Differently Difficult

Tue, 29 Sep 2026 00:00:00 +0000

In AI Didn’t Make Programming Easier. It Just Made It Differently Difficult, Jeremy Osborn writes:

In other words, the hard part moves from recall (“How do I write this?”) to judgment (“Does this actually make sense?”). This shift from recall-based to judgment-based programming represents the fundamental cognitive transformation at the heart of AI-assisted development. Where traditional programming demanded that developers maintain vast internal libraries of syntax, patterns, and idioms, AI-enabled programming demands instead they maintain robust evaluative frameworks for assessing correctness, coherence, and appropriateness. The cognitive burden has not disappeared—it has relocated from retrieval to reasoning.

If You Make Software, You Should Self-Host Something

Mon, 21 Sep 2026 00:00:00 +0000

If you write software for your job, you probably write software that runs “in the cloud” somewhere that users access it over the internet.

Do you know how all of this works?

Probably not.

I don’t doubt your skills and knowledge as a developer. Software deployments are so complex, even small companies have teams dedicated to managing deployment and uptime.

Self-hosting something–anything–can teach you a lot about how software runs on the web. Knowledge that is essential to being an excellent engineer.

While your company might deploy with Kubernetes triggered by your git workflow, the fundamentals of how software runs on a computer aren’t that different between a small self-hosted VPS and a k8s deployment.

What Should You Self Host?

There are plenty of open source projects you can self-host these days. You can deploy any of these just to try them out and then tear down your server. Here are a few ideas:

Host your blog with a Caddy or NGINX server in front of it.
Run a kan instance for your own todo list.
Deploy a WordPress site on a VPS.
Deploy a MiniFlux RSS reader (you do use RSS, right?)
Run your own password manager with Vaultwarden.
Run Trivabble, a Scrabble-like game with no rules.

Where Should You Host?

Your own computer.
1. Start here. You already have this computer! Edit your local /etc/hosts file to give yourself a fun domain that you can access from your local system. But you write software for the web, right? So you should deploy to a virtual private server.
A Virtual Private Server
1. Find a provider of your choosing and deploy a small VPS. Get this connected to the internet and deploy an app. Find a free subdomain provider and connect it to your VPS.
A Computer at Home
1. If you have a spare computer you can keep running, set up a web server on it. This will require more tinkering and probably require a reverse proxy to expose it to the public internet.

How To Host?

Manual! You’ll learn the most this way. Follow the install instructions on the app you chose to get it up and running. Once you can log in, celebrate!
Automated(ish). YunoHost is a software for managing your server. Once you’ve done it manually, you’ll appreciate all the work that’s gone int to YunoHost. The docs help you understand how user roles work on the operating system and how applications are protected from reading one another’s data.

Self Host for Fun

You really don’t need to keep apps up and running. Remember that the point is to get something out here, break it, and learn to fix it. Along the way you’ll learn about unix systems, application processes, resource management, backups, downtime and application resiliance.

Try self-host something and have some fun.

Feeling Stuck at Work

Tue, 18 Mar 2025 00:00:00 +0000

Early in my career, a mentor cautioned me, “One day, you won’t feel like you’ve learned anything in weeks. Work will feel slow and difficult. " They said, “But that’s okay. Learning comes in spikes and plateaus.” I am paraphrasing, of course, but their observation has been accurate throughout my career.

I started at my current company three and a half years ago. In my roles, I’ve made technical contributions to multiple teams, guided single, impactful teams, and written the company’s architecture strategy.

A colleague recently observed that when we started working together, I doubted everything I did, and now, I have broad technical influence at the company. “What changed?” he asked.

I didn’t have a great answer then, but shortly after we chatted, he sent me Katie Sylor-Miller’s article, “The Staff+ Performance Cliff.”

“Yes!” I thought, “But it’s not a cliff.”

During growth periods, I learn something new daily. Each line of code I write is thrilling, every project plan has a broad impact, and I receive positive feedback every minute.

Plateaus come abruptly.

A plateau is a period of slowing down. Work seems more challenging and ambiguous, and my impact is unclear or absent. I often also experience a hit to my confidence because I feel less impactful and less relevant.

Plateaus are expected, and I can think of two reasons for them:

I have other things going on in life.
I’m learning to apply my new skills at a higher level.

Life Happens

Work is a part of my life, but not my whole life. Many life events can cause a plateau at work.

Becoming a parent, coming out, going through a breakup, or experiencing a death in the family–all these things take time and energy, and they are IMPORTANT. Work comes second to these things.

In some communities, periods like this are called a “Skill Regression.” In my own words, this is a period where things that previously seemed easy to you are challenging. This might be because you are overwhelmed or processing new stuff you’ve never experienced.

In one Redditor’s words:

Think of your brain as a series of highways connecting a dozen towns. Each town represents a skill or ability that you have developed over your lifetime. The roads are the synapses and connections our brain creates to access those skills and our brain loves efficiency. We have a lot of roads that can get to those towns and those roads are developed over time from childhood.

Then. Boom. Something new happens in life, and all those roads don’t make sense anymore. All your old ways of accessing skills are gone because your brain is occupied learning new skills.

Suddenly, every single one of those efficient roads that kept you going every day has been blocked off by road construction and you can no longer access that town. The towns are still there, but you have a really rough route getting there as your learned experience is no longer accessible to you.

Life happens. And that’s okay. Plateaus, cliffs, skill regressions, or whatever you call them, are complicated. They are times to take care of ourselves and build support networks.

What to do when life happens

Know your capacity. Determine for yourself what scope of work feels right. Recognize that you might not make a flashy impact in your work, but you will do essential work for the business.
Tell someone. Once you know your capacity, talk to your manager about it. Tell them where you are at and what kind of work you are most capable of doing. Communicate your capacity. You don’t have to tell anyone why you need space; only that you need space.
Know your strengths. You worked hard to get here, and while you might be at a plateau, this plateau is higher than the level you were at before. Remember to take a moment to enjoy the view. Even this version of you produces better work than you were a year ago.
Expect pushback. Your manager or colleagues may expect you to perform and grow at the same rate you previously did. Lean on your strengths and continue to do the work you are skilled at. Accept feedback and set reasonable boundaries that acknowledge your current capacity. Continue to communicate your capacity clearly, and don’t over-commit yourself.

When life happens, your job is to take care of yourself. You are already good at your job. You’ve done fantastic work to get here. Let work take a back seat while you learn new life skills outside of work.

Working at A New Level

Working at a new level brings on a different kind of plateau. One where the growth and learning that got you to this new position are suddenly not relevant to your work. You may have gotten promoted by leading a project and shipping a new feature. Congratulations! But now you are being asked for architectural direction that affects the longevity of a whole software system. Shipping features and setting architecture direction are two wildly different things! The skills needed to ship are not those needed to design resilient systems.

You may have heard about “The Peter Principle,” or at least heard it summarized as “people rise to their respective level of incompetence.” In a hierarchy, everyone is skilled at the job below them but not the job they have.

The Peter Principle is a bleak way of saying that people hit plateaus when promoted. However, they can learn new skills if they have the insight to recognize this plateau.

I have encountered these plateaus in my career, requiring a thoughtful pause to create a learning strategy.

What do you do when you’re learning new skills?

First, read Katie Sylor-Miller’s article. I highly recommend reading her suggestions. Here is my take on a few things that have worked for me.

Find your peers. You are now at a new level, and you have new peers. But your peers don’t always have the same title. Recognize the people you work well with who are doing jobs you admire. These people can be across the organization, in another department, or adjacent roles on other teams. Having peers working at the same level, regardless of title, will help you see how your work fits into the organization.
Build your network outside of work. This is a hard one for me. As a natural introvert and a horrible small-talker, I value a few deep relationships that cut through the small talk and get right to the point. I challenge myself to attend social events or reach out to people. These relationships can provide invaluable insight into how other companies work.
Write everything down. I recently started a work log. I book a half hour at the end of the week to journal everything I did that week. These journals are succinct and focus on impact. I use this time to reflect on shaping my priorities to ensure I am consistent in the direction and impetus of my work.
Seek feedback. When you work at a higher level, you will get feedback less often and rarely get positive feedback. Reach out to your peers and those above you for feedback frequently. Feedback in the moment is usually the best. After a meeting or when a project is wrapping up, I ask other leaders for input while their memory is fresh. Ask for actionable feedback. Don’t expect it to be positive; expect it to have your best interests in mind. This helps me adapt on the fly.
Say no. It is easy to have too many priorities because, in your new position, you want to help everyone you can. You have to learn to say no and let go. Saying “no” frees up your energy to focus on priorities that matter to you, your peers, and your manager.

Conclusion

Plateaus caused by live events or working at a new level are similar. As you learn, you are reorganizing how you operate in the world. The skills that got you to this place are not the skills you need to continue to succeed.

If you are conscientious of this, you can build the support you need into your work environment to get through the challenging parts of this new learning period. One day, this hard work will all come together, and you’ll feel like you’re back on a rocket ship, making an impact with every keystroke.

Career-Growth on enumerator.dev