How to Manage Your Calendar 

UPDATED: February 1, 2024
PUBLISHED: March 15, 2022
How to Manage Your Calendar 

This week on the SUCCESS Line we discuss the repetition of fundamentals, particularly as it relates to protecting your time. Ben, who has been in the insurance industry for the past 10 years, struck out on his own last year as an independent agent. While he enjoys the opportunities he now has for greater diversification, he also no longer has a manager dictating his daily schedule. Ben is therefore having issues with how to lay out his time and calendar to maximize his efficiency and productivity.

We took a deep dive into the actionable changes he can implement to find success.

Understand how you’re spending your time.

Have you ever gotten to the end of your day and knew you were busy, but couldn’t really name what you had accomplished? Before you can decide how to best allocate your time and put systems in place to enable that, you have to understand how you’re currently divvying up your attention. What task takes up the most time in a given week? Is there a task that’s getting lost in the shuffle? And what are the items you need to be devoting time to that will pay dividends in the future? Once you have a complete sense of the flow of your current weeks, you can more accurately rejigger your day-to-day.

Ben spends a lot of time building rapport with potential clients and businesses as a means of prospecting, but sometimes wonders if he’s talking to enough of the right people, given the mental stamina he exerts during the conversations. He also often weighs if prospecting comes at the expense of servicing existing clients, potentially resulting in their dissatisfaction or a bad review.

It’s not an either/or situation.

I challenged Ben to reframe his thought process. He has to figure out a way to carve out time to perform both servicing and prospecting duties, not one or the other. I once had a mentor that told me that success day-to-day looks incredibly boring. Anyone who has reached that high level—through grit, grind, blood, sweat and tears—has done so by the repetition of fundamentals, or a few things that they do consistently every day. 

Entrepreneurs can often get distracted by the shiniest thing or the next bright object, but what gets us to where we want to go is, again, that repetition.

Make the appointment with yourself.

As I told Ben, servicing and prospecting are appointments you have to keep with yourself, and consider sacred time, every day. You can’t treat this dedicated time any differently than any other appointment, as these two items are some of the biggest levers to move your business to where you want it to go. So if you wouldn’t cancel an appointment with your best customer, then why cancel one with yourself?

Block it.

The key to effective time blocking is to begin with blocking 50% of your calendar for the drivers that will move your business ahead. If you honor that part of your schedule, you’ve honored your commitments to yourself and still won the day, no matter what else occurs.

One way to maintain these dedicated time blocks is to use a scheduling software such as Calendly. That way, when you have clients wanting to book an appointment with you, they are only offered the times outside of the appointments you’ve already made with yourself.

This discipline with your time actually gives you freedom, because otherwise we’re just jumping from one thing to the next. This way, you’re forcing everything and everyone else to fall around these core buckets. 

There’s a very fitting expression in regards to your time blocking: If you erase, you must replace. For example, let’s say that during Ben’s servicing time there’s a networking meeting he would like to attend. He should give himself the grace to move that prospecting time in order to attend the meeting, but make sure he finds a different block for it that same day. Make that commitment to yourself, so that you’re not completely missing that appointment. 

Build good habits.

The week before someone goes on vacation, I often refer to them as being a productivity ninja or making a vacation miracle, they’re that efficient. You need to ask yourself how you can develop your habits to incorporate a percentage of that productivity in every day. You’ll be getting more done overall because you’re being more purposeful.

When people attempt to establish a habit they often overcommit, so start with the most important things first. The small, specific buckets that move the needle toward what you want. And if you’re consistently sticking with it, you’ll eventually reach success—the further out you go from staying consistent in a habit, the easier it is for the habit to never come back.


The SUCCESS Line is no longer releasing new episodes on the SUCCESS Podcast Network, but you can still listen to the full conversation below.

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Ben Fairfield is the Managing Director of SUCCESS Coaching & a SUCCESS Certified Coach.