Planning, productivity, and getting through the never-ending to-do list are some of the biggest concerns of the small business owners we work with. They certainly were some of my biggest concerns for years.
I’d come up with a “great” plan at the beginning of every year and then promptly forget about it by April. I’d log into Asana and it would greet with a list of overdue tasks that didn’t excite me (or seem remotely connected to my goals). I’d sprint through creating a bunch of articles, videos, or explainers only to crash hard the next week.
It was often hard to know what to focus on, what was most important at any given time, and how to fit it all in—I felt like there just weren’t enough hours in the day to get it all done.
Something had to change.
A couple of years ago, I got curious about how I could be objectively productive and always feel disconnected from my work and behind on important things.
In other words, if I was legitimately getting a ton of good stuff done every day, how was it that I still didn’t feel like I had the time or energy to focus on the important stuff?
I was curious as to why I could streamline my to-do list only to feel short on time and results at the end of the day.
Of course, time wasn’t really the problem. And neither was my productivity.
I couldn’t see the connection between how I was spending my time on a daily basis and what mattered most to me and my small business—that was my biggest problem when it came to how I planned my week and workload.
I was either head down, banging out my to-do list—or I was head-in-the-clouds, only thinking about my plans and strategy.
I ended up trying to squeeze more and more onto my plate to hedge my bets on what would help me actually make good on my plans.
I needed a way to move seamlessly between daily work and big picture thinking, to regularly make the connection between what I was doing on a weekly basis and where I wanted to be going…
…so I could stop trying to do more and start focusing on what mattered.
And, I needed to take control of what I was working on instead of feeling like my work was controlling me.
In a bigger business, connecting tasks and big picture priorities is often the role of the manager.
Managers are the ones connecting the company’s priorities to the projects and tasks their team is working on. They’re the go-betweens that help to ensure that small tasks add up to meaningful progress on bigger initiatives.
A good manager stays curious about how they can move themselves, their teams, and the projects under their management forward in line with their company’s key priorities.
I needed to become a better manager to myself.
To do that, I needed a new system and a new tool to track that system—a new way to connect the dots, organize my priorities, and focus on what mattered most.
The tools I had used in the past—task management apps like Asana and Trello, note-taking apps like Evernote, and big-picturing planning tools like mind maps and spreadsheets—all were good at helping me focus on a particular thing. But they weren’t so great at helping me manage myself by connecting my daily work to my projects and priorities.
I needed a new system.
This dashboard allows me to see my current personal commitments (I stopped setting goals), my business’s strategic priorities, and the projects I have planned for the year. It also has a more detailed view of the projects I’m working on that quarter and the tasks I have allocated for the week.
By using this dashboard, I have the ultimate control center for managing myself and my small business—so I’m always focused on what matters most at any given time. I track my longer-term priorities & projects there, as well as my projects for the quarter, daily tasks, and key metrics.
Using my dashboard, I can always stay curious about what needs to be done, how it should be done, and why it matters.
Of course, the dashboard itself only goes so far, though. I need to allocate my work and plan effectively for how I use my time in order to make sure that I’m actually building a stronger business as I go.
Here’s how I plan each week as I manage myself and my small business.
First thing every Monday morning, I set my agenda for the week.
I clear out the old tasks from the previous week and I look at what needs to get done for the current week—and what I want to move forward on that’s not “due” yet.
I start by addressing my routine tasks—the things that happen every week (which have a special spot on my agenda) and the things that happen every month. Because this kind of work is routine (i.e. it just happens, right?!), it’s really easy to miss when I’m planning things out—and when I miss it, I overestimate my capacity to get other things done. #frustrating
Next, I transfer any meetings, appointments, or time off from my calendar into my agenda. And, I add any prep work that needs to be done for them so that I’m not caught off guard or trying to remember to prepare. This is the work that limits my personal capacity to get stuff done the most, so it’s important that it’s recorded in my planning for the week. Otherwise, I’ll have unrealistic expectations and get down on myself.
Finally, I look at the projects I’m currently working on (typically about 3 per quarter). I try to allocate items from these projects to my workload each week so that I’m moving forward on them, even just a bit at a time. I also look ahead to see what doesn’t yet feel “urgent” but could be really helpful to work on now instead of later.
As I plan, I don’t just make one long to-do list. I spread my work out throughout the week, day by day and task by task. By doing that, I’ve gotten a much better handle at what I can get done and when I can do it, which makes planning much easier. It’s also helped me to have clearer expectations for the day at hand, which makes it much easier to be kind to myself.
Inevitably, I have to make choices as I plan my week.
And to make these choices, I use my planning process as opportunity for reflection and analysis.
Sometimes I prioritize one project over another or accept that a week with a lot of meetings means that I won’t make much forward progress on my projects. Sometimes I ignore things that are interesting to me but not important. Sometimes I coach myself to followthrough on something I’m a little bored with. Sometimes I examine what form of self-sabotage I’ve been indulging recently.
To figure that out, I basically get to have a heart-to-heart with myself every week!
And each week, I learn something new about myself, my small business, and what matters most right now.
Here are 5 key questions I ask myself to get clear on the choices I want to make, what work I want to tackle first, and what is most important for the strength of my small business:
1. Given my capacity & commitments, what is most important right now?
I always want to be clear on what I’m committed to (personally & business-wise) as well as the factors that are limiting my capacity to get stuff done or move things forward (meetings, illness, team needs, mental health, family responsibilities, time off, current events, etc…).
I’ve found that I need to check in with this each and every week in order to stay on top of it. There are always so many things vying for my attention and I need to maintain my focus while, of course, staying flexible and open to new information, too.
My commitments and capacity also heavily influence what is, in fact, most important at any given time. I may be committed to a project that’s nearing completion and needs my full attention. I might be committed to an event or a group that needs my full emotional and psychological presence. Or, I might have some open space that I can use to work on a number of things that are important given the capacity of my time and attention.
2. What always needs to be done? (And is that true?)
As I mentioned above, one area of my workload that’s really easy to loose track of is the work that’s always due. It’s the podcast that needs to be published every week, the community newsletter that needs a message to be written to be sent out every Tuesday, the team meeting that happens every Friday.
Because these activities become so integrated into how we work, it’s easy to take them for granted and forget that they impact our capacity to get other things done.
I’ve made checking in with my routine work part of my planning process so that I don’t forget about it and so that I can reassess if it really deserves to be something taking up my time and capacity, too.
Priorities and commitments change—and that can impact our routine work. If we don’t reevaluate whether it still fits into what’s most important, we’ll keep doing it even when we don’t need to anymore.
3. What can I move forward today that my future self will thank me for?
I got so tired of always feeling like I was trying to catch up.
So I make a point of working ahead now. When I plan out my week, I think about what’s urgent now—but I also think about what will be urgent next week or the week after (or even a month or two in advance) and how I can do even one small thing to move that forward, no matter how “busy” I might be right now.
This has been a game-changer.
The idea of “working ahead” might feel like a real luxury right now—and I get it. But the effects of incorporating one small thing per day or every just a few small things per week into your planning are exponential.
Each time you move something forward ahead of schedule, you make extra space in the next week and then extra space in the week after that. That either adds up to plenty of time off or the chance to complete a big project you didn’t expect to get done—or both.
4. What is distracting me?
This is similar to getting to clear on my capacity… but I extend it to the great ideas, “shoulds,” and shiny objects that might be tempting me away from what matters most right now.
The truth is, these things could be legitimately great or interesting and still not matter most right now. Even great ideas are distractions when they pull me away from what matters most.
So I want to look at whether I’m trying to fit things into my agenda for the week that are just distractions (for now). If I am, I make sure to take note of them (I have an Idea Island for those things).
It’s not about judging these ideas or myself for being distracted by them. I’m just recognizing that they’re a distraction that I can set aside for later.
5. What am I avoiding?
Just as I can be eager to jump into work that’s not truly important right now, I can be avoiding work that really matters.
Am I shirking an important conversation? Am I procrastinating on a key project? Am I ignoring an impending deadline? Do I just really not want to answer those emails?
I get clear on what I’m avoiding and work it into my schedule so that I can activate my personal accountability and get it done.
Planning my week this way has helped me to stay curious about what’s working and what’s not working in my small business. It’s also allowed me to step up my ownership of the work that I do and the projects that are truly important to me and help make my business stronger.
Instead of waiting for a task management app to tell me what’s due or relying on a team member to “manage up,” I’m curious about what’s important and how it fits into my day, week, or month.
This has given me a greater sense of control and confidence—even when things feel uncertain. This system has also allowed me to stay nimble as priorities shift and new projects come into focus.
I believe that the way we manage ourselves as small business owners is an opportunity to learn something new about ourselves and our businesses—but we have to stay curious.