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The Wonderful Life Problem (TWLP): Dealing with Disappointments in our Work Lives

July 23, 2024 By Eyvonne Leave a Comment

In the classic Christmas film “It’s a Wonderful Life”, the iconic Jimmy Steward plays George Bailey, a struggling businessman and father who sacrifices his own ambitions for the good of his family and their small town of Bedford Falls. In deep despair because of his perceived failures, George contemplates suicide. Through a series of flashbacks prompted by the hapless angel Clarence, George glimpses the world absent his influence. He sees how his actions – from saving his younger brother to helping his neighbors – dramatically alter the world for the better. Realizing his impact, George chooses to live. It’s the feel-good Christmas movie by which all other Christmas movies are judged.

For the evidence based technologist, our individual careers present an interesting challenge. While we can make educated plans for our careers by reading and studying others, we have no way to re-run the experiment of our lives. Unlike George Bailey, we never get to see the outcome of our road not taken. Likewise, we cannot see the collective impact of our presence day-to-day.

There are some things we can measure. We can measure projects completed, pull requests submitted, presentations made, and tickets closed. Yet, there are times that our best efforts don’t accomplish all that we want them to. Maybe we complete the migration, but with more downtime than expected. Or the startup we join and toil for doesn’t survive. Or the technology we expect to become industry standard is subsumed by a similar but less elegant competitor. We do all that we can, yet there are outages, bugs, inefficiencies, organizational changes, and economic realities. The world is subject to entropy and decay and we feel like the proverbial Sysiphus forever pushing the boulder up a hill.

I once had a leader say that technologists are eternal optimists. When I looked at him with disbelief, he explained: For the most part, we believe that the fix for the current outage is just around the corner, that we’re a few lines of code away from completing the project, or that the implementation will go smoothly and be done within a tiny outage window. He chose to frame the technologist’s tendency to underestimate time and difficulty as optimism. The more I observe incredible technical talent, the more I agree with his assessment.

Our frustrations come not because we lack impact, or because we didn’t apply significant effort or skill, but because we cannot seem to realize the perfect outcomes we envision: the reality of the result of our efforts does not align with the imagined outcomes we expect. Or even worse, the technology we thought was going to change the world does – with many unintended negative consequences.

Most of our careers, and indeed our lives, exist not in magical high-functioning times, or in the deep despair of failure, but in the liminal mundane day-to-day. Here the project almost works, we make progress in the midst of setbacks, we move forward but not quickly enough. Our best efforts often fall short of the perfect outcome we imagine. We lament the imperfection around us while at the same time we cannot accurately gauge the impact our efforts are having. I’ve come to think of this as “The Wonderful Life” problem.

What then, is the remedy? How do we move forward when the most certain outcome, at best, falls short of what we envision?

First, make note of the great things. I have experienced times when my professional life seemed like magic: the team was functioning at a high level, we were accomplishing goals, having fun, and making profound and incredible progress. During those times, take note. Remember them and know they are precious and fleeting. At best, you can create the conditions in which magic can happen. You cannot force it to happen. Enjoy great times with gratitude. They won’t last forever.

Second, learn from the challenging times. Are there things you could have done differently? Were there circumstances, technical, organizational, or cultural, you did not see at the time? Was it merely bad timing? Were circumstances beyond your control? Learn from the things you could have done differently, accept realities outside of your control. Improve and adjust as you learn. Remember, challenging times won’t last forever.

Lastly, understand the mindset of those who’ve demonstrated greatness in their own careers. Michael Jordan famously said, “I’ve missed more than 9,000 shots in my career. I’ve lost almost 300 games. Twenty-six times I’ve been trusted to take the game-winning shot and missed. I’ve failed over and over and over again in my life. And that is why I succeed.” Even at the pinnacle of success, the greats experience failure. Likewise, we will survey our work and see missteps, outages, and breeches.

Most of us will have times when we experience “The Wonderful Life Problem” – we’ll look around in moments of disappointment and difficulty and wonder if our work has mattered. Ultimately, though, our introspective questions affirm our impact. Those who desire to do great work, do great work. We’ll go further, faster, as we accept TWLP as a natural consequence of caring about our work, and as evidence of our meaningful contribution.

The Second Act: Thriving as an Experienced Technologist

July 5, 2024 By Eyvonne 1 Comment

When people embark on a tech career, there’s a plethora of available advice – some good and some terrible. Most advice centers around getting training and certification, developing hands-on experience, and finding a role in which you can grow. This guidance is helpful for the first decade or more of one’s career. As I once told an aspiring young developer, “No experience in tech is bad experience” in the early years.

At a certain point, though, even the most eager and talented technologist reaches a boundary by merely learning more. Even though there’s always more to learn and explore, ever-deepening technical capability without scaling your knowledge through others will meet a law of diminishing returns. Your ability to grow and learn as an individual no longer has the same outsized impact on your career it once had. Eventually, you no longer get more opportunities because you know more than the next person.

And so, what are the options? What change is necessary to grow in effectiveness and opportunity? Some choose management as their path to growth – they formally step into a leadership role in their organization. This will require a step back from daily deep technical work and will demand entirely new skills. Formal management roles, often unpalatable for deeply technical people, are not the only option. The other path will require the technical individual contributor to transform into a technical leader.

Many people wrongly believe that leadership requires a title, positional authority, and the commiserate ability to hire, fire, and make salary decisions for others. At its core, however, leadership is the ability to influence people to move in a particular direction. A technologist who profoundly understands the tech and can marshal people becomes a powerful organizational asset and will unlock career opportunities previously unimaginable.

Think of the technical people you admire — Kelsey Hightower is a great example. For all of his technical knowledge and hard work, his work in the community — public speaking, mentoring, human interaction — has elevated his career. As you catalog the people you admire, you’ll realize they all exhibit this trait. You know their names precisely because they’ve worked to influence and grow others.

Some of you will be nonplussed by the idea of engaging broadly and focusing on other people after a decade or more of deep technical work on yourself. You may tell yourself that you’re not good at it, it’s not what you want to do, or you “just don’t like people.” Your life and career are your own. However, you will limit your career opportunities as an expert-level technologist if you don’t learn to lead and develop others.

There’s no single way to scale your knowledge and experience — and you don’t have to be an extreme extrovert. You can:

Write articles or blog posts or build a formal or informal community of practice at your job.
Join and then lead a community user group, attend conferences, and organize a meetup.
Seek out peers and schedule one-to-one conversations to learn and share knowledge.
Build documentation and then share it broadly within your company.
Write a book or develop training content.
Develop and maintain tools that codify your knowledge into repeatable processes.
Identify the areas where you have significant expertise and invite colleagues to shadow, reverse shadow, and then deliver by themselves.

I’ve personally seen technologists apply one or more of these strategies to become technical leaders and enable thousands of other engineers. These activities will scale your expertise and cement you as an expert of experts.

The work we want

August 30, 2022 By Eyvonne 1 Comment

I’ve observed a trend in technical people.

There’s the work that we’re good at. Then, there’s the work that we love. In a world that is fair and beautiful, the Venn diagrams of these two categories complete a perfect circle.

Alas, we do not live in a perfect world.

For the driven, early career goals focus on expanding our competence circle. Engineers need skills, they need to demonstrate those skills, they need to earn their spot on the team, and they need to establish themselves. For a long time, a decade or two even, the acquisition of competence provides enough positive feedback to adequately satisfy both circles, competence leads to fulfillment. For some, this dynamic never shifts. They continue to dive deep, grow, learn ever-deepening skills, branch into new tech, and find satisfaction in this stream of work.

For others, technical competence follows a law of diminishing returns. They acquire skills such that they can do work in minutes and hours that take others days and weeks. At the same time, the work loses its fascination. It becomes, dare I say, boring. These skilled engineers work with such efficiency they become the de-facto owner of the work. They find themselves being the unenviable do-er of work they no longer find interesting.

Some accept their fate, they lean into their skills, continue to make quick work of tasks that are hard for everyone else, and become the “person” for that skill. For many, this is the path of least resistance. The work comes easily, they can do it in their sleep, they receive accolades, and they’re generally admired by junior people. The risks here are, at first, subtle but become more pronounced over time. First, there’s the boredom. The work isn’t interesting anymore. There’s also the risk that, over time, the particular skills have less value. The longer one identifies with a particular skillset — without substantive growth — the more difficult it becomes to change. One can find themselves in command of very specialized skills that have diminishing market value.

There are other options. For example, as an engineer you can resist the urge to become the de-facto owner of anything. As you develop deep skills, refuse to be the only person who owns that skill. The next time you get a request to “do your thing”, refuse to do it alone. Invite someone along by saying something like, “I think Michelle can help with this one. Why don’t we let her own the deliverable and I’ll be there to support her the whole time?” Note, that you’re not saying no to the request. Assuming Michelle is a bit junior, needs to learn the skills you have, and has the resources to work alongside you, it’s a win for everyone.

You’ll no longer be the only person who can complete the task, Michelle grows in her skills, and the business is no longer single-threaded. This takes discipline. The first time you bring along a peer, it will be more work for you. You’ll have to improve your processes and your documentation. You’ll have to iron out some of your personal quirks. In the long run, you’ll get to accomplish more and won’t be shackled to a particular skill.

To grow in your career, you will eventually reach the point at which individual improvement is no longer enough. Even if you remain an individual contributor, you must learn to make the people and systems around you better. Anyone who’s read “The Phoenix Project” knows the peril a Brent — the smart condescending, information-hoarding engineer — brings to an organization. It feels good to be the one with all the answers, until it doesn’t.

As you get better at enabling your peers, you’ll have opportunities to do more interesting things. Once you develop a pattern for learning hard things and teaching hard things, you will be more valuable — not less. You’ll have opportunities to explore and broaden your horizons. You won’t get trapped underneath the weight of your own competence.

The world of tech has no end. The depth and breadth are unquantifiable in every direction. The opportunities for gainful employment, however, are more nuanced. We each approach a unique confluence of technical, economic, business, geographic, and personal factors. For me, the clarifying question of my career has always been, “How can I help?” This personality trait has been fortuitous for me for a few reasons. First, it’s caused me to pursue work that has objective value to my employer and my team — for work to be helpful, it must be valuable. Also, when I know I’ve been helpful, the work feels meaningful. It’s made me more willing to shift my technical focus over time as the needs of my team, my employer, and the industry continue to change.

Your clarifying question may be different. Regardless, it’s important to understand what motivates you, what work you are great at, what work fulfills you, and what work will be needed in the future.

Work and Values: Why it matters

August 16, 2022 By Eyvonne 1 Comment

A few weeks ago, my team had our first in-person offsite. It’s inexplicably wonderful to meet people in three dimensions whom you’ve come to know in two. Some people closely matched the model I had constructed for them in my imagination. Others were surprising, taller or shorter than expected, unique in their profile, or warmer in person than at a distance.

Before coming together, our manager asked us to complete a Values Exercise from the wonderful Brené Brown. The accompanying podcast is helpful. On its face, the exercise sounds simple: review the list of common values on page 3 and circle the ones that resonate with you. Then, narrow the list down to two core values, the qualities you lean on when life gets hard — the source from which all your other values flow.

If you want to know more about the exercise, listen to the podcast or read Brené’s Book, Dare to Lead. I won’t attempt to improve on her explanations. Instead, I want to talk about the impact of this work, both on me personally and on our team.

The act of thinking through your personal values is powerful enough. It causes you to ask hard questions. Why do I do what I do? What drives me? When I’m offended or wounded, when one of my core values is being disregarded? For example, competence, love, integrity, trust, and excellence are all important values to me. But are they core? Which values most deeply influence my decisions and behaviors? Ultimately, I concluded my core values are wisdom and faith. I love books because I deeply desire wisdom. I talk about books because great wisdom demands to be shared.

Most of the other values I hold roll up under faith. This value has been through the wringer in the last few years but even as institutions and people have disappointed me, I cannot escape the centrality of faith to my values and actions. Your values most certainly will be different, and may come from a different place. The power of the exercise stems from understanding your values and how you live them out.

Brené dives into what it means to live into your values followed by the challenges that arise when we live outside of them. We may sense that something is off, feel deflated or tired, lose our motivation, or dread daily activities. Through this exercise I realized pandemic life changed my routines which impacted how I was living into my values. I was no longer dedicating the time to prayer, meditation, and journaling as I once had. The loss of those reflective moments not only affected my connection with my faith, they removed the opportunity for the wisdom of the day to settle and crystallize in my mind.

Up until now, this sounds more like personal self reflection and therapy than a work exercise. What do our values have to do with our day jobs? It’s a good and important question. When we understand and lean into our values we’re more energized in our work. Our boundaries give us built-in guardrails to help us define the work that matters most.

What does this have to do with our work lives?

Knowing our own values does indeed help us navigate our careers. If you value helping, you will likely gravitate toward projects you believe will benefit a large number of people. When you know your values and chose work that supports them, you will be energized and intrinsically motivated. Conversely, if you have the opportunity to work on a project that doesn’t seem to help anyone, you may decline. It’s not a judgement of the project, it’s an expression of your values.

Don’t mistake me here. Our work often includes tasks that are not energizing. Boring work must be done and every tasks will not fulfill our deepest personal goals. However, when we get the chance, we can look for opportunities that fuel us, lean into them, and decline ones that don’t. Over time, we will develop a portfolio of meaningful work which aligns with our values and can become a true expression of ourselves.

How does this help a team

If you’re engaged in any kind of knowledge work, your job requires a degree of creativity, critical thinking, and collaboration. Typically, this also requires you work well with a team. The more you know your team’s values, the more you can lean into their strengths and energize them at the same time.

Consider a situation in which one of your team members values curiosity. As you work on a problem, you discover a system that isn’t working as intended. You’ve checked documentation, you’ve run a few tests and the output makes no sense. Instead of solving it alone, you share your observations with your curious coworker. Their eyes light up, their words come quickly, and they rattle off a series of tests that could be run to explore more deeply. Because they’re energized by curiosity, you have a willing ally in solving your problem. You are not burdening your coworker, you’re providing an opportunity for them to express what they most deeply value.

In conclusion

The last few years have been a struggle on a global scale. We’ve all been required to adjust. Some of those adjustments became permanent, others continue to morph and change with our world. It’s entirely possible that, for many of us, our values have shifted as our world has changed around us. As the dust settles, and we work to build a new way forward, defining our values can help shape our decisions and actions. We are all building our lives, our careers, our futures. We all ought to build in the direction we ultimately want to go.

Change – Personal, Professional, Organizational

August 3, 2022 By Eyvonne 2 Comments

Over the past several years, my career has undergone a metamorphosis. In the early days, I was convinced that my best contributions to work would be learning to solve hard problems, making things work, being helpful and understanding the systems everyone needed to do their jobs, making them better, and solving technical puzzles. I built an identity around solving problems, around understanding technology, around filling gaps in capabilities and knowledge and finding ways to make myself valuable. In many ways, I still do these things, but it manifests differently now.

Several years ago, I made a job change. The divisional leader had big dreams. He was leading change at his organization, he wanted to do things differently and he had a clearly articulated vision for where he wanted to go. I was excited.

However, when I joined the organization, it became clear that the behaviors inside the company did not align with the vision the leader espoused. The disconnect between the stated vision and the team’s behavior clearly signaled impending failure. One fateful day, I met with my leader and tried to discuss the ways in which lower level leaders were thwarting the vision. For example, one cannot say they want a “self-healing network” (whatever that means) and continue to demand the deployment of static routes (I digress).

My feedback was not well received. My divisional leader never spoke to me again and I found new opportunities and moved on.

We often don’t realize we’re in the middle of a sea change as it’s happening. Personal transformation becomes more clear in hindsight and we understand the narrative of our lives more as we look back. My toxic work experience birthed a new realization in me. While technical problems are often challenging and require tremendous skill and focus, toxic cultures and organizational structures will thwart even the most skilled engineers. I came to see I was wholly unprepared to address the cultural, organizational, and human components that were larger barriers to success.

As I struggled to make sense of my work world and find a better way, I discovered Westrum’s typology and began reading about effectives teams and organizational change. I became more concerned about influence and relational leadership and how I could effect change — for the good of my organization — without positional authority. I came to see that, in many circumstances, enterprise leaders listen to their vendors more than their employees.

I made the shift from enterprise network engineering to vendor customer engineering — leaning on over a decade solving real problems with technology in the enterprise. I observed the different personalities of enterprise organizations, what makes some relatively healthy and what makes others relatively sick. And, I continued to ask the question, how can I help?

These days, I find myself less enamored with the latest technical implementation details. These are important. But I find my thinking drifts toward business problems. How do we gain clarity and agreement across an organization around what problems we are trying to solve? How do we most clearly articulate what we’re trying to accomplish to reduce confusion, rework, unneeded expense, and ultimate failure? How do we marry technology to business problems and solve them in better ways? What barriers, technical and non-technical, inhibit success?

Earlier in my career, these questions and answers seemed obvious, simple, and not nearly engaging enough. Now, I believe ignoring them, or assuming they’re obvious, is the single greatest reason for technology failure.

Where does all of this leave me? I came into my own as a network engineer and the network engineering community has been good to me. At my core, I still view IT infrastructure through a lens shaped by networking and infrastructure. At the same time, I’m more comfortable focusing less on deeply technical implementation details and more on the larger organizational barriers the impede progress. I’m concerned about healthy teams and psychological safety and how we, as fully embodied humans, work in sustainable and effective ways to solve real problems.