1. Home ›
2. Blog ›
3. Entrepreneurship ›
4. 9 Strategies to Help Manage Multiple Projects at Once (Without Losing Your Head)

9 Strategies to Help Manage Multiple Projects at Once (Without Losing Your Head)

“Ooooh, shiny!”

This could be the distracted murmur of an attention-deficit friend at a car dealership, a cooing toddler mesmerized by car keys, or … perhaps you, my friend.

As an online entrepreneur, your mind is in approximately one million places at once. On any given day, you’re likely managing daily operations, employee and customer issues, meetings, trainings, company growth strategies, new projects, and everything in between.

From the time you start work (early) to the time you finish (late), your mind is abuzz with activity.

You might frequently have days bursting with activity, but when you finally fall into bed, you ask yourself, “What did I actually do today?”

Not to mention the fact that every day is not only full to the brim with things you’re already doing, but things you want and plan to do: businesses you haven’t started, connections you haven’t made, ideas you haven’t pursued. As you try to fall asleep, the “what ifs” come raining down.

It’s a common feeling in this day and age. You push yourself to do all the things ––probably at the same time. The result? You end up actually doing none of the things… Or at least, significantly less than you would have if you had approached your crazy life a little more tactically.

Because let’s face it –– the life of the perpetually overworked, overstressed, overtired (sensing a theme?) entrepreneur does not make you a hero. It just means you’re bad at time management.

Fear not –– there is a way out of the kaleidoscope that is your brain.

We’ve come up with a 9-step, one-at-a-time game plan for doing just that. On the other side, you will feel clearer, calmer, and more collected; you’ll feel ready to take on all parts of your world, not just the shiny ones.

1. Admit that you have a problem.

I know, I know. This sounds like another step one you’ve likely heard of that relates to booze, not productivity.

But the sentiment applies here, too. If you don’t think you have a problem when it comes to managing your time, you will definitely not benefit from the following steps and will ultimately fall right back into your current methods of operation.

This guide is going to require some work on your part. So if you don’t already have a notebook and pen handy (Yes, a paper notebook –– you remember things more when you write them down. Stop whining, it’s science.), go ahead and get one out and flip to a clean page here.

Take a minute to think about your strengths and weaknesses when it comes to your time management. Here are some questions you can ask to self-assess:

• What things never get done, or end up being completed half-assedly (your new favorite word –– you’re welcome)?
• What parts of your life –– inside or outside of work –– do you wish you had more time for? Creative exploration? Friendships? Netflix binges?
• What are the most frequent emotions you feel while you’re working? Stressed? Content? Panicked? Energized? Alive?

No matter who you are, there is room for growth. Look at and think critically about your answers to the above questions. Where are your areas for development?

We will be using your answers to these questions as we dive deep into your time management plan, so make sure to keep all your notes handy as we go forward.

2. Solidify your goals and priorities.

Spend several minutes and make a big list, journal, draw pictures, make a mind map, or whatever works for your brain about what’s important to you and what your goals are. At this stage of the game, don’t worry about whether they relate to work, life, or your fictional alter ego. Just write them down.

Got ‘em?

Now, group them together however it makes sense to you. Mine tend to fall into personal life, work, and creative projects, but your categories might look different –– that’s ok! Try not to make more than four, or it’s hard to keep track.

Once you’ve done that, go through and number them in order of importance. It might be hard to do, but there can only be one top priority in each. When you have many number one priorities, you have no number one priorities. Be a little strict with yourself here.

Ok –– so now you’ve got a pretty organized look at what matters to you in the world. These lists are not set in stone, but they’re a great way to give you some perspective into that messy lil’ brain of yours.

3. Know thyself.

At this point, you might be thinking that this feels more like therapy than time management. I get it. But as I mentioned above, if you don’t spend some time at the beginning peering into your own brain and habits, the work we do in the following steps won’t matter.

So, we have one more step dedicated to crawling inside yourself. Turn the page in your notebook and let’s look at something of particular importance –– your work habits.

Divide your paper into four sections: turf, time, tools, and tasks. Under each one, describe that aspect of your work life. Answer the questions below to get some good details:

Turf –– Where do you work?

• Do you work from home? In a café? In bed? In a cubicle? On a spaceship (calling all astronauts)?
• Who else is around? Coworkers? Strangers? Your dog? Siri?
• What’s the noise in the background? Silence? Smooth jazz? Fire truck sirens?
• What is the space like? Is it a big, open room with natural light? An office with fluorescent lamps? Outer space (again, astronauts)?

Time –– When do you work?

• Morning bird, night owl, or perpetual pigeon?
• Do you work in several hour chunks, or short bursts?
• Do you find yourself watching the clock, or do hours pass without you even realizing it?

Tools –– How do you work?

• What pieces of technology or other tools do you use on a daily basis? Think hardware or tangible tools.
• What programs do you use to get work done? Think software and apps.
• What’s your typical tab preference? One to two open ones, or so many that you can’t even see the icons?

Tasks –– What do you work on?

• How do you determine what you will work on in a given day? Do you have a system of to-do lists or another method you use?
• Do you normally work on one thing at a time, or frequently switch between many tasks simultaneously?
• Which tasks tend to get priority? Which ones keep falling into the “I’ll do it tomorrow” stack?

Once you’ve answered these questions, go into label mode.

First, with the positives –– go through and star the elements of your work life that you find are productive, effective, and make you happy. We’re holding onto these.

4. Make a “keep” pile, and integrate it into your schedule

The idea here is to take these positive elements and mold your schedule to reflect them as much as possible.

Depending on what situation you’re coming from, maybe your time is not all your own. In other words, you might spend a large quantity of time working for someone else, and some things will be somewhat out of your control.

Long term, your goal is to move into a situation where you can indeed change these things, but for now we have to work around them.

Now you can come back to the digital world and get out your calendar. Don’t have a digital calendar or planner? Google is a great place to start.

On your calendar spaces, put these fixed things in there first. Think mandatory meetings, check-ins, deadlines, and the like.

Then, plan out the rest of your time to optimize the positive elements we wrote above, starting with time and tasks. Schedule blocks of time in your calendar for the creative stuff that best works for you. This could mean early morning 5 AM wakeups, or late night 2 AM frenzies. Important: this time will only be for your creative work! No emails, phone calls, or the like.

In these hours, you’re set to do not disturb. Note it as such on your calendar and on any communication channels. This chunk of work should also be completed in your prime creative environment if possible.

Rinse and repeat with the other elements of your work and goals. Schedule the more mindless tasks during your lower-energy moments. If you’re a very active soul, incorporate plenty of short breaks for bursts of exercise, snacks, and social interaction.

Make your calendar reflect you, to the best of your abilities. Put your time in when, where, and how you will make the most of it.

5. Name and strategize against your productivity thieves

With the positive elements accounted for, let’s focus our energy on the “need a change” elements of your work –– they can get a triangle or delta symbol. For these parts, brainstorm how you can possibly change that element to make them better.

• Are your officemates too loud? → Look into noise cancelling headphones or talk to them about keeping it down.
• Is your schedule inconducive to your peak productivity and creativity times? → See what adjustments you could make to when you work.
• Do you find yourself wasting precious times on Facebook Messenger while you work? → Shut that shit down! We believe in you.

As you go through this process, you might find that you don’t have all of the answers to defeat the time thieves and creativity sucks. Here are a few tools that might come in handy:

• Headspace: a gamified app that brings daily meditations and mindfulness practices to the everyday person.
• Pomodoro Technique: task-based 25-minute bursts of activity to keep your productivity boosted.
• RescueTime: tracks and limits your use of timesuck sites like Facebook, Twitter, etc. and cuts you off when you reach your limit.
• Trello: a digital bulletin board to help you track your progress on different projects.
• Slack: replace email with a souped up chat service that contains public and private channels for communication.
• Asana: like Trello + Slack on steroids. More on this below.
• Evernote: all your ideas in one place, organized.

You can use these tools in order to prioritize your most important tasks, and keep the info you need to remember out of your head and in a digital system where you can easily access them later.

6. When in doubt, break into smaller chunks

Even as you organize your time more efficiently, you might still feel a bit overwhelmed by all the things you need to do across projects. A tried and true strategy involves –– you guessed it –– lists. Now that you can see more clearly when, where, and how you will be working, take the opportunity to break down your workflow into parts so that you can make it more manageable.

Using a task master like Asana can help you stay on track by ticking off items as you complete them, and also assigning tasks to others who might be collaborating with you on the project.

Try not to overwhelm yourself with a to-do list 20 items long for a given day or work block. Put one or two things as the priority for the project or task you are working on at the time, and don’t spread yourself across more than one at a time. Multitasking just doesn’t work, folks.

For a level up on your task master challenge, keep a clock nearby, and — as you check off your tasks — take note of how long they approximately took you, so you can plan your time even more effectively in the future.

7. Give yourself the gift of free time

Before we put the calendar away, let’s schedule in one last very important piece of your week: free time.

At first, it might feel counterintuitive to schedule free time, but it’s completely necessary.

Choose at least two two-hour blocks during the week for complete and total you-time, with absolutely nothing planned. This can be your naptime, your Netflix time, bathtime, whatever. The important thing here is that you deliberately choose not to focus on work things during this time slot.

Why? Your brain needs time away from your projects in order to come up with new ideas and develop new connections. Ever wonder why you get great ideas in the shower?

Obviously, you will have free time and you know –– a life –– outside of these two-hour blocks, but consider these your mental health moments, and protect them as such! Your brain does you no good if it’s swamped with stress.

8. Test and Reflect

We’re almost there!

Obviously, no system is perfect. If you’re an entrepreneur or creative of any type, the first draft rarely looks the same as the final one. Make sure to follow suit with your time management strategies as well.

Maybe you imagined that joining the 5 AM club would be hip and cool, but you just ended up eating cereal alone in the dark before most people wake up and not actually accomplishing anything. Time for a tweak.

Keep a notebook beside your bed, and before you go to sleep, take a few minutes to reflect on the day. What were the high and low points? When were you most productive? What did you accomplish? What were any problems you came across that day that you couldn’t solve?

Touch back to the questions from the beginning of the exercise to keep tabs on your ongoing progress.

9. Give yourself a pat on the back

Wahoo! If you’ve made it this far, you deserve some self love and appreciation.

Committing to revamping your time management systems can be a daunting task, and many people do not take the energy to step back and truly evaluate the way they work.

Apart from increasing productivity and efficiency, managing your calendar also helps you be less stressed, and ultimately happier and more fulfilled. Some people might see that as a delightful side effect, but it’s actually an extremely important element of any entrepreneur’s (or person’s for that matter) world.

Your Life in a Busy Nutshell

You might be the kind of person who is always asking yourself when your life will calm down or become less hectic, and all the while continually adding things to your plate. Such is the gift and the curse of the motivated business owner.

A calm life of no responsibility sipping booze by the beach might seem like the dream, but most people are actually happier overall if they can do the work they love and that challenges them –– in a smart way.

The busy life is awesome and rewarding if you know yourself and plan accordingly:

• Start by admitting to and identifying your problem.
• Next, write out and categorize your goals and priorities.
• From there, take an assessment of your turf, time, tools, and tasks.
• Break out Google Calendar and schedule in your mandatory events and positive qualities first.
• Then brainstorm how to improve upon your weaknesses, and incorporate tools to help you do so.
• When overwhelmed, chunkify your projects.
• Don’t forget to give yourself time and space to breathe and relax.
• Try out your new systems and tweak/revamp as needed.
• Congratulate yourself on a job well done.

Set aside some time to walk through the steps listed here, and feel free to go back from time to time and do it all again.

Your business and brain will thank you for it.

Photo credit: Peus