Blog Creativity & Creative Business Personal & Professional Development

Insightful Mid-Year Reflection and Planning Questions

31st May 2019

Insightful Mid-Year Reflection and Planning Questions | Natasha Denness Coaching | (photo of a desk)

Celebrating the middle of the year

I love reaching yearly milestones. They remind me to reflect on how far I’ve come and make adjustments to those things that are no longer working. They also encourage me to be grateful – for where I am, what I’ve achieved and what I can learn from things that haven’t gone so well. It’s maybe because I take this time to reflect that I’m no longer afraid of failure, because it always precedes growth. In fact, throughout my life, I’ve embraced some wonderful opportunities when things haven’t gone to plan!

‘Failure is not the opposite of success: it’s part of success.’ – Arianna Huffington

Journaling prompts

At the beginning of the year, I started journaling. I was inspired to start this practice while reading Julia Cameron’s The Artist’s Way. As an art student, I wrote a diary, but the habit slowly dwindled when I graduated and moved to London – too many wonderful distractions! I’ve loved writing again and connecting with myself in this way. I’ve also enjoyed the daily ritual of getting my thoughts and ideas out of my head and down on paper. The regular reflection and planning has given me an enormous amount of insight and clarity, both in my life and in my work.

As we approach the mid-year point, I always take a little time to think about where I am and where I’m heading, and this year I’m considering the following questions as I reflect on the time that has passed. If you’d like to explore where you are in your life and work right now, you might wish to use these as journaling prompts. They’re gentle questions to help you to explore and celebrate the months that have passed. I’ve also noted a few questions to help you plan what you’d like from the months ahead.

Insightful Mid-Year Reflection and Planning Questions | Natasha Denness Coaching | (photo of palms)

Reflection and planning questions..

1. Gratitude

What worked well and felt good?
What were you grateful for?
What brought you happiness, contentment and joy?

2. Growth

What did you learn?
What did you discover about yourself?
Has anything surprised you?

3. Accomplishments

What did you accomplish?
What are you most proud of?
Did you reach any of your goals? And did you celebrate?

4. Challenges

What wasn’t working or feeling good?
Was there anything missing?
Was there anything draining you of your energy, motivation and time?

5. Plans

What would you like the second half of the year to look and feel like?
How do you want to be spending your days, weeks and months?
What do you want more of and what do you want less of?
Do you have an overarching ambition, vision or goal?

Finding fulfilment and joy – whatever that means for you

I hope the questions help you to gain some insight and clarity while enabling you to consider what you’d like moving forward. When making plans and setting goals, remember that it’s okay to change your mind and that you can reset, refocus and restart as often as you need to. For the most part, there are no rules so please give yourself permission to live the life you want to lead!

Insightful Mid-Year Reflection and Planning Questions | Natasha Denness Coaching | (photo of a desk)

Are you seeking some support and accountability?

If you’re feeling overwhelmed or stuck and would like to explore your options and ideas with a coach, then I would love to hear from you. I can help you move forward and find clarity, focus, fulfilment and joy – whatever that looks and feels like for you. And of course, we’ll have a lot of fun along the way! If you’d like to find out how my coaching can help you just drop me an email and we can have a chat about the support you’re looking for. I very much look forward to hearing from you.

Further reading

Practical tips to help you reach your goals
Bring your dreams and goals to life with a vision board

Thank you for reading. I wish you a beautiful and inspiring day!

Previous Post | Next Post

You Might Also Like


  • Avatar
    Reply Kirsty 31st May 2019 at 10:47 am

    This is such a great post and I feel like I need to start journaling and free writing more. People talk about how beneficial it is and I think it would be good for me. Thank you for the prompts xxx

    • Natasha
      Reply Natasha 31st May 2019 at 10:58 am

      Thank you, Kirsty. I’ve wanted to re-start my journaling practice for years! I can thoroughly recommend giving it a try – if the time feels right for you, of course! I hope you have a great weekend. 🙂

  • Avatar
    Reply Lucy 31st May 2019 at 9:31 pm

    You’ve reminded me of how important it is to keep a journal. I love your posts, Natasha. They’re always full of wisdom x

    • Natasha
      Reply Natasha 2nd June 2019 at 4:35 pm

      Thanks so much, Lucy. I’m certainly enjoying keeping one! 🙂

    Leave a Reply