One of the top questions I get every year is: How do I make a plan I can stick to?
Everyone wants to know a magical formula for choosing goals and making plans that they can glue themselves to for a month, a quarter, or a year.
After all, not sticking with a plan is a sign of failure, right? And we want nothing more than to avoid any signal that we have failed ourselves or others.
Look, that’s pretty messed up. But I’m not here to psychoanalyze your (or myself). Thank god. I’m here to share that I don’t think sticking to your plan is the real goal.
Instead, I want to propose that you intentionally, purposefully, joyfully change your plans as you work them.
Sticking To A Plan vs Working A Plan
Let’s define terms. When I say “sticking to the plan,” I mean the idea that we can make a plan to reach a goal or complete a project and execute it as is, from top to bottom. Sticking to the plan means checking every item off your list and hitting all your deadlines. It means not changing course or giving up on anything from the plan.
When I say “working the plan,” I mean engaging with your plan as a learning process. The more you learn, the more your plan evolves and adapts. You might discover the objective is something totally different than you expected. You might find out that a part of your plan just isn’t very important. Or, you might see that there is more learning to be done before the plan can be completed.
With everything you check off the list of your plan, you learn something new.
You have new information. If you execute the plan exactly as you created it when you had less information, you’re inevitably missing ways to make it better.
That doesn’t necessarily mean you’ll discover you need to do more. No, often it means you’ll discover that you can do less. Or you can do something differently. Or that you need to take a different direction entirely.
It also doesn’t mean you’ll necessarily want to strive for more. Working your plan might mean that you realize you are happy with a simpler target or that there are ways to make working on a project more satisfying.
One of the reasons we don’t see our plans this way—as a learning process that we can use to adapt into an even better outcome—is because we’re trying to “get it right.” We’re trying to follow a perceived set of instructions to the letter. After all, the imperative to “follow the instructions” is engrained in most of us from an early age.
There truly is no set of instructions, no manual for how to create what you want to create. No one before has created what you’re creating. No one has executed your project or developed your system. People have done similar things—and we can learn from them. But we can’t hope to land on a preexisting set of instructions and then just follow it.
For every step of the plan, you only ever have your best guess based on the information you have right now. So why not utilize new information to make a better guess than you did a week or month or year ago?
Another reason we fail to see our plans as evolving is that we’re afraid we’re not up to the task. We create a plan based on who we are and what we think we’re capable of as much as we do on how we think it’s “supposed to” be done. Letting the plan evolve adds a new variable into the mix. What if the plan becomes something we’re no longer skilled for? What if the plan becomes something that “people like me” can’t or, worse, shouldn’t do?
Letting a plan evolve may force us to reckon with our identities, resources, and skills. It may teach us lessons that we didn’t know we needed to learn. It might create uncomfortable choices that we don’t feel prepared for.
None of that is bad. It’s growth.
We’re wired for growth.
We’re constantly changing. After all, as you might have heard, our bodies’ completely replace themselves every 7 years.
We can’t execute a plan the way a computer executes a program because we’re not made of software. We’re made of “liveware” as neuroscientist David Eagleman calls it. He says, “all of [the brain’s] experiences reshape it. So that you’ve got these 86 billion neurons, these brain cells, and each one of these has about 10,000 connections to its neighbors … Every moment of your life, every experience you have, changes the physical structure of your brain.”
adrienne maree brown takes this further with the concept of emergent strategy. Emergent strategy is utilizing change to grow, become more whole, and embody our vision. She writes, “We are already emergent beings, just by our very existence. But we’ve been tricked away from it.”
Teachers, managers, and even some parents taught us to act like unadaptable machines. They taught us to follow the instructions. To check the items off of a list. To be accountable to teachers, managers, and cultures by meeting expectations—with the chief expectation being that you don’t get creative with the way you do the work.
Your ability to adapt your plans is part of your very nature. Let’s commit to our natures.
So what does that actually look like?
First, we can tune into the growth we’ve already made and bring attention to how we’ve already evolved our plans and systems based on what we’ve learned.
Then, we can start to incorporate mechanisms for recognizing learning and adaptation into our plans themselves.
I’ll break it down.
Recognize what you’ve already learned.
You’ve already learned so much—but we rarely stop to examine how they’ve changed and acknowledge what we’ve learned. Take a look at the systems, routines, meetings, to-dos that make up your work and ask yourself how your understanding of them has evolved. Have the processes themselves changed, too? If these are things you’re doing with any sort of regularity, you’re learning something about them every time you complete the task and it’s very likely that you’re approaching them differently than you did before.
Even if you haven’t intentionally changed the way you do things, it’s helpful to examine how you could or even should.
Shannon, our community advocate, and I just did that a few weeks ago. We started a new weekly event in March when people were craving a place to process all of the things that were impacting them and their businesses.
We designed the event to be a way for people to connect, check-in, and share what they needed to share with people who understood. The weekly event, called the Monday Huddle, was a much bigger hit than we anticipated! Now, there are many community members who have come to rely on it as a touchstone of their workweek. And that is wonderful.
It also means that there are a number of people who have strong feelings about how they want that meeting to evolve. To be clear, that is also wonderful. And, it introduces questions that we need to consider from a leadership perspective.
So I asked Shannon (because she’s the host of this event) to consider how the purpose behind the event has evolved as the year has gone on. What has she learned about how attendees value that meeting? What has she learned about how people experience it? Why they show up? How they use it?
Before we can consider any kind of structural or logistical change, we need to get to the root of its purpose and how that’s already changed.
With those questions in mind, Shannon can talk to the people who have the most investment in the Huddle and pay attention to patterns and needs. From there, we can adapt the plan.
By pausing to recognize what you’ve already learned, you can integrate the process of “working the plan” into your daily work before you start rearranging your plans for the future.
Plan for repetition.
We often create plans that include experiments we’ll repeat if they’re successful. The problem is…
We’re way too quick to declare, “That didn’t work!” I find that it is almost a default response for people (which is its own challenge when we’re thinking about the process of planning).
In coaching and facilitation, I’m often in the position of asking people to repeat the things they think didn’t work but with the new information they gathered in mind. I help them see that one experiment is almost never “statistically significant,” which essentially means that, while we can learn from how we experimented, we don’t have enough information yet to learn from the outcome.
If you’re planning for a project that is designed to be repeated if it’s successful (like teaching a workshop, creating a sales campaign, hiring a team member, hosting an event), plan to repeat it whether it’s successful or not the first 3 times you try it. Of course, don’t plan to repeat it as is! Plan to repeat it with modifications based on what you learned the first, second, or third time you tried it.
By baking repetition into the way you plan, you can temper your inclination to declare your project a failure before it’s even had a chance to succeed.
Make room for margin.
Margin has a couple of meanings—but 2 matter most here. Margin is the outside edge, the border of something, like a page, a park, or a community. Margin is also the difference between things, like the spread of the score in a game or the difference between revenue and expenses.
Margin is space. And one thing our plans often (always?) lack is space. We don’t allow for margin at the start or finish. We don’t leave margin between projects or items in a check list. We certainly don’t leave margin for error.
Everything starts to feel rushed, harried, and full of anxiety as a result.
In a conversation on What Works, my friend Kate Strathmann told me that she noticed she’s more likely to cause harm when she’s feeling urgency. We were talking about sales in that conversation, but I think this idea applies to many things—including planning.
We often plan in a way that begets urgency. We try to tackle too many things at once. We think we can do things faster than we really can. We forget to factor in preexisting commitments. We don’t take stock of our resources before we start doling them out—literally and figuratively.
It’s no wonder then that we so often feel “the crunch” when we’re trying to stick to our plans. And when we’re feeling “the crunch” we’re much more likely to take action that causes harm to ourselves, to others, and to our communities.
Maybe we ignore our families or intimate relationships. Maybe we pull too many all-nighters. Maybe we resort to choices and tactics that damage the community or industry ecosystem we’re a part of. Maybe we start to believe the horrible things we say about ourselves: how slow we are, how unprepared we are, how unskilled we are.
When we’re constantly executing our plans in a state of urgency, we’re exposing ourselves to all sorts of triggers and negative influences.
So we cause harm. And then we quit the plan.
How do you make room for margin? I’ll be honest: it’s quite difficult for me and for many others.
First, you can make sure to always take account of your routine work and preexisting commitments. Don’t fool yourself into thinking you have more time than you do.
Second, you can find creative ways to use your resources (skills, money, knowledge, support, etc…) to create more margin where you need it. Hire help. Learn how to DIY it. Ask questions of people who know more. Carve out space to work when you’re most energized. Be resource-full instead of slogging through and wishing you had more time, energy, or money.
And yes, the slog is where quite a bit of our margin ends up going.
Last year, I realized that I had stopped setting deadlines for myself. Instead of trying to force myself into action by certain dates, I simply let my projects stay top of mind. I reviewed what I was working on daily, running through my ongoing projects as I checked my list for the day, and then incorporated that work into my day whenever I could. When I couldn’t, I didn’t feel like I was failing.
I didn’t just not lose my edge or lessen my productivity by eliminating deadlines. I started to create more than I had ever created before. I felt more ownership over what I was doing. I felt more in control of how I spent my time and what I focused on.
Look, I’m not denying that some people are served by setting deadlines. I’m also not denying that natural deadlines exist (and yes, I still use those).
But what I am trying to say is that we have inherited a pattern of over-scheduling, over-planning, and over-committing, as well as tools (like deadlines and the software we use to set them) that eliminate our margins and induce urgency—and, with it, anxiety.
That’s not a helpful way to engage your work. It’s not the state of mind you need to do creative and critical thinking.
What could leaving more space in your plans do for you? And what would it mean about the choices you need to make?
Plan for your patterns.
We all have patterns that we’ve come to know and, likely, fear when it comes to how we work. We procrastinate. We deny help from others. We wait for our projects to be perfect. We berate ourselves when things go wrong. We hide out when things get challenging.
Self-sabotage is often one of the core reasons we don’t stick to our plans. And I absolutely believe we can rewrite these patterns. But to do so, we need to integrate our self-knowledge into our plans.
Sharon Salzberg explains in her book, Real Change:
As a habit, certain thought patterns arise that we tend to get lost in, overcome by, defined by, even as we resent or fear them. We can retrain our whole mental attitude by first learning to recognize these patterns and perhaps even calmly naming them: “Oh, here is the pattern of thinking, Everything is wrong, the pattern of thinking, I’m a failure, the pattern of thinking, I can never do enough.” Once we recognize them, we can remind ourselves that they are just visiting. They are not essentially who we are.
If you know you have a tendency to procrastinate, consider why you put off getting started. Is it because you often feel unprepared? Is it because you’re afraid of the result of finishing?
Procrastination doesn’t have to define you. You are capable of planning ahead, doing work before it’s due, and making the space to create great things.
If you have a pattern of denying help, consider why you don’t accept help when it’s offered or ask for help when you need it. Is it because you think you’ll be a burden? Is it because you’re afraid of looking ill-equipped or stupid? Is it because you only believe the work is good enough if you do it all on your own?
Denying help doesn’t have to define you. You are capable of receiving the support of your colleagues, your community, your family, and your team. You are also capable of asking for support with openness.
Our patterns stem from our beliefs and assumptions about how the world and our relationships work. When we start to notice our patterns and then begin to uncover those beliefs, we can build self-awareness into our plans so that we can begin to make different choices.
For instance, I know I have a tendency to stop following through when I reach some “good enough” result. It’s a pattern I’ve developed to save myself from not hitting the real target and triggering a feeling of failure. If I don’t actually commit to working my plan, when it “inevitably” fails, I can give myself an out.
“Good enough” doesn’t have to define me. I am capable of stretching toward greatness and accepting failure or disappointment if greatness doesn’t take the form I expect it to.
When I make my plans, I think about this “good enough” pattern. There’s rarely a logistical way that I can accommodate for it. But by considering it, I can bring awareness to it and be on the lookout for that pattern when it happens. Then, when I feel compelled to let things slide, I can work the plan by addressing the fear, adjusting course as necessary, and continuing to follow through toward the ultimate objective.
For patterns of procrastination, or denying help, or perfectionism, you may be able to include mechanisms in your plans that help you continue to follow through. A peer support group, developing a daily habit, or creating set milestones for shipping might help you work the plan. Remember, it’s not about “sticking to the plan,” it’s about learning, adapting, and continuing to follow through. These mechanisms can help you learn more about how you work and create plans that help you grow.
Finally, you don’t need to fear not “sticking to the plan.”
There’s no need to hedge on your plans or stop yourself from planning “too far” in advance. And we certainly don’t need to avoid planning! We can accept and embrace the fact that plans always change because we learn something new at every turn.
Whether you end up making big changes or small adjustments, letting your plan flex and breathe will give you a greater sense of ownership to how you lead yourself and your business.
So start making that plan and then commit to working it mindfully and deliberately, even as it evolves.