The Problem With Small Business Planning Season (And How To Fix It) | What Works

The Problem With Small Business Planning Season (And How To Fix It)

Oct 1, 2020 | Mindset & Identity, Productivity

It’s pumpkin spice season.

It’s apple cider donut season. It’s even getting to be jacket season.

And, soon…

…it will be ​small business planning​ season.

You know, the time of year when everyone (including me) encourages you to take a step back, think about what you want out of the next 12 months, and make a plan to achieve it.

I love planning–and I know that the vast majority of plans either get forgotten or they fail.

What happens for me is that I look out at the glorious future-time–so empty of the usual hustle & bustle of daily life, so fertile with possibility–and create what I believe to be the ​perfect​ picture of life and business-to-come.

When I’m planning, I mostly forget about my pre-existing commitments and the unexpected events that inevitably pop up. 

And so, in the past, my plans have rarely reflected reality. My guess is that yours haven’t either.

This is frustrating as all get out, right?

You start off the new year, the new quarter, even the new week with an idea of everything you’re going to accomplish and how everything is going to fall into place. But within weeks, days, or even hours, the plan is out the window and you’re back to making it up as you go.

Now, I this might be a tad dramatic. I’ll own it. 

I will ​also​ own that I have ​lived​ this experience so I know it’s not a complete exaggeration!

So what do we do about this?

Is there a way to make a plan and actually stick to it? 

Yes. But we need to refine what “sticking to it” actually looks and feels like.

And we need to refine how “sticking to it” plays out in our daily work lives.

The first step is recognizing that having a plan is not, in and of itself, a silver bullet for solving business problems or achieving next-level goals.

That’s how we tend to treat plans, of course. We throw our weight behind the projects, the lists, and the deadlines hoping that whatever we cooked up will transmute itself into our ultimate desires.

The plan is more like a hypothesis. It’s your best guess for how to close the gap between where you’re at and where you want to be. 

Since it’s a hypothesis, that means that a key part of executing your plan becomes experimenting, learning, and updating the hypothesis–and ​that​ means that the goal of making a plan isn’t so much to stick to it but to make it better with every action you take.

 And that leads us to the second step.

The second step is to make planning something that actually happens every single day instead of something that happens on a monthly, quarterly, or annual basis. 

Every day, the goal is to look back to learn something from the day before and to look forward to consider the future. Every day is an opportunity for execution and it’s ​also​ an opportunity for recalibrating your plan.

I firmly believe that the small business owners who are the most successful, most grounded, and most at peace are the ones who are sitting with a near-term, mid-term, and long-term view daily. They’re considering how what they do today impacts their plan and how their plan impacts what they do today. 

All of this to say that I ​love​ planning season (like I love apple cider donut season) but I hope that you don’t relegate “planning” just to this season.

I encourage you to make it part of your daily routine.

Host of What Works

Tara is a podcaster, small business community leader, strategist, and speaker. She’s been helping small business owners build stronger businesses for over a decade.  

Tara McMullin, What Works Weekly Newsletter

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