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How to Review Your Year as an Entrepreneur

November 14, 2023

8 minread

byCasey Clark

Casey Clark
Casey Clark

CEO, Co-Founder

Chicago, IL

As a business partner, he helps his clients get a holistic view of their financial health by slowing down to talk about numbers. Then, he breaks down even complex problems into one or two elements to help them break through their barriers of growth.

How was your year?

What may seem like an innocent question is actually a serious inquiry everyone should be asking themselves this time of year, especially as entrepreneurs.

Let’s face it, sometimes the answer to this question is a bit more complex, with layers of wins and losses.

But, with the new year around the corner, it’s important to take a moment to reflect. By putting your last year under the microscope, you can learn a great deal and take stock of how you’re doing to see if you’re on track towards hitting your long-term vision. It opens your eyes to past achievements, as well as some areas you can improve. All of which can inform future goal planning. So before jumping into a new year, set aside an hour to reflect. Grab a pen and invite a friend or mentor to run through this exercise.

  1. Outline 3 Areas of Success

    What are three of your most significant achievements over the last year? Hopefully, you can think of many wins throughout the year, but identifying three wins that significantly impacted your business. Here, you’ll want to pull in the numbers, and look at the data you’ve collected over the last year. How much revenue did you pull in each month? How many leads did you generate? How many clients did you win? Were there months that you did exceptionally well? Were you trying a new tactic? Or were there some outside factors that contributed to your success? Maybe you hired your first employee, opening up space to take on new clients. Whatever it is, write it down. Don’t stop there. Once you have three, take a moment to reflect on those achievements. Think about how you got there and, more importantly, how you might be able to build off this momentum.

  2. Write Down 3 Areas to Improve

    What are three areas of your business that didn’t go so well? Again, look at the data. How many clients did you lose? Did you have a low revenue month? What were the factors surrounding this failure? Were they environmental? Maybe you had a bad sales month, or you tried a new initiative that never took off. It happens. Identify those areas and drill down to the root issue. Once you do, recognize what you learned from it and how your business has evolved because of it.

  3. Identify 3 Initiatives For the New Year

    Flash forward one year: Where do you see yourself? What are three things you can do now to put yourself on the path to that ideal state in 1 year? Take a minute to analyze those highs and lows. How do you keep the momentum going? What needs to change? Remember, it’s essential to look at the data. If you only use your gut, you’ll make emotional decisions and focus on the wrong things. Reviewing the data first and using that to identify the wins and losses will keep you focused holistically versus acting on how you feel in the moment.

The purpose of writing down your answers or sharing them with someone else is that it forces you to get your thoughts out clearly and intentionally recognize your current state of work. Better still is that once you complete this exercise, you’ll walk away with a baseline.

Once you’ve gone through this exercise to analyze your business, you can follow the same steps to reflect on your personal goals.

Often, entrepreneurs struggle to separate their work from their personal lives since they dedicate so much time to their business. But separating the two can help you put more focus into both areas of your life.

  • What are 3 wins you are most proud of in your personal life? Think of those personal experiences from the past 12 months that bring a smile to your face. Maybe it was a major event like buying a home or a memorable trip abroad or smaller wins like going to a World Series game or crushing your PR in that 5k.
  • What are 3 things that didn’t go well? No one is perfect. The best thing we can do is recognize areas we can do better, learn from it, and keep moving forward.
  • Flash FORWARD one year: How do you picture yourself? What did you accomplish?

What are 2 things you can do now to put yourself on the path to that ideal state of self in 1 year? How do you keep the momentum going? What needs to change? Why or why not?
Once you have completed this exercise, you should walk away with clarity on what really changed in the last year and focus on where you are headed. Then next year, when you repeat the exercise, you will have a reference point to measure against. You can even set up checkpoints with yourself throughout the year to review and hold yourself accountable.

Perhaps the biggest benefit is that you now have precise conversation pieces to discuss the next time someone asks you, “How was your year?” Start talking about the momentum of your wins and where you are going, and just maybe that conversation will start moving things forward.

If you’re not sure where to start, you don’t have to go at it alone. Schedule a free two-hour session with Cultivate Advisors to dig into your business to uncover bottlenecks and develop a roadmap based on where you are in your business and where you would like to be. With this roadmap, you’ll have a tangible plan you can implement to reach your long-term goals.

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