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Scheduling Productivity Tips for Solo Entrepreneurs

(and maybe others too)


Photo courtesy of DAHC on nappy.co

When someone asks you what you’re doing later, do you immediately whip out your phone to check your calendar? #alsome. I truly live by my calendar. If it’s not on that thing, it likely is not happening or being remembered.

Que joke: “My dependency is so heavy. There are times when I have to check my own calendar just to see what I did earlier the same day.” 😂 Some say that I have a memory problem. Some say I’m truly living in the moment.

Regardless of your opinion of my calendar's dominion over my day-to-day activities, if you’re interested in improving your own schedule organization, I’m sharing some rules of thumb that I apply. I hope you find them helpful. I’ve listed them below in no particular order of importance and gone into detail for each.

  1. Schedule only 30-minute meetings

  2. Leave 30-minute gaps between meetings

  3. Always leave time for food

  4. Take all meetings one day of the week

  5. Batch repeat tasks per day

  6. Stop asking people to put time on your calendar

  7. Always confirm meetings for the day in the morning

  8. Do things remotely whenever possible

  9. Leave your mornings open and maximize your nights

Rule numero uno:

Schedule only 30-minute meetings. During my tenure at LivePerson Inc. I had the pleasure of working with several excellent managers. One of them was Craig Condon Siegal. I was in a new position and was having trouble getting my colleagues to accept my meeting requests. This was delaying my projects because I couldn't get feedback or loop in other parties.

Craig took a look and advised me that I should try scheduling 30-minute meetings instead of an hour. This helped a lot! Think about it. Do you really need to meet with people for an hour?

In 30 minutes, I’m able to catch up and connect with the person or people I’m meeting with, discuss the meeting purpose, and take the actions needed to move forward as long as I stay focused. When you only have 30 minutes, it forces you to stay focused. It also encourages whoever you are meeting with to respect your time. Often I find we don’t even need the full 30 and can spend time, in the end, continuing to connect. That is the best part of “meeting” people anyway!

Rule numero dos:

Leave 30-minute gaps between meetings. This gap time is key to your sanity and productivity. It will account for people that are running late, and it will account for the occasional meeting that runs over. Have you ever run late to a meeting because another ran over? This happens when you schedule back-to-back. I promise you this gap will give you the freedom to breathe, which will result in a higher return on investment and rate of happiness.

I find it extremely frustrating when people, including myself, run late. It makes my heart rate go up. At the end of the day, only I can control not letting the frustration affect my mood. Starting a meeting in that mode of operation will put obstacles in your way of connecting with the other person. Giving myself the gap is truly a preventative measure.

When I have that gap, I can remind myself that it’s going to be ok even though this person ran late. Surely they didn’t intend to disrespect my time and upset me. I try to remember I have no idea what they had to do before meeting with me!

This is not to say disregard the behavior. Absolutely not it mentally, and take it into account when making future choices, but in the present moment, give yourself the flexibility to proceed with the meeting as planned. Handle their tardiness with grace and stay focused on the purpose of the meeting. If you cancel the meeting or go into it being upset because one was late, no one gets what they want.

Rule numero tres:


Photo courtesy of Cayo Ferreira from Nappy.co

Always leave time for food. Food is fuel. Food is connected x 1000 when shared with others. Food is life. I’d like to take this opportunity to also say that if you are eating crappy food, that is no Bueno. But we’ll save that for a different post. Back to the point. Schedule time for eating! If you’re choosing to fill up your days with things that you love to do, aka you are “busy” you may forget to eat, which causes an array of problems including low energy! Lord knows I need the energy to keep my cool with people running late to everything! Scheduling food time is another preventative! It’s called #hangryprevention.

Sidenote - It’s totally ok to bump up a meeting to an hour if you decide to “meet” over a meal. Remember to still apply rule numero dos.

Meeting over food is also a great way to slow down your day a bit. If you have a meeting with someone who is particularly fast-paced, and you need them to focus for a bit, invite them for lunch or breakfast. Choose a location with good food, but slow service. #bizhack #protip #halfkidding.

Scheduling time for food breaks is also important when it comes to your self-care. If you keep up with my content, especially on the other platforms I contribute on, you know this is a topic that comes up frequently. Ever since I was a child my mom always allowed me to take “mental health days.” Even if it meant staying home from school!

I don’t want to beat a dead horse here. Plenty of buzz going around stressing this topic. Exhibit B:


Snippet of google “self care quotes” image search results

Rule numero cuatro:

Take all meetings one day of the week. This. Is. Key. Possibly the most important tip that I’m sharing. If you can take all of your meetings in one location, this is also preferred and will be 10x this hack. Ok, back to the all-in-one-day point because I know some of you may have a look like this on your face:


This is a radical approach. I know. People tell me all the time that they don’t know how I do this, but it has so many benefits especially if you are a solo entrepreneur. Think about it; if you’re taking meetings all the time when are you actually getting work done? Is anything THAT urgent that you need to squeeze in a zillion meetings into one week? The answer is no. Unless you are saving lives, and people will literally die if you don’t meet with them, the answer is no.

Just try it. Try it for a month. See the difference in your life. Doing this will keep you in your “meeting” mode of operation, maximizing your efficiency which is a perfect segway into our next rule of thumb."

Rule numero cinco:

Batch repeat tasks per day. If you are not doing this, you could be leaving up to 40% of your productivity on the table. That is what Psychology Today estimates if you switch tasks. In that article, they gave examples and tips like checking your email once a day. I’m going to expand a bit to include tasks solo entrepreneurs have and suggest you do them all in one day per week.

We already talked about meetings above so that’s one day. Another day should be dedicated to accounting. Balancing el books, squaring up receipts, sending invoices, inputting expenses, etc. Use a different day to review all paperwork. This includes your mail, filing, and writing cards.

Everyone’s batch days will be different because we all have different things that we need to do to run our businesses. Think about the tasks you do repeatedly and take a lot of time. Another benefit besides maximizing your brain power is that once you start batching these tasks you’ll be able to more accurately forecast when you’ll be done with a project. This will lead to better relationships with clients and yourself.

Rule numero seis:


Courtesy of the internet

Stop asking people to put time on your calendar. This doesn't really need much explaining. Or does it? What is it about this petty workplace dominance over who sends the calendar request? It’s as if it’s a competition of who is less quote, unquote “busy” and has the time to send over the email.

This is super inefficient people. If you’re so busy that you can’t take a minute to send over the calendar invite you’re not thinking about time sustainably. You are actually wasting more time by doing this. Once the meeting is confirmed the calendar confirmation should be sent by the reader of the confirmed.

If you choose the petty route you likely are going to get more emails back and forth. I present Exhibit A:

This all could have been wrapped up with one less email if silly M had just sent the calendar invite.

Rule numero seite:

Always confirm meetings for the day in the morning. No matter if people have accepted or not, this is especially important if you are planning on driving somewhere for a meeting. This is doubly important if someone else schedules meetings for you, or you’re scheduled to meet with multiple people.

I heard a horror story once where a CEO had a really important meeting scheduled. It was put on the calendar, and confirmed by the client, and two of his staff. He drove up to the meeting and no one was there. Turned out the client was at his office. Also, one of his staff members had completely forgotten about the meeting, and the other drove to the wrong place!

Don’t let this happen to you. Confirm your meetings with quick text messages, phone calls, or emails. The morning of is fine, or the night before. Things change for people last minute. Taking a few minutes to do this will save you in the long run.

Rule numero ocho:

Do things remotely whenever possible. There is a time and place for an in-person meeting. Those times are few and far between, and until Lyft or self-driving cars become mobile offices you’re best suited to not schedule in-person meetings.

Porque you ask? Well, avoiding time in your vehicle is literally one of the best things. It reduces your chances of experiencing road rage, stopping at a fast food place for junk, hitting traffic, ingesting pollution, and adding to the pollution in the air, plus saving you time and money.

In most cases, you don’t need to meet in person. You can use video meeting technology and do meetings from the comfort of wherever you choose. Of course, you do want to spend some IRL (in real life) “face time” with people, so if you’ve met remotely with people multiple times in a row, request an “in person!”

'Remember to factor in drive time into your schedule, and if you have to do a presentation upon arrival, build in time to test all the tech and check into the facility you’re meeting at if it’s not your own. The reason for this is best summed up by Eric Jerome Dickey.

“Early is on time, on time is late, and late is unacceptable!”

Rule numero nueve:

Leave your mornings open and maximize your nights. Mornings are the best time for you to do things for yourself. Like the ever-important AM routine. Or calling a dreaded 1800 number. Protip — customer service reps are always in better moods when they first arrive because they haven’t had to deal with as much of the wrath of humanity yet. Also, appointments at the doctor or dentist should always be scheduled for the first appointment of the day. That’s my hack to make sure I get seen on time.

Gif credit to HollyMcCammack

Evenings are great for networkers and events! You can pair them with “catch up” meetings with colleagues that you have a more casual relationship with, or if you think it will be of value for the client to also attend the event. This is a great way to “multi-meet.”

If you’ve made it to the bottom of my list I hope you found at least one of these rules of thumb new, or useful. Feel free to drop me a clap or a comment. If you want to meet to discuss them, I take meetings on Thursdays. 😉

Until next time! Besos,

This was originally posted here: https://medium.com/@mdorsettnow/scheduling-productivity-tips-for-solo-entrepreneurs-and-maybe-others-too-e375fcfc12df


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