How to break a system that no longer works for you
Start small, and keep going
Welcome to Every Day is a Strategy Day, where I make strategy personal, practical, and just a little provocative.
The last edition - about how to reclaim your life - struck a chord with many of you based on the feedback I received (thank you!). So, I decided to delve deeper into the topic in this edition, focusing on this question:
What if the very structure you rely on - your routines, your habits, your ways of working - is the thing holding you back?
Think.
Every organisation knows the danger of brittle systems. It could be through too much dependence on one supplier, too many decisions stuck in a bottleneck, or a lack of resilience when something substantial changes in the context (customer sentiment, competitor launches, economic conditions). A strategist would flag those as critical, if not existential, risks to deal with.
Yet in our own lives, we often tolerate — even defend — fragile setups. I have. Maybe it’s a family routine that works only if everything works precisely. Or a work structure that depends on you never getting sick. Or a personal way of working that is too rigid when there’s a need for flexibility.
When we’re inside the system, we don’t see the problem. In fact, we normalise it; we think it’s just how things are or have to be.
That’s where strategy can help - taking an outside-in perspective, naming the constraints, and, when needed, breaking the system to build something stronger.
Breaking a system can feel radical and risky, which explains why we avoid it.
Yet often it involves:
Subtraction — removing one dependency.
Redistribution — moving a responsibility across the team.
Redesign — building some slack, variety, and resilience back in to the system.
As Viktor Frankl argued in Man’s Search for Meaning, even under the harshest constraints, choice still exists. In this case, the choice is to stop running on a system that was never built to sustain you, and to imagine building one that will.
Listen.
New possibilities emerge when we slow down, create space, and let curiosity guide the system forward. This principle guided me when I talked with
for his Getting Under The Skin (GUTS) podcast.I open up about the hardest decisions of my life: leaving a prestigious partnership, reshaping family systems around my son, and rediscovering what it means to thrive.
We talk about:
How to find agency and possibility even under severe constraints.
The tension between security, loyalty, and self-care.
The combinations and perspectives that form my “superpower” (even if I felt uncomfortable talking about them).
The emptiness of success when it isn’t tied to a deeper impact.
What parenting a disabled child has taught me about resilience, labels, and connections.
Topaz was masterful in creating a space for me to reflect, think, and share more than I have elsewhere - you’ll see and sense his genuine curiosity, intensity, and quality of questions.
Visualise.
Imagine holding up your life as a strategist would hold up a company:
What are the bottlenecks draining energy and joy?
Where is resilience dangerously thin?
Which assumptions (“we’ve always done it this way”) are limiting possibility?
Mapping your life like a system helps to sharpen and crystalise your vision. It reveals hidden fragilities and overlooked dependencies that explain why pressure builds in some places and energy leaks in others.
Read.
For a stark reminder that choice exists even under the harshest constraints, read Viktor Frankl’s seminal work, Man’s Search for Meaning.
Drill down into the art of subtraction in this article, which focuses on organisations but is relevant to us, as individuals, too.
Challenge yourself.
Now, move from noticing to doing:
Choose one bottleneck or weak spot you identified — and remove, redesign, or redistribute it this week.
Subtract something small but draining: a meeting, a habit, a commitment that no longer serves you.
Set one boundary that strengthens your resilience — a pause, a reset, a redistribution of your commitments.
Each step shows that you can intervene in the system, rather than letting it run you. these small steps accumulate over time and help you create the space to explore and design a new system.
Strategy Shift.
In the last edition, I shared a draft guide called Strategy in the Moment. I hope many of you have an opportunity to read it, and, most of all, use it. If you haven’t, you can check it out here (and download it).
Let me know what you learned about yourself and what you’re trying now in the moments that matter most. I’m exploring how to evolve this guide, specifically how to use it so I would be grateful if you would take two minutes to share your feedback and advice here.
Warmly,
David.
***
That’s all for this edition. Thanks for your interest, encouragement, and inspiration.
Subscribe for free to receive new posts and support my work: