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Zero to $100K: How I'd Build My IT Career All Over Again Knowing What I Know Now
Before I got into IT, things weren't exactly going according to plan. I'd delivered pizzas for Domino's. Later, I ended up academically suspended from university. I wasn't exactly on track for a six-figure career. Going back to a traditional four-year school wasn't really an option, but I knew I wanted to make good money. So I went online and searched something along the lines of "How to make six figures without a degree." That's how I discovered IT. I wasn't particularly passionate about...
CyberAndChill Brief #1: You probably don’t need to start over
One of my best-performing posts last week started like this: “I used to deliver pizzas. Now I make over $200k in tech, work remotely… I’m not some genius FAANG engineer either…” It reached 260,000+ people. I care about that number for one reason: It shows me what you’re paying attention to. Experienced IT people want more from their careers without throwing away everything they already spent years learning. The rest of that thread was basically my answer: “I just got really good at figuring...
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How to Choose Your Next IT Role So You Earn More Without Making Your Life Worse
I’ve gotten a lot more specific about what I want from my next career move. I want roughly 50% more income. I want to stay remote. I want control over my schedule. I want to be able to live where I want, visit family and friends, and build my life without asking an employer for permission to relocate. And I want the role to keep me relevant enough that I can continue earning at that level for a long time. The last part matters more than it used to. Part of the reason I want higher...
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How to Stay Valuable in IT Even When the Technology Changes
A customer problem can land in front of me and I’ll have no idea what the answer is yet. That doesn’t bother me nearly as much as it used to. At some point I realized the job isn’t to already know the answer. The job is to reduce the uncertainty fast enough that the problem becomes manageable. So before I disappear into documentation or start troubleshooting, I try to understand the consequence. Is this actually important right now? What happens if it sits? Who is affected? Is there money, a...
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How to Find IT Roles Where High Pay and Flexibility Come Together
Some of the best tech interviews I’ve had barely felt like interviews. You talk shop. Some technical stuff comes up. Then eventually everyone is mostly figuring out whether they can work with you. Game sees game. That started making more sense once I looked at the kinds of jobs I had ended up targeting. For me, the sweet spot has been consulting-like technical positions: Sales Engineer, Architect, Customer Engineer, Customer Success Engineer. Companies use different titles, but the actual job...
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How to Know If You’re Already Qualified for a Better IT Job
You can be 80% qualified for an IT job and still talk yourself out of applying because of one requirement you don’t know. The problem is treating every unknown like it will take months to fix. After enough years in IT, some gaps are really a Saturday afternoon. Others might take a weekend of building and breaking something in a lab. A few actually require experience you can’t create on your own. Knowing the difference is how I’d decide whether I’m technical enough to make the move. Judge...
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How to Find Career Moves That Have Already Worked for People Like You
I used to use LinkedIn backwards. Instead of starting with job postings, I would look for people who used to have my job. Then I’d see where they went. The best example was someone who had worked in the same position at the same company. They already had roughly the same environment, the same type of problems, and many of the same constraints I had. Their profile gave me a glimpse of what could happen after my seat. Then I would find another person. And another. One went somewhere...
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How to Stop Studying Random IT Skills and Start Qualifying for Better Jobs
You can spend six months doing everything that looks productive in IT and still be no closer to a better job. Finish a course. Get certified. Build a lab. Watch hours of technical content. You’ll know more than you did six months ago. You might even feel like you’ve made serious progress. Then you open LinkedIn and realize you still don’t know what job you’re applying for. That’s what I call knowledge entertainment. It’s not necessarily bad. Learning technology is probably a better use of...
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#5 How to Position Your Resume for the $200k Tier in IT (Non-Management)
Edition #5 of Get Paid in Tech (the newsletter) How to Position Your Resume for the $200k Tier in IT (Non-Management) The next level of IT blends into business, but you can still be very very technical. You just need to communicate well across the board from the development team all the way to the C-Suite. The rest of the sales stuff is usually handled by your counterpart. I'm talking about Solutions Engineer. Solutions Architect. Sales Engineer. Technical Consultant. Customer Success...
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#4 How to Make More Money from IT Experience
Edition #4 of Get Paid in Tech (the newsletter) How to Make More Money from IT Experience The usual IT career plan is simple: Get experience. Use that experience to get the next job. Repeat until the money starts looking respectable. That has been my route, and honestly, it has served me well. But once you have enough IT experience, you start realizing there are more ways to make money from it than just waiting for the next title bump. You can climb. You can stack. You can build something...
Get the best of CyberAndChill delivered weekly. My top posts, career insights, and practical advice to help you earn more and land better roles. Join 1,300+ subscribers. It's free.