• Sara Torpey

Plan Ahead by Looking Back

The new year is quickly approaching!

If your life is anything like mine, you’re surrounded by a growing collection of holiday decorations (not in my house yet, but everywhere else…), songs, and a little bit of pre-holiday/new year panic. Your social media feeds are filled with a combination of holiday deals, other people’s angst about the holiday season, and advertisements for planners.

In the world of small business, ’tis the season for planning ahead.

If you own a business, you know, at least intellectually, that planning for the new year is vital; you can’t get where you’re going if you don’t actually know where your destination is.

If this is your favorite part of the year, high fives! If planning for the new year to come (in the midst of the holiday craziness no less) is easier said than done, keep reading...

We agree that planning is important. What you might not know, though, is that far too many business people only kind-of plan ahead for the new year.

What does a ‘kind-of’ plan look like? Maybe you set some new goals and targets. Maybe you think on what you’d like to achieve in the next year. But that’s kind-of it…

And while having goals and ideas are great, that’s only part of the planning process, and it’s leaving a big piece undone.

What’s that piece?

Looking back.

Reflection is so important. And doing it well isn’t easy, especially if your business didn’t exactly meet what you had hoped for the year. It takes a fair amount of work and fortitude to look back and reflect on your prior year effectively.

That being said, I would contend that looking back is one of the (if not THE) most important steps in planning ahead.


As much as looking back can be a pain - collecting all the right data points, reviewing the numbers, making sense of both the numerical and non-numerical results - reflection gives you two super important gifts.

The first gift is a likely unexpected shot of confidence when your data shows you that you have come further than you might think or feel. I have done lots (and lots) of end of year review sessions with clients, colleagues, friends, and my own businesses, and I have never not walked away thinking ‘Huh, things went better than I thought they did in ____ way.”

You may or may not have met your goals from last year. Sometimes we avoid reflecting because we know we didn’t make the number we set in our plans. But as much as some things may not have grown the way you wanted, there are other aspects of your business that went great - you just haven’t focused on them. I can say for certain that you learned new things, adopted new tools and processes, grew your following or forged a new and unexpected path of some sort. You DID succeed. And when we don’t take the time to give reflection its due, those ‘hidden wins’ often go overlooked.

The other gift of reflection is that it provides you with a real, solid, and definite starting line to move forward from, into the new year. Setting a new goal is great, but if your new goal is to make X more dollars, and you don’t know how many dollars you made last year, it’s a pretty squishy goal. When you reflect, and you really dig in, you can actually see how your business has grown in different ways over time. Once you know the details of how you’ve grown you can use that real data to inform your new goals. When new goals are created from actual data, they tend to be more concrete, more well defined, and more manageable. And concrete, well defined, and manageable goals in turn have a better chance to actually get met. When you know where you are coming from, it’s a whole lot easier to plan where you want to go next.

So, how do you effectively reflect on your prior year? Ask yourself some good questions!

Here are the questions I ask clients (and myself!) to prompt reflection:

  • How has your business changed in the last 12 months? How can you quantify those changes?

To answer this, think about where you were 12 months ago, and where you are today. What’s the same? What’s different? Don’t judge the results, just collect the data. Think carefully about the numbers that you can use to show the various changes (these might include numbers of followers or subscribers, sales numbers, content creation amounts, percent change from month to month…).

  • What went well last year? What’s on your ‘highlight reel’? Why?

To answer this, think about your best moments. What were they? Why were they awesome?

  • What didn’t work as planned? What would you like to avoid next year? Why?

This is where you think about the things that you aren’t loving. What’s not working for your business and your life, and why aren’t they working?

  • What surprised you last year? Why?

This is a valuable question to ask simply because it brings out interesting stories and ideas. Some surprises were great, some were less so, but it’s useful to consider the things that happened that hadn’t been planned for if you haven’t already, and how they may have changed your trajectory.

Once you have the answers to these questions, you’ll be ready to use what you now know for sure about your business to create a clear plan for the year to come.

If you find that you are struggling to reflect, or to take the steps that come after reflection to create a clear, focused, and manageable plan for the year to come, we should talk. I work with people like you, one-on-one to create plans that they can actually use to grow their businesses. Click here to schedule a time to talk.

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