Jeff Shearer

I took a Lyft on my way to the airport recently that had a tablet mounted to the back of the seat with a bunch of ad-supported games. Trivia, mostly.

And I love trivia, so I had to check it out.

But I quickly realized the questions were all stupidly easy. A few samplings from the photo trivia:

What’s the name of this famous building? – The White House

Who is this famous scientist? Benjamin Franklin

My point isn’t to call out this company for crappy trivia. More an observation that trivia loses its fun when the challenge level doesn’t line up. We like trivia when it is just at the edge, or slightly beyond the edge of our abilities. When we have to think, and summon up some piece of insight from a dusty corner of our minds.

Meanwhile, Trivia that’s too easy is dull, and trivia that is far outside our knowledge is demoralizing.

I think most satisfying work follows the same trajectory. We often think we want the easy assignments and straightforward projects. Yet we’re surprised when we find little satisfaction to show for the work. And when we’re completely out of our depth, we feel like we’re drowning.

All along, what we really crave is the work that sits right in that sweet spot – not the “comfort zone” – but just a little bit beyond it.

Fall as told by TV and popular media is an orderly affair. The tree leaves change colors from burnt orange to deep amber, and eventually they all fall off.

But if you actually pay attention to the trees around your home, as I did yesterday on a walk, this transition is not uniform at all. One tree may be just sticks by Halloween, while the one next to it is still full of leaves. Even on an individual tree, the leaves change at different rates.

Now that we’re here in November, we’re entering that period of fall where the pretty part of the transition is (mostly) over, and we’re left with the piles of wet leaves rotting in the gutters and clogging the drains. There’s even a decent argument that this period of fall isn’t even really fall – but a sixth season called “Locking”.

The point is – we always hope for these nice, tidy transitions. where one stage becomes the next. Where one day we’re planning, and the next, we’re executing. Yet we fail to recognize that rarely does such dramatic transition exist anywhere else. Certainly not in nature, and probably nowhere outside our own imagined standards.

Instead, change is a gradual, messy process. Worth keeping in mind if you’re ever feeling like your efforts are stalling – it could be you need to give it a little while longer, and let the rest of the trees lose their leaves.

You’re fooling yourself if you think you’ll remember all the important work you did a year or two from now. Sure you may remember a few of the big, visible projects, but the more subtle work you did may be tough to recall.

So when it comes time to update your resume, you’re up a creek if you are just relying on memory.

I recently came across a solution though: the “Career Management Document” , which serves as a way of cataloging your milestones as they occur.

It’s a pretty simple idea, but saves you the trouble of trying to remember all the details of your past at once.

I recently built one, and I check the document every month or so and add new items and projects that seem noteworthy to me at the time. The beauty of the process is that I don’t really need to be selective – I can list anything on my mind at the time. It just translate to more ammo for me to use whenever updating my resume might be necessary.

The key is to not forget about it, and ensure you regularly check in. I just set a monthly reminder to take a look, and that seems to do the trick.

With just a bit of attention a few times a year, this document can be a truly valuable resource for you- not just in keeping a resume current, but as a way of reflecting on what you’ve achieved so far.

A few years back, I got completely sucked into the business and self improvement book genre, reading basically everything I could find of value. My favorites?

Rework, Anything You Want, the Lean Startup, Let My People Go Surfing.

But at some point, I started hitting a rut. Maybe it was the retreading of popular anecdotes. Or the fact that many books ended up leaning on the same tired and outdated examples to draw their conclusions. The process of reading started to feel like a chore, and I found I wasn’t retaining much from the books I was reading. I ended up taking a break from reading for most of a year.

Once I got the urge to start reading again, I decided to focus entirely on reading for pleasure. Initially I thought this would mean a lot of fiction, but the reality is that I was especially drawn to non-fiction, namely history.

The more eclectic my reading got – whether I was reading a book about Theodore Roosevelt or the environmentalism movement, I was drawing connections and analogies to my everyday work.

As someone who works in a highly specialized and technical field, being able to clearly convey complex ideas to non-technical audiences is a big part of my role. And the value of my eclectic reading has paid off in helpful anecdotes and analogies alone, not to mention expansion of my worldview.

I do still read plenty of business and marketing books – but I feel less inclined to guide my reading by what I “should” read, and instead what genuinely sparks my interest at the time. Chances are, if I’m absorbed by the reading, I’ll find a way to apply the material in some useful way in my life. But there’s no need to try and force it.

Early in my career, I made a few enemies. Mostly because a disagreement in my mind turned into an attitude of “they’re out to get me”. I created these enemies myself, and the animosity I held towards them lasted for years.

Looking back on those times is embarrassing – disagreement & conflict are natural parts of the workplace, but I had let it get much more personal than that.

These days I think I’m a lot more cool headed and ambivalent about conflict and disagreement at work. It can be frustrating at times. It’s still easy to interpret disagreement as a sign of a personal slight. But the difference today is that I rarely let these feelings evoke a response.

Whenever I speak to people just starting their careers, I always try and emphasis this point. The easy choice is to let our emotions get the better of us. To treat conflict at work as if it’s theater. But the reality is usually far less interesting, and the consequences of behaving that way just don’t work out well for you in the end.

The perfect feature set. The perfect structure. The perfect circumstances. We never quite seem to reach any of them.

It’s worth knowing where perfect lies for getting your bearings, but endlessly chasing it is like trying to catch your shadow. Settle for “good enough for now” instead.

When CD burning first became popular, I was obsessed with getting a burner of my own. How cool would it be to make my own CDs? I could have my own mixes for car rides, and give them out to my friends.

That year for Christmas, my parents got me a CD burner. I hooked up the bulky beige box to our family computer, installed the software, and then realized – I had nothing to put on my new CDs.

I was so distracted by the idea of burning a CD, yet hadn’t really considered the circumstances – that I wasn’t really in a place to make use of such a tool. In fact, my first few CDs were basically wasted on a bunch of free .WAV sound loops I found online. My first few CDs were basically tracklists of Powerpoint sound effects.

Eventually I got some music and figured out how to use the thing, but it was an early lesson in the difference between expectation and reality.

It’s so easy to get wrapped up in the excitement of a new piece of technology and the possibilities it affords. But if you’re not equipped to make use of that technology now—If you don’t have a specific problem to solve or use case to pursue—then it’s not worth devoting many mental cycles to thinking about any further. Buying technology for “What if” is a pretty quick way to end up in integration purgatory, and a finance team questioning your budget decisions.

Or, to put it another way, you have no use for a spindle of blank CDs if you have nothing to put on them.

The daily vitamin/pill reminder may seem like a mundane, boring product, but it’s in fact the perfect habit forming tool.

To borrow the framework set forth by James Clear in Atomic Habits, the steps to design good habits are:

• Make it obvious: Simply setting out your vitamin reminder on the counter you pass every morning will do the trick here.
• Make it attractive: Your daily vitamin is typically something you take with food. So taking your vitamin = time to eat a tasty breakfast
• Make it easy: You’ve already done the legwork of laying out exactly the pills you need to take — all you need to do is swallow them.
• Make it satisfying: The weekly pill reminder is its own checklist — the empty segments mean another day you successfully completed. And who doesn’t love to cross off an item on a list?

Daily vitamins solved, surely there must be other areas of life solved with a similarly simple and elegant solution.

A little while back I wrote about the lessons I’ve learned from remote work, and the experience of working from home full time over the last year has been a net-positive for me. In fact, I love remote work—It’d be hard for me to adjust back to an in-office life again.

But there is one big downside I’ve been forced to reckon with: Isolation.

This is perhaps obvious, yet something I ultimately underestimated. It’s hard to appreciate the value of the social dynamic of an in-person work environment until you no longer have it to fall back on. Even for introverts like myself, isolation and the lack of that face to face experience can make the dynamics and communication styles in a workplace challenging at times.

Video conferencing helps immensely here, but even it is not a perfect substitute.

When an issue arises, or a problem needs to be escalated, it can be challenging to convey meaning and get everyone on the same page when emotions are raw. There’s something about sitting down face to face to resolve a dispute that technology just hasn’t quite solved yet.

The solution here, oddly, is more meetings. It’s easy to try and burn the candle from both ends—striving to be both a distributed team and embracing a meeting-light culture, but at least in the beginning, and especially with new team members, face to face time, whether virtual or in-person is crucial.

I’m typically up before the sun is, 5-5:30 AM, and this is the time when I’m most productive and creative. I’m an early bird.

But I’ve been reading Matthew Walker’s Why We Sleep and early on, he mentions that early birds and night owls are genetically determined—chronotypes. Some of us simply are wired differently for sleep.

Living in a society that views and encourages “normal” as waking early and starting at 8 or 9am, I feel right at home. But the night owls in our society really get a raw deal. Not only are they expected, both through cultural norms and company policies, to adhere to an unnatural schedule, they’re at a distinct disadvantage in how their success is measured. For a night owl that does their best work in the evenings, the expectation of creative excellence at 9am is a tall order.

So it’s no surprise that there’s a rise of non-traditional schedules and organizations with flexible work hours to help address this. But I think we’re a long way from an even playing field. Remote roles and distributed companies feel like the perfect fit to solving this issue. If you can work from anywhere, and rely on asynchronous tools to stay in touch – where’s the problem in keeping different schedules?

Economics may have set the early-rising mentality of the workforce early on, but as sleep science advances, and workplace options diversify, the traditional, clock-punching, 9-5 companies lose a lot of their power. Adapt or get left behind.