The Questions High Performers Skip in Their Annual Planning (And Why That’s the Problem)
If you started the new year thinking both “I crushed it last year” and “2025 almost broke me,” it’s time for you to level up in how to dive into the coming year. Maybe you got the promotion, expanded your team, or checked off every box on your vision board. But if you’re honest? Something still feels off.
You came back from vacation more tired than ever. You snapped at someone you love over a topic so insignificant you can barely remember. More days than you’d like to admit feel like going through the motions, where you’re performing your own life instead of living it.
Since we suspect you’ve already downloaded your fair share of strategic planning documents to design the life you want in 2026, let us share information that might be more helpful.
Here’s what you’ve missed: you’ve been looking in the wrong direction.
(Bookmark this page so you can reference the list of questions below and return to it throughout the year.)
Most annual planning asks What do you want to achieve next year? But it leapfrogs over the critical questions that actually end up shaping your success. Those are questions like What are you still carrying from last year? What patterns showed up that you didn’t deal with? What did you avoid because there was always something more urgent?
Driven New Yorkers are exceptional at forward momentum. We live at the nexus of innovation. But momentum without reflection isn’t strategy–it’s just speed. And moving fast while shackled to outdated coping patterns and unresolved pain from the past is how you reach the end of the year feeling like you’ve run the NY Marathon with a 50-lb weight tied to your ankle. We don’t want to gas you. There’s no superficial helium hiding in this post to carry you to new heights. We’re going to help you get rid of the weights around your ankles.
The Missing Piece in Annual Planning for High Achievers
Most strategic planning frameworks focus on external metrics like career milestones, financial goals, fitness benchmarks, and relationship status. They’re all the same: set an objective, identify the KPIs, and nail down the actions that’ll get you to your goal. But here’s what rarely makes it onto the spreadsheet: your capacity, your patterns, your emotional sustainability, and the cost of what you’re carrying.
Let’s say the quiet part out loud: you can’t outperform unresolved patterns. You can’t time block your way out of an anxiety attack. Your vision board isn’t helping you manifest courage; it’s cataloging your need for control.
This isn’t about being broken. This is about being honest. The most successful New Yorkers aren’t the people who never struggle. They’re the high-performers who deal with what’s real instead of pretending it isn’t there.
So let’s get real. What follows are some deep cut questions your annual planning is missing. Some will feel easy. Some will make you uncomfortable. A few are NSFS (that’s not suitable for subway) and might stop you in your tracks. That’s the point. If every question feels comfortable, you’re not going deep enough.
End-of-Year Reflection Questions from Top NYC Therapists
These aren’t journal prompts just to help you break in that new moleskine. These are diagnostic questions to help you get under the hood of your life. Answer them honestly. Notice which questions make you want to scroll faster and which make you feel something. Everything is data. This is how to reflect on the past year in a way that leads to real life transformation.
Grab your notes app, a journal, or scribble the answers in your mind. Be honest because no one else will read your answers. Then hop to the bottom of this article for a wrap up idea.
What You’re Still Carrying
The stuff that didn’t resolve just because the calendar year ended.
What situation from last year are you still replaying in your head?
What conversation do you wish you’d had but didn’t?
What are you still angry about, even if you’ve told yourself you’re over it?
What loss (a person, an opportunity a version of yourself) are you still grieving but haven’t named out loud?
Patterns You Keep Running
The behaviors, reactions, and cycles that showed up more than once.
What did you promise yourself you’d stop doing last year that you’re still doing?
When you felt most overwhelmed in the past year, what did you do? (Work more? Withdraw? Numb out? Pick a fight?)
What criticism did you hear more than once from people you trust?
Where do you keep choosing the path that feels safe over the path that feels true?
What You’ve Been Avoiding
The things you’ve been too busy, too scared, or too tired to face.
What hard conversation have you been postponing?
What part of your life feels like it’s on autopilot—and what would it cost to actually examine it?
What are you afraid would fall apart if you stopped holding it together?
If you stopped moving for a second, what feeling would catch up to you?
The Gaps Between Who You Are and Who You Pretend to Be
Where the performance is exhausting you.
Where are you performing confidence but feeling doubt?
What do people assume about you that isn’t actually true—and why haven’t you corrected them?
What part of your success feels hollow, even though it looks good from the outside?
If someone asked, “How are you really?”—what would you say if you were being honest?
Capacity and Sustainability
Whether you’re building something that lasts or just running faster.
What are you doing that’s working against your energy instead of with it?
Where are you sacrificing your presence (in relationships, in moments, in your own life) for productivity?
If you kept operating at this pace for another five years, what would break first?
What would it feel like to be ambitious and at peace? (And why does that feel impossible right now?)
What Happens When You Sit with Self-Reflection Questions for Goal-Setting
Around question 7 or 12, you probably recognized that some of these end of year reflection questions aren’t the type that you can just “think your way” through. Step one is awareness. But without support and action, you’re just ruminating on record.
In Life Starts Now, I talk about the difference between coping and transforming. After decades of working with clients, I’ve seen what it looks like for people to just manage their symptoms or actually start addressing what’s underneath. The high performers who plateau are those who stop inviting feedback and support. They are great at analyzing their problems, but they don’t get traction on goals because they try to make change alone.
Here’s the thing: the ability to ask for help isn’t weakness; it’s strategy. The GOATs (folks like Lebron James, Beyoncé, or Steve Jobs) get better over time because they outsource their development, leveraging the brain power of experts to enhance their performance in one area, while they dedicate their energy to living dynamically in other areas.
The Difference Between Reflection and Transformation in Therapy or Coaching
Sure, you can do reflection exercises and strategic planning alone. Journal, process, note the threads, and craft an action plan all by yourself. That’s valuable. But for high achievers in particular, there’s a limit to what self-awareness can do without expert guidance.
“Momentum without reflection isn’t strategy—it’s just speed.”
Transformation happens in relationships. It’s the reason why all the ChatGPT prompts in the world aren’t actually solving your mental health challenges long-term. You need someone, a real human, who can see your patterns before you can, who won’t let you intellectualize or perform your way around the hard stuff, and who can hold space for what you’re carrying so you don’t have to carry it alone.
That’s the difference between annual planning and actually changing. One happens in a Google doc around midnight. The other requires you to stop performing and start being honest with a trusted guide who knows how to help.
Partner with the Best Therapists in New York City
If you’re ready to go deeper and climb higher in the year ahead, you don’t have to dive into your personal growth alone.
Healthy Minds NYC helps high achievers stop performing and start being present. We don’t do therapy that tiptoes–we do the kind that creates shifts you can feel in weeks, not years. Let’s get clear on what’s been keeping you stuck.
Schedule a free consultation call with our dedicated care coordinator to explore your options for care. We’ll listen to your needs and goals, nail down the right provider for your wellness journey, and start getting traction on your plan for the year.
