These 10 Questions Will Take Your Career to the Next Level in 2026

A short, honest exercise designed to help you figure out what you want next in your career

and

Dec 08, 2025

Welcome back to Reframed! Work is complex, career advice shouldn’t be. I’m Ashley Rudolph and I write this newsletter for people who are ready for the next level in their careers.

This week, I’m partnering with

Kate Citron

, former marketing executive turned freelancer and author of False Start where she shares career advice for early to mid-career marketers. Today, we’re sharing our advice for making 2026 your most successful and fulfilling year in your career.

Want to level up in 2026? Your biggest career moves will be shaped by clarity, smart choices, and creating the right plan. Here’s your blueprint.

Together, we’ve completed 25+ performance review cycles.

Reviews serve a purpose, but rarely is that purpose meaningful (and vulnerable!) self-reflection. That’s why we’re teaming up to bring you a more human year-end review reflection exercise: one that’s actually for you, not your manager.

We know a thing or two about the role self-reflection plays in career growth — both from our own experiences and from helping other people uplevel at work.

We designed this exercise to help you:

Get clearer on what energizes (and drains) you
Name what no longer works for you
Set a direction that feels inspiring for next year

Below you’ll find three sections, each with a few prompts and a short anecdote from one of us. You’ll see how this kind of reflection has shaped both our careers as executives and, now, as entrepreneurs.

Journal through the prompts, talk them out with a friend or partner, or jot down notes while you’re traveling this holiday season. There’s no right or wrong way to approach it.

Let’s jump in.

Level Up Next Year with These 10 Questions

PART 1

Looking Back – What This Year Revealed About You

So, you know how you enjoy reading our Substacks because we share lessons rooted in our personal experiences? There’s a reason for that! Personal experience is the best guide when you’re trying to uncover what’s next. Below are four questions to bring you more clarity about what the future holds for your career next year.

What kind of leader did you become this year? Everyone is a leader in their own way, even if you don’t have the title or lead a team.
Where did you feel most like yourself at work?
What did you keep telling yourself wasn’t “that big of a deal” but actually bothered you this year?
What felt hard this year that used to feel easy? What changed? Was it you or your environment?

Kate’s Story

At the end of 2016, I was wrapping up my role at my second job, an early-stage media startup. I had secured a new role for January and was excited for something different. As I reflected on my experience at the startup, I realized I was embarrassed by the way I had handled myself in several situations. A few examples: I had gossiped with coworkers, cried in front of my boss, and reacted irrationally to organizational change. (Don’t judge, I was 25.) I wanted to be proud of how I conducted myself, and I had noticed that my more experienced coworkers carried themself much more professionally. This became my goal for 2017, and it’s stuck ever since.

PART 2

Defining Your Edge – An Energy & Strengths Audit

Before you roll your eyes, this is not the standard interview question: “What are your greatest strengths?” Even if you’re self-aware, it’s a difficult question to answer honestly. So we created a slightly different approach to helping you figure out what you’re best at, what you love doing, and what you might want for the future.

What parts of your work or projects made you feel energized vs. drained?
When teams come to you for help and what are they usually hoping you’ll do?
What or who did you feel envious of this year? Jealousy can tell us a lot about what we want but may not be ready to consciously acknowledge yet.

Kate’s Story

I realized I was unhappy in my job around August of 2024, but I had no idea what I wanted to do instead. I was burnt out and exhausted, and every time I tried to imagine a path that might energize me, I came up empty. So I started paying attention to my envy. I noticed it was always directed at people who had more freedom and flexibility in their careers — people who started their own brands, went freelance, or stepped out of marketing entirely.

Jealousy is uncomfortable, but it turned out to be the most useful signal I had. Paying attention to that feeling pushed me to go freelance and start writing on Substack. In hindsight, both were undoubtedly the right decision.

PART 3

Building Your 2026 Career Plan

This is where you turn everything you’ve learned from the earlier prompts into a plan that moves you closer to the version of yourself you want to become next year. As you think about what 2026 could look like, use these questions to define your direction and sharpen your focus:

If nothing changed for 12 months, would you still be happy about where you’re at?
What are 1-2 skills or qualities that you want to work on? These can come from feedback you’ve gotten, things you’re envious of in other people, etc.
What are 3 things you can do to help yourself level up? What support systems do you have vs. need? Examples: presentation or public speaking workshops, professional development resources (HBR or newsletter subscriptions), a buddy at work who has skills that you don’t, a coach

You’ll start to notice that intentional action makes your goals feel possible, instead of feeling theoretical.

Ashley’s Story

When Kate and I were talking about this part of the exercise, I thought back to one of the most defining times in my career: when I made the shift from Manager to Director and eventually to VP in 5 years.

Before my initial promotion, I was a program manager at a startup, fully leaning into the fantasy of “cool startup life”. I loved the casual clothes, the freedom, the energy. But over time, I noticed something: the people I admired in leadership didn’t look or operate the way I did. They were always “polished” and prepared. They dressed the part, and they seemed to know what to say in spaces where I stayed quiet, afraid of sounding out of my depth.

So I made two goals that year:

I found a “lewk” that felt like me but more elevated. I revamped my wardrobe (Rent the Runway Unlimited was my bff). This one small shift made me feel more serious and more grounded when I walked into work every day.
I stopped waiting to be invited into higher-stakes work. I started talking to colleagues and superiors about what I was good at and what I wanted to do more of. I sent thoughtful emails to leadership. And eventually, I found myself presenting 1:1 to the CEO and nailing the conversation (after obsessing maniacally about it for days).

Those choices shifted how the organization saw me before my title changed. I focused on what was fully in my control: how I showed up, what I took on, and how prepared I was.

And when the opportunities came, I landed them.