Understanding Your Goals, Evaluating Your Path, and Embracing the Seasons of Life
I remember a few years ago, I sat across the table from a senior executive, bright-eyed, ready to soak in his wisdom. I asked him what I thought was a smart question: “How do you know if you’re on the right path in your career?” He smiled, leaned back, and said, “That depends on the season of your life.” At the time, I didn’t fully grasp what he meant, but as the years unfolded, that statement echoed back to me in boardrooms, career talks, and during those lonely reflections when life throws you into unexpected corners.
Today, let’s talk about that—what really matters most in your career right now. Not what mattered five years ago, not what will matter five years from now, but what is crucial in this moment.
Let’s also talk about how your personal goals and career ambitions can sometimes walk on separate roads and the courage it takes to merge them, realign them, or even redraw the entire map when life demands it.
Understanding Your Personal Goals: The Compass of Your Career
For most of us, our careers are not straight highways with clear signs and predictable exits. They are more like winding country roads, full of unexpected detours, potholes, and sometimes, stunning scenic routes we never planned for. But at the heart of all these journeys is your personal compass: your goals, values, and what you define as success.
The truth is, many of us enter the workforce running on society’s GPS:
- Get a “good job.”
- Climb the corporate ladder
- Make six or seven figures
- Retire early or at least in comfort
While there’s nothing wrong with these ambitions, they are often not rooted in self-awareness but in external validations. This is why many people achieve these milestones only to feel an emptiness they can’t quite name.
So, what does it mean to truly understand your personal goals?
It means stepping back and asking yourself:
- What does success mean to me right now?
- What kind of life do I want to build outside of work?
- What do I want people to say about me when I’m not in the room?
- What brings me joy, not just accolades?
These are confronting questions. They strip away the glossy titles, the awards, and the corner offices and force you to look inwards. And the answers might change, many times over, as you move from one life season to another.
Evaluating Your Current Career Path: Are You on the Right Road?
Once you have a sense of what your personal compass is pointing to, the next step is to honestly evaluate your current career path.
This can be hard, especially when you’ve invested years, energy, and your sense of identity into a particular industry or role. But staying on a path that no longer serves you is like running on a treadmill—you sweat, you pant, but you remain in the same spot emotionally.
Ask yourself:
- Does my current career path allow me to live out my personal values and goals?
- Am I growing in ways that matter to me?
- Do I still wake up with curiosity and hunger for what I do?
Sometimes, the answers might sting. You might realise that the role you once dreamed of no longer excites you. Or that the industry you fought to enter doesn’t align with your evolving values.
And that’s okay. Life is fluid and so are we.
Evaluating your career path is not about quitting overnight or taking drastic turns without preparation. It’s about gaining clarity on what’s working, what’s draining you, and what adjustments—big or small—you might need to make.
Merging Personal Goals with Career Ambitions
This is where the real work begins.
Merging your personal goals with your career isn’t always a perfect science. Sometimes it feels like trying to mix oil and water. But it is possible to find intersections where they feed into each other rather than fight against each other.
For instance:
- If you value flexibility and freedom, seek roles that allow remote work, freelance projects, or reduced hours.
- If you crave impact over income, explore nonprofit, advocacy, or purpose-driven organisations.
- If you’re passionate about mentorship, start incorporating coaching or leadership into your current role, even informally.
This process requires you to be brutally honest about your non-negotiables. It also demands that you stop waiting for your employer or industry to give you permission to pursue the life you want. You might need to carve your own path, create your own projects, or switch directions entirely.
The Seasons of Life: How Time Changes Our Definitions of Success
One of the most humbling lessons life teaches us is that what lights us up at 25 might feel like a heavy chain at 40.
When you’re in your early career, it’s natural to be driven by ambition, recognition, and proving yourself. You want the promotions, the accolades, and the visible markers of progress, and that’s okay. But as you grow, life invites you to pause, reflect, and sometimes, change course.
Maybe you had dreams of making it to the C-suite by 35. But somewhere along the way, you discovered that your true calling is in teaching, or writing, or starting a social enterprise that serves marginalised communities.
Or perhaps you planned to travel the world as a digital nomad, only to find that you now crave roots, family, and stability more than adventure.
These shifts are not failures. They are reflections of growth.
Time, experience, and sometimes hardship bring clarity to the things we once held sacred. They help us shed the borrowed goals of society, mentors, or peers and embrace what truly aligns with our souls.
The courage lies in being willing to pivot when those realisations hit you. To stop chasing outdated dreams simply because you once declared them boldly on LinkedIn.
Making Peace with Evolving Dreams
One of the greatest traps in career-building is the fear of “starting over.”
We stay in jobs, industries, or paths that drain us because we fear being labelled inconsistent, lost, or directionless.
But the truth is, evolution is not confusion. It is growth. Your calling might evolve. Your definition of success might change. Your values might shift.
That doesn’t make your past seasons invalid—it makes them stepping stones toward deeper self-awareness.
So give yourself permission to:
- Leave the table when the menu no longer feeds your soul.
- Walk away from titles that no longer define your worth.
- Redefine success as often as you need to.
Aligning Career and Life: A Journey, Not a Destination
Alignment is not a one-time event. It’s a continuous process of checking in with yourself, recalibrating your path, and making adjustments as life unfolds.
Practical steps to help you on this journey:
Create a Personal and Career Vision Board Every Year
- Reflect on what you want in your personal life and how your career supports or hinders that.
- Make it visual, tangible, and review it quarterly.
Practice Regular Self-Check-Ins
- Use journal prompts like:
- What brings me joy in my current work?
- What drains me?
- What skills am I excited to develop next?
- Listen to your answers without judgement.
Surround Yourself with Reflective Conversations
- Engage with mentors, peers, and friends who aren’t afraid to question the status quo.
- Attend workshops or retreats that focus on holistic career planning, not just skills development.
Be Gentle with Yourself in Times of Transition
- Career realignments can be messy, emotional, and filled with uncertainty.
- Embrace the discomfort as part of the process.
What Matters Most Right Now?
At the end of the day, what really matters most in your career right now is not what your LinkedIn headline says, how many followers you have, or how impressive your job title sounds.
It’s about how your work feeds your life, not the other way around.
It’s about how your career allows you to live in alignment with your evolving values.
It’s about embracing the beauty of seasons—where some things bloom, others die, and new dreams are planted in fertile ground.
So, as you read this, take a breath. Ask yourself: What matters to me in this season of my life?
The answers may surprise you. They may unsettle you. But they will always, always set you free.
Stay frosty!
