October 20, 2023


I’ve been a software engineer for over 20 years, building systems for hundreds of millions of people. It’s been a wild ride and I’ve enjoyed every day of it (well, most days of it πŸ˜†).

Along the way, I’ve identified a set of career principles that guide my decision-making. I’ve been writing them down in my personal journal. Eventually I realized that they might be helpful to others, so I cleaned them up and published as a single post. The post you are reading right now is the most recent version of the principles.

Before I dive in, I’d like to start with a caveat. These principles have been useful to me, however people are unique and these principles may not be applicable to everyone. This is my personal experience and your mileage may vary. Some examples of what I mean:

  • Role – I’ve been a software engineer for most of my career. For other roles there may be other principles that are more important.
  • Individual Contributor - I was a people manager for two years, but for the rest of the time I’ve been an individual contributor (IC). An IC is someone who does not have direct reports.
  • Industry – I’ve spent my career in tech and finance. Perhaps other industries are different.
  • Region – I live and work in the U.S.
  • Privilege – I come from a place of privilege (middle-aged, white, man, raised middle-class, etc.). Principles might be different for folks in under-represented groups.

Each section describes one principle. The sections are sorted approximately in order of importance. Below is a list of the principles, with relative links to bring you directly to each one.

This post will be a work in progress. If you have any comments or questions and would like to share, by all means let me know. Thank you for reading, and enjoy!


Persistence is key

If you remember one thing from this document, let it be this one.

Success doesn’t always happen on the first try. Sometimes you pick the wrong solution, or you don’t execute well enough, or something happens that is out of your control. All of these things might happen (and have happened to me). This is ok, it is a part of life.

  • “Never confuse a single defeat with a final defeat."
    • F. Scott Fitzgerald

Try to figure out why the failure occurred, learn from it, adjust your approach, and then…try again. If anything, you’ll have more knowledge about the problem space and your chance of success will be higher.


Fall into the pit of success

I think of this principle as the following:

  • Position yourself in such a way that success is nearly inevitable.

What do I mean by “position yourself”? This could mean changing either the tasks that you are working on, the role you are in, the tools you use, the team you are a member of, or your employer. I often encountered highlights in my career just after re-positioning myself or my surroundings. Like switching a role or switching a team. Don’t be afraid to re-position if you feel that it will increase your chances of success. You are probably correct.

Another way to look at this:

  • What small change can I make to my environment to make my desired outcome achievable?

Sometimes all it takes is a simple change to your surroundings to unlock your potential.

This doesn’t mean that success is guaranteed. It also doesn’t mean that there won’t be hard work. But I feel that positioning yourself correctly is a key part of success.


Choose experiences that energize you

A common career question I hear is “where do you want to be in 5 years?”

I’ll be honest - I struggle answering this question. I really have no idea “where I want to be”. However, I find it easier to identify what types of activities and experiences keep me most engaged at work. Tasks where I often find myself “in the zone”.

Given this, I reframe the original question as the following:

  • Which experiences will energize you over the next 5 years?

This helps me decide what next steps I might want to take in my career.

When I’m energized by my workload, I’m happier and more successful. This is a sign that I’m in a role that’s right for me. The opposite is also true - if I’m not feeling engaged or energized, this is a signal that I might need to make a change in role or position.


Build a brick wall

Another way to frame the above principle is to “build a brick wall” 🧱.

Early in my career, I was focused on being the best software engineer I could possibly be. An expert in the field. Every career step I took was in support of that path.

Nowadays, I’m looking for varied experiences. Things outside of that original path. Presentations, coordination across teams, planning events, temporary v-teams, social media, etc. I see these experiences as individual bricks to place on my career wall.

Why the change in philosophy? At first I was just looking to try new things that are fun and interesting. But along the way I’ve noticed that I’m learning new tools that I can put in my career toolbox.


You’re not alone, find people in your shoes

It’s worthwhile to build up a network of peers in your company and industry. This network can help in various ways – you can learn from each other, help each other through difficulties, collaborate on projects, share successes and failures, provide job opportunities, etc.

I sometimes fall into the trap of thinking “nobody else on earth is experiencing this thing that’s happening to me.” The reality is that there are usually many folks experiencing the same things. The trick is finding some of these folks and comparing notes.

How do you find folks? Social media is one way. Every social media platform is different, and my general advice is to pick the one that best fits your personality and then be consistent with your engagement. Offline pursuits are also helpful here – both internal resource groups, as well as external hobbies. Basically anything where you are spending time with others on a subject that you care about and enjoy. And the subject doesn’t really need to be work-related, it can be anything.

A recent example: my role at work shifted from software engineering tasks (coding, data analysis, etc.) to what I would consider “non-software engineering tasks” (recruiting, driving meetings, building consensus on process, etc). I was very engaged in these tasks, however I no longer felt like a Software Engineer, and I struggled to find a vocabulary to describe this new role I was in. Then one day I had a chat with someone in an adjacent org and mentioned the situation, and discovered they were in the exact same situation. It was AMAZING to have someone to compare notes with and confide in. This discovery will probably result in us meeting periodically to compare notes and help each other.


Have a mix of “Preparation” and “Highlight” years

When I look back at the years of my career, each of those years can be classified as either a “preparation” year or a “highlight” year:

  • Preparation year – you are laying groundwork for a highlight year, either by learning new skills, starting on a new team or in a new company, or putting together some building blocks (tools/code/libraries/analyses/etc.) that will come in handy later. Preparation years sometimes feel difficult. You might feel like you aren’t providing enough value to the business. Don’t worry, this hard work will pay off soon. You are preparing for your highlight.
  • Highlight year - an opportunity has appeared where you can utilize prior preparation to create a highlight! Highlights can be delivering a high-value project, getting a promotion, or something else that is just plain awesome. All of that hard work in the preparation years has now paid off!

When I look back at my Microsoft career, I’ve had four major project-related highlights. And in between those I’ve had years where I was learning or otherwise positioning myself for an upcoming highlight.

It’s natural to have a mix of both. Not every year will be a highlight. But make sure you occasionally experience the highlights.

Looking back at my career highlights, what are the common themes for all of them?

  • Opportunity - a large opportunity appears (huge challenge/problem/business need)
  • Positioning - I’m positioned near it (right team/role)
  • Preparation - I’m prepared for it (skills/tools)
  • Subject Matter Expertise - I’m a SME on the topic or the project allows me to become one (perf, network, data analysis/viz)
  • Clarity - I have clarity about the “right path” and feel strongly about that path
  • Autonomy - I have autonomy to explore that path and lead folks down it
  • Work Product - my “work product” is being directly used (toolset, analysis, etc)
  • Pressure - there’s high pressure, and almost feels hectic at times


Test your assumptions

This principle manifests itself in several ways, but the general idea is:

  • If you are making an assumption, be sure to verify the assumption with tests or observations.

The earliest example of this I can remember from my career is unit testing. Prior to unit testing, I was always nervous about refactoring code, and I made assumptions about the correctness of the code based on code review and manually testing. Once I started writing unit tests, refactoring became way easier, and I found a ton of problems with my initial assumptions. To this day, unit testing is one of the subjects that fundamentally changed how I approach software engineering.

A more recent example of this is data engineering. Let’s say I’m evaluating a new data source for visualization, and I find a column in a data table named “US State”. My initial assumption would be “Oh, this will have data for all 50 U.S. States”. It’s important to test that assumption. Many times I find that my assumption is wrong – either some data is missing, or some data is duplicated, or I misunderstood the purpose of the column, or something else. Often when I am starting a new data project, the first thing I’ll do is create visualizations that test my assumptions about the data. Besides initially verifying my assumptions, these visualizations help when issues arise with a data source. I can send a screenshot of the chart and say, “this data doesn’t look right, can we investigate?”

This principle applies to non-technical situations, too. One example of this is when you are working on a team across multiple cultures. Don’t assume that you fully understand the nuances of folks that live and work in cultures that you are unfamiliar with. Communication styles and behaviors may be slightly different. Ask questions and replace assumption with curiosity to ensure that communication is effective.

One a similar note – don’t be afraid to ask questions. If you are in a meeting or on an email thread, and you are making an assumption but you’re not quite sure about it – ask a question. There’s a good chance that other folks are wondering the same thing you are. Also if you are a more senior person in the group, it’s good to ask questions to set the right example for the entire team.


Start with the unanswered questions

When you are working on a new project, sometimes it’s difficult to figure out where to begin.

For example, let’s say you’re building a full-stack application. Do you start by building out a backend database? Or do you instead work on the frontend user interface? You’ve got choices.

I like to start projects by focusing on the unanswered questions first. These are things like “will a SQL database support the size of data we expect to receive?” or “does this user interface library contain features to support our user scenarios?”

Why do it this way? I like this approach because it tells you as soon as possible if an idea won’t work, which in turn minimizes the amount of time wasted. The alternative is spending large amounts of time on an idea that ultimately will not be successful. You might learn some things along the way, but you won’t deliver a working project.


Document the important things

This is something I’ve started doing more recently in my career. At first it feels like too much time and energy to stop what I am doing and write a document, but later I find that it provides so much value. It’s something you need to try once to really understand fully.

Some situations where I’ve found this to be useful:

  • Documenting an existing system. There are some software systems that I get asked questions about a lot, and it’s really great to be able to say “first read this document I wrote, and then if you have more questions, please ask.” It helps save me time and provides information to the folks that need it.
  • Gaining consensus on a plan. Sometimes there is a path forward on a project, and it would help to get consensus from the team on the plan. Writing a document and letting folks comment on it is a great way to gain consensus.
  • Learning about a topic. I often will write something as I’m trying to learn it. I like the saying – “you don’t really know a topic until you can teach it.”
  • Documenting experience. For example, documenting principles of being an Individual Contributor. 😊
  • Taking notes. Sometimes it’s good to just take personal notes for later. I have a OneNote notebook that I’ve been using for over 10 years. I refer back to notes all the time.

I urge everyone to create a few documents on topics they care about. You might be surprised at how useful these documents become.


Know your tools

Software engineering requires a lot of tools - IDEs, programming languages, version control, graphical tools, etc. All of these tools assist you in solving your scenarios and problems.

Here’s the trick though - if you don’t know how your tools work, you’ll spend too much time fighting with the tools themselves, instead of solving your customer problems. That’s why I like to spend a small % of my time dedicated to learning.

When do I decide to spend time learning? In some cases, the team or organization has mandated use of a tool (build system, programming language, etc.), and I have no choice but to learn it. In other cases, I’ll be using a toolset on my own, and I’ll notice that it has a downside that may be fixed by migrating to something else. In either case I’ll pause what I’m working on and shift my focus to learning.

Here are a few examples:

  • Power BI - prior to learning Power BI, I had been building reports at work using things like JS and D3, and hosting them on my own server. The analyses were going well, but I was spending too much time on things like server maintenance, authentication, and report look-and-feel. I just wanted to focus on the analyses instead. I had heard that Power BI was getting popular within the company and I decided to give it a try. I’m glad I did - since then I’ve been using it successfully for our team’s analyses.
  • Affinity Designer - I like to make comics. For a while I used a raster-based tool for drawing the Threddy comics. The problem, though, was that if I wanted to scale the characters larger or smaller, the raster drawings wouldn’t scale well and I would need to redraw them. I had heard that a vector-based approach might fix this. During a long flight to China I decided to practice using Affinity Designer, which is a popular vector drawing tool. By the end of the flight I had learned enough about the software to be able to use it for the comics. And ever since then I’ve been using only Affinity Designer for Threddy comics.

If you find yourself thinking “if I learn tool XYZ it will be good for my project or career”, you’re probably right. Spend that time on learning and you won’t regret it.


Move to adjacent roles

You may love your current role, but at some point you will reach a moment where it’s time for a change. Maybe a move to a different team, or a different role, or a different company or career.

When making these moves, I like to pick an adjacent role. What does this mean? I try to pick something where my current experience will be useful and help me in the new role, but the new role has new tasks and activities that I can learn and grow with. The adjacency provides familiarity that helps me learn and grow into the new role.

An example of this: I was on a team doing data analysis and performance engineering. For my next role, I chose a team where I could continue doing these types of tasks, however it was for a new product, in a new org, with different strategies for how we approached the tasks. I was able to lean on my past experience, while learning new things and growing.


Try things that scare you

I am a risk-averse person. I like to stay in my comfort zone. It is safe there.

This is Ok at times, but if I stay there always, I’ll never learn or experience new things. Occasionally I like to try things that scare me.

An example of this is when I was invited to give a talk at Microsoft Ignite 2019. I was invited in early 2019, and I spent the entire year worrying about it until the conference in the Fall. Would I fail? Would people not like it? What if I tripped off the stage and broke something? Despite all these worries, I got up on stage anyways and gave what I think was an acceptable talk. And I’m glad I did – it is an experience I will never forget and I consider it to be one of my career highlights.


Trust your instincts

A few times during my career I’ve found myself in a position where there was a status quo, and I felt strongly that it should be changed (and I had the skill and power to change it). During these times, I chose to trust my instincts and attempt to make a change and follow the path I thought was correct. So far, these have been good decisions.

I will often ask permission in these cases. But not always. Sometimes you need to put your head down, crank out a solution, then come up for air and show it to folks (and apologize later if needed). It’s like that saying – it’s easier to ask for forgiveness than to ask for permission. 😊

Use this sparingly and wisely. Weigh the risks/rewards, and if it makes sense to try it, go for it. There is higher risk here, but the reward is wonderful.


Life is not a competition

In our always-connected online lives, we often see peers celebrating successes. New jobs, promotions, etc. It’s wonderful seeing these successes and joining in the celebration.

But sometimes it’s difficult to not be jealous of those successes. Why haven’t I achieved that yet? Why only them? When will I have similar success?

Avoid this line of thinking. Don’t compare against your peers - compare against your past self. Are you learning and growing? Are you farther along now then you were last year and last decade? That’s all that matters.


Know when to log out

Working hard is great, but it’s equally important to know when to log out. Work/life balance is critical for maintaining a successful, happy, and healthy life. Don’t be afraid to take breaks. Enjoy life. The work will be here when you return.