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As small business owners, a mid-year check-in is a great opportunity to take stock of our progress and reconnect with our vision. Often, we’re so focused on the day-to-day that we lose sight of the bigger picture. That’s why it’s crucial to take periodic time out for reflection to make sure we’re aligned with who we are and where we’re going. I use the following mid-year check-in to evaluate my progress and realign with my goals and intentions. As we head into the second half of the year, I encourage you to set aside sacred time for yourself. It doesn’t have to be a long, drawn-out process; blocking out an hour or so on your calendar should provide plenty of time. Light a candle, grab a notebook and pen, and your favorite cuppa, and let’s get started. 

Begin with Celebration.

Start your mid-year check-in by celebrating your wins and acknowledging the progress you’ve made thus far. Take a moment to savor your accomplishments and let the positive energy fuel your motivation for the next phase. Remember to celebrate each step, no matter how small, because it’s moving you toward your dream.

 Reflection Questions:

  • Over the past 6 months, what have you accomplished (big or small)?
  • How have you celebrated?

Reflect on Your Vision.

Close your eyes, take a deep breath, and reconnect with your vision for your life and your business. Reflect on your initial aspirations, your purpose, and the impact you want to have in the world. Check-in to make sure that your vision still feels energizing and inspiring – that provides the fuel to help you stay motivated even on ‘meh’ days. Evaluate your daily actions as well as your future plans, and see how they align (or not) with your goals. 

Reflection Questions:

  • Does your vision still feel energizing? If not, what needs to be tweaked?
  • Do your current actions align with your vision?
  • Are there any areas that require adjustments or fine-tuning?

Evaluate Key Metrics and Milestones.

Now it’s time to check in on your numbers. Review your business metrics to gauge how your business is performing. If you haven’t already, take this opportunity to identify key performance indicators (KPIs) that are relevant to your business and how you will track them. Celebrate the progress you’ve made so far and identify any areas for optimization or improvement. (Note: If you’re not exactly where you wanted to be, don’t fret, and please don’t beat yourself up over it. Whether you’ve hit your targets or not, it is all good information that you can use in moving forward!)

Reflection Questions:

  • Do your current KPIs align with your vision, or do they need adjustment?
  • Which areas are on track?
  • Which areas need extra attention?
  • How can you approach those areas with curiosity rather than judgment?

Assess Challenges and Learnings.

Acknowledge the obstacles you’ve faced and the lessons you’ve learned along the way. Remember, as entrepreneurs, we are always learning, and every challenge is a valuable opportunity for growth. Reflect on how you’ve navigated through obstacles over the past 6 months, and identify any anticipated challenges you see moving forward.

Reflection Questions:

  • What challenges has this year brought so far?
  • What strategies and support systems helped you through them?
  • What hasn’t worked (and why)?
  • What challenges do you anticipate as you move forward?
  • How can you support yourself through them? 

Realign and Set New Goals.

Now that you have a clearer perspective on where you’ve been, it’s time to realign with where you’re going. What goals do you have for the next 6 months? Remember to set ambitious yet achievable goals that excite and challenge you – you want to feel inspired, not overwhelmed. Break them down into actionable steps and create a roadmap that will guide you toward their realization.

Reflection Questions:

  • What are your top 2-3 goals for the next 6 months?
  • Are they SMART (specific, measurable, action-oriented, realistic, and time-bound)?
  • How will you measure success?
  • How will it FEEL when you achieve these goals?
  • For each goal, what are the top 3-5 actions that will move you toward that goal?
  • Are these action steps aligned with your strengths? If not, how can you get some help?
  • For each goal, what’s the very next step you need to take?

Cultivate Self-Care and Renewal.

Creating a business you love requires a lot of energy, especially when you’re just starting out or when you’re pivoting to something new. Similar to riding a bike, it takes a big push to get things going, but things start rolling more easily as you build momentum. As entrepreneurs, it’s important to prioritize self-care and rejuvenation as part of our mid-year check-ins. Take time to replenish your energy, engage in things that bring you joy, and surround yourself with positive influences. Refilling your well is not optional, it’s essential to maintaining both resilience and enthusiasm as you move forward.

Reflection Questions:

  • What gives you energy?
  • What drains you?
  • What are some simple ways you can weave these energizing practices into your daily routine?
  • Of the things that drain you, what can you say NO to in order to say yes to more of the things that light you up? 

In my business, I tend to view this mid-year check-in as a sacred practice. It’s non-negotiable for me. From experience, I know taking time out for reflection creates the necessary space for insights to emerge—ones that will guide me in moving forward. I hope this inspires you in your own business as well!

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