How to Sync Your Short-Term and Long-Term Planning

This year, for the first time ever, I’m offering Breakthrough Sessions to target focus areas where clients often feel stuck. During these 50-minute sessions, I help clients make substantive and compelling improvements to their websites, pitch/sponsorship decks, or organizational habi ts.

Over the course of three weeks, I’m taking a closer look at how these offerings can benefit clients and discussing typical problem areas. Why is website messaging so important? What is the outcome of a standout pitch deck? How much can new organizational habits really help?

For more information about Breakthrough Sessions, click here. For now, read on, and check out my previous posts about common website makes entrepreneurs make and how to create a great pitch or sponsorship deck.


When you run a business, staying organized is imperative. You can’t function without some kind of organizational systems in place, and many business owners realize this early on and take steps to get organized. And yet, for many new entrepreneurs, it’s still a struggle to make progress over the long term, even if they’re accomplishing everything on their daily to-do list.

When I work with clients to restructure their organizational habits, my goal is to make it easier for them to focus on their day-to-day needs without neglecting the things that need to be done in the future or over an extended period time.

The challenge for entrepreneurs is the fact that both of these organizational systems have to work together. If they’re not in sync, it can lead to feeling stuck, overwhelmed, and at a loss for how to fix it.

In my experience, I’ve found that some clients excel at doing short-term planning, while others are more comfortable when operating in long-term planning or big-picture mode. 

Whether you’re struggling to check off items on your to-do list, make progress on your long-term business goals, or some combination of both, these tips can help you get new systems in place to ensure your days, weeks, and months ahead feel manageable and productive.

1. Create a master to-do list and put everything on it.

A master to-do list is your best friend when it comes to organization. This is your comprehensive reference point for every task that needs to be accomplished over the course of the next day, week, and months.  Which is why, when I say put everything on it, I mean everything!

Then, use that master list to create your daily to-do list, pulling items off the list that you need or hope to accomplish that day. I recommend to clients that they do this at night before they shut down their computer or first thing in the morning--whatever works best for their schedule.

The trick is to be realistic about your time and only put items on your daily to-do lists if they are truly important. That doesn’t mean you have to restrict your work to urgent items; long-term projects are just as important. But be realistic about your time, and don’t overload your daily to-do lists with things that you know aren’t a priority. Lots of people put things on their to-do lists without any intention of completing them that day; they just don’t want to forget. The beauty of the master to-do list is that nothing is forgotten, but your daily to-do lists are more manageable.

2. Rely on a calendar, especially for long-term planning and repeating events.

I encourage all my clients to use some kind of calendar for long-term planning. A calendar provides a visual representation of deadlines, which is helpful when your average day is jam-packed and time seems to be flying by at warp speed.

A calendar is a reality check, and it can help you quickly eyeball what’s ahead. I block out my big projects, known deadlines, and other items to remember six months in advance. I also use my calendar for events or reminders that happen on a weekly basis. If I didn’t have a note in my calendar on the 4th of every month, I would likely forget to send my monthly bank and credit card statements to my bookkeeper, which would start a cycle of playing catch-up. While it seems like a minor detail, being on top of the little things helps me feel like I’m in control of my business.

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3. Explore whether digital or analog tools (or a combination) work best for you.

There are countless organization apps out there. Some of my favorites for managing to-do lists are Wunderlist, Evernote, and Trello, but there’s also something really satisfying about checking things off in a notebook. Logistically, I like having all of my lists on my phone so they’re always accessible and I don’t have to carry around a notebook, but I do go through bursts of time when I’m all about pen and paper. For me, both methods of organization are productive.

Some people feel very strongly one way or the other: they love the process of recording in a notebook, or they thrive on the convenience of apps that basically do it all. Others, like me, like a combination of methods. The key is to explore a variety of approaches before ruling one out. If you’ve never relied on apps but are looking for ways to be more organized, it’s worth trying one (or several). And similarly, if you’ve never gone the analog route, it might be a way to change up (and improve) your process.

4. Remember to hold yourself accountable.

One important aspect of developing any new habit is accountability. When I work with clients, accountability is built into our process. But it’s also critical to establish ways of sticking to your own habits, especially when you’re managing your daily routines AND your long-term goals.

One easy way? Reflect on how your new organization methods serve you and your business. How do you feel on days or weeks when you aim for organization and stick to your new habits versus weeks when you abandon them? Taking note of the value of habits is one good way to cement them as a more permanent practice. And it can also help you identify habits or tools that might not be a good fit for your organization or working style. Sure, in one sense, taking the time to hold yourself accountable is just one more thing to do. But in reality, it’s a critical piece of the puzzle. Accountability helps you transform your habits into a natural element of your business.