Do you experiment with your schedule to optimize your time and productivity? I do, and I recently ran a test that failed miserably and left me anxious and feeling awful.

I don’t love writing about productivity, but I am endlessly fascinated by human physiology and psychology. True fact – I was almost a psychology major in university, following in the footsteps of both of my parents, but decided to do something more reasonable (writing/web development) which I would say has paid off in spades.

So I run productivity experiments on myself. They’ve ranged from working from different coffee shops around the city to see which I work at best (and has the best food) to whether eating early in the morning or mid-morning is better for productivity (early morning), and where I work best (from my kitchen counter with my laptop unplugged from power). I’ve also tried Pomodoros (failed) and working with and without music (depends on my mood, really).

This brings me to my latest test – moving sales calls to the afternoon. I failed miserably.

Why This Test Failed (For Me)

I’m 32 years old. My body is tired and feels like it’s getting older every month. I know I’m still young, but this is my reality.

As I said at the top, I’m also super interested in my own psychology and figuring out how to optimize my mood and motivation to get the maximum output from a reasonable input.

This test failed for me because I got less done in the last two weeks and felt horrible about it when compared with the few weeks before where I was traveling and not even putting in as much time as the last few weeks. To preempt any questions, the few weeks leading up to traveling I was putting in as many hours as the last two weeks and felt great.

I’ve learned a few things about myself over the last year:

I am maybe more extroverted than I thought

I get inspired and energized by talking with smart people. My best ideas come from talking with others too. When I go a few days or even mornings without speaking to anyone, my brain gets wrapped up in being busy and I never move anything forward. Speaking with others brings clarity.

Deep Work is Hard Solo

I also need time to get into “deep work”, which is a few hours of uninterrupted focus to work through complicated problems or create new features for my product. This is not possible for me when I know that I have a hard stop coming up with an obligation.

I need to create open-ended space in my schedule to get into deep focused work, and that’s not possible with afternoon calls or appointments.

Mornings are also a great time to get started accomplishing things

Whether that’s a phone call or taking your car to the mechanic, mornings can be great for life tasks. When I do sales calls in the morning, I can simply schedule being out of the office and no calls get scheduled or done that day, which is fine for my company’s rate of growth (perks of bootstrapping). But if phone calls are in the afternoon, then these morning tasks which should be motivating for the rest of the day become stressful because I know I won’t get any work other than calls done that day.

My energy and ability to deal well with other humans is highest in the morning, and in the afternoon I need to retreat into my computer and feel like I’ve gotten things done.

Flipping my schedule went against my own physiology and psychology.

How I Organized My Time Before This Test

Part of being productive is understanding your own body, how it gets and stores energy, and how to get yourself into peak performance when needed (which also means there are periods that you need to recharge).

I am not a morning person. I’ve never been. I mentally love the feeling of waking up early and getting a lot done in the morning, but my body hates early mornings partially because I am hypoglycemic and always feel like I am going to vomit in the morning when I wake up. It’s a terrible way to be, but it’s my life until I get some protein (I eat a couple eggs cooked in butter every morning) and have no more than one cup of coffee (otherwise I crash in the afternoon).

For the last four months my schedule was something like this:

• 8am – get out of bed, say hi to wife and dog, drink coffee
• ASAP – sit down with my laptop, process email quickly, get a handle on what I want to get done that day.
• Start sales calls around 9/10am and go no later than noon.
• Noon-end of the day – retreat to a coffee shop or somewhere else to write/write code/handle business admin things.

The last few months have been quite productive and my business has grown a lot, but I’ve still hated doing calls early enough to where I may not have had time to drink some coffee and wake up enough.

I decided to run the test of What if I move sales calls to the afternoon, 2-4pm PST, and do my writing and product development in the morning?

What Happened?

I moved my Calendly times for scheduling calls to the afternoon and people started scheduling calls in the afternoon, starting September 22nd. By the end of the next week (September 30th), I realized I felt:

• Harried, because I had a deadline (2pm each day) within which to get things done otherwise I’d have to work in the evening (and with life right now, moving cities and travel coming up) which I cannot afford to do right now.
• Anxious. Instead of starting my day with talking to others, which always inspires me, I was stuck in my own head working on things. I was never getting wins early in the day, so my brain got mired in “everything is broken and sucks and I’m a failure” thinking.
• Tired by the time I got on phone calls. I kid you not, two days ago on Monday I asked someone how their Friday was going. By the afternoon, my brain is foggy and I don’t do a good job on phone calls.

I hadn’t felt this way in months, but in retrospect it’s how I felt constantly from January -> May of this year when I did not have a set schedule.

Not good. I’ve changed the hours on my calendar back to the morning as of yesterday.

How I Schedule Calls

Let me take you through my process for scheduling calls.

I hate scheduling phone calls. Scheduling on calendars is possibly an unsolvable problem because calendars are simultaneously private and have a need to be (partially) open so that others can fit into your schedule.

If you’re inside a big company and use Outlook, you can often see the calendars of others at least so far as when they are available or not. That works well.

But if you’re working across companies and types of calendars, the process usually goes this way:

• One person initiates the idea of a meeting, gives a stretch of times available;
• Second person writes back when their availability is, but that it’s filling up quickly.
• First person sends a meeting request, not knowing if 30 or 60 minutes is the right amount of time, so they schedule 30 and everyone’s schedule gets messed up for the rest of the day or they both end up with extra time to do nothing of consequence because 20-30 minutes isn’t enough time to really get anything deep done.

Or, even worse, one person sends through a meeting invite that doesn’t work for you, then there’s no good way to request a different time and even if you do, then you can’t be sure that time works for them. It’s a mess.

I’ve managed to make scheduling easier on myself by sending people links to my Calendly account, which is linked to my Google Calendar and won’t allow people to schedule a meeting when I am already busy or have blocked it off. Warning: Calendly does not do well with international time zones and meetings, so be careful when using them for that. I am actually looking for a new scheduling tool because of this.

Anyways, this has made scheduling a lot easier and I see a lot of entrepreneurs using tools like this to give people limited access to their availability. That’s great.

The Importance of Tests

I’ll keep running tests on myself and my productivity because I want to be as efficient as possible in reaching my dream of living a life of freedom while running my own business from where my wife and I want to be as opposed to where we need to be for a job.

I’m a digital marketer by trade. I preach about the importance of conversion rate optimization to clients and run my own tests on my marketplace. In fact, I have three separate tests running right now as I write this post in early October.

As a Type-A person married to a Type-A person (we literally made a spreadsheet to narrow down our potential places to move based off of what we care about in life), I can’t sit still. I spent two weeks between jobs back in 2013 that were supposed to be vacation, but I went stir crazy and worked on what became Credo a few years later.

As such, tests are important to me because I can figure out how I operate at my best which further enables me to live the life I want. If something is off, I want to figure out why and work to solve it. This could be optimizing your schedule, moving to a new city, seeking to make new friends, getting more exercise, or even seeing a therapist.

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As an entrepreneur, you have to test things constantly. Your business model might be wrong, your customers might be having an issue because of your business’s growth, you might need to take your product in a new direction. You only lose in business if you stop moving forward and give up, so keep testing and moving forward towards that ultimate goal, whatever that is.

So that’s my lesson from these last two weeks. Keep moving, know yourself, and good luck.

Cover image via Unsplash.