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How to Conduct a Mid-Year Business Review (That Actually Moves the Needle)

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How do you conduct a mid-year business review without spiraling into self-criticism or getting stuck in overwhelm?

In this solo episode of The Jewish Entrepreneur Podcast, I’m coming to you from Los Angeles—grateful, grounded, and fresh from a whirlwind of expected/unexpected travel and family time. After navigating war, travel logistics, and life’s interruptions, I’m here to remind you of the importance of pressing pause, reviewing what worked in your business over the last 6 months, what didn’t, and what you’re going to change up during the second half of the year.

I’m diving into exactly how to conduct a powerful mid-year performance review—for both you as the CEO and you as the employee of your business. Because here’s the truth: if you don’t measure what’s working (and what’s not), you’ll struggle to compound your business growth.

This episode is packed with journal prompts, CEO insights, and strategic wisdom to help you honor how far you’ve come and plan your next six months on purpose.

Whether your first half of the year looked like building foundations, navigating challenges, or running full speed ahead—this review will help you achieve the results you’re aiming for.

Whether you’ve had a strong start or a slow season, this episode will help you get honest about where you are—and chart a meaningful path forward.

What You’ll Learn from this Episode:

      • Why summer is the best time for a business review—especially for women and even if you’re by the pool!
      • The difference between a performance review as a CEO vs. an employee
      • How to celebrate your growth instead of shaming yourself into action
        Transcendent Active
      • My personal insights from migrating my membership platform—and what it taught me
      • The “review and renew” mindset that helps you avoid burnout and grow sustainably
      • Key journal questions to help you reflect, reassess, and recommit to your goals
      • How to identify where your standards, boundaries, or focus need an upgrade
      • A step-by-step guide to planning your next six months

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Read the full transcript now

You're listening to The Jewish Entrepreneur Podcast with Debbie Sassen, Episode 177.

Welcome to The Jewish Entrepreneur Podcast. I'm your host, Debbie Sassen. I went from being a financial advisor, author, and chronic under-earner to building my business to six figures as a financial planner and money mindset coach, and then onto multiple six figures as a full-time money and business coach. I help entrepreneurs create money-making businesses and build wealth using sales and money mindset strategies, all in alignment with authentic Jewish values. Now let’s dive into today’s show.

Hello my friends, and welcome back to the podcast. I’m recording this episode today from Los Angeles. As you might recall—though I don’t know how you’d remember—the last time I recorded a podcast, I was in Israel, and we were at the end of the 12-day war with Iran. Thankfully, that finished, the skies opened up, and today, as I record this, it is July 2nd—my father’s birthday—and I am so, so grateful to be here and spending time with my family. My husband is arriving today. I’ve been spending time in Los Angeles with my sister, who is going through some medical issues and treatments over the next few months. It’s been such a blessed opportunity to be with my family. There is nothing like a war to remind you what is really important in life. I’m truly filled with gratitude—thank you, God, for bringing me here. I have nothing but praise. And thank you to El Al, our national airline, because it was all so quick. I actually had a flight scheduled for Thursday, but it was canceled. Then, supposedly, there were only flights going out with 50 people at a time, and you had to get on a list. I wasn’t even thinking about it. I mean, my family is in Israel, and as much as I wanted to be with my family in Los Angeles, I didn’t think it would happen. But my travel agent said, "Sign up—you never know." And then, Wednesday afternoon, I got word that I was scheduled to fly out between Thursday night and Friday. Thank God, I’m here.

Now I want to share a podcast episode with you that is critically important for every person in business, especially every woman in business. Why do I say that? Because I get it—I’m a mom. I’m here now with my family. And what often happens during the summer is that some of us turn down the fire in our business. We have other things going on, and that’s part of the beauty of running your own business. There is a work-life harmony—not necessarily balance—but a harmony, where you integrate your family, your holidays, your body needing to rest and renew. And doing a mid-year performance review might be something you put on the back burner. You tell yourself, "I’ll get to it tomorrow, maybe next week, after the holidays," and it gets pushed aside and never happens. So I want to talk to you today about what a mid-year performance 

 

review is, why it’s important, and I’m going to give you some steps and journaling questions so it will be useful and successful for you in your business.

We wear two hats as entrepreneurs: the CEO and the employee. You are the boss, the strategist, the leader—and you are the worker bee, the executor, the doer. This review is about evaluating how you performed in both roles. Did you show up fully? Did you follow through? Did your leadership drive results? Or were you flying by the seat of your pants, distracted, reactive, and unstructured? This review is not about beating yourself up. It’s about gathering data and noticing what worked, what didn’t, and where you can improve.

I did this review myself, and for example, I realized that migrating my membership platform from Thinkific to Kartra went really well. I had a year to plan, and we executed step-by-step with my assistant. Yes, there were hiccups—there always are—but we stayed the course and even finished early. That’s something to celebrate. On the other hand, I noticed that when I ran a five-day masterclass, it took way too much out of me. It didn’t fit with the way I manage my energy. Three-day masterclasses work better for me, and I won’t run a five-day one again.

Here are a few questions to guide you:

  • What are you most proud of from the last six months?
  • What challenges did you face, and how did you handle them?
  • What did you learn about yourself as a leader? As an employee?
  • What worked in your business? What didn’t, and why?
  • What are your goals for the next six months?
  • What do you need to say no to in order to say yes to your priorities?
  • What positive money beliefs do you hold now?
  • What new money beliefs do you want to adopt and embody?

Don’t just listen to this podcast. Please take action. Schedule time in your calendar. Put two hours aside. Reflect deeply. Write it all down. Celebrate your progress. Notice your patterns. Recommit to your goals. And then take aligned action so that your next six months are even more powerful than the last.

Thank you so much for tuning in today. I look forward to seeing you next week on The Jewish Entrepreneur Podcast. Bye for now.

Thanks for listening to The Jewish Entrepreneur Podcast. If you want to stop underselling and under-earning and close more sales, you need to clear the limiting money beliefs that are sabotaging your business growth. Head over to debbiesassen.com/mindset and download my free Money Mindset Workbook. Uncover and dissolve money blocks like hundreds of other entrepreneurs who are now building six-, multi-six-, and seven-figure businesses—and creating true financial freedom.

 

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Debbie Sassen is a Messaging Strategist, Business Mentor, and host of the Jewish Entrepreneur Podcast. She helps established entrepreneurs clarify their messaging, increase their profits, and scale their businesses.

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