“I’m so far behind!”
Get a few small business owners together and it’s only a matter time until you hear that line. Our brains are always a few steps ahead and our execution always feels like it’s lagging behind.
It might seem absurd to even imagine feeling caught up or—dare I say it—ahead as a small business owner. But I do think it’s possible. Because I’ve done it.
I used to operate in a constant state of feeling behind.
Every morning, I’d cobble together a list of things that absolutely must get done and then have a mental temper tantrum every time something else got added to that list.
The reason was pretty simple: I was always aiming to get my work done just-in-time.
My lists were full of things that were due on or near the date that I was working on them.
That’s deadline orientation.
Deadline orientation is how the vast majority of our meetings, to do lists, and project management tools are organized. We give things a due date and then we arrange our workflow around that deadline.
Deadline orientation is so engrained in the way we work that it has become part of the way many of us think of ourselves. It’s become part of our identity.
“Deadline-oriented” has been part of my identity since at least high school. For a long time, I thought deadline orientation was my nature, my natural way of operating in the world.
I no longer believe that.
Instead, I see triggers for deadline orientation all around me. In high school, it was the reaction to having a project due on a certain date. In my retail management days, it was having to swap out displays on a certain date. In my business, it was using tools that organize work by deadlines.
I was trained to focus on the due date.
I was accountable to the deadline and (virtually) nothing else. Deadlines were a sense of order—but an order that was imposed on me by outside forces. Yuck.
Of course, I’m not alone in this. Even if you don’t have a crushing sense of deadline orientation, we live in a society that worships the deadline.
How many times have you heard, “Give me a deadline or it won’t get done?”
Deadline orientation might be an effective way to ensure things get done when they need to get done. But it makes us cranky. It means most of us are living on the edge of falling behind—which leads to feeling anxious and out of control.
So last year, I started to wonder what it would look and feel like to not always have that sense of impending doom brought on by deadline after deadline creeping up on me.
I started to rewire the way I work.
Before I get into my experience and how I’ve personally solved the problem of feeling behind, I want to say that this is my experience as a neurotypical, college-educated white woman. Your brain chemistry, past trauma, or school/work experience might very well create different patterns and experiences for you.
At first, I just wanted to get a better handle on what I was doing, make sure I was prioritizing the right things, and create a clearer sense of routine.
But now I know that I was starting to break away from the deadline orientation I’d learned over decades while starting to create a greater sense of personal accountability.
Personal accountability is knowing what I want to do, why I want to do it, and actively choosing when I do it. And it feels so much better than deadline orientation—even when I’m choosing to do something I don’t love to do.
Today, I manage my work by reviewing where I’m at in context of my plan for the year, my quarterly projects, and my weekly routines.
I choose what I’m going to work on for the week and I manually place each task on the day when I want to get it done.
I don’t always get it right. Sometimes I get more done in a day than I expect and can start working ahead. Other times, I end the day with a few things left to do and I choose to move them to another day or into the next week.
But… here’s the kicker…
I’ve completely eliminated due dates from the way I manage my work.
(I don’t know that I even really realized that until I typed that sentence just now.)
My work is my choice.
And I so notice when I’m choosing not to get something done. I can either push through and do it or I can examine what is causing so much friction in order to eliminate it (or I can choose to do both).
That’s not to say that I’ve eliminated priorities or order of operations. I still take the time to think through what’s important now, what’s important in the future, and what I need to do first thing every day. It’s just that those priorities aren’t dictated by due dates—they’re dictated by my commitment to the projects I’m working on and the way I’ve chosen to complete those projects.
Now, how does this help you stop feeling (so far) behind?
Deadlines are a big part of what make us feel behind. That externally imposed order of the calendar is what makes us feel like we’re lagging.
When you choose your work, it’s easier to start owning what’s important, what matters, what is truly needed (and what’s not).
And that is incredibly important today as we work in an environment of uncertainty—with children who want our attention, with parents that need to be convinced not to go to the grocery store for fun, with a thick mental fog that limits our capacity, with new routines, new styles of relationships, new information.
I won’t go so far as to say that deadlines are becoming obsolete. Deadlines and due dates can help us work with other people and measure progress.
But I do think our relationship to deadlines—even productivity and time management—is changing rapidly whether we like it or not.
We can try to hold on to the old way of working, where office life was structured with 8-hour workdays and tidy calendars.
Or, we can create a new way of working that allows for flexibility, choice, and personal agency.
I know getting rid of deadlines probably feel pretty radical. Even impossible.
Maybe you’re wondering if you would get your work done and move your plans forward at all. Maybe you’re wondering if you could keep up with your clients or communicate with your team members effectively. Maybe you’re wondering how you would know what to do on any given day.
Whatever your hesitation, consider what your objection is telling you about your commitment to the work you’re supposed to be doing. If you’re unwilling to prioritize work that doesn’t have an impending due, is it really that important to you? And if it is important, why are you unwilling (or unable) to do it before it’s due?
Here’s what I know:
Working for external accountability, imposed order, and deadlines made me angry and filled my life with friction. Orienting my work to choice, ownership, and commitment has made me a happier person who has created more things I’m incredibly proud of.
What could it do for you?
Get the planning and task management system I created so I could break free from deadlines.
The Leadership Dashboard will walk you through creating the commitments that shape your life, the strategic priorities that shape your business, and the projects and plans that will shape your schedule.
You’ll get video guidance every step of the way, plus a done-for-you Notion template to track your work and choose your tasks. You’ll be able to adapt for today while planning for the future.