Now let’s talk about how, in 2026, to get there starting from scratch.

First off: you’re gonna have to pay your dues one way or the other. There is no such thing as a free ride in life, unless you’re a nepo baby or kid born with generational wealth. For the rest of us, you’ll need to work your ass off.

You’re going to need a roadmap though, and that’s what I’m here to help you with, so you can avoid wasting your time on things that don’t matter, and focus like a laser on the things that move the needle. It still won’t be easy but it will be possible if you don’t quit.

Gut Check

Take a step back and take an honest inventory of your skills, personality and weaknesses: does a high-stakes infrastructure role fit you? Better to answer this directly right now rather than waste time on something you aren’t a good fit for.

1. Do you enjoy tinkering with technology? Were you the type of kid that would take gadgets apart to see how they work? Did you like building things like Lego, or electronics kits?

2. Do you work well under pressure? Have you ever been attracted to high-stakes roles like firefighter, EMS, police, ER nurse, etc?

3. Do you have technical aptitude? Especially in 2026, if you’re young, do you actually own a computer (not just a phone or tablet)? Have you ever installed or run Linux? Do you know what a command line terminal is, and have you used one?

I know the last question seems basic, but I’ve been shocked at the number of Zoomers that are almost completely tech-illiterate, don’t have or have hardly used an actual computer, and basically live their lives on touchscreens.

If you answered no to most or all of those questions, reconsider whether DevOps or any operational role is a good fit for you. Otherwise, continue on!

Two Hop Strategy

The hard truth is this: junior roles barely exist. To the extent that they do exist in established companies, they’re almost always filled by temp consultants. Intern roles only really exist on the SWE (Software Engineering) side, I’ve never seen any kind of operational DevOps/SRE intern role (the exception are CS-pipeline internships, but if you’re going the university path this roadmap doesn’t apply). If you can find one, great, but you probably won’t.

The solution is the Two Hop Strategy:

• Hop 1: Build relevant real-world experience

• Hop 2: Transfer into industry, build career from there

Hop 1: Building Experience

This is the hardest step because it means going from zero to one. It will take the most time and resolve. But it’s the hop with no gatekeeper and no credentials needed, just work.

You have a few options for this one:

• Junior helpdesk role, NOC, junior sysadmin, cloud support agent. Anything entry level that is operations-adjacent.

• Be careful about generic “IT Support” positions. Sometimes these can be good and useful, but if it involves things like helping 50 year old office workers use Outlook it’s a dead end. If you’re doing real hands-on work at least some of the time with either cloud infrastructure like Azure, or actual hardware, it fits.

• Visible, public project that you actually care about. This can be almost anything: a website you’ve built, open source work, an interesting Kickstarter project, or whatever. As long as it’s something real that you’re putting effort into and actually care about (not some dead Github resume-padding thing), that’s what matters.

• Focused, demonstrable homelab tinkering. Build something complex with hardware you own. Some random examples: build a full multi-node Kubernetes cluster and run NextCloud on it. Run your own mailserver and email domain. Run a website from your garage. Set up IP cameras and your own self-hosted NVR. There’s no limit, do something neat and impressive that you can talk about in detail.

Couple things I want to note up front:

If you are going for the Junior helpdesk route, be aware that your goal IS NOT to just do the work, get “Meets Expectations” every performance review, and somehow expect the next hop to just happen. Your goal is to use that first job as an EXCUSE and OPPORTUNITY to do the real work that matters, which means getting the official work done early and then use the remaining time to do actual infrastructure work and build up your experience. This could be as simple as using the company’s AWS account to provision test infrastructure and get familiar with networking and security concepts, or whatever. Point is: do adequate work (don’t get fired), then put the bulk of your time and energy into educating and bootcamping yourself on company time. If you play this right, you can come off to your boss like an ambitious guy who’s interested in the work and going above and beyond. Just be careful not to run up the AWS bill or do anything stupid, security or ethics-wise.

If you’re going the homelab route, you need to be disciplined and carve out time. This is why the helpdesk role is nice, because you have a luxurious 8 hours per day to get the boring work out of the way so you can focus on the things you care about. If you’re working some non-tech job, that means you have to carve out additional time to get this done. Not impossible, but will take longer.

Timeline is 1-2 years for the helpdesk training-on-the-job option. 2-3 years for the homelab option if you’re dedicated about it. Both are easier the younger you are with fewer responsibilities: kids and family make it harder and slower. Fast learners have an advantage: the main requirement is skill acquisition, so judge by that and not strictly calendar time.

A Word on AI Tools

AI is amazing and it can do a lot. Too much. You might be tempted to build your homelab by buying an AI subscription and then letting an agent do it over the course of a few hours. This misses the entire point of the exercise. You are building systems as a proxy and substitute for a formal certification program: the point is the learning, not the end state. If AI does it all, you’ve accomplished nothing and you will fall apart at the most basic intro questions of any interview.

AI can be super-helpful at getting you unstuck when you run into tough problems. I wish I had it back in the day when I was mystified by Linux kernel oops messages or couldn’t figure out how to script something. Just be sure that each time you use AI, you spend the effort to learn WHY the problem occurred, how to prevent it next time, and WHY the AI-suggested fix works.

Foundational Skills

Your goal in Hop 1 is to get enough skills and experience that you have something to put into a resume, and hopefully make it interesting and unusual enough to convince a hiring manager to take a chance on you. Beyond that, you want enough of the basic skills down so that you can pass a set of interviews and actually do OK at the job initially, while you ramp up.

Here’s the bare minimum to consider Hop 1 complete:

1. Linux sysadmin experience. I don’t care if you’ve only worked in Microsoft shops at a helpdesk, there’s no excuse not to get some Linux experience. “Sysadmin” means the ability to set up a new system, set up users and permissions, install and reconfigure software, add or remove hardware, reformat disks, and fix the system when it breaks.

2. You should know where system logs are and how to read them. You should know where to look when things go wrong and the different types of logs (dmesg, journald, application logs).

3. Unix CLI. You need to be familiar enough with the CLI to do sysadmin tasks. You should know what ps aux or du -hs |sort -h does offhand and be able to explain it. Knowledge of how to use pipes, standard utilities like cut, awk, uniq is essential.

4. Bash scripting. Building on the point above. You don’t have to be a programmer, but you should have some ability to write basic bash scripts to automate tasks. You should understand shell functions, variable expansion and how to pass parameters from the command line through to the logic in the script.

Certifications

Certifications like AWS Solutions Architect Associate, or CKA (Certified Kubernetes Administrator) have limited usefulness, in my view. The one thing they get you is a pass through possible keyword filters for Hop 1 positions. When I’m hiring mid-levels or higher, I almost completely disregard them in favor of actual industry experience: what you did, the companies you worked at. If getting certified in a structured environment helps you learn, go right ahead, but be realistic about what it gets you especially given that those exams aren’t free.

Hop 2: Move into industry

This is where your prep work in Hop 1 really matters. If you don’t pay your dues adequately, you will run into a brick wall here. Better to spend the time in Hop 1 to do it right rather than prematurely try to move into Hop 2 and fail completely. One clue: if you’re anxious to get on with Hop 2, it might be because you’re not actually passionate about technology or fixing things and this is all just an income/job play for you. Nothing wrong with maximizing income of course, but if you’re not a die-hard tech nerd this probably isn’t the right path for you. Figure out sales or e-com or something.

Remember when I wrote that there are basically no junior positions? That’s true in established companies, but your goal is to find the smaller companies, startups, non-tech companies that have some kind of tech department, and so on, that would be willing to take a chance on you.

And let’s be real: you have zero chance of getting into Meta, Google, Apple, etc at this level. Maybe a tiny chance at Amazon if you land on a manager who wants to hire-to-fire, but you don’t want that. You’re looking for the tiny company, cash-strapped startup, or one-man operation who wants someone cheap who can work hard, has initiative and will grow into the role.

Here are places to look:

• Hacker News “Who’s Hiring?” threads. They post this monthly. Scour the posts looking for infrastructure/cloud engineer/SRE/DevOps roles.

• Social Media. X is probably your biggest opportunity area. Facebook is mostly boomers but worth looking at. You could try Bluesky but the vibe is…different, so be aware of that.

• Niche job boards. There’s a surprising number of these out there for specific industry areas or technologies. For example: bitcoinerjobs.com, golangprojects.com. Search for “<technology/area> job boards” and see what comes up.

• Standard job boards. Don’t neglect these, even in 2026. Indeed and ZipRecruiter can sometimes have interesting posts.

Relocation

In this Hop 2 job search, you’re going to need to give yourself every possible advantage. Even if you succeed in everything up to this point, if you put too many conditionals on the job you’re willing to take (“must make $X/year”, “must involve technology Y”, “needs to be fully remote”) you can shoot yourself in the foot. When you find that hiring manager that likes you and is willing to take a chance, you need to jump on it immediately.

Commit up front, before even starting, to make this happen. If you don’t live in a top 5 metro area, your chances of finding a position that will both accept your junior level, and also allow you to work fully remotely, is way less. You likely will have to pass on what otherwise would be golden ticket opportunities. Even if you DO live near a major city (say, Chicago), if an opportunity in New York opens up, you don’t want to have to say no to it.

Keep in mind that all metro areas are not the same for your purposes. The areas with strongest tech and startup cultures are San Francisco, NYC, LA, Austin, Seattle. In contrast, major cities like Houston, Atlanta, Phoenix, Miami, not so much.

Personally, I’m sympathetic and conflicted because I’m a fan of strong, local communities and I hate that young people often have to leave their families to follow their careers. That said, we don’t live in a perfect world and this roadmap is all about how pragmatically to get where you want to go. So be realistic.

In the Job

So now you’ve gotten your first industry job. Congrats! Now get ready to work harder than you likely have ever worked in your life. Especially if you’re in a startup, expect to work stretches of 10-12 hour days, 5-6 days per week plus on-call duties. You’re likely making just enough to survive, not much more. If this sounds like hell, keep in mind that this job is your paid bootcamp. Unlike a university or private bootcamp that you have to pay for, this bootcamp pays you. Your goal is to grow in this position for 1-2 years, then make your step-change transition into a mid-level role where you will greatly increase your income and career.

Patience and willingness to learn is key. Try to keep a sense of gratitude and humility: you don’t really know what you’re doing, you’re going to screw up, and these people took a chance on you. Own your mistakes, don’t be arrogant or entitled, and do everything you can to both level up yourself and also contribute to the company to make it a better place and succeed.

How do you know when you’re ready to move on? Probably when you start to feel comfortable, and when start to feel limited both in terms of work assignments and advancement. You’ll likely only get incremental promotions and comp increases in this role, so changing companies into a mid-level role will give you way higher upside.

Polish up your resume now that you have real, demonstrable industry experience and see what’s out there. Hit LinkedIn, find industry recruiters (CyberCoders, etc) and apply directly to companies. It will still be an uphill battle for the highest tier of companies like Google and Meta, but it’s not impossible either depending upon your skill.

If you play this right, you can likely double your income. Maybe more, if you include equity and perks. Tech roles like this are some of the only W2 roles in existence where you can routinely get meaningful equity (BowTiedBull makes the valid point that this is increasingly the only way to generate real wealth). This is the step-change payoff that you’ve been working for years doing the Two Hop method. This is also why the operations area is relatively uncrowded: paying dues isn’t fun and not a lot of people have the drive or persistence to make it work. If you’ve done it, be proud.

What’s Next

Next up: the homelab roadmap. What to build, in what order, and what skills each project proves. This is the 18-month version of the one that took me a decade to stumble through by accident. Subscribe and you'll get it the day it drops.

I'm opening paid mock interviews soon: a full SRE/DevOps interview loop run by me—the guy who actually runs these loops for a living—followed by a written scorecard telling you exactly how you did, where you can improve, and my honest assessment of whether you’re ready. Slots will be limited and waitlist gets first crack. Email hello@bowtiedcessna.com with "coaching" in the subject line to get on it.

For the previous 10 years or so, at home I was a Linux nerd. I got started in the early days of the 2.4 kernel and package managers that were glorified tarball unpacks with no dependency tracking. Back in those days there was no GUI email client, so I spent a week getting sendmail MTA set up, and then used fetchmail to download via POP3 into my mutt terminal email client. It was obviously insane and nothing that any normal person would put up with, but I was young, broke and had a lot of time so to me it was fun. I broke my systems constantly just messing around, then spent days fixing them. The odd thing is, I never considered it any kind of career path. In fact, I was kind of embarrassed and was afraid of being labeled a “nerd” because I thought Unix and Linux systems were cool.

That all changed as I sat in my cubicle, in my shirt and tie, bored to tears and terrified that this would be my life until I die. I realized, very belatedly, as I saw how my coworkers and boss interacted with technology, that I had skills that were not typical. Maybe even marketable. But I had a science degree unrelated to computers and no formal tech experience whatsoever. What could I do?

First thing I did was use a fortunate assignment at work to teach myself the beginnings of programming. First using R, then Python. I already had a lot of the sysadmin foundation, I just needed the time and motivation to learn the basics of coding and my job gave me that opportunity. By the end of it, I could put together scripts and even (for me) fairly complex PyQt graphical applications. I wasn’t any good, obviously, but I had the rough beginnings.

I spent the next year—not an exaggeration, a full year—sending out my resume and applying to every vaguely-related tech job posting I could find. The hook in my resume was the 10 years of Linux experience (I was honest about it being unpaid home hobbyist work) and then some perhaps slightly embellished items about my R and Python work. I got a fair number of callbacks surprisingly, but I almost never made it past the recruiter screen. I was obviously totally inexperienced and it showed, but I kept persisting. At times I thought I was crazy and this would never work out, but I kept sending in applications and taking recruiter calls during my lunch breaks.

One day, I got an actual interview. It was with a startup I had never heard of, on the other side of the country, in an industry I knew nothing about, but they were friendly and interested. I made it clear that I was motivated, wanted to work in tech and I was willing to move across the country in 30 days. After a few more calls with them, I got the offer letter for a Junior DevOps Engineer position.

The offer was essentially exactly what I was making in my current job. Except this was in a city with one of the highest costs of living in the country, so it was an effective pay cut. It also was about half of what a typical mid-level DevOps role was going for, in the startup world. But it was a job, in the field I wanted, in an exciting location. I decided to go for it, and packed up everything and drove across the country.

I’m not going to sugar-coat this: it was hard. I’ve never worked as hard in my life as I did for those first few months, trying to prove myself in the pressure cooker of a VC-backed startup of a few dozen people. I was used to a 9-5 office job, not grinding from 9:30AM to 8-9PM every day and dealing with production outages. But that’s what my coworkers did so I followed along. Eventually, I learned some things. Got promoted. Was mentored by the CTO. Things were looking good.

Two years later, now I’m making about 20% more. Definitely better, but even more significantly, now I had actual professional experience and I was living in an area with a real tech ecosystem.

I reached out to some independent tech recruiters, gave them my availability, and to my shock, started getting solid leads. It was surreal to have a recruiter working for me—it felt like having a Hollywood agent or something. She was setting up my interviews and negotiating terms with the companies, it was unreal. I landed a job with a hot, well-known startup and their opening offer was double what I was making, plus equity.

To this day, it’s the largest percentage income jump I’ve ever landed in a single job change, and certainly the most satisfying. This validated the gamble I made a couple years earlier, and turned all my Linux tinkering from a quirky hobby into a solid career investment.

I won’t bore you with what happened next—promotions, startup exits, move into management—but I want you to understand that this career opportunity is still available today for those with the motivation and skill set. Regardless of formal credentials.

Why? Operations skill is provable and demonstrable. You prove you have the skill by doing it. You don’t need a million dollar lab or permission from anyone to practice, you can build skills yourself on your own time using easily-obtainable consumer hardware.

What you need to take away from this: there’s nothing special about me. Although the details differ a bit now some years later, the door I stumbled upon by accident is the same door that’s available to you right now. The story is the same, but you can do it better because I’ve already mapped out how to get there and I’m ready to share it with you and help you step by step.

Let me be real though: it won’t be easy. You have to pay your dues any way you look at it: either the way I did it, over 10 long years of unfocused tinkering + 2 years of intense industry “boot camp” of sorts. Or you can do it faster and better because you’ll know the skills you need and you won’t waste time on things that don’t matter.

In Part II, I’ll share the roadmap as it exists in 2026: focused training areas, roughly how you know when you’re “ready”, where the industry entry points are, and the roles and jobs that can serve as your bootcamp, and the ones that are a waste of time and should be avoided.

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And if any of this sounds like where you are right now—stuck somewhere with a weird hobby that might be worth more than you think—tell me in the comments. I read all of them.

Follow @BowTiedCessna on X for more.

Need help getting hired in DevOps/SRE or want to chat about whether your background is a fit? Reach out at hello@bowtiedcessna.com

Let’s dive into why this is such a great career choice:

No Degree Needed

Not only is there no degree required, no such degree even exists. This is the type of thing that you learn in the school of hard knocks: tinkering, breaking things, fixing them. Do that over and over again, then do it at scale in production where millions of dollars are at stake.

Uncrowded

No high school senior says they want to be a “Systems Engineer” or a “DevOps Engineer” at graduation. Who even knows what that is, outside of industry? Nobody. If you have the job, try explaining what you do to your aunt or grandmother. Nearly impossible. Yet there is a need for these roles everywhere. They tend to be invisible and taken for granted when everything is going well, suddenly indispensable when things break.

Pays Well

At the mid-level and especially senior/staff levels, these roles have the same earning potential as Software Developer roles with equivalent experience, but with less entry competition and few or no credential gates. Once beyond junior level, you will be considered a peer of the software development teams in terms of expertise and engineering skill. Check out levels.fyi for real numbers, but 200-400k in total comp (incl. equity) isn’t unusual for the senior level at top-tier companies.

Developers Don’t Want to Do It

Generally speaking, software developers want to write code. They want to write beautiful, clean, abstract code in their language of choice and sit back and marvel at the complexity and elegance of it. Operations work is anything but clean and abstract: it’s messy, complicated, things always breaking. The reality is real world machines intersect with theoretical elegance quite poorly, and operations roles are the ones to bridge the gap. Although there are exceptions, developers are happy to let that be someone else’s job. This aversion is your opportunity.

“The Cloud” Didn’t Fix It

In the early 2000s, companies ran their own datacenters and deploying a new service meant buying physical hardware, hiring someone to set it up, turn it on, configure it and keep it running. This is the classic “sysadmin” role of that time. When Amazon invented the modern cloud with AWS, this was supposed to fix all of this. In some sense it did, but it also introduced a whole new world of complexity, failure modes and an ecosystem of tooling to understand and use. DevOps/SRE is needed more than ever, even if your company never touches a physical server.

AI isn’t Eating Operations (as much)

It’s pretty obvious at this point in 2026 that agentic coding and AI tools generally are eating up the low and even middle tiers of software development. AI is also affecting operations roles, but it’s more about tooling and surfacing information, diagnostics and insights faster, not about doing the work itself. Think of AI in operations like advanced avionics: it helps the pilot do their job more efficiently and removes toil, but at the end of the day nothing replaces the human being in the cockpit. Operations roles are still needed to get everything running again, whether AI is helping or not.

Room For Growth

These roles at the junior level usually start out purely operations: managing cloud or server fleets, provisioning new infra, managing code deployments. However there’s an open lane to grow into a hybrid software development/operations role. Simplified, this is Google’s well-known definition of SRE (Site Reliability Engineering): a software developer who also knows how to manage ops, or an ops guy who also learns how to do software development. Building up your development skills on the job is a demonstrated way to grow into bigger comp roles, more responsibility and greater scope of work.

What’s the Downside?

If you’re thinking there must be a catch, you’re right because in this world there are always tradeoffs. Operations work often is stressful. You don’t get to plan out your day ahead of time, you react when things break which is usually at the worst possible time. You will get paged at 3AM with a 15 min response expectation more times than you can count. You have to be comfortable working under pressure with incomplete information and no defined way out other than what you figure out on your own. When the whole company including the CEO is riding you for updates because the site is down and nobody can figure out why, you have to be able to calmly relay information and go through diagnostic procedures without panicking. If that doesn’t mesh with your personality type, you might want to look elsewhere.

Who Am I?

I’ve been doing operations roles (and managing teams of DevOps/SREs) for over 15 years in companies big and small. I started with 10 years of tinkering with Linux on my own, never thinking it could be a career, until I got a job at a cash-strapped startup looking for someone to help, at around half the market rate (within two years I doubled my income, more on that later). I learned a lot since then and now I run teams and mentor new people who want to get into the field. If you want an SRE job, I’m the guy that screens the resumes and runs the interviews.

What’s Coming

• How to break into DevOps/SRE without a degree

• How SRE interviews actually work

• What to do (and not to do) when everything falls apart and you’re on call

• War stories from production and how failures didn’t kill my career

All of it free—subscribe and it lands in your inbox.

Follow @BowTiedCessna on X for more.

Need help getting hired or want to chat about whether your background is a fit? Reach out at hello@bowtiedcessna.com