Happy start to the week 🌞

June is my birthday month, and historically the month I use to reflect on goals. Things have been more full over here so I wasn’t able to reflect on my birthday, but I feel close to reaching two of my goals and I feel like that achievement will help me reflect on what’s next.

One of the biggest things about creating systems in life and work is finding the ones that work for you, not creating them for an outside reason.

For years, I followed the same goal-setting approach and it worked really well for me (this is the approach) but in the last ~five years life has been different. I’ve had two kids, moved twice, grown into a leadership role at work, and returned to jiu-jitsu after a break. Life is simply different, especially as a parent, and my systems and expectations have needed to adjust.

This year, I decided to try something new: setting monthly themes for my goals. Whereas previously I did annual or quarterly goals, I felt I needed smaller goals with faster achievements in this current season.

Here are a few examples from my year so far:

• January was for habits — I focused on getting to the gym more consistently
• February was for career — I spent time in a coaching program
• March was for creation — I dedicated energy to content projects (like this newsletter!)

I really like the more frequent reflections combined with the shorter timeframe. It feels much more manageable than trying to sustain motivation for three months at a time, especially with how quickly life changes right now. I’ll share more about this approach close to the end of the year when I’ve had more time with it.

Regardless of how you approach your yearly planning: mid-year is the perfect time for reflection on goals or any other intentions you set for the year.

Even if your birthday is not in June, which is likely the case for most folks reading this, June is still a natural time to start reflecting or adjusting goals for the rest of the year since you’re about halfway through it.

Here are three basic questions I’m using to broadly reflect on the year so far:

1️⃣ What has gone well?

For me: Getting back to the gym more often has been a huge win. I’m feeling stronger and more energized.

2️⃣ What do you want more of?

For me: I want to carve out more mornings for myself either for yoga, writing, or just a cup of tea on my own.

3️⃣ What hasn’t gone well?

For me: I’m still struggling with having too many things on my to-do list and solidifying a better email system — something I wrote about a few weeks ago.

You can use these reflections to set goals or not, but the act of reflecting is usually clarifying. Sometimes just naming what’s working and what isn’t is enough to help you make small adjustments for the second half of the year.

I hope you have a lovely week ahead. As always, feel free to reply if this sparks any thoughts or questions. ✨

See you next Monday,

Hailley

• I'm a big fan of the Enneagram and knowing my type has created a lot of clarity for me in my work, life, and decisions over the years. I recently came across this post about the different leadership strengths and struggles across the Enneagram. If you know your type, or you know the type of others in leadership positions that you work with, this can be quite a resource.
• Have you ever wondered how others are using AI? This HBR piece gets into how people are using AI in 2025 and it was a fascinating read. The top three reasons were: therapy/companionship, organizing my life, and finding purpose.
• There are a lot of tools I use daily, one tool is AI, specifically Claude, which I use for writing, processing, summarizing, and a ton of other daily tasks. If you haven't yet, I highly recommend checking out Claude. (Full transparency: That's a referral link so I can enter to win a few free months of Claude if you sign up.)

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