After I published my post on the Perfect Day exercise, a colleague reached out with something that stuck with me. She shared my resistance to the “where do you see yourself in five to ten years” question, but she named a specific version of the trap I hadn’t fully articulated: the way we default to planning our futures in terms of roles.
I want to be a director. I want to run my own firm. I want to make partner.
These sound like ambitions. They feel concrete. But they are actually some of the most limiting ways to think about what comes next, because they lock your imagination into a structure someone else designed. A title tells you almost nothing about how you’ll spend your Tuesday afternoon. And yet, when most people plan their futures, that’s where they start.
I know this because I lived it.
The credentials that didn’t open the doors I expected
When I moved to the United States, I arrived with years of leadership experience, including C-level positions, and a career I had built in my home country. I had real ground under my ambitions. I did what seemed logical: I set about verifying every credential I could. I passed my PMP certification again. I earned a Change Management certification. I updated my résumé and started applying for the roles that matched my background.
The rejections came steadily. Not one or two, but enough to make me question whether everything I had built before was transferable at all. I was making decisions based on roles I had held, qualifications I could prove on paper, and what seemed like a rational next step. I was asking the labor market to confirm an identity I had carried with me across an ocean. It kept saying no.
At the time, this felt like failure. I was qualified. I had done the work. The logic was sound. Why wasn’t it working?
Looking back, I can see what I couldn’t then: I was trying to fit myself into a shape that had already served its purpose. The roles I was chasing belonged to a version of my career that was complete. But I didn’t have language for that yet, so I kept applying for variations of what I already knew.
What the exercise showed me that my résumé couldn’t
Somewhere in the middle of all those rejections, I did the Perfect Day exercise.
I didn’t write about a title. I didn’t describe an office or a reporting structure. What came out, when I let myself write freely, was this: I saw myself working with people. Having real conversations. Sharing ideas. Asking questions that mattered.
That was it. No company name, no industry, no level. Just the texture of a day that felt like mine.
I shared this with a friend. Her response was immediate: “What about coaching?”
It was one of those moments where someone sees something in your own writing that you haven’t seen yourself. The Perfect Day exercise had bypassed all the categories I had been sorting myself into, the titles, the credentials, the logical next steps, and revealed what I actually wanted to do with my time. Not what I was qualified for. Not what made sense on paper. What I wanted the hours to feel like.
Why roles are a trap and days are a compass
Here is what I have come to understand, both from my own experience and from years of working with clients who face similar crossroads: when you define your future by a role, you are borrowing someone else’s structure for your life. You are saying, “I’ll know I’ve arrived when I have this title, at this kind of organization, at this level.” But titles describe positions in systems. They don’t describe the quality of your experience inside those systems.
Two people can hold the same title and live completely different days. One is energized. The other is depleted. The title is identical. The days are nothing alike.
The Perfect Day exercise cuts through this because it asks you to describe experience, not position. When you write about a day, you can’t hide behind abstractions. You have to say what you’re actually doing, how it feels, who you’re with, what the rhythm is. And what emerges is often different from what you would have put on a goal sheet.
I’ve watched this happen with clients who come to coaching convinced they need a promotion, a lateral move, a new company. Sometimes they do. But sometimes, when they write their perfect day, the surprise is that the change they need has nothing to do with their title and everything to do with how they’re spending the hours inside it.
What the rejections actually gave me
That was five years ago, and I have never been happier in my work. The rejections that felt so discouraging at the time turned out to be the most productive thing that happened to my career, because they made it impossible to keep following the old map. They forced me to stop asking “what role should I have?” and start asking “what kind of day do I want to live?”
Coaching is the answer I found. My days are filled with exactly what surfaced in that exercise: working with people, having conversations that matter, asking the questions that open something up. But also reading, learning, writing, making sense of patterns I notice across clients and situations, and a constant process of creation. The day I imagined is the day I live.
But the point of this story isn’t that everyone should become a coach. The point is that the future I actually wanted was invisible to me for as long as I was looking through the lens of roles and titles. The moment I described a day instead, it appeared. And someone who knew me recognized it before I did.
If this sounds familiar
If you’re in a place where the roles available to you don’t feel right, if you’re wondering what comes next but every option you can name feels like a variation of something you’ve already done, try a different question. Don’t ask what you want to be. Ask what you want a day to look like.
You might discover, as I did, that the answer has been waiting for you to stop looking in the wrong direction.
You can start with the Perfect Day exercise. If you’d like a guided version with prompts and reflection questions, I’ve created a free workbook to walk you through the process.
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