How do I maintain balance and avoid overwhelm as an entrepreneur?

As an entrepreneur or small business owner, there may be lots of times where you feel overwhelmed, over-extended, and underwater, especially when you’re just getting started and trying to bootstrap everything. This is not uncommon, and concepts like “hustle culture” and thinking that you just need to work harder to be able to get it all done are not helpful in finding your way out of this mess. If you have ADHD or other types of neurodivergence, trying to work harder can quite literally make it worse.

It’s easy to think that the period of overwhelm is just a phase, or a necessary growing pain, or some other cliched thing. I fall for it myself, even. A few years ago, I was working with a partner on planning the first WordCamp Pittsburgh. It was August, and there were several things that needed to get done, and I felt overwhelmed, and I kept telling my co-organizer that I would have more time in a few weeks, when the kids were back in school.

Spoiler: I was wrong.

The school year started, and even though the kids were in school during the day for several hours, the magical “more time” that I thought I was going to have never seemed to materialize. What actually happened is that my working hours because filled with other things, interrupted by school drop-off and pick-up, and requests to bring things that had been left at home. Additionally, many others who had been in a similar boat were taking advantage of their new-found perceived extra time to make requests, so my work load bumped up a bit, effectively taking up any extra time I may have had.

Not to sound ungrateful, but it all became a different kind of overwhelming. I had to find a way out, and something that going to last longer than a few weeks. It was right around this time that I began to “live by” my Google Calendar, and rely heavily on it when planning out my time and evaluating commitments.

Tip: You can use the same ideas even if you use a different calendaring system, such out Outlook.

Use multiple calendars in your main calendar

This is one of the things that really helped the most. I wanted to have one place where I could look to see everything, but I also wanted to be able to filter out some things when necessary, or focus on a particular type of calendar item. Some of the different calendars I use are:

  • Kids activities – this calendar is shared with my ex so we can both see the same info about the kids school activities, medical appointments, etc.
  • Bills – I put my routine bills in as recurring full-day events, so I can easily see what’s due when, and I include the amount (or approximate amount) in the title, so I can quickly look at that for budgeting. This is especially helpful with quarterly or bills that fall on a non-monthly schedule, so I don’t forget when they are due next.
  • Blog topics – even though I use an editorial calendar plugin on my site, I live to add the planned blog topics to my calendar, which makes it easier to shift them around or make sure they are aligned with (or at least not at odds with) upcoming holidays and events.
  • Marketing – I use this for planning marketing goals. This can include things like your own launches, affiliate offers, webinars, etc.
  • School calendar – our school district publishes the calendar for the following academic year usually in about March or April of the current one. As soon as it is published, I print out a hard copy for the wall near my desk, and make sure to add first and last day of school, as well as an days off and major events to main calendar so I don’t plan webinars or marketing launches during a day off from school. I also add things like PTA meetings, band practice, and turn in deadlines for school forms.

When I first started using Google Workspace for my business, I tried to be really strict about only adding business-related events to that calendar. But that proved to be ill-advised because it was easier to end up double booking myself, or missing deadlines because I have been focusing too much on the wrong calendar. The reality is that when you’re an entrepreneur, school and family related events are business-related events, so its important to have them all in one place.

Printable Calendars

If electronic calendars aren’t your thing, you can do the same kind of thing with paper calendars and different colored pens or highlighters. You can get a printable calendar here. Even with my digital calendars, sometimes I print off calendars for the next few months and pencil in plans on there while I’m figuring out where I want it all to land. Sometimes, the tactile experience of using a pen/pencil and a paper calendar is more conducive to the process.

Put things in your chosen calendar as soon as possible

As soon as you get/make an appointment, put it in your chosen calendar system as soon as possible. Since I use Google Calendar, this means entering appointments using the app on my phone before leaving the pediatrician’s office, or using my browser to add the appointment while I’m still on the phone.

Using services like Calendly or TidyCal for booking appointments with your customers makes it easy for the appointment to get added to both calendars – yours and theirs – instantly so neither one of you have a chance to forget.

Balancing different areas

Balancing the different areas of your life is a lot easier when everything is all in one place, and you’re using different colors for those different areas. When you look at your calendar for the week, you can quickly tell if one color is dominating, especially when it’s showing up a lot in a time frame that’s usually reserved for a different color/area of your life.

Put time off in your calendar

When you’re working on your calendar and you’re putting in all the doctor’s appointments, blog posts, webinars, and other important dates, make sure you also put in some time off. I try to add at least one day a month (or two part-days) where appointments cannot be booked through the calendar system, and I know not to book things directly. These days can be used for catching up on important things like bookkeeping, planning and goal tracking, or naps.

I was recently talking with a client who I know goes away with her family every year around the 4th of July. During our call, she looked very tired. I know her kids had had very active weeks, and she had lots of family obligations. While we were talking, she mentioned some work she planned to do while she was away with her family and I admonished her not to do this. It’s easy to think that minimally planned weeks can be a good time to “get caught up” on things like planning and content writing, especially when your kids are older and don’t need to be entertained as much. But, even if you don’t have kids or you’re not going away with family, it’s important to give your self some down time. Just like we need to sleep every night to have enough energy to make it through the next day, we need to have some larger breaks in order to give our brains the ability to carry on with the rest of the plan.

What are some calendar tips and techniques that have been helpful for you? Although I feel like I’ve got a good handle on things, I’m always open to learning better ways to optimize my time.

Download your Printable Calendars here

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