title: "Navigating Life's Crossroads: The Power of The Sunday Evening Question" date: 2025-10-25 author: David Sanker
The house gets quiet on Sunday evenings in a particular way. The kids have settled, the week's noise fades, and there's this brief pocket of stillness before Monday starts its slow approach. I've learned to sit inside that stillness rather than fill it.
It was during one of those quiet evenings, maybe three years into simultaneously practicing law and writing code in the margins of my life, that I realized something uncomfortable: I was answering someone else's questions about who I should be. The Sunday evening ritual I've built since then is my attempt to ask better ones — ones that are actually mine.
Key Facts
- Three years ago, the author was practicing law while developing code projects on the side.
- That dual life led to a transition into building AI systems specifically for law firms.
- The Sunday Evening Question is a weekly reflective practice for making intentional life and career choices.
- Embracing uncertainty — and learning from failures — shaped the path through startups and career pivots.
- The practice has since become central to the author's coaching work with others navigating their own crossroads.
How the Question Found Me
I didn't invent this ritual. It invented itself out of necessity.
There's a particular cognitive dissonance that comes with living two professional identities at once. By day, I was drafting contracts and thinking in legal frameworks. By night, I was building things in code — small projects, experiments, ideas that didn't have a billing code or a client file. Both lives felt real. Both felt incomplete on their own.
The question that kept surfacing on those Sunday evenings wasn't grand. It started small: What did I actually do this week, versus what I intended to do — and what does that gap tell me?
Over time, it evolved into something more searching: What is one thing I learned this past week, and what does that tell me about the future I want to shape?
What I discovered is that the honest answer to that question — not the polished version, but the one you give yourself before you've had time to rationalize — is usually the one worth following.
What the Question Is Actually Doing
Here's what I think is happening beneath the surface of this kind of reflection: it's catching you before the week's momentum carries you somewhere you didn't consciously choose.
Most of us are remarkably good at being busy. We optimize, we respond, we deliver. But being busy is not the same as being directional. The Sunday Evening Question interrupts that pattern. It asks: Is where you've been going actually where you want to go?
When I was writing code until midnight while billing hours during the day, the honest answer to that question was pointing somewhere my professional identity hadn't caught up to yet. The late-night work wasn't just a hobby. It was a signal. It took months of Sunday evenings to admit that, and then a few more to act on it.
That's what eventually led me toward the intersection of law and technology — building AI tools for law firms, a space where both languages I'd been learning suddenly mattered. Not a clean pivot. More like a slow convergence that the weekly question kept nudging me toward.
Applying the Practice: What This Actually Looks Like
This isn't journaling for its own sake, and it's not therapy. It's closer to navigation — checking your heading before you're too far off course.
I keep it simple. Sunday evening, usually after dinner, I give myself twenty minutes. No phone. Sometimes a cup of tea. And I work through a few questions:
- What surprised me this week — and why was I surprised?
- Where did I feel most like myself, and where did I feel like I was performing?
- What am I avoiding, and is the avoidance costing me something?
- What would I do differently if this week were practice for the one that actually matters?
That last question is the sharpest. Because every week is practice for the one that matters. They're also the same week.
Embracing Uncertainty Without Romanticizing It
I want to be honest about something: the pivot from law to tech-focused work was not a confident leap. It was a series of uncertain, sometimes humbling steps. Startups that ran out of runway. Projects that didn't find their market. Code that worked perfectly and solved the wrong problem.
The Sunday Evening Question didn't make those failures not happen. What it did was prevent me from treating them as verdicts. Instead of I failed, therefore I was wrong to try, the question helped me ask What did this teach me, and how does that change what I do next?
That reframe is not a trick. It's a discipline. And like most disciplines, it gets easier with practice and harder to skip once you've felt the cost of skipping it.
Unshackling from the 'Shoulds'
A version of this question sits at the center of most coaching conversations I have. People come to me not because they lack direction, but because they have too many directions — and most of them were handed to them by someone else.
The legal career because it was stable. The corporate track because it was the obvious next step. The title because it looked right on paper. These aren't bad choices, but they're often unchosen ones — and there's a difference.
One client I worked with had spent a decade building technical expertise in software infrastructure. Genuinely excellent at it. Also quietly miserable. During our sessions, something kept surfacing in his Sunday reflections: he kept writing about stories. Books he was reading. Ideas he wanted to explore in long form. A narrative instinct that had no outlet in his current work.
We didn't manufacture a career change out of thin air. But we followed the thread. He started writing about technology — not documentation, but actual human stories about what it feels like to build systems that other people depend on. That writing opened doors. He's now doing work that uses both the engineering depth and the storytelling voice, and it happened because he stopped treating the storytelling as a distraction and started treating it as data.
The Sunday Evening Question is how you gather that data about yourself.
A Note on Robert Frost
People sometimes expect me to lean heavily on the "road not taken" metaphor — it's in my brand name, after all. But I think Frost's real insight is subtler than the inspirational poster version. The speaker in that poem isn't certain he took the better road. He just knows he made a choice, and that he'll tell the story of it as though it mattered — because it did.
That's what I try to hold onto. Not the romance of the unconventional path, but the discipline of choosing consciously. The Sunday Evening Question is how I keep choosing, week after week, rather than drifting.
FAQ
Q: What is the Sunday Evening Question and how can it help my career? The Sunday Evening Question is a weekly reflective practice — a structured pause at the end of each week to examine the gap between your intentions and your actual choices. Rather than a single fixed question, it's a practice of honest inquiry that helps surface what you actually want versus what you've been assuming you want. Over time, it creates a kind of internal compass that makes larger career decisions feel less like leaps and more like natural next steps.
Q: How does embracing uncertainty benefit my career path? Uncertainty is uncomfortable, but it's also information-rich. When you're uncertain, it usually means you're at the edge of what you already know — which is exactly where growth happens. The practice of weekly reflection helps you stay oriented inside that uncertainty rather than retreating to familiar but unsatisfying ground. It won't eliminate the discomfort, but it gives you a way to keep moving through it.
Q: How can I overcome the societal pressure of the 'shoulds' in my career? Slowly, and with some patience for yourself. The 'shoulds' are deeply embedded — they come from people who cared about us, from institutions that shaped us, from narratives we absorbed before we had the language to question them. The Sunday Evening Question creates a regular opportunity to notice when you're operating from a 'should' versus a genuine choice. That noticing is the beginning. You can't unlearn the 'shoulds' all at once, but you can start catching them.
What question do you find yourself avoiding on Sunday evenings? That might be exactly the one worth sitting with.