar realm. It’s no coincidence to me that The Cheshire Cat is one of the only creatures in Wonderland that commands any respect from Alice whatsoever. ![](https://cdn.mymidnight.blog/a14ac55a4f27472c5d894ec1c3c743d2/substack-post-media-s3-amazonaws-com/public/images/ba31cdb0-2986-45a6-bf58-9b2ccb4b267d_2240x1260.png) [Subscribe now](#/portal/signup) And he isn’t afraid to mess with the other characters of Wonderland and their senseless actions either, seen when he derides the court proceedings for a short while when various members of the “Hearts” are trying to prosecute Alice. It’s clear that The Cheshire Cat has no real ulterior motive or agenda other than to experience the happenings of Wonderland and provide his insights on the workings of this world where relevant - reminding Alice in the only way he knows how that this world they are in truly is absurd. For me, there are many parallels with the Cheshire Cat and how some of the best guides and mentors can show up in our lives. Good mentors, like the Cheshire Cat, lead with curiosity first and foremost. Yes, their insight can frustrate and confuse us if we do not have the tools or experience to fully make sense of it or put into action - and yet they never impose their worldview on us. Good mentors realise that everyone’s path is different, and the Cheshire Cat’s approach encourages Alice to forge her own path through Wonderland for him to observe and learn from. As someone called to guide and mentor others, I’m using my piece this week to look at a few lines from the Cheshire Cat that I’m increasingly finding wisdom in. Let’s dive in: “Every adventure requires a first step.” Starting anything is always the most important, and often most difficult, step in a journey of mine, as it’s what breaks me out of whatever patterns of behaviour I may subconsciously fall into that end up preventing me from making progress. It is the first step that opens the door to other ways of living that are possible. It doesn’t matter if what I have accomplished at the end is (by whatever metric) “good” or “bad”, what matters most is that I began. The act of doing will naturally get me closer to “good”, and that living in the fear of what might happen at the end of the road is often not founded in reality. The Cheshire Cat understands this. “I am not crazy; my reality is just different from yours.” This is the quote that got me interested in re-reading *Alice’s Adventures in Wonderland* in preparation for this piece - one I shared [via Substack Notes](https://tomshawwritings.substack.com/notes) some months ago: This line rings especially true for me in a day and age where pretty much anyone can be derided as “crazy” for having contrarian views - even when the “mainstream” is, by many standards, the “crazy” one. For the Cheshire Cat, this absolutely it true: the reality of Wonderland *is* different from Alice’s reality. And I feel more and more like the realities of those caught in groupthinks are very much different to the one I am experiencing. I’m not complaining. “Not all who wander are lost.” This may well be the most well-known of the Cheshire Cat’s lines, although I suspect many people who know of it don’t realise that this is its origin. Taking a very narrow definition of what constitutes as “wandering”, I often enjoy taking a hike without a planned or known route in mind, just to see what I can find that surprises me. I’m purposefully choosing to do this, and not at all “lost”. Like I explored earlier, it’s taking that first step into the unknown and “wandering” down that path with intention that allows me to grow - and you as well! “Imagination is the only weapon in the war with reality.” Out of the many lines said by the Cheshire Cat, this may well be my favourite. Imagination is vital for creating things that bring us out of our self-limiting belief systems and, by extension, society’s self-limiting ways of being and the challenges that creates. It seems that, so often, we brush aside our children’s expressions of imagination because we’re too busy thinking about something “more important”, or that we only want them to focus on something like academic expression. What are we teaching children when this happens? That their imagination is not welcome. Is it any wonder, therefore, that [we seem to be drowning in problems](https://www.tom-shaw.uk/lament-of-a-dying-dragonfly/) with no way of being able to find solutions? “Only a few find the way, some don’t recognise it when they do – some… don’t ever want to.” Where are *you* afraid to take the path you know, deep down, you need to take? [Leave a comment](#ghost-comments-root) “I never get involved in politics.” There were several occasions in school where I was identified by other classmates as “most likely to become Prime Minister”. Perhaps if I’d [continued on a path of appeasing whoever was above me](https://www.tom-shaw.uk/my-marionette/) in the structures I operated in, that might well be the case. Life, however, had other plans. Politics is a messy game, especially in the modern day. I’m a firm believer that most change comes from outside those systems. The biggest change I can see us needing right now is a reminder of our soul’s existence. Political quabbles mainly serve to keep us divided, rather than realising that we are all real people trying to do the best in our lives (no matter how twisted our idea of “best” might be). More often than not, [politics is only triggering people](https://www.tom-shaw.uk/the-badgers-path/) to the point that people’s minds cannot be changed on topics they believe they are correct on, even when they’re not. I’d rather connect with people directly through their souls, then work outwards. “I can’t know everything.” This line comes in response to Alice claiming that the Cheshire Cat seems to know everything. This line is key to showing that, even though he has wisdom to impart at various points on Alice’s journey (where she would not be able to figure something out by herself), he maintains humility in acknowledging the limits of his capabilities. This is something that any aspiring, and even current, leader could learn much from. Whether they will remains to be seen. --- With that, we come to the end of this exploration. Thank you all for reading, and I hope these words sparked something within you. If they did, please consider leaving a tip to support my work, and subscribe for free if you aren’t already to make sure you don’t miss my future pieces. With gratitude, Tom ![](https://cdn.mymidnight.blog/a14ac55a4f27472c5d894ec1c3c743d2/substack-post-media-s3-amazonaws-com/public/images/6c70cd50-c872-48fb-a222-0695da0274b0_750x990.png) [Leave a Tip](https://tom-shaw.uk/product/one-time-donation-or-tip/?ref=tom-shaw.uk) [Subscribe now](#/portal/signup) --- ## Further Reading [Books That Changed My LifeI’m still astounded by the power of books to change my perspectives on issues and the trajectory on which I approach my life and my own works. I want to use this pi…![](https://cdn.mymidnight.blog/a14ac55a4f27472c5d894ec1c3c743d2/substack-post-media-s3-amazonaws-com/public/images/10bb0009-5e84-44ee-a718-12b501f3eb7a_1280x1280.png)Tom ShawTom Shaw![](https://images.unsplash.com/photo-1521587760476-6c12a4b040da?crop=entropy&cs=tinysrgb&fit=max&fm=jpg&ixid=M3wzMDAzMzh8MHwxfHNlYXJjaHwzfHxib29rc2hlbGZ8ZW58MHx8fHwxNzE1NDI4NzYxfDA&ixlib=rb-4.0.3&q=80&w=1080)](https://www.tom-shaw.uk/books-that-changed-my-life/) [Who Am I Writing For?How much delusional thought is required in order to be remembered as an artist? Will I benefit from some loose screws leaving holes where ideas can pour out? Or doe…![](https://cdn.mymidnight.blog/a14ac55a4f27472c5d894ec1c3c743d2/substack-post-media-s3-amazonaws-com/public/images/10bb0009-5e84-44ee-a718-12b501f3eb7a_1280x1280.png)Tom ShawTom Shaw![](https://images.unsplash.com/photo-1560523159-6b681a1e1852?crop=entropy&cs=tinysrgb&fit=max&fm=jpg&ixid=M3wzMDAzMzh8MHwxfHNlYXJjaHw4fHxwcmVzZW50YXRpb258ZW58MHx8fHwxNzE1ODAzNTg1fDA&ixlib=rb-4.0.3&q=80&w=1080)](https://www.tom-shaw.uk/who-am-i-writing-for/) [Judgement is Inevitable. Offence is Optional.Credit to Midnight, whose following note sparked me to begin writing this piece:![](https://cdn.mymidnight.blog/a14ac55a4f27472c5d894ec1c3c743d2/substack-post-media-s3-amazonaws-com/public/images/10bb0009-5e84-44ee-a718-12b501f3eb7a_1280x1280.png)Tom ShawTom Shaw![](https://cdn.mymidnight.blog/a14ac55a4f27472c5d894ec1c3c743d2/substack-post-media-s3-amazonaws-com/public/images/760480a8-d30e-47cc-b48f-ffdd41f8e593_1180x842.jpg)](https://www.tom-shaw.uk/judgement-is-inevitable-offence-is/)