5 Powerful Midyear Reflection Questions for Leaders

As we cross the halfway mark of the year, many of us feel the quiet urge to pause, reflect, and realign. Whether you're a founder, creative, or leader, this midpoint isn’t just a calendar milestone: it’s a strategic opportunity.

According to James Clear, author of Atomic Habits, “You do not rise to the level of your goals. You fall to the level of your systems.” And midyear is the ideal time to evaluate both: the goals we set and the systems (or lack thereof) we’ve used to pursue them.

Here are five powerful, grounding questions that can help you check in with yourself and reset with intention:

1. What’s been the most energising part of this year so far? Often, we remember what drained us more than what inspired us. But energy is a compass. Noticing where it lifted you can guide your second-half strategy.
   

2. What have I outgrown in my work or habits? Growth requires shedding. Maybe a project, mindset, or even a client no longer aligns. As leadership expert Marshall Goldsmith puts it, "What got you here won’t get you there."
   

3. Where am I overcommitted or under-nourished? Busyness doesn’t equal momentum. If your calendar is full but your spirit is depleted, it’s time to re-evaluate what you’re saying yes to, and why.
   

4. What kind of support would actually serve me now? We often wait until we're overwhelmed to ask for help. But real leadership includes resourcing yourself before the burnout. Support can mean mentorship, coaching, or simply better boundaries.
   

5. What does "success" feel like in this season? Not just what it looks like, but what it feels like. Is it peace? Is it space? Is it creative flow? Redefining success midyear can give you permission to pursue goals that are truly aligned.
   

Taking time to reflect with these questions isn't indulgent; it's strategic. Research from Harvard Business School found that employees who spent just 15 minutes reflecting at the end of their day performed 23% better after 10 days than those who did not.

Midyear is an invitation: not to double down on what’s not working, but to lead from a more aligned, strategic version of you.

Ready to explore your answers more deeply?

Our signature midyear offer, the Power Hour Reset, is designed for founders, creatives, and leaders who are ready to move from scattered to strategic. In a single, high-impact session, we’ll clarify where you are, where you're heading, and what needs to shift now to lead from your most aligned self.

📅 Limited slots only.

Book your Power Hour Reset now and start the second half of the year with clarity, energy, and focus.

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