3 Simple Ideas if 2020 Planning Is Overwhelming

I love planning and reflection. That “big picture” time is usually the most satisfying and peaceful part of my work.

But sometimes a bigger reflection process feels overwhelming. For instance, this month, we are doing a big batch of Wholesale In a Box improvements. And when you combine that with all the rest of life and holidays and management and family -- currently I’m planning more like 12 hours in advance than 12 months in advance.

No doubt about it: I will eventually make time to pause in a meaningful way. And we will eventually have a 2020 plan for Wholesale In a Box. But right now, I’m realizing that it can be helpful to have a structure for Basics Only planning. Like a 7-minute workout, you may not get all the benefits of the full version, but you do get an efficient burst of what you need. So today I’m sharing three simple ideas to consider if a full planning process isn’t in the cards, but you still want to get pointed in the right direction for future months.

3 SIMPLE IDEAS IF 2020 PLANNING IS OVERWHELMING

1. Get closer to your inspiration.
Sometimes the reason that planning feels overwhelming is that we’re just used up. And that’s not necessarily a bad thing! In my opinion, it’s one of the great joys of life to work or love or live to capacity. But when we’ve just spent a period of time producing and giving and creating fully, we can’t jump immediately to reflection and planning the future. First, we need to fill up our reserves and return ourselves to ourselves.

For me, one way to do that is to get back to what inspires me. The word “inspire” comes from a root meaning “to fill with breath.” Doesn’t that feel like just what is needed when you arrive at the finish line of a big work race, breathless, red-cheeked, and exhilarated?

Whether that means an hour in a museum, reading great books, 30 minutes in a cafe with a notebook, an afternoon volunteering, or a Saturday spent painting for no productive purpose... the idea is simply to do something that you know reconnects you to what inspires you. And trust that as you get renewed and inspired, you will gradually feel more able to reflect on where you’ve been and plan where you’re going.


2. Get closer to the people you serve.
Another time planning can feel hard is when we feel like we’ve lost clarity about the path forward. Maybe you’re not sure where to invest your marketing time. Maybe you don’t know whether to create new products or just sell the ones you have. Maybe it feels like there are 100 things you could do in your work and you have no idea which ones to choose.

When I feel this way in Wholesale In a Box, it’s always because I’ve gotten too much in my own head. I have found that clarity about our best path forward always comes from a vivid understanding of what our makers most need. Do my vision and our values matter? Of course -- our ideal strategy will always be at the intersection of what our makers need and our vision and values. But I’ve found that when I feel unclear, it’s because I’ve gotten too much in the trenches of my own laptop and become too distant from the makers we serve.

This happened to us a few months ago and so we spent a solid month having conversations and doing observations with our makers to gain a deeper understanding. What is working about what we do? What isn’t working? What could we change or add in order to be more in service to the people we serve?

As a maker, the questions you ask will be different… but talking to your best customers (that could be individuals or stores) can be extraordinarily powerful. What do they love about your line? What do they wish you would add? What is their experience more generally? I think you’ll find you gain a lot of clarity about your 2020 strategy from sitting with what you hear.


3. Get closer to your ultimate vision
The third big reason that it’s sometimes difficult or overwhelming to plan is if you’ve lost touch with the bigger vision of what you’re trying to do. My friend and coach Melissa calls this your “compelling reason.” Simon Sinek calls it “starting with why.”

The way I think about it is simply answering the question: “What would I want if I could snap my fingers and make anything real?” I find answering that question a bit easier than thinking about my personal mission, core values, or 10-year plan (all of which make me feel a little panicked.)

You don’t necessarily need to use your answer to this question as something to “work backward” from or create a plan from. Sometimes I find it deeply supportive to just reclaim that vision of my ideal. And it brings into obvious contrast things on my to-do list that have nothing to do with my vision… or things that I really want to make time for.


You probably have an intuitive sense of which of the above three ideas would help you feel more clarity. So if you’re feeling overwhelmed about taking on a full planning or strategy session, try picking one of the above approaches -- and let it be easy.


PS - We’ve shared some good planning and year reflection articles in past years, too! Worth a look: some planning resources, one thing to remember as you reflect, and two easeful approaches to planning here and here.