When I work with business owners to develop a plan for their business, I always make sure we keep going until they know exactly what they are doing tomorrow, and the next day, and the next week. This makes the difference between a plan that gets executed and a plan that looks nice on the wall but rarely comes to fruition. It also ensures that everything you do on a daily basis is contributing to progressing a big goal, which is critical to remaining motivated and energized about your business.
Think about planning in three “layers”: goals, milestones and tasks. Imagine a funnel, into which you pour your great ideas that flow down from big picture goals to very detailed tasks, leaving you with an actionable, short term work schedule that directly contributes to the progression of your business in the direction you have chosen. These tasks can be both one-time activities that you cross off a list, or ongoing habits that you would like to cultivate in order to support a bigger picture objective.
I use different tools for each layer of my plan because I tend to think differently about how I want to manage each layer. For instance, when managing my detailed tasks, I want to be able to work from grouped checklists in a tool. Alternatively, when I am working on a strategic plan, I want to be able to create free form maps that can morph and grow as my mind wraps itself around a topic. I don’t need to worry about details at this level.
Your Goals
Start by throwing everything out there that comes to you when you think about the vision you have for your business and your life. These goals might be financial, ethical, personal, operational, charitable, or anything else that really represents your ideal state. Think in a 3-5 year term here, and be completely honest with yourself about what you really want.
The best way to keep track of these goals is in a free-form tool that lets you jump around and build on your ideas in a non-structured way. I like to use a mind-mapping tool like MindMeister, because it has so much flexibility and a great interface. There are plenty of others available and which you choose just depends on your preferences. You can even do this on a whiteboard or flip charts – just don’t constrain yourself too much and make sure whatever you use allows you to be flexible.
Think of a goal as any objective which you can’t imagine just doing right this minute and being finished in a short duration. It should seem far away, and lofty. Don’t be afraid to be a dreamer – if you don’t set a goal, you most definitely will not reach it. We will work on making your goals more realistic next. During this process, it is easy to get sidetracked by more tactical objectives, but just note them and put them off to the side for later.
Once you have established your first draft of your goals, try and add some measures to them – timelines, financial targets, counts of some sort. For example, if one of your goals is to make $100,000 annually, think about when you would like to achieve that. One year? Two years? Add these measures. If you have a goal of making an impact on your community, try and quantify that. Does this mean contributing 100 hours to volunteer organizations every year? Or perhaps donating 2% of your profits to a charitable organization related to your community?
Adding measures to your goals will help you make them more specific. Specificity enables you to create goals that are realistic and meaningful. If you know there is a specific type of community you would like to contribute to, also include that in your goal description. Review each of your goals for specificity and add where you can.
Your Milestones
Now that you have established your goals, start thinking about what needs to be done in order to achieve them. Ask yourself what stands between your business now and the achievement of that goal. What is missing that is preventing you from reaching your objective? Start listing these milestones and try putting them in chronological order if you can. If there are dependencies amongst these milestones, make sure you note these and order them accordingly. I use a tool like SmartSheet in Gantt view to create this chronological sequence of milestones.
A milestone is something you think of as a step that gets you closer to your goal. This is the “how” part of your plan. A great way of deciding if something belongs in this level is to ask yourself “Is this something I could do in a day?”. If the answer is “no”, then it belongs in your milestones. You may have multiple levels of milestones, as you may break these down into sub-milestones.  When you start thinking of quick, detailed tasks, those will belong in the next level of your plan.
Once you have built your milestones, add some dates to each milestone, such that they correspond to your goals. If you cannot correlate your milestones to your goals, then you need to ask yourself why they are in your plan. You don’t need to be painfully accurate right now about your estimated completion dates. A ballpark is acceptable, so long as the dependencies amongst the milestones make sense (i.e. “Create a logo” might come before “Build marketing material”).
If you are using a tool like SmartSheet’s Gantt view, you should now see your plan being displayed in both a milestone view and a calendar view, so you can see what needs to be done when. A visual reference like this is really helpful when it comes to staying on track and trusting that all of these pieces combined, and done in the right order, will eventually result in your vision being realized.
Your Tasks
Now’s the fun part where everything starts to become tangible. You are going to create a work schedule for the next 12 weeks which will allow you to get up in the morning and just go, with your day already fully planned out and with the knowledge that everything you are doing is inching you towards the business and life you have envisioned.
Look at your milestone plan and zoom in to the next 12 weeks. You want to constrain your task schedule to a shorter, more realistic timeline than the typical 12 months. By building your work schedule around a shorter time line  you are able to be more realistic about what you are trying to achieve, and you can pivot more frequently if you find that you need to change direction. You can learn more about the rationale behind the 12-week schedule by reading The 12-Week Year (I highlight recommend this for every business owner).
Considering the goals and milestones that you would like to achieve, or contribute to, over the next 12 weeks, start noting all of the tasks that you will need to finish in order to get to that goal. For instance, if one of your tactical goals is “Create a logo”, then you may need to do the following:
  1. Search for designers
  2. Shortlist designers
  3. Interview shortlist
  4. Check references
  5. Hire designer
  6. Discovery session
  7. Review Round 1
  8. Review Round 2
  9. Sign off on final design
Using a bit of visualization during this step is often helpful. Draw out what you imagine the process will look like for achieving this task. Work backwards from the end date that you have assigned to the goal and assign due dates for each of these tasks, and an estimated duration. Then you will know exactly when you should be scheduling them. I use Trello for managing my tasks because I can group them into boards that align with the way I organize my days. Additionally, I can create nested checklists of tasks that I can quickly drag from one status to another, Kanban-style.
Your Daily Schedule
Every day that you sit down to start your work, you are in your freshest and most productive state. The last thing you want to do in that precious time is to start trying to figure out what you want to do today. Spending a few minutes every evening to plan the following day means you can wake up and get going right away.
Your daily schedule should include more than just your tasks. This is also where you can ensure you are building in time for creating habits, and doing all of the other things that are important to you. I use a journal from Best Self Co. to manage my daily schedule – I find I want to be able to write my daily schedule down, and have it with me all the time. Best Self has also built in sections to encourage habits that balance out our busy work lives. Every evening while sitting in bed, I review the day and reflect on what I learned, what went well, and what I am thankful for. Then, I look at my tasks, and decide which I will be working on the following day, remind myself of the goals and milestones that these are contributing to, and identify targets for the day.
When we break our schedules down to these micro levels of planning, we are far more likely to make progress on the things we have been having trouble getting done. Even small, incremental progress is better than none. For instance, I set aside half an hour every morning to write, first thing. I used to have such a difficult time finding any time to write and it would fall further and further behind. Now I produce at least one post a week, which I would never have done before I had scheduled time for it every day.
Additionally, because my schedule has already been set the night before, I don’t question it in the morning, and am far more likely to just sit down, plow through and get it done. I’ve already thought through any of the challenges I might have the night before, and adjusted accordingly. While there is always the chance something can come up, for the most part I can run through my day and move from one task to the next without too much trouble.
The Review
To wrap this all up: if you want to be successful getting things done, you need to break your big goals down to little tasks, and create a system for managing and scheduling these. Leaving ambiguity in your system means you will spend time wondering about the right way to approach what you need to do. Plan your day the night before, and stick to a consistent regimented schedule where you can deliver on tasks every day that have been derived from bigger goals.
Don’t forget to review your progress every day, use what you’ve learned to make your next day better, and remind yourself of what went well, and what you have to be thankful for. Use tools and systems to help you manage your planning, and remind yourself daily why you are doing what you do.
If you are already committed to your success, a system like this will be your best path to ensuring you can deliver on those intentions. Good luck and happy planning!
Disclosure: Some of the products I have added links to within my articles may compensate me for sales generated by visitors to my site. I have used and tested these products myself and will only post links to products that I trust and value.