Digital Strategist & Entrepreneur

Scheduling for Multiple Ventures

Lately my days have consisted of working on a number of my own ventures which I either fully or partially own, as well as maintaining consulting clients.

I know that I tend to be a “top of mind” and reactionary sort of person when it comes to what I work on, if I don’t actively manage my time to prevent that.


  • Waking up to a customer email about a priority change for their website
  • An agency I provide subcontract consulting for, saying they have a new priority
  • Positive emails regarding projects of mine
  • Recurring / ongoing projects I feel behind on, or with deadlines looming
  • Busy work

I realized last December, that I needed a better way of managing my time, which will ensure that my smaller projects receive the attention they are warranted, instead of being passed over for what might feel more important at the time. All while also managing client projects / priorities placed on me from others.

The only way I knew I could do this, and maintain full control of my own schedule, was if I scheduled out 100% of my hours, sleep/etc. included.

I sat down with a notepad, and listed out all of my existing ventures, and other demands of my time, along with how many hours I felt each thing should have attributed to it each month. Also then figured how many consulting hours I need each week to make sure I cover clients and bill enough hours each month to afford myself the time to work on other projects.

The result:

  • Personal A/B/C are companies I own or co-own, and have their requirements of attention each week/month
  • Racquetball is generally scheduled for the same hours each week and were easy to put in
  • One of my businesses is a product company, and combined with my eBay flipping, they require I go to the post office most days, so that’s scheduled in as well. Keeping me from packing/shipping orders as they come in, which while fun, is not efficient
  • The remaining business-day hours are allocated towards working with clients in various consulting roles, mostly digital work ( dev / SEO / tech consulting )
  • After-hours I schedule in a good amount of time to spend with my S/O for tv/dinner/etc.
  • Then I write for an hour on the computer, before TRYING to shut down the electronics and read or hand-write for an hour to try and get to sleep
  • Unallocated hours from there were marked as flex, and tend to be overflow or get burnt up with more gym/cycling time or fires needing put out

Now that hours are appropriated, we need to fill them with tasks!

All of my todo’s are managed in a massive combined trello account, with a separate board per project. Each morning ( or sometimes the night before ) I will put any/all meetings in a blank version of my calendar, then backfill the rest based on the hour-spread from my plan for the day. I don’t necessarily schedule tasks in the given order, but reference it for how many hours each venture/etc. should get each day. I pull the appropriate hours worth of task from trello and put them in the blank calendar from there.

So far, so good!

Moving forward, I’m attempting to fill out my “blank” calendar further and further into the future, in the hopes of making sure new tasks have less chance of taking precedence, and instead always go into trello to be prioritized/scheduled with respect to everything else.

Poke me on twitter if you have any questions about my current process!


My trello setup is loosely based on this post ( )

My current calendar, anonymized for this post is here ( )

A blank one I use each week is here ( )

Date: March 23rd at 3:53pm
Tags: productivity