Imposter Syndrome and Systems (& Why It's Not "Just In Your Head")

TL;DR: Systemic patterns in work that lead towards imposter syndrome — complexity and continual learning — the certification of knowledge — different types of work — know-how versus know-tools — communication and networks.

I think that there are certain professional patterns in tech and tech-adjacent work that make imposter syndrome much more common there than anywhere else. And I think by recognizing that, we can build systems that can help mitigate that feeling.  

1. Complexity

In “Overcomplicated,” Samuel Arbesman describes how we’re moving increasingly quickly towards a world of complex systems.¹ These systems are often entangled with each other and display unpredictable and unanticipated emergent behaviors.

This is as true for the design of laws guiding us (creative accounting loopholes!) as it is for code development and engineering. Anyone working in computer engineering and technology-adjacent fields — with their quick cycle between development and feedback — is privy to experiencing a headlong rush of dealing with the side effects of overcomplication.

But more to the point, this means that many people are dealing with a) more time troubleshooting than creating work, and b) working with systems the are increasingly out of their control and domain.

In the first case, dealing with inevitable bugs and fixes is a death-by-a-thousand-cuts blow to the ego, a constant reminder of things not working as they should. Little things end up having big, unanticipated, cascading effects. At some point, it’s natural to begin to wonder: ‘Is it the code, or is it me?'

In the second case, most people are unable to grasp the broader implications of their actions within a system. In any business (as in any team), a large number of people work together to succeed. But unlike professional sports teams — where there is constant training to reinforce individual skills and practice collaboration before a game — most businesses operate in game mode nearly 100% of the time, with little energy devoted to practicing and understanding collaboration.²

Which bring us to the second point:

2. Specialists vs. Generalists

There are two types of people in the workforce - generalists and specialists.
The imposter feeling that specialists tend to have can come out of recognizing the depth of their field and the amount to learn and practice within it, set against a backdrop of many other fields that have just as much to learn — “As the island of our knowledge grows, so do the shores of our ignorance."

Generalists have the opposite problem: toggling across a breadth of roles, they flit against the edges of knowledge everywhere. Enough to sound confident, but not enough to tackle any problem on their own. Without a solid anchor somewhere, it’s easy to feel inadequate and lack confidence or a sense of belonging.

3. Rapid Change

The rapid rate of change in tech and tech-adjacent fields is nearly a truism. Every new hire seems to come with their preferred favorite language, there is a new must-use framework out every year, and best practices seem to go out of style faster than the season’s fashions. Then there’s the cacophony of online opinions whenever you try to do your research: each voice proclaiming the best this or that, with hundreds of reasons for why.

So yeah, even if things for you don’t change quickly, one is exposed to an environment where stillness = death. It’s easy to ask - "Are my skills still relevant? Am I doing enough?"

4. Slow Certification

As a corollary to that, the process of certifying knowledge and experience has never been more behind the times.

On one hand, it seems like code academies are popping up like mushrooms after a gentle rain, each one promising certifications in the latest and trendiest anythings. But are some of these fields even old enough to have ‘best’ practices? Who knows if it will be around in five years… or even two years? Moreover, with the proliferation of certifications and certifying institutes, they become meaningless: a) most of these places don’t carry weight, and b) if even your landlady took a coding class, what’s the value of it?

On the other hand, traditional institutions haven’t kept pace. It’s hard to build a 4-year program around a 2-year trend, harder to know if it is worth choosing a trendy program over the tried-and-true majors for incoming freshman, and hardest to justify taking six-digit lumps of debt out if the alternatives are cheaper, quicker programs (see above).

But without certification, most people find themselves in fields they didn’t really ‘practice’ for. Especially when junior employees are hired for their potential, as opposed to their experience.

Which points to:

5. In Theory, In Practice

“Everyone has a plan until they get punched in the face.” Everyone ³ also has a traditional four-year education with a breadth of study that suggests they’ll be doing not just interesting work in their field, but tackling “fundamental” and “big” problems.

Then you actually get your first job, and if you’re lucky enough to work in the field you studied, it's likely doing the sort of menial grunt work that you were never trained for... The sort of work composed of hacks, compromises, and duct tape. It’s only at the highest levels of your career ladder that you’ll may get a chance to think again and act on the fun things you studied, and that’s only if you haven’t forgotten things by then.

“In theory, there’s no difference between theory and practice. In practice, there is.” There’s a big difference between the study that is done in school, and the nitty-gritty of real work. Real work has constraints, compromises, politics, egos, disappointments, unforeseen direction changes, and often bad management and troublesome coworkers in an uncontrolled environment. The only way to prepare for real work is to actually do real work. There’s no substitute, and it’s easy to feel over-your-head when you start, especially as expectations are high and if there aren't safe spaces to fail.

6. Accessible Tooling & Self Directed Learning

But let’s assume you got into the field untraditionally — that is, not through a four-year college pipeline somewhere. This is more and more the case, especially with fields like technology. I can’t count how many people I know got into their field because they picked up some tools or projects as a kid (or adult) and felt a sandbox of possibilities.

Today’s tools are designed with accessibility in mind. It’s a growth tactic: make it as open and easy to use for the maximum amount of people, to encourage uptake. If something is complex, less people will work with it or support it. Especially when it comes to programming languages and frameworks — and this is more and more true tools in the arts, design, marketing, video games, and other create-ive fields as well. There’s a whole army of such eager, enthusiastic, self-starting folks out there.

But everything has a trade off. Tools that focus on accessibility trade off more complex possibilities which lead to a superficiality to skills that are developed — enough to create something that looks good, but not enough to actually know what you’re doing. You’re not a web designer if you use SquareSpace and Unsplash to build a site. You’re not a creative director if your core experience is from curating other people’s work and phone-edited selfies.

While those skills and projects kick off the habit of lifelong learning and enthusiasm and passion that gets your foot in the door, it’s easy to confuse small early victories with expertise and versatile/flexible knowledge. The transition from one to the other can be rough, especially in unforgiving corporate environments. Self-education and tooling choices can also leave massive gaps in foundational knowledge that are easy to miss… things you don’t know you don’t know.

7. Open Ended Problems

What we’ve talked about so far is often limited to people in the early stages of their careers. But there’s totally different instance of imposter syndrome that strikes people later on. I think of this as arising when people deal with open-ended problems, things that have no preconceived answers.

I’ve often been enamored with blue-sky work of the sort done at Lockheed Martin’s Skunk Works, Google X, Bell Labs, and the likes. I’ve been lucky enough to spend half of my career doing something like that — coming up with something new that never existed before — with various companies as well. I even like to tell people that this is the most fun you can have at work, regardless if you’re a CEO charting a new course, a product manager designing new tools and features, a researcher figuring out new opportunities, or a creative director coming up with a hot new campaign.

But the flip side of the adrenaline that comes from figuring something new out is the deep and relentless fear that you are not the right person to do it, the questioning if you’ve got what it takes, and the fear that you won’t make the right choice. Precisely because there is no pre-selected answer, that nagging feeling is adjacent to feeling like an imposter. It’s the questioning of ‘why me?’ and ‘am I doing the right thing?' with no one to turn to.

8. Communities, Communication

That last line is important: without having someone to talk to about a problem, even a small thing can get amplified and out of proportion in your personal echo chamber. Some cases of imposter syndrome are easily resolved through communication and empathy: “I deal with that too! Here’s my story!” Other are resolved through both professional and personal communities that support each other, much like anywhere else. Sometimes, the feeling of being an imposter goes away on its own — you either get enough experience to feel adequate, or notice that other people flounder around as well. Other people just get over it through philosophy or other paths of self realization. But without new information coming into your head — from coworkers, from communities, from writers and gurus and dead trees — it’s hard to change the patterns of thinking that make you feel like an imposter.

Now What?

I wrote this in hopes of trying to understand what imposter syndrome is, and why it seems to happen more often in one line of work than anywhere else. Having put together a framework that seems to make sense for me, the next steps for dealing with it suggest themselves:

1. Invest in (Better) Professional Onboarding
   As seasoned professionals, invest in thoughtful internship programs (that focus on teaching skills, rather than coffee-work) and mentoring programs in your space. Not only will this be beneficial for you (practicing foundational knowledge, teaching as learning-reinforcement), but you’ll create more capable and more confident new employees, cement better team practices, and make your company a more desirable place to work.
   
2. Make Time For Better Communication + Support Networks
   Go out with people and talk to them about what you feel and why. Hear their stories and how they overcame it. Even if there are no easy answers, vulnerability is the first step to self growth, overcoming fear, and is a leading indicator for building trust and high-performing communities.
   
3. Pick Something Where You Want To Keep Learning
   If you pick a field you’re interested in, it’s never a challenge to keep discovering new things. As someone once wrote: “If you don’t like learning new things, you’ll like feeling outdated even less.” Continual learning is a shield against the feeling of inadequacy that comes from lack of knowledge. It also helps make work more fun and interesting, especially if you can experiment with your new learnings.

Special thanks to Max G for a long conversation on how modern tooling allows for accessible lifelong learning, and how knowledge gaps can form based on the tools you choose.

Footnotes

¹ - Complex systems have a very specific definition:

• Simple systems are... well, simple. "A causes B". They are easily knowable.
• Complicated systems are where there are a lot of different elements but the nature of the system is still knowable and predictable. A car is a complicated system.
• Complex systems are systems that are sometimes but not always predictable (as in, the follow general patterns). They tend to lead to unpredicted emergent properties.
• Chaotic systems are unpredictable and and generally unknowable (either because of the level of complexity or because we don't have enough knowledge.

² - Not to generalize, but I strongly believe that there is a survivor bias associated with everything we read about high-performing teams vs. what the real world actually does. Those articles cover a minuscule breadth of actually existing companies, and are written about precisely because they deviate from the norm.

³ - Not everyone.