How I Planned Every Minute of 2019

I’ve never been one to make New Year’s resolutions.  My thinking has always been, if I need to make an important change, then I should do it today, rather than wait for an imaginary moment on the calendar.  Therefore, I completely surprised myself when I spent nearly 6 hours on Wednesday planning out 2019.  I really don’t know what came over me, but I’m guessing it had something to do with how 2018 finished.  You can read my last couple of posts and correctly hypothesize that I haven’t been living the way I want to recently.  My days haven’t been fulfilling and I have only myself to blame.  F the blame game, it was time to get back to living life to the fullest (my fullest).

As I sat down at my desk for the first work day in 2019, I had a list of things I wanted to get done.  Most had to do with my real estate business and I had a full day planned.  I didn’t get any of those tasks done and it was the best failure of a day I’ve had in a long time.

I once remarked to a friend that, I was really good at planning out my home life (morning routine, weekend activities, and annual trips), but I was really bad at planning out my work life.  I told him how I was usually super reactive, versus proactive – living out of Outlook and responding immediately to every email, text, or phone call that came my way.  Hearing this, my friend said, “why not just plan out your work day the same way you’ve planned your home stuff?”  Hearing his wise words, I shrugged my shoulders and said that it was too hard.  Three years later and I finally took his advice.

Rather than searching the internet for templates on goal setting (and eventually finding my way to some website that would trap my attention for hours on end), I decided to tap into the supercomputer up in my head and see if I could develop a process that worked for me.  Having read plenty of management, optimization, and planning books, attending a Stephen Covey course, and been a project manager in a previous life, what follows is a conglomeration of all that I’ve learned and put in a tidy package for me.  In my opinion, that’s the key.  This was created to work for Dan and might be a complete disaster for you.

I began by creating the buckets of my life that I want to focus on this year – Personal, Business, Mindfulness, Family & Friends, and Community.  I then tried to fast forward to Jan 2, 2020 and imagine looking back on the year that was 2019.  What did I want to look back and see?  What goals did I want to have accomplished?  Taking this 2020 mindset, I created “smart goals” (as best I could), that were clear and measurable.  As an example, one goal is to continue to improve my relationship with my wife.  Except this is really hard to measure.  Therefore, the goal was turned into – spend 1 night out with Jenny a month, away from the kids.  Achieving this will lead to at least 12 nights away from the kids for the year and hopefully result in Jenny and Dan leveling up their marriage to Lucy and Ricky status.

From here, I continued to work backwards, until I had developed goals for all of my “Life Buckets”, given daily/weekly/monthly tasks for each to ensure I succeed at the goal and also listed a “why” as to why the goal was important to me.  If I developed a goal and I didn’t connect with the “why”, I removed it.

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Fair warning, throughout this entire goal setting process, I wanted to throw my computer out the window.  I love to plan, but I HATED this process.  There’s a reason it has taken me years to do this – my ego was in constant fight mode.  I’ve always been a goal-oriented person, but my goals are usually reserved for a place in my journal and something I will look back on every so often, but never really hold myself to.  My goals are usually “time flexible” (a month here or a year there).  With this exercise, I am holding myself to not only a period of time, but also a daily and weekly time schedule.  While I’m super proud of myself for pulling this plan together, there’s another side of me that wishes I could go back to my “time flexible” goals where if I didn’t achieve them, I just gave myself some more time!

After developing the annual plan, I then created a daily structure as to how my days need to run in order for my goals to be achievable.  What I quickly realized is HOW MUCH FREAKING TIME I WASTE.  There was time to achieve everything I wanted, yet I haven’t been as efficient with my days over the past couple of years.  Where has the time gone?  Nope, not Twitter or Facebook – I’m a proud “facedeleter,” it’s gone to Bryce Harper free agent rumor stories, searching funny memes to text to friends, reading random population stats on Wikipedia, and watching Joe Rogan podcast clips on youtube (you read that correctly – watching video of a podcast).

daily routine

Like Frodo wants his ring, I want this time back.  To do so, I added maybe the most important goals to my planning sheet – under the Mindfulness bucket, you will find two goals with the category of “Mindful” where I plan to batch my email and web consumption.  Rather than “checking” stuff throughout the day, I will only do so during prescriptive times.  Having experimented with this in the past, what I have found is that EVERYTHING can wait.  If there is truly an emergency and someone needs to get in touch with me, they will find a way (like calling three straight times).  The battle is with myself and not giving in to those FOMO tendencies.

While my daily schedule isn’t as interesting as Mark Wahlberg’s with his 2:30am wake up time, 2 workouts a day, and 9:30am cryo chamber recovery time (is that what Jabba the Hut put Han Solo in?), I think it does the trick for me.  And that’s just it, there are plenty of optimization gurus and efficiency wizards out there to take advice from, but what’s important to me is finding techniques that work for Dan.

To wrap things up, I also planned out my reading list (for the first 6 months), when I should schedule meetings/lunches, exercise schedule and a summary of my annual travel plans.  My guess is that putting all of these items in one easy to read place should help keep me on task over the year.

weekly guidance

Now for the important part – being a visual person, I have printed a copy of this plan and put it up next to my bathroom mirror and above my computer.  It is obnoxiously in my face, which is the point.  I can’t run from these goals and sending them out onto the internet is the final piece to the puzzle.  That’s all for now, I’m off to the gym where each rep brings me one step closer to a 2019 goal.

Author Bio: Dan started Fired and Free in 2017, to provide his “truth” after being fired as CEO of the company he started and led. After a diverse 17-year career in management consulting and entrepreneurship, Dan now leads 3Sixty Leadership, where he provides coaching and consulting to business owners with 5 to 500 employees, helping them to work “on” their business not “in” their business.

10 thoughts on “How I Planned Every Minute of 2019

  1. Anonymous

    Thank you for sharing your template! It’s truly incredible to see how much time we really do have once we take accountability for it. Btw, I watch the Rich Roll podcast on YouTube. You’re not the only one! I also highly recommend you check out his podcast. Start with his most recent ones, the “best of 2018”.


  2. Steph

    Great job on your schedules and goals, I think it’s entirely doable. As you’ve put this out for all to see, I’m thinking you might want some feedback? Perhaps you might want to tweak the daddy/kid time goal a little?


  3. Bridgette

    Really interested to see how this method works out for you as the year progress. I began doing something similar with scheduling my tasks on a weekly basis… on paper away from my computer so it would stare at me. Like you, very eye opening to see big empty chunks of time. It lit a fire under my butt, habits are hard to change but you gotta keep trying, right?


    1. Fired and Free

      Yes! If you don’t get right, keep modifying, changing and adapting! What worked for me when I was younger (ie – eating Big Bite Hot Dogs and downing Big Gulps at 7Eleven) certainly doesn’t work today. Best of luck with your scheduling efforts – I too am a big fan of doing this away from the computer.


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