This question was originally posted on Quora. Here are some selected answers: Opinion from: "Noah Parsons", COO @ www.liveplan.com Creating a plan is critical, but you also need to make sure that you have some flexibility as you follow your plan. Just like going on a road trip, unexpected things will happen. You might get a flat tire or you might find a new shortcut. Instead of just following the plan blindly, you need to be prepared to adjust on the fly and change your schedule as new information becomes available. Even if you do make adjustments, you will want to try and stay "on plan" - meaning that your high-level goals probably aren't changing too much. You still want to end up at the same destination, but how you arrive at that destination might change. Here are a few tips to help you stick to your schedule: Use a tool. You'll need something to create tasks, assign responsibility, and track progress. Basecamp and Asana are both good options. You could also look at a "to do" tool such as Todoist or Wunderlist. Break down your tasks into manageable chunks so that you can estimate correctly. As a general rule of thumb, if any task gets estimated to take more than one day, the task is probably too big and should be broken down into sub-tasks. The more specific you can get with your tasks and sub-tasks, the better your estimates will be. Follow up with regular check-ins. Daily "standups" are a good idea so that everyone on your team can quickly share progress and bring up issues that may require a change in schedule. These follow up meetings are a great time to brainstorm solutions to problems that have come up as you implement the plan. Adjust the schedule in real time as you find out new information. No schedule or plan is perfect and you're going to learn new things as you implement the plan. Don't be afraid to adjust the schedule or change what you expect to finish by a certain date. Artificial deadlines don't do anyone any good. You have to be realistic and adjust your plan as you go. At the end of the day, a plan is nothing without implementation. Be sure to balance the amount of time spent planning and the amount of time spent "doing" so that you can learn quickly about the parts of your plan that will work and the parts that don't. Second opinion from: "Laura Ling" The best way to build a new habit is to tie it in to an existing habit after the triggering event (as opposed to the beginning). Here's a visual on the "Habit Loop" as identified by Charles Duhigg: Source