We toast New Year's Eve with resolutions. We celebrate birthdays with well wishes. We post highlight reels to social media. But how often do we actually pause - long enough and honestly enough - to ask ourselves questions like:
Is this still the life I want?
Am I growing toward the version of me I respect?
Am I building a career that matches my definition of success - or someone else’s?
Most of us are moving too fast to stop and look. Or worse, we avoid it because what if we don't like what we see?
Reflection is not a luxury. It doesn’t have to involve a silent retreat. It's not mystical (tho I love woo woo). Reflection is leadership. It’s self direction. Without it, we let our lives fall victim to distraction or inertia.
Recently I made a big change in my life, I transitioned away from running a billion dollar public company. It would have been easy to step into the next big executive job. My ego wanted me to do exactly that, but reflection revealed to me what I actually wanted is FREEDOM - to be on my own schedule, to invest in my interests, and to teach. Years of effort had given me the financial cushion to allow for this moment - to take a step off the treadmill. My ego was so loud:
You can only grind for so long, keep going! More, more, more…
What if I become irrelevant?
What if when I am ready to go back, nobody wants me?
My ego was pointing me to external measures unrelated to what matters to me: energy, alignment, and impact. Reflection revealed: Yes, I am in prime so why wait for “retirement,” which sounds like a reward for a lifetime of hard work when you can least enjoy it. Irrelevant to who? If you don’t care about me because I don’t have “CEO” after my name, then you’re not someone I need in my life anyway. And finally, the idea that my decades of experience would suddenly be rendered useless with the passing of time is a default setting at it’s worst: a false narrative to bust. I believe that stepping back will only make me stronger and more inspired. Eventually, I may take the seat of CEO again, but that’s not what I want today.
Instead I exchanged earnings calls and town halls for Namaste and Professor. Since stepping away from my operating role, I completed my 200 hour yoga teacher training, and even taught my first class. I have also developed a new course curriculum for Duke University, which I will teach this Fall called, The Women’s Leadership Lab. I get to live a portfolio life serving as a Board Director, Investor, and Advisor. All these fulfilling changes as a result of following the 4 simple prompts below, and reflecting truthfully on the answers.
You are Not Vin Diesel - Don’t Drift
Momentum is seductive. When you're busy, you don't have to confront discomfort. You don't have to ask hard questions. You just keep moving, producing, performing. If you never stop to reassess, you are at risk of waking up five years from now wondering: How did I get here?
Intentional reflection - at least once a year - is how you course-correct before you drift too far. Honor the fact that you’re not the same person you were 12 months ago, and neither is the life you’re meant to lead.
You don’t need a silent retreat in Bali, but that does sound really amazing. You need a quiet afternoon, a journal, and your own radical honesty.
How to Reflect, Reset, and Reclaim Your Path
Here’s a simple framework to get started:
1. Audit Your Energy, Not Your Outcomes
Instead of asking What did I achieve?
What gave me energy this year?
What drained me - even if it “looked good” from the outside?
The work, the relationships, the habits that light you up are data. The things that leave you empty are data too. Combine that data with your intuition and inner knowing.
2. Assess Your Alignment, Not Just Your Ambition
Instead of asking What goals did I hit?
Are my goals still mine?
Do they align with who I’m becoming, not just who I was?
Reassess your definition of ambition because all too often we can let old paradigms and expectations of success keep us static.
3. Identify What Needs Shedding, Not Just Starting
We love to set resolutions: I’ll do more! I’ll add more! But often, evolution isn’t about stacking more on top. It’s about clearing space.
Ask yourself:
What needs to end, dissolve, or be gracefully released this year?
Where am I holding on out of fear, not love?
Letting go isn’t failure. It’s making room for what’s next.
4. Choose Your Guiding Question for the Next Year
Instead of rigid goals, set a living, breathing question to guide you. That allows a constant calibration throughout the year until you get to your next time for deep reflection. I like to keep my question on a post-it note on the inside of my bedside table.
For example:
What would it look like to trust myself more deeply?
Where could I choose creativity?
How can I build a life that feels as good on the inside as it looks on the outside?
Inquiry invites curiosity. Curiosity invites change without judgement or punishment.
We are Meant to Evolve
There is plenty of science to back up the cognitive and performance benefits of reflection but what we rarely talk about is the emotional truth: it is perfectly human to want different things for yourself. Over my career I have zigged and zagged across industries and disciplines in ways I could have never predicted: finance (Goldman Sachs), entertainment (CAA), tech (Yahoo!), consumer products (L’Oreal), and gaming (Epic Games). You are allowed to choose a path that your past self couldn’t even imagine. Reflection isn’t about judging where you are, it’s about remembering that you get to begin again as many times as you need.
Be the pirate of your own ship! “Look at me, I am the Captain now.”
If you’ve read this far, then I know you’re ready to be in a habit of reflection. Here are a couple exercise to help expand your practice.
Expansion Exercise for Today: If I could change one thing about my life or work today - small or big - what would it be? What comes to mind, without overcomplicating it. You have now tapped into your inner knowing.
Expansion Exercise for Tomorrow: Write two quick lists. What gave me energy this year? What drained my energy this year? After writing, circle one item from each list. For the energized item: How could you expand it next year? For the draining item: How could you reduce or rethink it?
Expansion Exercise for next Month: Small actions build momentum. So for the next 30 days spend 5 minutes (commit to a time of day) thinking about this simple question: What felt true for me today? It can be about your work, a conversation, your mood, your body - anything that was asking for your attention. Capture it in a voice memo or notes app so that it's easy to do anytime and to revisit. If reflection is new to you, this becomes a way to train yourself to notice alignment daily, not just once a year. Tiny reflections stack up into self-awareness shifts.
✨ I'd love to hear your progress and questions - reply and tell me. What will be your guiding question for this year? Let’s stay aligned and energized.
Thank you for the framework. I'm old and retired and drifting. I think this just might be the thing I have been looking for.
Hi Sima, thanks so much for taking the time to put this together! This looks like a great exercise to do. I’m 28 years old, trying to figure out my next step and stumbling upon your Substack came at the perfect time :)