Blog: Stress-Free Time Management Tips for Busy Entrepreneurs, Managers, Executives

Upon some serious self-assessment, I’ve decided to demonstrate some professional vulnerability with my peers: I’m terrible at managing my time. There, I said it. Well, I actually think the reality of it is that I’m not that bad at time management, but, historically, I’ve been awful at estimating what I can accomplish in the next day, week, month, and year. I’ve been even worse at acknowledging and respecting what I’ve accomplished yesterday, last week, last month, last year, and even in the last five to 10 years.
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Derek Gaskins
Derek Gaskins // Courtesy photo

Upon some serious self-assessment, I’ve decided to demonstrate some professional vulnerability with my peers: I’m terrible at managing my time. There, I said it. Well, I actually think the reality of it is that I’m not that bad at time management, but, historically, I’ve been awful at estimating what I can accomplish in the next day, week, month, and year. I’ve been even worse at acknowledging and respecting what I’ve accomplished yesterday, last week, last month, last year, and even in the last five to 10 years.

What do I mean by that? A maxim I’ve heard iterated a variety of ways says:

“People overestimate what can be done in one year and underestimate what can be done in five.” – Anonymous

I couldn’t quite find who to credit for that so forgive me, but it’s spot-on, for me at least.

I always think I can accomplish more today and tomorrow then I can realistically. By doing that, I set false expectations for myself (maybe even for my team) and often feel as though I’ve fallen short. It’s not until I look retrospectively that I realize how much I’ve truly accomplished. I’m finding it increasingly important to spend time each day evaluating what I did the day prior and acknowledging the progress that was made. Give it a go yourself, it takes a few minutes each day.

The moral of the story: give yourself some credit. Show yourself some love. Be proud of your accomplishments and don’t lose sight of that. Maintain that as the framework for advancing yourself personally and professionally. You may be here reading this on a mission to improve your time management skills, but take a look back first. Improved efficiency and time management may be unnecessary. There’s a good chance you’re already killing it and just haven’t taken the time to realize that.

Now, if you still think you suck at time management, then let me take a few minutes to share some tips that have helped me tremendously. Before moving on, I’d like to add that I’ve tried a lot of time management and task tools and have yet to find one that meets my needs. This patchwork approach has worked really well for me, and I hope it helps you as well.

Prioritize it
First off, where do you begin with managing your time if you can’t define the level of importance each task carries? Prioritizing your outstanding tasks is paramount. You have to start here. The best tool I’ve found for this is the Eisenhower matrix:

Here’s a Google Sheets version of this tool. Make a copy of it and use it for yourself. Is it important or not? Is it urgent or not? Using this tool, take some time to go through your list of outstanding tasks and ask yourself those questions. Bucket them within the matrix accordingly to determine whether it’s something you should do now, delegate, plan, or drop from the list entirely. Focus on what’s going to move the needle. Spend your time there.

Delegate it
Before you even consider planning the tasks you need to accomplish, first determine whether you have tasks worthy of delegation. If you’re struggling to find time, then there’s a good chance you’re doing something that someone else could do. Stop wasting your time.

Evaluate what you’re doing on a daily basis, document it over a few weeks, and then take some time to challenge everything to ensure you have time to focus on what’s most important. It’s as simple as:

  • Is this task repeatable? Yes. Delegate it.
  • Does this task require managerial/executive judgment? No. Delegate it.
  • Is this task simple to execute? Yes. Delegate it.

Use some common sense and don’t kill yourself by putting too much on your plate. If you don’t want to lose sight of the delegated task, then use a tool like Boomerang for Gmail or Boomerang for Outlook. I swear by Boomerang. When you send an email delegating a task, you can set the email to “boomerang” (return to your inbox) at a set time/date if the recipient fails to respond to you. It helps facilitate worry-free delegation, freeing you up mentally to focus on something else.

Plan it
Now that you’ve set your priorities and have managed to delegate some tasks, it’s time to organize your day to make the most of it. I like to divide my day into three buckets based primarily on the complexity of the task:

  • Complex (Morning) – Is the task complex? Does it require a lot of mental effort? Is it more “project” in nature? If so, plan to tackle it in the morning when your brain is sharpest, assuming your brain is similar to mine, of course (after my morning coffee that is). Don’t wait until after lunch when your caffeine fix is depleted, and your carb-induced coma is setting in.
  • Simple (Midday / Afternoon) – Is the task simple in nature? Something that requires basic attention and mental effort? A great example of this would be a phone call with a colleague or vendor. These are still important tasks, but typically don’t require the same level of “sharpness” as the tasks I book during the morning hours. I like to book these after lunch and into the early afternoon hours.
  • Mundane (End of Day) – These tasks are as basic as they get. Examples would be filing an expense report or responding to emails. It’s easy to start your day with tasks like these as you can quickly check things off the list and feel accomplished, but why waste your mornings, when you’re peaking mentally, on tasks like these? Save these for the very end of your day. Sure, the bloated inbox may bother you during the day, but you’ll go home feeling more accomplished than ever.

Looking for some help committing to an approach like this? Try calendar blocks. I’ve found if my calendar is open, then I’ll book something – a meeting, phone call, etc. Yet, if I book myself and set alerts, I tend to remain far more committed, and sometimes that audible alert yelling at me is just what I need to light the fire.

Try it. Set aside some blocks in your calendar and don’t let yourself book anything during those windows. Set up a morning block for complex tasks, a midday/early afternoon block for simple tasks, and an afternoon/end-of-day block for anything mundane in nature. And stick to it. Treat your calendar blocks as if they are actual meetings and try not to cave. Stay strong, stay committed, and see your productivity skyrocket.

Keyboard shortcuts
Never underestimate the power of the shortcut. Time away from your keyboard adds up fast. If you consistently use the same software applications, then take the time to learn the keyboard shortcuts. Keeping your digits focused on nothing but keys will save more time than you realize. We use Slack regularly for internal communication, and I almost never use my mouse. If you use Slack, learn the shortcuts today – game changing. Same goes for email and even navigating MS Windows. You may need a cheat sheet for the first week or two, but you’ll establish muscle memory in no time and will save a ton of time.

Don’t forget you
Soap box time. The quality of the soil determines the fruitfulness of the seed. If you neglect yourself, you’re neglecting your team. Burning out will be detrimental to your efficiency, and your time management efforts will quickly become moot. It’s imperative you take care of yourself – your physical and mental well-being. Take time for yourself, even if during the day. Eat healthy, nutrient-dense foods, meditate on your accomplishments, dream about the future. Just get lost in your thoughts, even if only for five to 10 minutes a day. And, if you’re struggling to find time for your health, try:

  • Meal Services – I love Trifecta Nutrition (not an affiliate URL here – I really just love their food). Whether you’re looking for paleo, vegan, clean, keto or vegetarian, they have it all, and it’s delicious.
  • 5-minute workouts – Don’t tell me you can’t find 5 minutes. In fact, I bet you could find at least three 5-minute windows a day for a quick bodyweight workout. When you’re ready for a screen break, try some of these 5-minute circuits instead:
    • Repeat for 5 minutes: 20 jumping jacks, 15 crunches, 10 lunges, 5 burpees
    • Repeat for 5 minutes: 20 jumping jacks, 10 lunges, 30 second boat pose
    • Repeat for 5 minutes: 9 pushups, 9 crunches, 12 squats

That felt good – definitely needed to remind myself of these things. Prioritize it, delegate it, and plan it; find some hacks like the keyboard shortcuts above; and, most importantly, don’t forget about yourself. This combination has worked wonders for me when it comes to time management, efficiency, and well-being. I hope you’ve found something helpful that you can apply to your life.

Derek Gaskins is an eCommerce executive, internet marketing professional, marketplace expert, investor, and entrepreneur. His passion to help others succeed drives his desire to create content that is both thoughtful and actionable.

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