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Let Your Past Inform Your Future with the Rearview Mirror Exercise

Business PlanningThe interesting thing about planning for a new year is, if you are not careful, it can become a drug we take this time every year to numb the pain and discomfort of goals unmet.

By ignoring the past and turning our gaze to the future where hope and possibility lie, we miss the opportunity to draw wisdom from the 12 months we just lived.

I know, because for years, I would roll into December with great anticipation and leap headlong into crafting a vision for the coming year. With my “Pollyanna Persona” in tow, I would dream of new products, triumphant launches, and a rapidly expanding network and community – all without a moment of reflection on the past year.

While I am all about looking at the “bright side” of life and focusing on what we want rather than what is, when you fail to take time to look in the rearview mirror and reflect the year you just lived, you miss the true wisdom your past has to offer.

It was this truth, three years ago, that inspired me to create the Rearview Mirror Exercise, which now represents Step 1 in my annual planning process.

By reflecting on 10 powerful questions (5 on what went well and 5 on what missed the mark), you can gleam from your answers, clues to what you want more of and what you do not want to repeat in the coming year. Through these 10 questions, you become more informed and aligned with what’s important to you. Through these 10 questions, you gain wisdom and discover what works for you and what doesn’t.

In the end, you come away with greater clarity around what you want your entrepreneurial journey to be next year.

That’s a pretty good deal. By investing 30 minutes answering 10 questions, you can step into next year with new insights and greater clarity that enables you to make wise, conscious decisions about where to invest your time and resources.

If you have a team, ask them to complete the exercise as well. By celebrating your wins together and pinpointing what you don’t want to repeat, you’ll step into 2019 with a more aligned and solid team who is committed to a common vision.

When you take time to look back over the year you just lived before turning your attention to the where you want to go next year, you give yourself a gift. Through this exercise you get to celebrate where you kicked ass, honor where you stood in your power and acknowledge the times you moved through the fear and took courageous action.

But looking at the past is not always easy.

It requires a big dose of self-love and compassion as we forgive ourselves for the miss-steps, misses and disappointments. It also requires that you slow down long enough to reflect on where you’ve been, so you bring a more informed and conscious perspective into the year ahead.

If you are committed to make 2019 your best year yet, take time today to complete the Rearview Mirror Exercise – in the Annual Planning Guide.

Step 1: Let Your Past Inform Your Future

What went well?

  • What are you most proud of accomplishing last year?
  • What projects, campaigns, promotions or events brought you the most joy?
  • What projects, campaigns, promotions or events brought you the biggest results?
  • What 3 key business relationships did you nurture?
  • Where did the money flow from without a lot of stress or effort?

What didn’t go so well?

  • What projects or promotions didn’t turn out as planned and why?
  • Were there decisions or projects that you would have done differently?
  • If you had a “do-over card,” what would you have done differently last year?
  • What do you wish you had done more of last year?
  • What do you wish you had done less of last year?

Give yourself the gift of answering these 10 powerful questions and as you do, notice what comes up as a result. What often arises for me is a new level of clarity and distinctions that inform what I want next year to be.


Important Note: If you have NOT yet grabbed the Quick Start Guide to Planning Your Best Year Yetclick here to grab it.

Then, watch for tomorrow’s blog where I share my own experience of the Rearview Mirror exercise. In it I’ll come clean around what did not go well last year, honor a life-changing decision I made and used these past three months to recalibrate and recommit to the work I am here to do.

How about you… are you in?

If yes, my intent is to help you arrive at the end of this year feeling clear, confident and encouraged as to how you can make 2019 your best year yet.

2018-12-28T12:12:22+00:00December 4th, 2018|2018 Best Year Yet Series, Business Planning|2 Comments


  1. Toni December 9, 2018 at 8:06 pm - Reply

    I am in my 11th month in business which has been a slow start-up on purpose. I wanted to minimize the stress and pressure and can see many accomplishments as well as some things that didn’t go so well. Right now I can see that I don’t have a better plan for 2019.

  2. Bob E Forrester December 11, 2018 at 8:10 pm - Reply

    This guide has already opened my eyes to end the frustration and confusion about what to include in the initial website of my biz. The future vision of this biz has many phases which require learning and implementing the previous phases. It was a huge struggle to assemble all the parts and was stopping me. Your story about your dad’s visit in Monterey opened my blocked attempts to have everything complete and perfect out of the starting gate. It was so simple and so powerful to use the idea of a 1, 2, and 5 year plan. The first year plan is enough to put in the website for a beginning. I already have the outline and objectives of what follows and can add them in the 3rd or 4th qtr of the first year. Even though the concept of “Simplify” is one I use elsewhere, it took your story provide a precise perspective. Thank you for offering this guide to planning!

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