Career Checkpoints: Why You Need Them (No Matter What Field You're In)
Let us talk about why it is important for anyone building a career
Let’s talk about something I believe is vital for anyone building a career—career checkpoints. I recently did a video on this and thought it may be helpful to share more.
It doesn’t matter what field you’re in, or what stage you're at—whether you’re just starting out in your 20s, figuring things out in your 30s, or even pivoting in your 40s or 50s—if you’re serious about building a life that aligns with your values, you need to pause and reflect at key moments. These checkpoints allow you to re-evaluate your vision, goals, values, and how they may have shifted over time.
Without doing this, you risk moving forward with a mindset that's outdated—one that might’ve made sense when you started, but no longer serves who you are becoming.
What are Career Checkpoints?
Career checkpoints are moments—either planned or forced—where you intentionally sit down to ask yourself:
Where am I now?
What do I want?
What do I no longer want?
What’s changed in my life, my interests, or the world around me?
What’s next?
And trust me, life will give you these moments. The key is whether you’ll take them seriously.
My Checkpoints (So Far)
Let me share a few of mine:
1. Medical School – Choosing Between Public Health or Business School
In my fourth year of medical school, I had to decide if I continue medical school, pursue public health or go to business school. I took time to really think about what I wanted to learn, where I saw myself in the future, and what aligned with my interests at the time. I chose business school because I wanted to understand health systems, tech, and innovation. Public health was (and still is) important to me, but that wasn’t the season for it.
2. Post-Pandemic – Re-evaluating What Kind of Doctor I Wanted to Be
After the pandemic, I had another major checkpoint. That period forced so many of us to pause. For me, it became clear I needed to ask: How do I want to practise medicine? What kind of specialty fits who I am now? That reflection led me to take an F3 year out of training. During that time, I explored consulting, public health, and more. And while I liked consulting, I realised I didn’t want to leave medicine—I was just drawn to work that was community-focused and system-driven. That led me to GP training.
3. Now – The Freedom to Choose
I’m now approaching the end of my GP training, and I can feel another big checkpoint approaching. I have autonomy now—over how I work, where I work, what I focus on, how many days I do clinical work, and what other interests I want to pursue. And while that’s exciting, it also means I need to check in again: Where do I want to go? What do I want my next 5–10 years to look like?
How to Do Your Own Career Checkpoint
If you’re ready to do your own checkpoint, here’s a framework you can use:
How am I doing now?
What do I enjoy about my work? What drains me? What am I excited or bored by?What matters most to me right now?
Is it financial stability? Flexibility? Family time? Career growth? Travel? Purpose?Has my vision changed?
Look back at what your goals were a year or two ago. Do they still feel right? Or have they evolved because of life events, people you've met, or things you’ve learned?What external changes should I be aware of?
The world changes fast. Six years ago when I started practising, AI in healthcare wasn’t on my radar. Now, it’s a core interest of mine. Keep your eyes open—what’s happening around you can help guide what's next.What are my top 2 focus areas going forward?
Don’t feel like you have to pick one thing forever. Write out your interests, narrow them down, and focus on 1–2 areas for the next season of your career.
Final Thoughts
Checkpoints don’t have to be dramatic. They can be small moments of reflection or big life decisions. But they’re necessary. Your career will naturally give you opportunities to pause—your job is to notice them, and use them.
And don’t forget: you don’t need a 30-year plan. But you do need a direction, a vision, and a sense of what you care about. That’s how you build a career—and a life—that reflects who you are and who you’re becoming.
Let me know if you'd like more tools, prompts or videos on this—I'm happy to share more.
Podcasts for Goal Setting.
I am thinking of starting a podcast club because I absolutely love listening to them. Here are a few I have listened to that would be perfect for planning your new year ahead. Also lmk if you want to join the podcast club and if I should start one.
Ladies who Launch - How do you unlock success with purpose and mindset with Rochelle and Dior
I really loved this conversation with Rochelle and Dior. I listened to it earlier in the year, but so many of the points and discussions still feel incredibly relevant—especially for those of us exploring our interests and trying to figure out our purpose. They also break down some real gems from previous guests, which makes it even more insightful.
Diary of a CEO podcast with Jimmy Fallon
I was surprised by how interesting and relatable I found this interview. What I love about Jimmy Fallon is his ability to identify his dream and chase it—even when it didn’t seem likely to work out. Deep down, he believed he would end up where he wanted to be, and for him, that was Saturday Night Live. And he made it happen. He’s driven by a genuine purpose to bring joy to others and hasn’t looked back since. A great listen!
Opportunities, events & networking for you!
Upcoming events in June
ARA NINI Health: Sign up to our mailing list we have some exciting events this summer coming up and you do not want to miss. Our mailing list community will be the first to hear. LINK HERE
London Tech Week: June 9th -13th 2025 - London- Link here
HIMSS AI in Healthcare Forum: July 10 -11th 2025 - New York- Link here
Did you miss this?
Here’s a video I shared this week on career checkpoints and how I have used them so far in my career. Also check out my dump from an existing day in the city, graduation from my digital health fellowship, going to Parliament and having drinks with FIGS.
Again, THANK YOU for being here, let me know your thoughts in the comments, if you have any suggestions on topics, SHARE this with your friends & I will see you next week !
Signed, Dr J
(aka Joyce Omatseye)
I enjoyed reading this!! Thank you for sharing, I love the idea of the podcast club, I'd love to join!