How to Review Your 2018 as an Entrepreneur

As entrepreneurs and solo-preneurs hit the holiday parties, they are bound to face the common question: “How was your year?”

What may seem like innocent question asked by a semi-stranger over eggnog is actually a serious inquiry everyone should be asking themselves this time of year, especially an entrepreneur.

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

Admittedly, the party is probably not the ideal venue to share the ups and downs of being an entrepreneur. So you respond with, “Things are awesome!” and quickly change the subject.

While this may be a tactic to avoid an uncomfortable conversation if you feel it wasn’t a stellar year, it is important to own up to your year on your own time and recognize what is going well, what is not going well, and where you are headed.

Taking 30 minutes to dig in to the details and reflect on the previous 12 months is a smart way to evaluate your performance both professionally and personally.

So grab a pen, open an Evernote, or invite a trusted friend/advisor to coffee and run through the exercise below to evaluate your year. 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 and self.

Step 1: Business Life

How are you feeling about your business? Be honest. What is your general feeling of the state of your business right now vs. this time last year?

What are 2 wins that you are most proud of achieving this year in your business? Sure, there are many small wins throughout the year, but what are 2 that really made a difference in the business?

What are 2 things you failed at in your business? Yes, we all have failures. Admit it. Recognize what you learned from it and how your business has evolved because of it.

Step 2: Personal Life

How are you feeling about your personal life? Sure, many entrepreneurs have a hard time separating the work and personal buckets since they dedicate so much time to their business. However, where are you at outside of your business? We all have families, friends, relationships, hobbies, travel plans and more to recognize and appreciate.

What are 2 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 2 things that didn’t go well in your personal life? Ideally we are perfect humans, right? Not so. We all have that feeling of f*’n up on something. Share it, learn from it, and keep moving forward.

Step 3: Vision

The next step is to tie it in to where you are going.

Flash FORWARD one year: How do you picture yourself? Imagine tomorrow you wake up and it’s a couple weeks before your planned NYE trip to Patagonia. What is the feeling on your business? And your personal life? 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.

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.


Mike VonLunen is an Advisor for small business owners with Cultivate. Mike brings a strong background in entrepreneurship to Cultivate, after having worn multiple hats at startup companies. He has become a master at starting, growing, and maintaining small businesses. Schedule your free advising call to learn how you can grow your business.

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