Thinking About Your Career
A 4-step framework to consider, "what do I want to do next?"
Most people outsource their career plans and then wonder why they feel stuck or unsatisfied.
If you don’t plan out where you want your career to go, someone else will. A boss might map your path based on company needs. A family member might push you toward security. A career coach might project their formula onto your life. They’re all well intentioned, but none of them live with the consequences the way you do.
The truth is, the only person who can define a fulfilling career is you.
Over the years, speaking at universities and mentoring people, I’ve shared a simple 4-step framework that helps people reset, get clarity, and decide what’s next.
It works whether you’re choosing your first job, pivoting mid-career, or aiming for senior leadership.
Step 1: Vision — Define Your Destination
If you don’t know where you’re going, every job, degree, or certification looks like progress.
A lot of people are racing through their careers, adding credentials, attending industry events, and consuming thought pieces, without a clear sense of their destination.
If can feel like progress until you stop and ask:
Where do I actually want to end up in my career?
It sounds overly simplistic, but most people struggle to answer the question.
I don’t believe in rigid 10-year plans anymore. The world changes too fast and life is unpredictable, but it’s still worth investing the time to think about your long-term career trajectory or, at least, your next step on the road.
Your destination is not just a title or a paycheck. It’s the kind of work, impact, and life you want.
Ask yourself:
What problems do I want to solve?
What does my ideal day look like?
Do I primarily value money, time, or prestige?
Objection: “But I don’t know my 10-year plan.”
That’s fine. Your destination will evolve from season to season and that’s normal. What matters is defining it clearly enough to guide your next steps, so you’re steering with intention rather than drifting.
Step 2: Assessment — Take Inventory
Vision without honesty is just wishful thinking.
Assessment is about looking clearly at where you are today and what gaps exist between here and your destination.
One of my favorite exercises when I’m coaching people is to take 3–5 job descriptions they’re genuinely excited about, drop them into ChatGPT, and prompt engineer a composite of the “ideal candidate” for those roles.
We’ll ask things like:
What education shows up most often for these roles?
What experiences or track records do these candidates typically have?
How does this person’s resume compare to the ideal candidate profile?
This takes the guesswork out of career planning. Instead of assuming you know what’s missing, you get an objective snapshot of the gap between you and the roles you want.
Example: I once coached a mid-level manager who thought he was ready for a director job. His assessment told a different story: great technical expertise, but zero cross-functional leadership. Instead of sending out resumes and getting frustrated, he spent a year leading a cross-team project. That one shift unlocked the promotion.
Honest assessment stings sometimes, but it’s the fastest way to focus your energy on what actually matters.
Step 3: Planning — Identify Next Steps
Most careers stall because people are working hard on the wrong things.
This is where assessment turns into focus. Once you see the gaps between where you are and your destination, the next step is to pick one or two critical moves that unlock everything else.
When I work with people, I always push them to narrow down. Not five things. Not a laundry list. Just the one or two steps that will change the trajectory.
I’ve lived this myself. I was laid off while raising two young kids. My critical move was starting college as a husband and dad well past the “normal” age for college. It was awkward, humbling, and anything but convenient. But that uncomfortable step became the foundation for the next stage of my career.
Don’t underestimate the power of taking the nontraditional path when everything feels stacked against you.
Progress comes from identifying the one step that matters most right now and having the courage to take it.
Examples:
Student: Target the right internship, not just any internship.
Early in Career: Tell your manager that you are interested in working on a specific kind of project so that you can gain particular skills and experience.
Manager: Volunteer to lead a cross-functional initiative to break out of a silo.
Executive: Build visibility outside the company to prepare for board opportunities.
Objection: “But I don’t know which move matters most.”
That’s normal. Test it. Pick one and run a small career experiment. Momentum beats waiting years for certainty.
Step 4: Action — Execute Relentlessly
Clarity without execution is just a wish.
This is the part where most people stall. They’ve done the thinking, maybe even written down their goals, but nothing changes because they don’t take consistent action.
A simple time-based action plan with 2–3 outcomes is enough. Then find a way to hold yourself accountable: share it with a mentor, a peer, or even a spouse. Without action, even the best framework is just words on a page.
Practical ways to get moving:
Write a 90-day plan with clear, measurable outcomes.
Share your goals with someone who will check in with you.
Run small experiments: shadow another team, pitch a project, take on a stretch assignment, or sign up for a course.
Example: One mentee realized his gap was “executive presence.” He built a 90-day plan: deliver two presentations to senior leadership and ask for feedback. Three months later, he wasn’t just more confident, he was already being considered for more impactful roles.
Objection: “What if I fail?”
You will at times. Everyone does. But failure in motion is progress. You learn, adjust, and try again. Failure from standing still? That’s just wasted time.
Putting It All Together
Most people let their careers happen to them. They take the job that shows up, follow the path someone else laid out, and then wonder why they feel stuck.
This framework flips that. Instead of drifting, you’re steering:
Define your destination so you know where you’re headed.
Take an honest assessment of where you stand today.
Identify the critical moves that will actually move you forward.
And then take relentless action to build momentum.
I’ve seen this work for students landing their first job, managers breaking out of stagnation, and executives repositioning for the next stage of their career. The details change, but the system doesn’t.
If you have questions about the framework or would like a deeper dive on any of the steps, then please comment below or reach out 1:1 at justin.gillebo@gmail.com.
Rooting For You,
Justin
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