A Recovering Workaholic’s Insight on Time Management
Ever lift your head up and wonder where your day went?
Are you frustrated by a steady stream of meetings or endless tasks that fill your calendar? Does it ever feel like getting work done is damn near impossible? You’re not alone. I’ve been there: stretched thin, overweight, physically dizzy, tired, running from one place to the next. To the outsider, busy. In reality, a mess. This article is a collection of the lessons learned on my journey to the other side.
Not long ago, I was a 30 year old VP of Ops at a fast growing Silicon Valley tech startup. I was leading a rocketship organization with amateur training at best. Rewind time just a bit and I was a Director at the same company, a tiny bit more you’ll find me as a Manager, and before that a Team Lead. The world I lived in was slammed with stuff to do, and everything was important. People. Initiatives. Crisis. That was the norm. The looming reality was that there was never enough time.
My boss, Steve, would have me calculate how I was spending time. I’d work out percentages, analyze them against priorities. I made spreadsheets, which was a job in itself. Spoiler alert: way too much work, not enough time to do it.
The calculations and percentages were interesting at first, and did help me prioritize. But, the numbers made it obvious that I was drinking from the proverbial firehose, and there was no shut-off valve in sight. As an emerging leader, normalizing a state of consistently not delivering was defeating.
Over time I was connected with an Executive Coach, some advisors, and peers, and came to understand that my struggle was common. Later, I joined a strategy consulting & coaching firm that works with some of the darlings of Silicon Valley, and now acknowledge this as a universal leadership challenge.
Countless blog posts and research articles, coaching sessions, mentorship lunches, and broken promises later, I’ve produced five principles for taking total control of your time (and your life).
#1 — The Purge
The Purge is all about getting rid of stuff. Decreasing the volume. Reducing the “noise.” Think about your closet. All of those shirts and sweaters or shoes that you haven’t touched in 6 months, maybe even years. We all have meetings and blocks on our calendar that are just like those sweaters. Old. Not adding value. Taking up precious space.
The best piece of advice I received on time management actually came from a book about tidying up a home by Marie Kondo. In her book, “The Life Changing Magic of Tidying Up” (which I highly recommend you read) Marie suggests that we “start by discarding, all at once, intensely, and completely.” Without this kind of extreme approach to eliminating the clutter, we’re simply in perpetual maintenance mode. Now think about the clutter that exists on your calendar, and in your life. Don’t just take a look at the week ahead, or even the month ahead. Take a look at everything. The entire time landscape that exists for you. Personal. Work. Your dog’s calendar. What does the last year look like? You’ve collected meetings, commitments, and time blocks that are like old sweaters. A waste of space.
The true secret of The Purge comes from focusing strictly on discarding. Don’t allow yourself to organize or make things pretty. Simply purge. Do yourself a favor: carve out a few hours, pick a starting point on your calendars, and discard. This criteria helped me trim the fat:
Does this meeting/block of time add value to my life/job? If it doesn’t…discard.
Do I really need to be in the meeting? If not…discard.
Can this meeting/time block be delegated?
My Executive Coach, Regan, once told me, “Heroes don’t scale. Let someone else put on their Superman or Wonder Woman costume today. Put yours away, and take it out only when you absolutely need to save one of your people, or put out some fire”. Empowering the people around you to take an active voice and ownership role will transform your ability to manage your time and team.
If you purge properly, it shouldn’t be something you need to repeat often. Once a year, maybe twice if things are really crazy. Intensely discard.
#2 — Create White Space
A concept that I’d never really stopped to consider was that of creating space. Time on the calendar intentionally filled with nothing. Just broad swaths of time to ignite the spark. Sacred space.
Regan would tell me, “You aren’t training for the Olympics. Olympic athletes train for peak performance before the Olympics, then get to rest and recover. In the business world, every day is the Olympics. There is no rest and recovery period where you get to take your foot off the gas. You’ve gotta find ways to refuel and drive energy back into the system continually, instead of just constantly draining it.”
The takeaway here is to guard White Space with your life. It will become your secret weapon. Over time you can begin to fill it with activities that optimize for rest, recovery, creativity, and big picture thinking. The trap is when you allow the business to once again gobble that time up with all the stuff that drains you.
Your calendar should now have chunks of time. If it doesn’t, go back to the purge: discard, delegate, or defer. Somehow you need to reconcile that contrary to your instinct (which is to fill all of your time with traditional work), this space is your secret weapon, and needs to remain guarded.
‘You need to keep your calendar empty if you’re going to get anything significant done.’ - Warren Buffet
#3 — Design & Build a New Place to Spend Your Time
Now that you’ve decluttered, and created space, you’re ready to optimize how your time is structured. The end-goal is less about getting everything done, and more about allowing for peak performance. Getting everything done is the icing on the cake. This is the Design & Build phase. In this phase, there are five “lenses” that you need to push your time management efforts through. Think of these lenses as filters to view time through. They’ve been extracted from years of me searching for answers , and all the time I spent doing things the hard way.
The five lenses are: 1) Sandboxes; 2) Priorities; 3) Context Switching; 4) Decision Making; and, 5) Rituals.
This process begins with a brainstorm.
Think about what a good job for you at work looks like for you at work and at home…If you were checking all of the boxes, and absolutely crushing every area of life, how would you spend your time?
You’re gonna need some perspective on this one, so consider climbing the mountain a bit to see the logjam clearly. A great way to start is simply by scrolling back in your calendar. Look at the last 3–6 months. Take a look at your job description. Revisit notes from your 1-on-1s with the boss. What are the categories of work you’re expected to deliver on if you’re doing a kick ass job?
Let’s call these “sandboxes”.
You are encouraged to pull out the paper & pens to brainstorm your sandboxes. Once you’ve completed the capture — prioritize each of them. Step away, then return to validate the thinking. Iterate. Challenge conclusions. Solidify your sandboxes and priority level. This will serve as the order of operations for your rebuild, and will eventually become a guardrail of your weekly planning ritual. Sandboxes and Priorities serve as the first two lenses.
Set aside sandboxes and priorities for just a minute, and transition to a third lens: context switching. How much of this do you have happening in your day-to-day? Sure, the right amount can keep things exciting, but too much of it inhibits your performance, and drastically reduces the value & impact of your work.
In his book “Deep Work”, Cal Newton suggests that context switching with something as simple as -checking emails while you’re waiting for a file to load- has lasting and negative effects on the work you do after.
Newton introduces the concept of “deep work”, which are the distraction free activities that push our cognitive abilities to the limit. This is in contrast to “shallow work”, which is the low value, easily reproducible, tactical work many of us spend most of our time on. How are you going to build-out your time to allow for deep work everyday, and just enough shallow work to keep things moving?
Ever notice that President Obama wore either a blue or gray suit during his Presidency? Or Mark Zuckerberg’s gray t-shirt + hoodie uniform? These folks understand a universal truth of humanity: we all have a finite amount of mental energy each day to exhaust. This includes the amount of energy we have to devote to decisions.
The 4th lens is all about how we optimize for decision making.
Researchers at Ben Gurion University found that decision-making abilities deteriorate in quality as the day stretches on.
This phenomena: decision fatigue. Yes, it’s a real thing, and chances are it’s happening to you. In the instance of their research, it was happening to a parole board. Two prisoners, each convicted of the same crime, with the same sentence, and the same behavior while incarcerated were 70% likely to be granted parole in the mornings, versus 10% likely later in the day. Research suggests this is because the parole board was tired, hungry, and had depleted mental energy.
“Making decisions uses the very same willpower that you use to say no to doughnuts.” Roy Baumeister
Now apply this thinking to your build your calendar.
What are some of the ways you can pare down the volume of less impactful decisions?
How can you optimize your time to ensure that important decisions get made earlier in the day?
The 5th and final lens is all about identifying the rituals that energize you and empower others. Guarding certain behaviors & practices as though they’re sacred. Perhaps it’s making breakfast for your kids, sneaking in a workout, or having a brainstorming session with a direct report that’s blocked. These seemingly small things are what pumps energy back into the system. What do these energizing rituals look like for you? How good or bad are you at guarding them from sacrifice?
My rituals are waking up early, getting in a solid workout, 1:1s, team meetings, and spending time with my dogs. I’ll do everything short of a cartoon circus performance to protect these things.
#4 — “Rigorize” Your Meetings
An advisor, Louis, once told me the thing missing from my meetings was hygiene. Yes, meeting hygiene is a thing, just like brushing your teeth is. Some online research quickly yielded pathetic results. We worked up a set of meeting hygiene guidelines (which I’ll expand on in another post down the road), but here are some gold nuggets:
Make sure the intended outcome of the meeting is clear in advance. If you’re sending the invite, an agenda is nice (but, something I consider optional). I want to know — “What does success look like after the meeting?”. Put it in the invite. Say it when the meeting starts. Remind people when the meeting ends.
If you or anyone is going to be expected to make a decision, or have an informed dialogue, ask that data and other critical information be shared at least a day or two in advance. Looking at something for the first time and giving JIT feedback isn’t doing yourself or the business a service.
Challenge yourself and others to cut meeting times in half. If everyone has the data and info necessary to have an informed dialogue. And, the decisionmaker is in the room — the meeting manager should have everything they need to arrive at the intended outcome in less time.
Make sure the people in the room are the right folks to have at the table. If someone isn’t adding value, or in the critical path, they shouldn’t be there. Once you hit 8 people in the room — unless it’s a staff meeting or an all hands, that should be a red flag.
Unless it’s an Executive briefing, eliminate the status update meeting. This could be summarized in a deck, dashboard, or email.
#5 — Ritualize
If you’re purging, creating space, and categorizing more than once or twice a year, you’re doing something wrong. A critical piece to consider and build-in is a weekly planning ritual. This is a boringly predictable swath of time set aside to review the next week’s calendar, ensure it’s optimized for peak performance, intended outcomes, and that you’ve got space filled with the stuff that’s gonna energize you.
Some people carve out Sunday nights as their weekly planning ritual. I used to set aside time on Friday mornings, on my train ride down the Peninsula. I’d ask myself the same set of questions:
Do I need to be in all of these meetings? Then, ruthlessly extract myself from any where there wasn’t an absolute need.
Is there an opportunity to delegate & empower someone on my team? If you’re hiring & developing the right people opportunities will abound to offload. Bear in mind, all of this is in support of you continuing to level-up. A necessary behavior to scale.
What am I filling my white space with? Remember, if you don’t put something there, the business will gobble it up. Mine was usually a bike ride, or an urban hike. Always alone. Always low tech.
Am I optimized for decision-making, strategic work, tactical execution, and personal balance?
The purge is where the magic starts. This is where you shed the weight that slows you down. Then comes the white space, which is probably the biggest shift in how you plan and prioritize (I know it was for me). Suddenly you -the human- is prioritized, and getting energy back into the system as a building block for everything else. The planning process becomes all about optimizing for peak performance. Putting yourself in an ideal position to make decisions, collaborate, and focus when it matters. Introducing rigor in the form of hygiene becomes an operating norm. Rituals help you hold yourself accountable for managing time, and not the other way around.
Simply following one piece of this advice won’t transform the way you manage your time. In a week or two you’ll be back to square one. To transform the way you manage your time you must be willing to change the way you think, and operate. This means continually reevaluating and adjusting your habits, rituals, and mindset to operate as the best version of yourself.
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