Productivity and Me, Happily Ever After

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Finding the perfect productivity system is like finding the love of your life.

At first, you’re kind of clueless and don’t know what you’re looking for. You test the waters to see what’s out there, deflowering every productivity tool you can get your hands on.

After a while, you start to learn what you like. You lean into that. But there’s still so much to explore. You fall in love with one, the honeymoon phase ends, then you’re back on the App Store swiping to find the next.

If you’re like me, you might spend years (or more than a decade) trying to find “the one”. Family and friends start to get concerned. They begin telling you things like, “Stop being so picky and just settle down!”

But you know what? Screw them. Because I think I’ve finally done it. I found her. I finally found the one.

She’s been around every day of my life for the past year. You might not think that’s very impressive, but it’s literally 6x longer than my previous record. For the first time maybe ever, I’ve stopped wondering if the grass is greener on the other side.

My productivity system completes me. She makes me a better person. And that’s why I’m here today to tell you all about her.

Who knows, maybe this might help you find your own “happily ever after.”

What Makes a Productivity System a "Catch"

The good thing about dating around so much in my twenties was that I slowly learned what I valued in a productivity system. Turns out, I’m pretty picky.

But my system checks all the right boxes.

1. Simplicity. This is most important to me. I’m a one-woman kind of guy. If I have to juggle too many tools to do my work, I get overwhelmed and call it quits.

2. Ease of access. I must confess I’m a somewhat needy man. She must be available to me at all times of the day, at any location (at my desktop, on my laptop, on the couch, during a walk, while in the shower, etc).

3. Low maintenance. I don’t like to pay high recurring fees (I prefer none, actually). And I don’t want to spend more than a few minutes each day updating it. If it’s too much to manage, it’s only a matter of time before I re-download the app store and start swiping right and left again.

4. Flexibility. I’m a full-time engineer who enjoys writing on the side. I also have a family, friends, hobbies, and a home to clean. A true catch is a one-stop-shop for managing all facets of my life while staying true to the other 3 traits above.

5. Adds value. Overall, I need someone who adds to my life more than they subtract.

Maybe I am a bit picky, but I say I’m just a man who knows what he wants.

Now, here are the deets on why she’s so great:

1. We Share the Same Long-Term Goals, and They’re Written Down on a Whiteboard

My long-term goals are super important to me. Without them, I feel like a lost puppy (and I get pretty anxious, too). I need them so that my life has purpose and direction.

For this reason, I write all of my most valued long-term goals down on a whiteboard that hangs on the Camelot-colored wall in my office.

They’re not anything crazy, but they steer my ship in the right direction.

Once upon a time, I had a whiteboard goal to “make my net worth positive”. That year, I worked on things to eliminate my debt and improve my finances. After I achieved that, I wanted to hit a quarter of a million in net worth. And so I made that my focus. Now, I want to retire by age 45.

Will it happen? Maybe, but it definitely won’t if I don’t write it down.

Every January, I revisit my long-term goals and adjust accordingly. Keeping them on a giant whiteboard in my office makes it so that they’re always visible and somewhere on my mind.

Before moving on, I do have a quick confession. I’ve actually been using a whiteboard like this for over 3 years. It’s the one piece of my past productivity systems that I still use exactly the same way. It’s been that great for me.

2. We Both Trust Notion to Handle Pretty Much Everything for Weekly/Daily Tracking

The whiteboard is the cornerstone of my productivity system, but it’s really just a short, bulleted list that doesn’t change for an entire year.

I need something more robust that can manage the day-to-day.

Notion is what I’ve been using for this. After trying every other system out there, this one had just the right amount of customizability and simplicity. If I’m being honest, now that I’ve found the format I like, it probably doesn’t matter what app I use, as long as I can recreate the meat of my planning.

After much trial and error, I settled on weekly planning with each day broken down into a handful of tasks. I tried the whole quarterly and monthly goal-tracking thing, but I was never very good at it and didn’t really care to do major “reviews” that often. So, I said screw it.

Here’s what the format looks like at a glance:

The template came from Nat Eliason, who is apparently one of the guys I trust the most with my productivity dating life. If you’ve ever seen the movie Hitch, he’s my Will Smith.

I took his template, which had a few extra segments than the one above, and used that for a while. But I eventually gutted it down to the only three sections I consistently kept up with.

They are:

i) Priority 1, 2, 3

This is where I prioritize my tasks for each week.

• Priority 1’s are absolutely must-do’s

• Priority 2’s are probably should-do’s but not as important as Priority 1's

• Priority 3’s are nice-to-do’s (but usually just sit on my radar for a while)

This portion is also the bridge between my whiteboard goals and the actions I need to take to accomplish them.

For example, one of my whiteboard goals is to drastically improve my VO2 Max. To do that, one of my Priority 1’s is to finish all of my planned workouts. In fact, it’s my first Priority 1 each week, every week, because health and fitness are super important to me.

That doesn’t mean all of my Priority 1’s are whiteboard goals. Many, yes. But certainly not all. Because I work a full-time job, I often have deadlines to meet that require the bulk of my attention. These are obvious Priority 1’s.

Priority 2 and 3 items end up being things like non-urgent work tasks, laundry, paying bills, scheduling landscapers, and miscellaneous actions for my website, Twitter, etc.

If I ever get stuck (which happens more than you’d think), I simply turn around and look at my whiteboard goals. This almost always recalibrates me.

ii) The Week Ahead

Here’s where the bulk of the work happens.

Each week, I break down my 5 working days into daily tasks. Each task is actionable, concise, and generally takes somewhere between 5 minutes to 2 hours to complete. If an item takes longer than that, I’ll break it down into smaller segments.

I try to stick to 4–6 main things to do each day, where 1 or 2 are major tasks, and the others are minor. Any more than that and I’m only kidding myself.

Major tasks include things like engineering work for the day, writing, and intense workouts.

Minor things include updating my weekly plan, taking out the trash, publishing a tweet, or dropping something off at UPS.

At the beginning of each week, usually on Monday, I archive the previous week’s list and carry it over to the current. That’s when I start removing and populating tasks for the week.

Over time, I’ve noticed that:

• Mondays are medium workload days as I ease back into the week

• Tuesdays and Wednesdays are the days I get the most done

• Thursdays are another medium-ish day, and

• Fridays are typically light after completing the key stuff earlier in the week while winding down for the weekend

Every day is an exquisite blend of work-related tasks, writing, and personal stuff. It’s always been a struggle to find a system that can handle everything in one spot, but my “happily ever after” does the trick.

Also, I’m pretty flexible in how I manage my tasks. If I feel like I overbooked a day, I’ll just move it to another day later in the week or stage it for the following week. If a day is too light or something unexpected pops up, I’ll slot it in. It’s not a huge deal.

It’s kind of crazy how much I’ve learned about myself while searching for my productivity soulmate over the last decade. Pretty happy that now I know what gets me going, and I can lean into what works.

iii) Parking Lot Items

The final section of my Notion weekly tracker is essentially an ever-growing list of tasks. It’s a catch-all for anything and everything that I may or may not eventually want to do.

If something pops into my head, I write it down on the Parking Lot. I might pencil it into the current week, the week after, or 6 months down the line.

The Parking Lot is great for:

1. Never forgetting all the things I want to do

2. Being a buffet of actions that I can pick and choose from

So far, my Parking Lot hasn’t gotten too far away from me. New tasks pop up all the time, but I’m also knocking them out at a decent clip. Anytime it starts to get too crowded, I just spend an afternoon cleaning up the quick but annoying tasks I’ve been procrastinating on.

3. We Agree That Calendars Are ‘Meh’ but Necessary

These days everyone carries around some sort of baggage — a crazy ex, divorce, kids, debt, or you know, a calendar.

A calendar is the one thing I’ve learned to accept as a necessary evil in every productivity system. But I mean, let’s be real. There’s literally no other option for scheduling meetings and appointments.

Google Calendar is what I use for everything. It’s synced with my work meetings, appointments, events, and family things.

In the past, I tried scheduling tasks into my calendar so that I knew what to work on and when. But turns out I’m just not very good at following a plan with that much structure.

Today, 99% of my tasks don’t make it to my calendar. I know the important stuff I need to do thanks to my Notion priorities, and I just work around the various meetings and appointments I have on any given day.

Mornings (immediately after coffee) tend to be when I do my best work, so I do everything I can to schedule the bulk of my meetings in the afternoon. This way I finish all of the important actions first, then cruise through the rest of the day without the burden of unfinished business. Obviously, not every day works out perfectly, but this is what I shoot for.

As a side note, since I don’t have Facebook, my Google Calendar is the “trick” I use for remembering birthdays. It feels more special when someone reaches out and you know they aren’t just doing so because Facebook reminded them.

Let’s Wrap This Up

I feel like I’d regret not ending this with a cliche, so here it goes.

I will say though — she’s pretty damn close to perfection. After all, there’s really not much more to optimize when you’re only spending 5–10 minutes each week planning and prioritizing.

You might laugh, but before I found my “happily ever after”, I’d bet money that I spent more time optimizing my productivity than actually producing. Now, I’m spending peanuts and getting back…way bigger nuts.

Hopefully one day you’ll find the same.

Best,

Jason