3 Ways To Practice Planning When Planning Feels Impossible

Having a plan for your small business can give you a sense of control.

But how do you plan when just about everything feels out of control?

Our economic situation is changing rapidly—as is our public health, personal capacity, and work environments.

Over the last few weeks, I’ve had the privilege of talking to small business owners like you who are trying to assess where they’re at, make changes on the fly, and still—somehow—plan for the future.

What you are trying to accomplish right now is not an easy task, my friend.

So I wanted to offer some thoughts on ways you can practice planning even when planning feels impossible.

First, let’s define the practice of planning.

I’m stealing this concept from my favorite online yoga teacher, Jason Crandell.

He often cautions about getting hung up on the end result of yoga: how far you can get into any pose or what more difficult variation of a pose you can do.

He says, the point is not the end result—the point is the practice.

There is value in working hard, finding your edge, and even pushing yourself at times. But there is also value in letting each pose or movement be what it is. There’s value in practicing and finding peace in the flow or stillness.

The same is true of planning.

When we’re planning for our businesses, we’re normally focused on the end result. We want to be able to say we have a clear goal and solid plan for achieving it. We want to know each step along the way.

We want that plan so we can feel confident and in control.

In this moment, the plan isn’t nearly as important as the practice of planning—making the time to take stock, evaluate your options, and consider paths to move forward.

Of course, this is easier said than done especially if you’re busying holding space for your clients, supporting your community, or homeschooling your kids.

And yet, the space-making, the careful analysis, the curious question-asking can be a form of self-care.

It might be exactly the thing you need to build your capacity for continuing the generous service you are doing right now.

On the other hand, if your response has been to hunker down and get very still, the practice of planning might be the thing that helps you start moving again when you’re ready.

So let’s get into it.

1) Take stock of what’s worked before.

It’s tempting to think that you’ll need to do something new or different to weather this uncertainty. But what I’m finding the small business owners we work with say over & over again is that they’re rediscovering the things that have worked in the past.

“Taking stock” might not feel like planning since it’s not future-oriented but it gives you better information about what you can do next than you currently have. And if that’s not planning, I don’t know what is!

Even if you do nothing else, planning for a changing future by taking stock on what’s worked in the past can help you get centered and feel a little more focused.

2) Find the overlap.

During a planning session I led last week, I asked our participants to answer 4 key questions:

➡️What are your needs? What are your business’s needs?

➡️What do your customers need right now?

➡️How do your skills & your business’s capabilities meet those needs?

➡️How can you meet your needs & the needs of your customers in the short-term? Mid-term? Long-term?

Whether your revenue has completely dried up or you’re creating a contingency plan for possible fallout ahead, there is a way to meet your needs while meeting your customers’ needs. It just might mean getting paid for something you don’t normally get paid for.

Every business develops systems and capabilities that help it create, market, or deliver its product or service.

Those systems or capabilities are part of what makes the business work–but they’re not what drives revenue in and of themselves.

However, if you need to quickly develop a new offer (and lots of people do right now), figure out how to be of service (lots of people need help), or just create a contingency plan for the economic ripple effects coming our way, those systems and capabilities can help you make a move.

But since bandwidth is at a premium right now, you’ll want to make sure that you’re not just chasing potential revenue.

Instead, find the overlap between your needs and your customers’ needs and then meet that with a skill or capability you already have. Consider how this could serve you in the short-term, the mid-term, and the long-term.

3) Honor your capacity and adapt.

One reason that planning can feel so overwhelming right now is that our personal capacities vary from moment by moment depending on our family needs, our business’s needs, and the headlines.

So the idea of setting a deadline or even creating a timeline can be paralyzing.

It is possible to practice planning without setting hard & fast deadlines if you’re planning for the future while allowing yourself to adapt to today.

I’ve found that I am more productive when I take an active role in managing my workload and priorities instead of letting a rigid plan or project management software tell me what to do. That allows me to plan for the future while adapting to the specifics needs of today—whether they’re personal, business, or community needs.

While this is how I always manage my work now, it’s especially helpful now that I’m dealing with erratic changes in my personal capacity and schedule.

By staying hands-on with my workload, I can honor my capacity in the moment without dropping the ball on the most important things.

To do this, I lay out my anticipated projects in advance (usually 6-12 months at a time) on a month-by-month basis.


Then, I set goals for the current quarter based on those projects and the needs of the business. Once I know what I’m working towards, I lay out the high-level tasks related to those goals so that I can keep track of broad-strokes of the work that needs to be done (by me or by my team).


Finally, each week, I make a short-term plan for accomplishing my weekly work, work with pressing deadlines, and work that moves future projects forward.

This plan is flexible. I move tasks around in the week manually depending on my schedule and capacity.


The practice of planning doesn’t necessarily give you the (perhaps false) comfort of a clear roadmap or a hard-and-fast set of deadlines. But it does give you confidence in your ability to adapt and a sense of control over that creeping sense of overwhelm as your more detailed plans seem to slip away.

Remember, the plan itself isn’t nearly as important as the practice of planning.

You may not be able to make a plan that lasts for more than a week right now—but that shouldn’t stop you from planning. Whether you choose to look a few days or a few months ahead, the practice of planning can help you find your center as a small business owner.

Let go of the desire to have a solid plan and find some release in taking stock, figuring out how you can meet your needs and your customers needs, and adapting.

The Leadership Dashboard

I’ve made the planning system that I developed when all other systems fell short available as a done-for-you Notion template, with written & video planning guides. It’s currently Pay What You Want so you can get to the practice of planning for the future while adapting for today.

Click here to learn more.

Cover of What Works book by Tara McMullin

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