Engineering as Art: Embracing Creativity beyond Science

Achieving a staff+ engineering role is a considerable achievement that many engineers seek as the next step in their career growth. All staff+ positions are different, and precisely what your role entails can sometimes be murky.

Depending on the size of your organization, you could be the only staff+ engineer, or there may be dozens or hundreds of other engineers in similar roles to you. The number of staff+ engineers, the type of software you’re developing, and the management structure all play a part in shaping your role.

In this article, we’ll discuss the challenges that staff+ engineers can face and how our struggles are similar to those of artists. Specifically, we’ll look at the parallels between creating art, creating software, and dealing with organizational dynamics.

We’ll focus on such topics as:

• Leading without authority
• Dealing with psychological discomfort and impostor syndrome
• Finding and establishing relationships with your peers
• Bringing ideas from inception to completion
• Embracing discomfort, even failure, to grow

Before we dive into the challenges that staff+ engineers face, let’s review what shape these roles usually take within an organization and what the career ladder may look like for individual contributors versus managers.

Staff+ Archetypes

Will Larson’s Staff Engineer is a guide for many of us getting into the role of staff engineer or looking for guidance on how other individual contributors manage their careers. Larson identifies four common archetypes for staff engineers that he has encountered.

• The Tech Lead guides the approach and execution of a particular team. They partner closely with a single manager but sometimes with two or three managers within a focused area.
• The Architect is responsible for a critical area’s direction, quality, and approach. They combine in-depth knowledge of technical constraints, user needs, and organization-level leadership.
• The Solver digs deep into arbitrarily complex problems and finds an appropriate path forward. Some focus on a given area for long periods.
• The Right Hand extends an executive's attention, borrowing their scope and authority to operate particularly complex organizations.

I have primarily operated in the Tech Lead role for my career, but I have also dabbled in Architect.

Outside of these archetypes, I’ve found that our roles can be vague and shaped by personal experience and organizational dynamics. If you’ve grown at your organization over time from a senior position to staff+, you probably are filling a different need/role than someone hired from outside the company. Especially for older companies with tech debt or legacy systems, historical context plays a huge part in how well you can operate and influence the company. Starting a job where you’re hired as a staff+ engineer can be particularly challenging. I’ll discuss a few ways of overcoming these challenges later in the article.

Parallels to Art

I recently read a book called The Creative Act: A Way of Being by Rick Rubin. Some of you may have heard of Rubin (he is an American record executive famous for his eclectic mix of artists across musical genres, such as hip hop, heavy metal, alternative rock, etc.). He has produced albums for the Beastie Boys, Run DMC, Metallica, etc.

I picked up this book because I was feeling a pull towards creative pursuits in my life. Which, to be honest, I’ve always struggled with as an engineer.

"To live as an artist is a way of being in the world. A way of perceiving. A practice of paying attention. Refining our sensitivity to tune in to the more subtle notes. Looking for what draws us in and what pushes us away. Noticing what feeling tones arise and where they lead." - Rick Rubin

Get rid of the idea that you are not creative or a creator. Everything we make in our lives involves creativity, from writing software to writing documents. We’re not just technicians. Art and engineering are both about experimentation. Embracing ambiguity, performing discovery, and crafting a solution (either to a problem or crafting a masterpiece) is a process we all follow when solving problems or creating art.

Between the book and a few interviews I’ve listened to with Rubin, I’d like to draw on some of the lessons he shared and takeaways from a more artistic life that I think we can use to inspire our jobs as staff+ engineers.

Being open to new ideas

Rubin talks about this idea of creativity/clear thinking coming to us more effortlessly if you have a sensitive "antenna". I want to touch on this and his discussion on always being curious and looking for clues/transmissions.

Have you ever sat in a familiar room with nothing to do (no TV, phone, tablet, music, etc) and noticed something you never saw before? Something on the ceiling or wall? Being bored is something we’ve lost, and with distractions always stealing our focus and attention, we’re not as attuned to notice subtleties in daily life. This state of awareness is something artists curate in order to draw inspiration in their daily lives and the world around them. How much more attuned to our team and a better listener could we be if we increased our awareness?

Try meditation if you struggle with maintaining focus or feel pulled towards multiple tasks simultaneously. If mediation is not for you, try leaving your phone in another room during the workday or practice being bored. I know that sounds counterintuitive, but give it a chance. Go outside and sit on a park bench for 20 minutes with no distractions and after a few minutes, you’ll realize how much more attune to your surroundings you’ve become.

Cultivate a beginner’s mindset

The next topic I’d like to touch on is cultivating a beginner’s mindset. A beginner’s mindset can be summarized as approaching problems as if you have no knowledge or experience in the given arena.

Spending years gaining experience and refining skills may constrain our imagination, creativity, and focus. Cultivating a "Beginner's Mind" suggests that embracing this mindset can lead to acquiring new abilities, making wiser choices, and fostering empathy. The essence of a Beginner's Mind lies in liberating ourselves from preconceived notions about the future, thus reducing the risk of stress or disappointment.

Adopting a beginner's mindset proves beneficial for artists, allowing them to overcome creative blocks, initiate fresh ideas, and break free from self-imposed limitations. However, this mindset is broader than artists; engineers and less creative individuals can also benefit from it. Through years of dedicated practice and execution, our minds unconsciously develop recurring patterns, transforming them into mental shortcuts, rules, and best practices.

I’ve had success getting into a beginner’s mindset over the years by avoiding pre-judgment when learning new technologies and working with a beginner in the domain. Participating in exercises where you’re outside your comfort zone, asking questions, and listening shows your interest in learning but also helps you from jumping to conclusions about how you expect something should work based on experience.

Writer’s block

Do you often struggle to make progress on a challenging problem? Artists commonly struggle to break through creative or mental blocks, which we call writer’s block. In contrast, engineering challenges can take on a similar form. I want to discuss a few ways to tackle writer’s block head on.

Take small steps

I often feel overwhelmed by how large a task seems at the start. How I make progress and deal with the anxiety is to break up the work into manageable chunks - even scheduling time for myself in my calendar to work on it. For this post for instance, I knew how long I wanted it to be and a rough outline, so I said to myself, "write five minutes of content a day for five days next week". Just write down whatever comes into your head for each topic and the following week, edit.

As writers, we often get caught in the trap of trying to write and edit simultaneously, making us feel stuck in the loop of writing and re-writing. Taking these small steps towards a larger goal can give you a sense of accomplishment each day and make the more significant task seem less overwhelming.

Eliminate distractions / change your environment

I’m a big fan of the concept of Deep Work, popularized by Cal Newport. A story in his book resonated with me about a novelist who flew round-trip to Tokyo, writing during the whole flight to Japan. After landing, he drank an espresso, turned around, and flew back, again writing the entire way, arriving back home after 30 hours, now with a completed manuscript in tow.

This story resonated with me because I felt the same every time I flew. Being forced to sit in one place with little distraction helps me clear my head and focus on a single task. Making a radical change to your environment and investing significant effort or money into supporting a deep work task can increase the task's perceived importance.

Another thought exercise on this topic is how often we superficially consider solutions to a problem. For instance, we have a great idea in the shower but don’t allow ourselves more than a few minutes to dig in. We tackle issues "on the surface" but don’t get at the meat of the problem. Having the space and time to do this is where your best ideas shine.

Play with alternate mediums

Another "trick" I like to use for myself and my teams is changing how we communicate or think about a problem. One of the easiest and quickest ways to do that is to draw instead of talk about an issue.

Visual communication has gotten more complicated with virtual meetings, but it’s still beneficial. We tend to think things over in our heads and not write out a problem or draw it out. Both of these are excellent ways of forcing yourself to put down ideas to paper and work out the details.

If you’re familiar with the rubber duck paradigm in programming, you could also use this for drawing. Invite someone to listen to your idea, even if you don’t want or aren’t ready for feedback. Make sure to set the tone that this a safe space for ideas.

Be an anthropologist

Another area I often see folks needing help with is understanding and figuring out organizational dynamics and culture. It's not surprising in large organizations (>few thousand engineers), but have also seen it in smaller organizations (>100 but < 1k). As companies create management and corporate structures, engineers often need help with what happens above their immediate line manager.

To help folks understand better, I take on the task of being an anthropologist. An anthropologist’s job is to study the lives of humans in past and present societies worldwide. Parallel the world to your company and get exploring! Get to know people in other parts of the business, folks who’ve been at the company a while who can share context and give background. Most often, this happens serendipitously over time, but I find getting to it quicker, and intentionally, often helps. When I started at a new company recently, I set out to conduct 1:1s with at least 20% of the folks working in my organization in my first 30-60 days. The 1:1s helped me come up to speed quickly. It also was an opportunity to learn, through the interview questions I mention below, how engineers and managers feel about their roles and what struggles and challenges I need to develop.

Overcoming Staff+ Challenges

In this section, I’ll describe how approaching our role as an artist can help with some of the challenges of staff+ positions. We’ll touch on the parallels we drew to being an artist and how those can help navigate some of the challenges in your role.

Leading without authority

Many of you may have read a great book on this topic by Keith Ferazzi, called Leading Without Authority. The area I’d like to touch on here specifically is co-elevation.

Co-elevation is key

Co-elevation is a mission-driven approach to collaborative problem-solving through fluid partnerships and self-organizing teams. When we co-elevate with one or more of our associates, we turn them into teammates.

How do you establish relationships to build self-organizing teams and co-elevate? We talked earlier about being an anthropologist to learn your organization's and various teams' inner workings. Use this exercise to build relationships with different folks across the organization. Build trust and credibility with them.

Develop a set of questions you use to ask during the time you have with them. These questions will help set the tone for the interaction, but keep it light to not make it seem like an interview. Your goal here is to listen, not talk! Be an active listener.

Interview questions

Set the tone by first getting context from the interviewee. Ask them to give a talk about what they do at the company (team, job function), and if comfortable, a little about themselves on a personal level. Next, gather feedback on how they feel about their role at the company. What is working well for them and what is most frustrating. Lastly, ask for advice. What should I be aware of that I may be missing?

Use this set of questions to establish your relationships. For the ones you think are valuable, stay in touch with those folks every few months to keep the connection active. These interviews can help you understand a beginner’s mind, seeing problems from a perspective you are not the expert in.

Peer Relationships

Another challenge is building on leading without authority and establishing solid relationships with peers. If you happen to be in an organization that doesn’t have a ton of other folks in your role, you may struggle with this.

A few suggestions on how or where to build peer relationships:

• Look outside your immediate team. If your company doesn’t have one, try to form a peer group of all the staff+ engineers in your organization.
• Look outside your company. There are a few communities where staff+ engineers gather to discuss common topics and share feedback. Rand’s Leadership Slack is an excellent place to start if you’re looking for folks in the industry outside your company.

Be sure to maintain and nurture relationships with folks you used to work with who may have grown into a similar role. I have a peer group that I meet with regularly who now work across a few companies to keep this going. It’s a great resource for bouncing ideas, holding myself up to date with the challenges faced across companies and industries.

A few areas I think this can help in our staff+ roles:

• Someone who compliments your skill set
• Someone you can "rubber duck" ideas with
• Someone who can commiserate with you on shared struggles

Impostor Syndrome

The topic of impostor syndrome comes up fairly often in our industry. I have often faced this, especially when starting a new company. Artists often feel impostors syndrome as well (look at all these famous artists I’m comparing myself too, how can I possibly create something new that would be as good as that?).

Despite outward success and a set of successful work, you still feel like a fraud. These feelings are natural and many people have them, so take some comfort in that. Allow yourself to fail and feel uncomfortable and exposed to the challenge. You can overcome self-doubt and this feeling by being open and authentic, and sharing your experience with others.

We often only see others’ successes, but know that in the background they have had setbacks too (rejected conference proposals, causing a production outage at work, etc.). Find colleagues you can celebrate success with and share each other's failures. Remember to be open and authentic, no one is perfect.

Above all, find what works for you. Don’t assume that what someone else does will make you happy or help you overcome these feelings.

Embrace Discomfort

Artists, like us, suffer rejection quite often but you need to know you are good, your creation is worthwhile, and you will grow from experience.

For me, embracing discomfort is all about facing challenges you dislike and not taking the easy path. Tackle the complex problems, don’t "snack". Avoid low-effort, low impact work where possible. These tasks may feel rewarding to check off your list, but never tackling something of substance will hurt in the long run. Often, high effort, high impact tasks are the most challenging, which may result in failure or humiliation. Public humiliation is not ideal and hopefully you work in an environment that embraces failure. Still, we need to be comfortable putting ourselves out there (like artists do with paintings), taking criticism, and using it to improve.

Don’t try something because you think you might fail. There are a lot of cliques about failing, but at the core of it, many of them are true. You learn from mistakes, big and small. Make time to try hard things, get your hands dirty, and put your creations out in the world.

Part of embracing this sort of work and discomfort is making time for it.  Let’s discuss that in the next section.

Time Management Myths

I read this book recently about time management, Four Thousand Weeks, by Oliver Burkeman. It wasn’t really about time management, as much as a philosophical look at how much time we have in our lives. Four thousand weeks (assuming you live to be 80)!

The book gets at the core of how we should value our time and less about trying to squeeze every last minute out of the day to be more productive. In some ways, our obsession with productivity is making us more miserable. Your to-do list will never be done. We think if we can finish this project, presentation, etc., then we’ll be done. You’re never done.

We need to give ourselves time to think, daydream, and use the skills I discussed earlier (being an active listener and increasing the sensitivity of your antenna).

Make time for unplanned work in your day. Most of us wake up with a to-do list, jump on meetings, and immediately get caught up in our workday with email and Slack messages. Try to set aside some time when you have nothing planned. In this unplanned time, think about a problem you may have been trying to solve recently that doesn’t need an immediate solution. We talked before about changing up your environment or medium; use this time to do that. Go for a walk or draw, anything that could help you escape the usual trappings of your work day.

Conclusion

As we discussed, staff+ engineering roles vary in scope and responsibility across companies. Engineers in staff+ roles often struggle with where to focus their attention and how to juggle responsibilities. By comparing some of the struggles of a staff+ engineer to that of an artist, we’ve identified a few practices that can improve our focus, attention, and effectiveness as engineers.

Here are a few actionable things you can take away and try yourself:

• Don’t try to micromanage every aspect of your day
  • Set aside 1-2 hours in the morning or afternoon (block your calendars) at least twice a week for unplanned work
• Build new relationships
  • Try to meet at least one new person in your company once a month
  • Join (or start) some form of peer mentoring program
• Work on improving active listening
  • Mediation is not for everyone, but find something that works for you (walks, quiet time, etc.)
  • Commit to spending 30 minutes a few times a week exploring this space to improve