Within the last 12 months, I’ve gone from aimless to an SRE at Stack Overflow, my dream job. I was awarded the Microsoft MVP award and launched my first self-published book.

It’s easy to assume these accomplishments were all part of a plan. Truth be told, they weren’t. Instead they are results. Results of consistent and sustained effort.

What most don’t know is, I wrote You’re an Engineer, Be an Engineer to hold myself publicly accountable. It was a farewell letter to my past self, written while the version of myself that fell into complacency was still within sight.

Deciding to take back the driver’s seat of my career was only the first step. Since then I’ve been building, brick by painstaking brick, the evidence of a new identity.

I’ve become an engineer again, learning for the sake of learning. And have transformed a job back into a career.

Here’s what I’ve learned.

Listen with Polly

Your employer isn’t your success coach

You have a job. And you have a career. They are different things. What does this mean?

It means I don’t limit my learning to what’s applicable to my job. I find ways to demonstrate how the skills I want to acquire benefit my employer. Demonstrate is the keyword. I know I can only sell results, not ideas.

It also means I don’t expect my employer to design my career’s future. If my employer offers education programs, I’ll use them. But I do not expect nor depend on them.

What if there is no overlap between what I want and what benefits my employer?

You have a few choices. Outside of work, acquire the skills that secure a job with more alignment. Or work harder and smarter to provide enough slack in your workday to invest in your future.

“Change your job or change jobs” - @concentrateddon

When you are contemplating your future ask:

  • What do I enjoy?
  • What do I want to learn?
  • Where do I want my career to go?

Do not use your job to filter what you learn.

Establish a Habit of Growth

Each day left me defeated. Yet again, there was no time left for me. No time left to get better. No room left in the day to improve my craft.

I was a scavenger of time. Grabbing 5 minutes here and 10 minutes there. Within those reclaimed minutes I’d frantically pillage my social media feeds, wishlists, and bookmarks searching for the best use of my time. Paralyzed by context switching, I realized there just isn’t enough time in the day. All I could do was shallowly skim the surface of knowledge.

I knew something was missing. And I knew it would require sacrifice. What was missing was a habit of growth and dedicated time each day for myself. I have a full-time job and a family. I couldn’t take time from either of them. I had to take time from myself.

That’s why, before much of the world is awake, I’m up. I use this time to write, read, and to think. If there is a secret to the success I’ve had over the last 12 months, it’s making a daily investment in myself by taking time just for me.

You cannot make time. You can only take time. It’s a matter of choice. As with money, you must pay yourself first. If you want enough time to pursue what’s most important, schedule time with yourself. Establish a habit of growth and put the investment of your future self on autopay.

How would I recommend you establish a habit of growth?

The first problem is establishing the habit. For that, I recommend leveraging “The Four Laws of Habit Change”, which comes from the book Atomic Habits by James Clear.

Next, you’ll want to optimize that time with deep work to get more done in less time. Zero distractions are permitted. For that, I recommend a book called Deep Work by Cal Newport.

For a brief introduction check out The Complete Guide to Deep Work.

Consistency is your deposit. Growth is the interest you’re rewarded with.

Your future needs a direction, not an operating manual

As I sought to redefine my career aspirations, I made a critical mistake. I attempted to create a step by step plan that would ensure success. One that would guarantee I’d never fall back into the complacency I had stumbled into.

Here’s the thing, it didn’t work. I had over-engineered my own future…

Paralyzed by indecision. I felt stuck. Stuck in the suspended animation of my own mind. In motion, but not ever moving. Dreaming but never doing. I was overwhelmed by my thoughts, plans, and intentions. I mapped out my career for the next five years, listing out all of my required accomplishments and milestones.

It was a tortuous tactic. I had to constantly recalculate whenever circumstances changed or when I changed my mind, which happens often.

Then I found a cure. It turns out the future needs a direction not an operating manual. Instead of planning out every single step. I just needed a direction. It was a matter of motion vs. action. I overcame it by developing a bias toward action.

However, this doesn’t come without an internal struggle. You will second guess your decision. You will attempt to undermine yourself. A voice in your head will try and persuade you to undo all your work and to change course.

Commit. Hold the line. Reassess later.


Decide through action

When I’m focused I block everything else out. That’s part of the reason I loved writing my first book. Nothing else mattered. Every task that wasn’t contributing to the book was a distraction.

But there was a trap patiently waiting for me in the transition of tasks. In the void between projects, is when I become the most vulnerable. I often fall into a futuristic dream. Lining up milestones of achievement and slipping into overthinking everything.

If I wait long enough I go back to over engineering my future. Stuck in what I call the dreamer’s illusion. Planning makes you think you’re progressing but it’s an illusion. How I combat this is to continue to take action. I know it’s a mistake to think I can chart a map for my life. My life is a story that hasn’t been told, and therefore something I must explore.

“All direction comes from doing” — @jackbutcher

Direction is required to ignite action. And action is required to fuel direction. Constrain your direction to the point that it propels you into action.

What I mean by this is, if you cannot plan out a month, plan a week. And if you cannot plan a week, plan a day.

I work in sprints. And make the feedback loop short. Two weeks is a great starting point, but I aim for a month. A month is a healthy commitment. It’s long enough to get something meaningful done, like passing an exam. But not so long that it prevents me from pivoting when necessary.

Month > Week > Day

Write 3 Chapters > Write 1 Chapter > Write Chapter 1 Outline

Pass Exam > Watch Video Course > Watch 1 Hour

If you’re struggling with the dichotomy of persevere vs pivot, read my two favorite posts from @TinkeredThinker.


Action and direction are the connecting points of progress.

Learn enough to practice, practice until you understand

Information is abundant. And the skills I wanted to develop were moving targets. Combined, these facts make the perfect conditions for analysis paralysis. I had the time. I knew what I wanted to learn. Now I fought to figure out how.

Skill acquisition has no shortcuts. But there is an optimal method, deliberate practice. It’s easy to confuse skill acquisition with learning. Learning is what the doers scoff at. Why would I study? Why should I read that book? I’ll just do it, they say. That’s a fine way to make progress but it’s not an optimal way.

On the other hand you have the manual readers. They have tremendous amounts of knowledge. But they prefer to acquire knowledge instead of apply knowledge. Leaving them without experience.

What works best for me is to blend the two. It takes some creativity to design my own learning experience. But it’s also much more rewarding. I do this by finding the best resource available. I research it, I ask around for references, and I validate that reference with reviews.

After I’ve found a great resource, I dive in. I learn just enough that I can take what I learned and design a learning experiment for myself. I’m in the middle of doing this right now with Terraform. As I watched Terraform on Azure: Infrastructure as Code from Scratch on CloudSkills I started writing code examples of what I learned.

Having finished that course, I’m now reading Terraform Up and Running 2nd Edition. Guess what? I’m doing the same thing. After each chapter I do the lab and then design my own application exercise. All of which is on GitHub.


You can’t change the world with an hour a day. But you can certainly change yourself.

Analysis paralysis, mastery, & decision making

Analysis paralysis. Few things are more frustrating to me. I’d have the will, the time, and the drive to get something done but I would fail to decide. A few flaws in my decision making process were assuming I needed to master each new skill and not knowing which skills I should be acquiring.

Mastery. It’s a worthy goal. However, it’s not viable to master everything. You must be extremely selective in the areas you pursue mastery. You also cannot limit your learning to the single or few items you wish to master. You need to strive for T shaped knowledge.

Only after you’ve become competent can you determine if mastery is worth pursuing.

Another way to disarm analysis paralysis is to spend adequate time determining which skills belong in your tool belt and which do not. You can’t answer that question without knowing the direction you are headed.

Once you’ve decided on a new technology to learn or skill to acquire, make competence your only goal. Become comfortable being unproductive. Learning isn’t productive. Accept it and give yourself the freedom to experiment and learn.


Enjoy the process

I had gone from a job I hated to a job I loved. Would it surprise you if I said it was the same job? It’s true. My title didn’t change. I did. Somewhere along the way, I fell in love with the process. And I was only able to do that after I let go of the outcomes.

Outcomes are empty. Each goal is simply a mile marker of life. Bringing only a moment of reward as you approach it in anticipation. Its reward quickly fades as you drive past and move on to the next thing. Goals, outcomes, and objectives serve a single purpose, to provide direction. There is no need to delay all your enjoyment until you’ve arrived at the flagpole of your goals. Enjoy the process instead.

Find work that in and of itself is the reward. To find such work, pause on your climb to whom you want to be. And ask “Who am I?”, dig deep enough that the reply is met with your own disbelief. Then build evidence of that version of you.

Learn to enjoy the process instead of the outcome.

Compete against yourself and no one else

I spent my twenties sprinting towards ideals. Ideals drawn about myself but based on the life of others. Doing so propelled me towards the direction I aimed for. But come judgment day, I’d always fall short.

In comparison, I wouldn’t measure up to who they were. At least not the version of them I held in my mind. The metrics of my own success were woefully inaccurate. After all, how could I expect an accurate measurement by measuring the processes running on another system?

However, ignoring everyone puts you in a single player game. One without the narrative of others. You miss the opportunity to stand on the shoulders of giants. Maximize your growth by joining the open and infinite game of life. Look upon others to adjust your sights, dreams, and ambitions.

Compare only to who you were yesterday. They are the compass, you are the ship. The only thing that matters is the distance you’ve traveled.

Comparison is a killjoy. It demotivates, deflates, and disengages by robbing you of the satisfaction you deserve. Compare only to who you were yesterday.

Finding Work that Feels Like Play

Nothing stops me. I wake up every morning at 4:30 am and write. Sometimes I write hundreds of words and other times I write a single sentence. One I’ve obsessed over for an hour. It’s not the finished product that drives me. It’s the process.

It looks like work to others but feels like play to me. I have awoken the playful child within. The one who does for the sake of doing. I write to write. I write for the joy of writing. I write, simply, because I must.

It’s time to start building the evidence for another new identity. The evidence of a writer.

What’s Next?

Technology that once kept us connected now keeps us always-on. Without the walls and exit signs of a physical office we are left without the boundaries. Boundaries that kept our work confined to a set number of hours per day.

People need a kill switch. An andon cord. Some way to turn off the always-on chaos that’s been transplanted into the digital world. Higher productivity is found in less screen time, not more.

Attention matters more than time. And most people don’t realize that.

It’s said that you should write the book you want to read. Well, if that’s true what I most need is a way to unsubscribe. And that’s the idea I’ll be exploring in my next book.

As I learn to live in the digital world without being consumed by it I’ll be sharing my thoughts, insights, and progress.

If you’d like to learn more, check out:

Read: Detaching from Distraction

Read: The Digital Declutter

Listen to: Perspectives in Tech: Digital minimalism

When I need to escape the attention economy I disappear from social media. But I’m always writing.