There’s a cycle I’ve noticed in publishing my own thoughts.
Initial interest starts pretty high (otherwise why write about it?)
This rises steadily as I wrap my hands around the idea, feeling it’s edges. Gathering adjacent thoughts and ideas. Building a holistic view that explains in explicit terms of what I instrinsically feel is true.
Once I draft these thoughts, the loop feels complete. I’ve understood the topic, and communicated it. Of course there is much deeper I can go, but I’ve reached a natural milestone. In seeing my demonstration of understanding, the concept no longer holds power over my interest, which drops close to 0.
The tendency for me is to discard the draft at this point. It no longer feels novel to me, so why would it feel novel to anyone else?
But I’ve noticed another cycle too. Stumble across the draft weeks or months later, and I find a lot of value there. Things I forgot I had considered. Things I didn’t see before while I was in a flow state.
Now it holds a lot of new value for me, and I realize I should have published it in the moment. Now I’ve missed out on the some of the opportunity for others to see what I so clearly see now.
The effect of a culture & social platforms that encourage projecting perfection as a default state reinforces the hesitancy to publish.
I don’t know a good solution for this, other than to keep it in mind and try to press publish.
In rock climbing, a belayer is a partner who stays on the ground holding the safety rope attached to the climber’s harness. It’s a simple metaphor, but one that I’ve found a lot of mileage in lately.
There are 3 main things I draw from this metaphor:
It’s the climber’s journey
The role & responsibilities of leading
It’s a supporting role
It’s the climber’s journey
They’re doing the work
It’s up to the climber to choose whether they want to climb and initiate the process. Something my professional coach asked me that was really illuminating is “what do you want from your career at this stage of your life?”. I like that framing because it highlights the temporal nature of the answer. It’s ok to go through times where your career takes a backseat to other things in your life – and it’s equally ok if you want to challenge yourself and invest more heavily in your career. The important part is that the climber you are leading identifies this for themselves. Your role as a belayer is to provide support for whatever they choose.
Iteration is an important part of the learning process! That means going up and down many times – finding success and then surprising setbacks all on the same wall.
If you pull a butterfly out of the cocoon, it won’t be able to fly. What we think to be struggle or friction, that pendulation of going back and forth, is really a necessary part of the learning process.
Something I try to keep in mind is that if you encourage someone to challenge themselves, and then they fall, they’re really just doing what you’ve asked. It’s all a part of the process.
A process cannot be understood by stopping it. Understanding must move with the flow of the process, must join it and flow with it.
Frank Herbert, Dune
The role & responsibilities of leading
To encourage – the impact of wholehearted, honest belief in another’s potential is surprisingly powerful.
To coach – offering insight from your unique vantage point, which is different, and zoomed out from the perspective of the climber, who’s zoomed in doing the work.
Neither vantage point offers a superior view, but each offers unique value. When combined, they provide a richer context of the landscape.
There’s also an element of knowing when to be silent – allowing the climber to focus and do the work. Everything that is useful at the right dosage can be harmful at the wrong dosage.
To create an environment of safety that allows failure to be ok.
If you encourage someone to reach for a new hold, and they fall – it may be uncomfortable! You will feel their weight on the rope. They might be discouraged. They might even be angry. Your responsibility is to continue holding the rope. Let them feel that failure is ok – even safe. That safety you provide is what will allow them to come back and try again when they’re ready.
It’s a supporting role
And finally, it highlights that you’re not the main character in the story. Leading isn’t about ego – it’s not glamorous, or prestigious. It’s a minor character – one who’s added value is often overlooked, but whose contributions are also essential to the process.
It’s also a role that anyone can do, so long as they’re willing to take the responsibility seriously.
A few months ago I overheard my colleague Andrew Spittle say something that stuck with me:
I primarily think of risk tolerance as a question of, “When something bad has happened how quickly do we know about it and fix it?” and not one of, “How few bad things happen?” It can be a subtle difference but if we start with the latter framing it’s going to lead us to make less optimal decisions.
The first time I heard that, it passed me by without much notice. But two months later, while working through a tough problem, it came back to me, like a $20 bill I’d left in the pocket of last winter’s jacket. That’s it.
When we allow failure to be an option, we open ourselves up to gain all sorts of new insight. Insight that usually ends up being the key to success.
There’s a famous quote that touches on this, but when I looked it up for this article, I realized there was a longer version I’d never seen:
Would you like me to give you a formula for success? It’s quite simple, really. Double your rate of failure. You are thinking of failure as the enemy of success. But it isn’t at all. You can be discouraged by failure – or you can learn from it. So go ahead and make mistakes. Make all you can. Because, remember, that’s where you will find success.
Thomas J. Watson
Increasing Optionality
Think of a complex problem you’re working on.
Here’s a spectrum of what your options might look like:
A few options with a good chance at success
A few options with a good chance at failure
A lot of options that are unknown
The way you view failure is closely related to optionality. If you’re focused on avoiding failure, then you’ll limit your options. You won’t just ignore options that are known to cause failure, but any option that isn’t known to be successful. That’s most of the options.
One problem with this is an assumption that you can accurately assess up front which options are most likely to bring success. In my experience, that’s rarely the case. As my understanding of a problem grows, my analysis of the options changes quite a bit. It’s very rare that the solution I identify up front ends up being the right answer.
That flows nicely into this advice from Will Larson:
Prefer experimentation over analysis. It’s far more reliable to get good at cheap validation than it is to get great at consistently picking the right solution. Even if you’re brilliant, you are almost always missing essential information when you begin designing. Analysis can often uncover missing information, but it depends on knowing where to look, whereas experimentation allows you to find problems you didn’t anticipate.
Experimentation gives you many opportunities for small, recoverable failures. Counterintuitively, that’s a huge benefit. It allows you acquire first-hand knowledge about which options can demonstrate the potential for success.
Good Choices are Compounding, not Linear
Over time, the impact of experimentation is pronounced – but only if you allow for a range of possibilities.
Let’s look at the US stock market. Here is a chart of the S&P 500’s yearly % return from 1928-2021.
What if we decreased the range of possible failure & success only slightly? The red line shows what it would look like if we limited our gains or losses to a maximum of 25%.
Yikes!
Applications for Individuals
At an individual level, your decisions might feel small.
It’s easy to underestimate the compounding impact that experimentation + learning through failure have on your personal success.
One trend I’ve noticed is that all of the highly effective engineers I look up to are not better than average at picking winning solutions. They allow themselves more opportunities for failure than others do. In the end, everyone just remembers the successes.
When faced with a task that daunts you, a project that you find difficult, begin by doing something. Choose a small component that seems potentially relevant to the task. While it seems sensible to plan everything before you start, mostly you can’t: Objectives are not clearly enough defined, the nature of the problem keeps shifting, it is too complex and you lack sufficient information. The direct approach is simply impossible.
Obliquity: Why Our Goals Are Best Achieved Indirectly by John Kay, p191
Something my team lead wrote has become a mantra for me over the past few years, because it keeps my focus in the right place, with a bias for action:
What is the smallest change we can make today for a better tomorrow?
Applications for Leaders
If you believe it’s your responsibility as a leader to prevent your team from failing, then you will only give your staff opportunities within a narrow band of where you anticipate they can succeed. That ends up being extraordinarily stifling, whether it manifests as micromanaging or just limiting opportunities for your staff.
A good way to tell if you exhibit this behavior, is to ask yourself – Am I responsible in this role for ensuring things go well? Or am I responsible for responding reasonably to a myriad of situations beyond my control?
If it’s the former, then you’re aiming to prevent failure.
That can have a big impact on your personal performance as a leader too. In many complex situations, there isn’t a clear way to avoid failure and ensure things go well, which can arrest progress if that’s your aim. If your focus is on reasonable responses, then that unlocks many immediately actionable paths for you to take. That will improve your ability to take action, which reinforces the positive impact of small steps.
Applications for Teams + Larger Organizations
This perception that failure should be prevented shows up at all levels of organization, with a downward pressure exerted from the cultural environment onto the individual to follow an established norm.
There are 2 main implications for that at the org level: retention + output.
Retention
If your team leads are encouraged to prevent failure, then that will impact retention, as they obstruct their staff’s autonomy to remove failure from the range of possibilities.
Performance
Similar to the stock market example above, the cumulative network effect of many individuals pursuing either experimentation or failure prevention adds up quickly.
A good way to know which you’re pursuing is how you approach new initiatives:
Do you start with analysis, select the best path, and get started?
Or do you identify some small experiments to run, then scale up the winners?
Analysis can be used to identify which small experiments to run, but that’s different than embarking on a full project based on analysis alone.
This is the MVP approach, which everyone knows, but it’s easy to overlook all the places it applies. Projects born out of analysis without experimentation are likely to have a higher rate of failure.
The key is to identify failure quickly. Think about the initiatives in flight and how long it may take to identify if they fail:
6 hours, 6 days, 6 weeks, 6 months, or 6 years?
The longer it takes, the more painful it becomes to absorb that failure and move on.
There are many parallels to this idea of effective networked activity in the natural world, but this one I particularly like:
The mycelium starts in an exploratory mode, proliferating in all directions. Setting out to find water in a desert, we’d have to pick one direction to explore. Fungi can choose all possible routes at once. If the fungus discovers something to eat, it reinforces the links that connect it with the food and prunes back the links that don’t lead anywhere. One can think of it in terms of natural selection. Mycelium overproduced links. Some turn out to be more competitive than others. These links are thickened. Less competitive links are withdrawn, leaving a few mainline highways. By growing in one direction while pulling back from another, mycelia networks can even migrate through a landscape. The Latin root of the word extravagant means “to wander outside or beyond.” It is a good word for mycelium, which ceaselessly wanders outside and beyond its limits, none of which are preset as they are in most animal bodies. Mycelium is a body without a body plan.
Entangled Life, by Merlin Sheldrake, p48-49
That’s the best description I’ve come across of what a high performing team should be.
“which ceaselessly wanders outside and beyond its limits, none of which are preset”
How to Reframe Your Approach to Failure
I think of this approach to failure as a practice; not a one time decision. You’ll catch yourself in it many times, in many different situations. Even in this, it’s ok to fail. The important thing is identifying it and recovering quickly.
When are you feeling pressured to prevent failure?
Is the source of that pressure from within, from others, or from the environment you’re in?
Once you’ve identified that pressure, you can take steps in another direction.
The more times you rinse + repeat this process, the easier it gets. But the first time is always the hardest, because it’s often not enough to know intellectually that you should allow failure to be ok.
In that scenario, the lead domino is experiencing failure being ok. Until you do that, you can’t release control over needing to prevent it, even if you know you should.
One topic I’ve been monitoring during the pandemic is the availability of tools for producing better webcam quality. With so many more people suddenly logging onto Zoom to spend time with family and conduct their work, I’ve been waiting for capitalism to step in and offer better options.
Despite some interesting kickstarters, I haven’t seen what I’m looking for yet. Something elegant, affordable, and portable. That doesn’t mean there aren’t options.
This is my journey to much better video quality with very little effort.
If you’re interested in good image quality for video calls, I would start by reading these:
Matt’s 2021 Streaming Kit is probably the best example of what you can achieve if you want to go deep on this subject. But it means going deep.
In short, then, I recommend not going down this path. When you see someone on a video call with an impressive bokeh-ed image, just let it go and call yourself lucky. It’s not too late to save yourself.
Stephen O’Grady’s words of warning in So You’re Thinking About a Fancy Camera Rig rang true for me. I don’t take video calls often (2-8hrs/wk), so I’m not willing to invest a lot in it (time or money).
I strikes me that there’s a chasm of quality that exists between high-end setups using DSLR cameras, and the pinhole camera embedded in a laptop screen that almost everyone uses. Most people look at the cost of reaching 100% and choose to never get started. I hope that changes, mostly because I’d like to see people better on calls and feel like we’re both making eye contact.
Key Elements
That Bokeh
Obviously this is the big one. To get this, you’ll need 2 things:
Camera Quality: a decent camera with a wide aperture, allowing more light into the camera, which creates a narrow depth of field. You’ll see this represented in f-stop. In college I shot & developed b&w film on a Minolta x370 with an f1.4 50mm fixed lens, which was perfect.
Light Quality: Cameras capture light. Simple as that. It will be important to identify the location of your light, the color temperature of the light, and any natural light in the room where you work.
Eye Contact
This one is really important and was difficult to figure out. There’s just nothing as engaging as feeling like someone is looking directly at you when they’re speaking. As a society we’ve grown so used to seeing people looking elsewhere on video calls. Seeing someone making eye contact on a video call is especially engaging and surprising – like a dramatic demonstration of focus.
The only way to get this effect is by positioning the camera so you’re looking into it.
My Very Simple Setup
Camera
I use an iPhone XR, which is unique in that it only has one rear-facing camera, but still has portrait-mode. This gives me a slight bokeh out of the box with no effort.
Using Camo Studio, I connect the phone to my computer via a USB-C => Lightning cable, which gives me both a reliable video feed and a dedicated power source.
Lighting
In my home office, there are 3 recessed lights overhead, and a large window to my left. I noticed that calls during the daytime are pretty decent without additional lighting. But during the winter when it gets dark at 4pm, it’s really difficult to get a decent image, and the white balance shifts yellow.
I upgraded my workspace to use two Lume Edge Lights, which are anchored on the left & right sides of my desk as a 2-point system, ensuring there are no casted shadows on my face. These are great for a few reasons:
The light heads swivel, so I use them as downward-facing workspace lamps most of the time, and then flip the lights towards my face when I take a call.
You can adjust the color temperature (yellow=>white) and brightness of the lights easily, which allows you to compensate for natural light and tune the white balance of your image, naturally.
Eye Contact
I spent a bunch of time thinking about this, and decided to surf Amazon to see what I could find. I landed on a $15 flexible arm, which clamps to the stand for my monitor, and wraps around to hold my phone directly in front of my screen.
This means I reposition my call window to sit just below the camera, so I can see who I’m talking to, and I’m making eye contact with them at the same time. It mimics a teleprompter, but with so much less effort.
The great part about the flexible arm is that I can easily bend it out of the way behind the monitor when not in use.
Results
These are actual screenshots I took of my square during a series of Google Meet calls one day:
LG 5k Display WebcamiPhone XR + Camo with Room LightsiPhone XR + Camo with Lume Edge Lights
I’ve been using this setup for a little over a month now, and I’ve been pretty happy with it overall. It’s a little extra work to plug in my phone and mount it each time I jump on a call, but it feels like a good effort/value ratio.
It’s tempting to want to go further – maybe a nicer camera, or trying some different mounting options. But like Stephen O’Grady suggested, I’ll probably just consider myself lucky and let it go so I can focus on other things.
The easiest time to identify unnecessary complexity is when you’re an outsider. Before you’ve grown used to the way things have always been done. It’s the hidden value of not knowing. Your judgment isn’t clouded by knowledge. All you have is reasoning.
That’s when you’re in the mindset to ask the right questions. The high-level ones. Why is it like this?
We’ve all had experiences asking that question and getting an unexpected answer that betrays a very broken process. This post is about what to do next.
“What’s that on the stove?” “Oh, we ran out of dish soap, so I took the bar soap from the shower and I’m heating it up so we have liquid soap for washing dishes in the sink.”
It feels like the sound of a Shepard tone in a Christopher Nolan Film. A vibrating hum of anxiety like a slowly rising boil.
I guess you could do that…but I have so many questions about why you would. Isn’t there a store like 2 blocks from here?
What’s at the root of this? Complexity bias.
Complexity bias is a logical fallacy that leads us to give undue credence to complex concepts.
Faced with two competing hypotheses, we are likely to choose the most complex one. That’s usually the option with the most assumptions and regressions. As a result, when we need to solve a problem, we may ignore simple solutions — thinking “that will never work” — and instead favor complex ones.
As the observer of complexity bias, you’re unlikely to be the person with direct decision-making power to remove it. These things have a way of working their way into an organization. Like ivy weaving up a brick building, taking hold in the mortar in a motion that solidifies its position meanwhile deteriorating the structure itself.
Over time, I’ve found a simple series of steps that works reliably well in the pursuit of simplicity. It may not be easy, but I think it is effective in giving the best chance of unwinding complexity. Whether or not you are successful, you’ll gain a lot of knowledge taking this path. You might even find you’re mistaken and the complexity is necessary, but poorly explained!
Zoom Out
Gather your own data
Identify the components, and learn them deeply
Demonstrate your knowledge
1. Zoom Out
Zoom out as far as you can and ask the most basic question to start.
Avoid thinking of the problem on a technical level – think of it as if you were describing the problem to a toddler.
This is harder and takes much longer than it sounds.
2. Gather your own data
You never want to make decisions based on filtered data. Go to the source and examine it yourself.
“When a measure becomes a target, it ceases to be a good measure”
– Goodhart’s Law
Usually you’ll find a specific person who champions the value of the current setup. Ask them what specific parts are valuable to them. Be genuine in your interest to understand.
It can be tempting to use your inquiry as a launchpad to explain where they’re wrong. Instead, you’re more likely to win their support by understanding what they value in the current setup and finding a better way for them to get that value.
Exhibit curiosity.
There is a fine line between curiosity + obstruction, and the difference lies in interest. If your focus is on knowledge acquisition, then you will always find value in asking probing questions, and others will appreciate you for it.
3. Identify the components, and learn them deeply
You’ll probably hit a roadblock. It’ll feel like game over.
Well we can’t change Thing X because we need it to cover Need Y.
Instead, it’s an opportunity. Learn everything there is to possibly know about Thing X and Need Y.
How thing X works.
What it’s great at
What its limits are
How did we start using it
What alternatives exist, and what their strengths and weaknesses are
Learn why Need Y is so important.
What happens if that need isn’t met?
Who will it affect?
Optimize for the long term.
Assume you will interact with this component (Thing X) again and again, so it’s in your best interest to invest up front in learning it deeply. If you do, then every time you encounter it in the future, you’ll be adept and efficient in your work.
4. Demonstrate your knowledge
Write down what you have learned & observed, using simple, straightforward language. Whether it’s called documentation, or a proposal, or anything else does not matter. The act of writing it down is what matters.
This has 3 major benefits:
Its a gut check whether you know or not. You cannot explain something simply that you do not understand fully.
Writing will provide it’s own form of insight.
It’s the best way to help your colleagues in a growing organization to find effectiveness faster. The network effect of everyone providing good documentation yields an exponential increase in productivity over the long term.
Finally, when you need to make changes, here are a few suggestions that may help:
Separate problem identification from brainstorming solutions. Give yourself time to understand all the edges of the problem. You don’t want the first thing you can think of – you want the best thing you can think of.
Start small and build up. What is the smallest change you can make today that will result in a brighter tomorrow?
Ask around. Get creative and find unexpected places that a similar type of problem was worked on in the past, and ask for advice. There’s an element of confidence involved in this – navigating relationships with colleagues to gain insight but still possibly go in your own direction.
The best part?
Even if you fail to make any meaningful change, you’ll still be better off for taking this path. You’ll gain a deep understanding of the system that no one around you has. You’ll be able to make better decisions, and eventually, one way or another, those decisions will take you away from the frustrating complexity.
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