Planning -- 168 Hours at a Time

Last week, I talked about FULL weekly time tracking – accounting for all 168 hours. I learned so much just from seeing where my time went.

The next step was PLANNING a full week in advance, using the same tools. Doing this has been a revelation.

But I know – at first blush it seems both incredibly onerous and highly limiting. Let me address some of the key objections I typically get when I mention this approach:

• “It must take forever!” It doesn’t. The first time, it took about 2 hours. But now I typically finish in about 45 minutes, which includes setting weekly goals, doing a full calendar review of the upcoming week (and a quick scan of the week after that, in case there’s anything lurking that requires significant prep), and then allocating the full 168 hours. I have a standing time slot on Sunday morning, but find what works for you. I wouldn’t recommend Monday, though, because the whole point is to offload the mental effort required for planning to a time before the week actually starts.

• “How can you know on Sunday what you’ll need to do on Friday?” Let me turn that around: how can you NOT know? We create business strategies and roadmaps that often span years into the future, but we aren’t willing to commit to a time slot 5 days out? But to provide a more helpful answer, I start with weekly goals (decomposed from monthly goals), and I have a pretty good idea of how long it’ll take to get each of them done. At that point it’s just a matter of allocating enough blocks to each.

• “Won’t this just lead to working all the time?” Quite the opposite actually. I recommend starting with hours for sleep (and other non-negotiables like house chores), and then following with the stuff you always WANT to do but end up skipping because you run out of time and energy. Often that’s exercise, sometimes hobbies, sometimes going out with friends, and so on.  

THEN you start to fill in the work blocks, with a much better sense of what’s realistic to accomplish given the time – and energy – you have to spend. I prioritize “deep work” blocks for projects that directly contribute to goals. Then the time that remains, and there often isn’t much, is allocated to meetings, minor tasks, and follow-ups – you know, the stuff that actually DRIVES most people’s schedules.

• “You can’t be spontaneous!” Well, that depends on your definition. I don’t want to be “spontaneous” on Wednesday morning, I want to execute my plan and GSD. On Saturday afternoon, though? By that point I’ve accomplished (almost) all of my weekly goals already, and my templated schedule is pretty much a big block of hobby / leisure time. That actually promotes more spontaneity – and certainly less guilt – than the old way, where I’d probably be catching up on work I missed because I didn’t plan the earlier part of the week very well.

I’d love to hear from anyone else who has tried this, or is willing to give it a shot!

Time Tracking

I highly recommend EVERYONE try tracking their time, for at least a couple weeks.

It’ll reveal a lot.

But there’s a twist …

I don’t mean just your work time (which most of us can do with our calendars). I mean EVERYTHING. A full 168 hours each week.

I didn’t originate this idea; it comes from two great books by Laura Vanderkam – 168 Hours and I Know How She Does It (the latter, despite its title, is equally relevant to men). She even has templates on her website that will help get you started, though you’ll likely want to customize them. I made a version with conditional formatting so everything shows up colour-coded, and lots of other little nerdy twists to help me analyze it all.

But before we go there, start with some simple math. Sleep 8 hours a day (56 / week), work 45 hours, and you’re left with 67 hours – 9.5 a day. For those of us who say we have “no time” for anything but work, what are we doing with these?

The conclusions can be stunning. You’ll likely find, for one, that you work a LOT less than you think. The first full week I tracked, I ended up with 48 hours – had I been asked, I would have guesstimated 60. Especially in the before times, when “work” for most of us included commuting and a lot of water-cooler talk, it’s easy to think how 48 “real” hours could become 70+ in our minds.

You’ll also find that you sleep a lot MORE than you think. I feel like I get no sleep at all, but looking across the past 8 weeks, it’s actually quite consistent at around 47 hours a week. The “worst” was 45.5, which is still about 6.5 / night – probably less than ideal, but not seriously concerning.

What was concerning, though? Finally putting a number beside all the time I basically wasted. I always knew I spent too much time on mindless content browsing – for me it’s the three-headed hydra of unproductivity known as Instagram / Reddit / Youtube. But seeing the first week’s total was a massive kick in the pants (which I shudder to reveal): 21.5 hours on TV/Internet!

Even worse, this is actually an undercount, because quick hits at the gym or while doing something else don’t show up. I’m only counting 30-minute (or greater) blocks where I was doing nothing other than browsing / watching.

Everybody needs time to decompress, so I’m not suggesting that number needed to be zero. You might have a similar number and you might be perfectly fine with it – and that’s great! But for me, it certainly put the lie to being “too busy” for anything. And with everything I want to accomplish, I decided then and there that spending a half-time job’s worth of hours on Internet surfing was not acceptable.

As I did here, you’ll likely find that the observer effect comes into play, where your behaviour shifts even without an explicit plan. But there are also ways to turn this into more direct action, which I’ll articulate in a follow-up post.

Have you ever tracked your time? What did it reveal?

Clarity and Leadership

There are many ways to be a good leader …

But there’s one non-negotiable element.

You need to provide, at a minimum, MASSIVE CLARITY on priorities.

This doesn’t mean that you give each person a rank-ordered list and spell it out – do this, then that, then this other thing. Ideally that’s rarely necessary, as you provide clarity at a higher level: organizational values, team goals, and how each person fits in. Of course, learning to connect those dots is a career-long learning exercise in itself, so in some cases you might be guiding the pen a bit more than others.

Still, it’s remarkable how few of us can do this well. Thinking about the managers and leaders I’ve observed over my career, I’d break it down into four maturity levels:

• Level 1 managers (about 25%) provide absolutely no help when it comes to prioritization. Give them a list of 10 tasks and they’ll rank 9 of them as “high priority”. They and their teams play a never-ending game of whack-a-mole.

• Level 2 (60%) provide what seems like a reasonable list of key objectives, but then undermine the whole process with frequent tire fires, and/or constant “reminders” / requests for “updates” on the low-priority stuff.

• Level 3 (10-15%) provide massive clarity, and then get out of the way to let their team execute autonomously. I think just about everybody, on both sides of the equation, would be happy to get here on a regular basis.

• Level 4 (1-2%) provide massive clarity, get out of the way, AND then actively sweep for potential obstacles, blockers, and other distractions that could impede the team’s ability to focus on key priorities. My non-Canadian readers may struggle with this analogy, but I think about it a little like driving behind a snowplow during a blizzard. There could be utter chaos ahead of you, but the plow brushes everything aside so your path is clear.

What causes most of us to get stuck at Level 2? I can think of several reasons, but I’ll give you my top two. The first is that many of us misunderstand the real purpose of having a team and the leverage that it provides. I’m no mathematician, but I figured out years ago that if the teams I’ve led (anywhere from 3-30 people) were fully productive, at the cost of one person (me) being utterly unproductive, that would shake out way better than the opposite. The second is an unwillingness to have some potentially awkward conversations with other leaders to align on priorities and set ground rules – since many if not most of the distractions will originate outside of your direct team, you’re only doing half the job if you don’t get on the same page as your colleagues.

Got any stories of leaders who were amazing at setting priorities, or completely failed to do so? I’d be interested to hear them.

Meta-Work

So if meta-data = data about data

Then meta-work = work about work?

Except you probably don’t spend MORE time on your meta-data than your actual data …

(If you’re like a lot of companies I’ve worked with, you barely touch your meta-data at all, but that’s another topic entirely.)

Let’s broadly define meta-work as scheduling, planning, coordinating – all of the ancillary activities that surround “the work”. McKinsey looked at this a few years ago and found that, believe it or not, knowledge workers on average spend 1.5x as much time on meta-work as they do on “the work”. I’m sure it hasn’t gotten any better recently.

Sure, there’s value in meta-work, and a degree of necessity. I was a project manager for years, so if meta-work was cool, I’d be Miles Davis. But that’s sadly not the case. And more often than not, meta-work ends up being a massive distraction from what really moves the company forward. Yet the urgency that it’s often accorded means that a lot of people genuinely think meta-work is their key priority.

Here’s another way to think about this: being great at “the work” gets you promoted; being great at meta-work keeps you from getting fired. Far more true than any of us would like to admit, and fundamentally broken on so many levels.

How do we change this? There are lots of SaaS platforms that claim to have “solved” scheduling and tasking, and I’m sure I’m being added to all of their lead generation cadences as you read this. But I don’t think adding another system will solve much (maybe painful to admit, as a product guy). As everyone who follows us at Cinchy will know, if you’re doing something that is counterproductive (say, data integration) and you want to eliminate or at least minimize it, making it EASIER is a band-aid at best.

A better plan, I think, might be to re-examine the expectations we create around priorities – not through a “values” whiteboard exercise, but every day, through the interactions we have with our teams. So here’s what I’m doing for my team:

• Continually providing, and reinforcing, total clarity on objectives – ALL of which have to do with “the work”

• Ensuring that requests for things like status updates, touchpoints, plans etc. DON’T default to urgent (no matter who’s asking), and should be scheduled around “the work”

• From a systems perspective (you knew I wouldn’t completely leave this one alone), building user-friendly tools that support complete transparency, and limit the need to “reach out for a quick update”

What’s your work-to-meta-work ratio (as a reminder, the average per McKinsey is 40:60)? What would you like it to be, and what are you doing to get there?

On Vacations

“You shouldn’t be working while you’re on vacation!”

Says who?

Before I get eviscerated in the comments, I should probably elaborate on that …

I split time between two different worlds, with contrasting views on how people should work. The world of entrepreneurship glamourizes the nonstop grind. GSD. Whatever it takes. Suffer the pain of discipline.

It’s actually quite unfortunate. This kind of narrative discourages potentially great entrepreneurs from even trying, when the reality is that working 24/7 isn’t necessary and usually doesn’t even help. There’s abundant evidence that for most people, output drops off sharply after 50 hours per week, and once you exceed 55, the marginal gains are pretty much zero.

On the other hand, in the corporate world, I’ve seen a desire to promote “work-life balance” take the conversation pretty far in the opposite direction. Admittedly, being pressured NOT to work while you’re on vacation is a lot nicer than the converse. But I still have to shake my head at companies that actually remove employees’ email access when they’re away, or recommend to managers that “if you see them online, gently remind them that they are supposed to disconnect.”

These kinds of practices seem well-intentioned – if sometimes overly performative (a few weeks of enforced disconnection won’t make up for expecting 24/7 connectivity the rest of the time). But at the end of the day, we’re still reducing people’s flexibility to work in ways that suit their preference. We’re also being pretty paternalistic in assuming that we know why they’re online in the first place, and that we can help them make “better” choices.

There are, arguably, better ways. At Cinchy, we instituted an office closure between Christmas Eve and New Year’s so that everyone could take time off (over and above vacation allotments) simultaneously, without having to worry about our colleagues creating piles of work that would spoil our return. We also provided additional flexibility for staff who wished to carry over unused vacation from 2021. Contrast with other companies that responded to the pandemic by further restricting their carryover policies, forcing employees to take vacation during, shall we say, less preferable periods.

Going forward, my commitment as a leader is to spend less time nudging people to use vacation days, and more time engaging in dialogue about how I can support my team to work in ways that, well, work for them. I don’t know for sure where that will take us, but my guess is that the stark binary of “work days” vs. “vacation days” will become a little outmoded. With all of the technology we have to support work from anywhere, and the considerable advantages that a globally distributed team can provide, why wouldn’t we want to rethink these kinds of concepts?

Are you in favour of re-examining the relationship between work and vacation, or does that take us down a slippery slope?

Separation Season

I decided to give Separation Season a try this year.

What the heck is that? I’ll explain …

I first heard the term from Dan Martell, who succinctly describes it as “the time of the year when everyone takes their foot off the gas, and you keep pushing” – but it seems like it might have been Ed Mylett who coined the phrase.

For me, it was less about leaving my supposed rivals in the dust, and more about wanting to maximize an unprecedented 2.5 week span (counting some vacation I needed to take) when my calendar wouldn’t be full.

Being a “big data” nerd, I track all my time anyway. Analyzing the 18 days of “Separation Season” (December 17 to January 3) against the preceding two weeks (weekends included) yielded some interesting results:

• I spent less time on work (6h/day across various streams, vs 8.3h/day pre-holidays) but tripled the proportion of “deep work” I did

• Though I always spend a lot of time on self-improvement, I stepped it up over the past couple weeks (1.7 hours/day – 30% more than usual), and completed 3 fantastic online courses as well as finishing 4 great books

• I finally carved out time for a couple of neglected hobbies, managing to find 21 hours in Separation Season vs. a grand total of 1 hour in the first part of December

This isn’t meant to be a brag post; I’ve tried and failed at these kinds of efforts before, and didn’t have super high hopes going in.

What worked this time around was having a solid plan going into each day, and a set number of small but meaningful goals that I could fairly easily reach with a modicum of focused effort. Nothing earth-shattering here, but leagues better than my previous approach of “I really should spend some time on ABC today” – the only output that ever produced was guilt.

What’s your approach to the holidays? Do you prefer to disconnect completely and recharge, or keep grinding?