Leaving the map behind: building a life without a 5-year plan
What if it works out?
“I wake up every morning and feel like I’m wasting my life. I just need a plan. Any plan.”
That’s what a client told me, her hands tightly folded in her lap like she was bracing for impact. Her voice cracked. She wasn’t in crisis; at least not in the way we usually think of it. But she was facing something far more disorienting for a high-achiever: uncertainty.
She had left a prestigious job, was contemplating a moving to a new state, and most terrifyingly, didn’t know what came next. She had no clean answer for “So, what do you do?” No clear plan to hand to her inner critic, like a permission slip to exist.
High-achievers don’t just dislike uncertainty. They fear it. No plan means no control. No control means failure. And failure, in the high-achiever’s nervous system is terror.
This is something I explore more deeply in Toxic Productivity: the idea that planning becomes a form of emotional regulation for high-functioners. Toxic Productivity, is available everywhere books are sold and you can learn more about it on my website.
As a culture, we are so obsessed with direction, timelines, and milestones. People love talking about their ‘Five-year plans’. Job interviews ask about it. We ask little children, who are like 6, what they want to be when they ‘grow up’? (as though little children have any conceptualization of the world, let alone the skills to plan!) We live under the illusion that if we just chart the right course with the right degree, partner, job title, home, we’ll arrive somewhere that finally feels like enough. These plans give us more than structure. They give us a (false) sense of safety.
But what happens when life doesn’t follow the map?
Last week, I co-hosted a private dinner for 15 female founders with The Grand World. We kicked-off with asking the question: What’s one thing you accomplished recently but haven’t yet celebrated? We explored how to redefine ambition to make it more sustainable, how to let go of toxic productivity habits and be more intentional as leaders. The Grand World is a group coaching platform to support women founders, executives, and creatives in navigating transitions at the intersection of work and life.
Why high-achievers struggle with change?
Change disrupts more than routine, it disrupts identity.
Psychologically, many high-achievers have what’s called conditional self-worth: a belief that their value is dependent on what they can produce, prove, or control. This often stems from early attachment dynamics, where approval was tied to being competent, helpful, or emotionally restrained. Over time, achievement becomes not just a behavior but a strategy for safety.
Success (and therefore, a plan) reduces anxiety, offers predictability, and maintains a sense of control in a world that feels chaotic. This is why even positive change such as a new opportunity, a break from work, a shift in direction can feel overwhelming.
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Change also activates a specific type of cognitive distortion known as catastrophizing, which is the tendency to assume the worst possible outcome. Research in cognitive behavioral therapy shows that high-achievers are more prone to all-or-nothing thinking: If I don’t succeed, I’ve failed. If I’m uncertain, I’m lost. These distortions (harmful thought patterns) create an internal pressure to act decisively, quickly, and flawlessly, even when the situation calls for reflection or rest.
Finally, there’s also a cultural layer. In societies that glorify productivity, the unknown is equated with irresponsibility. We absorb the message that we must always have a plan, always be optimizing, always be a step ahead. So when a high-achiever enters a period of change, the discomfort is a existential crisis.
Understanding this is critical. Because without self-awareness, many high-achievers unconsciously seek premature closure. They rush into the next job, next project, next relationship, not out of alignment but out of anxiety.
Ask yourself: What parts of your five-year plan are rooted in fear, not desire?
This fear of change brings us to the deeper challenge: how do we make peace with not knowing?
Making peace with not knowing
The emotional skill of ambiguity
Psychologist Erik Erikson described identity development as a lifelong process, not something you accomplish once and move on from. In early adulthood, the goal isn’t certainty, it’s integration. Who are you, now that you’re no longer who others told you to be? What does a life look like when it’s shaped from the inside out?
Pop culture tends to polarize this moment. In The Devil Wears Prada, we’re shown a high-achieving young woman who burns out trying to prove herself in a system that doesn’t care about her. In Frances Ha, we watch the opposite - someone who drifts, resists structure, and fears she’s falling behind. The tension between these two narratives of rigid ambition vs. rootless wandering is exactly where most of us live.
And life isn’t either/or. We have to learn to move through the of uncertainty with intention. This is an emotional skill: ambiguity tolerance. In psychological terms, it’s the ability to hold uncertainty without rushing to resolve it. People with low ambiguity tolerance tend to overcommit, overfunction, or shut down. Those with higher tolerance can make thoughtful choices even in unclear conditions.
In moments of identity transition, we’re experiencing what James Marcia called ‘moratorium’: a period of exploration without commitment. It’s not a failure to decide. It’s an essential part of evolving as life evolves. And, it’s a muscle you can build.
Start by naming, not solving. When you feel that familiar discomfort, like you should “have it all figured out, pause. Ask: What’s actually uncertain here? Often, it’s not everything. It’s one corner of your life. Get specific.
Anchor to values, not outcomes. In the absence of a fixed plan, your values become your compass. Ask yourself: What do I want to stand for in this season? Not just what you want to do, but how you want to move through this fog.
Use metaphor to reframe. Ambiguity often feels like failure because we expect clarity to be linear. But nature rarely moves in straight lines. Think of this season like winter: a time of invisible growth, pruning, rest. Or like the tide: you may be pulled back before you surge forward. Your life isn’t stalled. It’s shifting shape.
Ask yourself: What’s one area of your life where you can allow space for uncertainty, without trying to control the outcome?
Satya Doyle Byock, in Quarterlife, reframes this period of searching as developmental, not pathological. She identifies a critical tension between “stability values” (the desire for safety, belonging, clarity) and “meaning values” (the drive toward growth, purpose, freedom). Many of us are pushed to resolve this too quickly: chasing stability and resenting the ambiguity, rather than learning to live inside it.
Psychologically, moments of not-knowing can lead to novelty, creativity, and deeper self-discovery. Research in positive psychology shows that uncertainty, when approached with openness, can heighten awe, wonder, and meaning. That’s because when you’re no longer locked into a script, life becomes textured again.
how to slow time
It’s July. It is the kind of day where the sun lingers like it’s not ready to go home, crickets hum, the air is thick with nothingness. As a child, this time of year felt slow - not boring, but spacious. I remember having no urgency to be anywhere but where I was.
Think about it: the most memorable moments in life usually didn’t go according to plan. They surprised you. They rerouted you. They asked you to respond, not perfectly, but with presence.
Expanding your tolerance for uncertainty
Learning to live without a five-year plan doesn’t mean abandoning goals or becoming passive. It means shifting the why behind our direction, from fear to curiosity, from rigidity to responsiveness.
Here are five tools to help:
1. Widen the lens
When you're in a moment of uncertainty, zoom out. Ask: What else is true? What are the multiple possible outcomes, not just the worst-case scenario my brain is fixating on? Research in cognitive behavioral therapy shows that identifying a range of outcomes can interrupt catastrophic thinking and reduce anxiety.
2. Somatic grounding
The body often reacts faster than the mind. When you feel foggy, frozen, or frantic - pause. Put your feet on the ground. Lengthen your exhale. Use your senses: name five things you can see, four you can touch, three you can hear. This brings you back to the present, where life is actually happening.
3. The “season” mindset
Your life is not a linear staircase, like I mentioned above, it’s more like a tide. Or a season. Some periods are about planting, others about pruning. You don’t have to be blooming all the time.
Ask yourself: How would you live differently if you trusted yourself to respond to whatever comes?
4. Create ‘micro-structure’
Uncertainty feels intolerable when everything is undefined. You don’t need a five-year plan, but you might need a Monday plan. Try creating gentle scaffolding: a weekly ritual, a 30-day focus, or a set of values you revisit every morning. These micro-structures offer stability without rigidity.
5. Practice ‘opposite action’
From DBT: when your instinct is to avoid, over-control, or shut down, practice the opposite. If uncertainty makes you want to rush to solve everything—slow down instead. Take one small action that aligns with curiosity, not fear. This could mean exploring a path you haven’t researched to death, or saying yes before you're 100% sure.
An invitation to live off the map
Leaving the map behind doesn’t mean being lost. It means learning to stay present, long enough to let a new path reveal itself.
Uncertainty, when we stop fighting it, is often where life becomes most vivid. Think about travel, falling in love, changing careers - our most expansive moments are rarely the ones we planned. They’re the ones we surrendered to.
There’s wisdom in learning to navigate with what you have: your values, your curiosity, your capacity to sit in the uncertainty without rushing toward clarity. A life lived without certainty is not aimless. You’re allowed to pivot. You’re allowed to not know. There may be a path that appears that you couldn’t have even imagined!
Think about the last time you let go of a plan, whether by choice or circumstance.
What happened that you didn’t expect?
What did you learn, gain, or experience that wouldn’t have happened if everything had gone “as planned”?
How did that moment shape your sense of self?
That’s all for now! May your tables, health, and happiness be always in abundance. Live well + be well xx,
Israa
WellGuide Watchlist:
Read: The Midnight Library by Matt Haig, a fictional lens on multiple lives and letting go of rigid paths.
Watch: Film: The Secret Life of Walter Mitty for a poetic exploration of purpose and stepping into the unknown. It has a fantastic soundtrack as well!
Listen: On Being with Krista Tippett - “The Future of Hope”
Connect: Join me and Ada Rose for a live conversation about toxic productivity at work and how to overcome it to boost genuine productivity. It’s free but RSVP required: link
Loved this so much. Thanks for sharing it.