This Wasn’t in the Itinerary: The Importance of Planning and Letting Go
- Isabelle Riche
- Oct 7
- 2 min read

Early on, I decided, “I would never pursue law.”
That is what I would tell my mom anytime she floated the idea of me becoming a lawyer. She was practicing as a Crown prosecutor throughout my youth, so it wasn’t like I could trust her to be unbiased.
I saw the giant factums she brought home: stacks of paper so thick and cumbersome that the pages could only be bound by large black plastic ringlets. The work reeked of “very serious business.”
And so, for the first few decades of my life, I had no interest in going to law school.
I made a mistake I am convinced we are all bound to repeat again; it is impossible to predict how one will feel in the future.
We can speak with unshakeable certainty in the present moment of our desires, but the factors and chaos that life throws our way make it impossible to guarantee anything beyond those fleeting moments.
Feelings possess the illusion of permanence.
Both the good and bad times feel like they will never end.
The reality is that you have to make plans for tomorrow. You must envision where you’ll be several years from now: where you’ll live, what you’ll do, what kind of partner or people will share life with you?
Without making these plans, we risk remaining adrift in a vast sea, piloting a tiny rowboat.
Yet, we simultaneously have to understand that our plans will never turn out exactly as written. We have to be amenable change, and embrace unfamiliar versions of ourselves that emerge during periods of duress and upheaval.
This past summer, as I prepared to begin a new chapter at law school, I’ve spent some time thinking about this paradox of planning – and how to make sense of it in the grand scheme of things.
Understanding everything is fragile and nothing is guaranteed can be liberating. It frees us from the intense judgement and expectations we often subject ourselves to.
The most important thing about the tiny rowboat we are piloting is to be paddling at all.
We must point our bow towards a distant landmark regardless of where we end up.
There is a better chance of drifting ashore with our oars in the water.
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