Hard Lessons I Learned from a High-Paying Job in Tech - Deepstash
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On the first day, I felt like a clown amongst Houdini magicians.

They were so damn good. They were polished as hell. And geez could they Powerpoint like nobody’s business. Compared to me, what they did was death-defying magic.


351 reads

My friend recommended me for the job. They worked me like a show pony, though, before pulling the trigger and rolling out the job offer. I hadn’t worked with her for a year or so. She left the world of banking to work inside a tech company. The growth trajectory was incredible.


147 reads

She learned more about AI in a few months than I learned about writing after seven years. The money can be good in tech, especially if the company is fast-growing. But pretty soon the allure of tech starts to change. What you think you’ll get from the experience turns out to be different.

If you dream of a high-paying job in tech, here are the lessons I learned.


121 reads

The laziness of developers is inspiring

Developers that write code for software often have to fill out a timesheet. It’s a factory worker feature from the dinosaur industrial age.

Developers love to automate stuff because it’s their job. A team of developers I worked with had enough one Friday. They refused to do their timesheet. It’s three clicks of mouse, but three too many clicks for developers.


148 reads

Instead, the devs built a Facebook Messenger script. Every Friday they would get a message about their timesheet that required a yes or a no. They’d almost always hit yes and get on with their day. No more filling out timesheets.

A simple hack, yes. But brilliance in my eyes. They didn’t just do this once either. They hacked many little annoyances in their lives. The really good developers learned to hack the problems of people beyond themselves. Those developers got all the opportunities and made the really big bucks.


125 reads

Developers taught me not to put up with bullshit. There are ways to automate parts of your life so you can focus your time on what matters.


139 reads

It’s easy to fall into the “work hard” trap and light your date

The disease slowly infects your life: working too much. There’s always another software release that needs to get out the door. There’s always more to do because the change in tech is astronomical.

If you can’t move quickly you end up getting left for dead. Plus, your skills get outdated much faster. That means excessive online learning to keep your certifications freshly updated. Before you know it, you’re working long hours.


122 reads

Early in my tech journey I missed an important date night with my partner. I traded time with her for time with this new client. The client ended up being coked up on their own ego. I left the dinner feeling disgustingly violated. They even wanted me to eat meat despite the fact I only eat plants. They laughed under their breath at my diet choices. So, I politely explained why I went from eating meat to all plants: a near-miss with cancer.


102 reads

I never did business with the client. But I missed that date night with my partner. She was angry, although hid it well.

Just because you earn good money from a job in tech, it doesn’t mean you need to abandon your family for glorified networking that can be done over a zoom call.


110 reads

Stoicism at work, works

People I worked with in tech valued thinking time. They even scheduled it. It’s as if they were a quiet fanboy/girl of stoicism on social media.


116 reads

If Marcus Aurelius were alive and working in tech wearing a google t-shirt, I reckon he’d have done the same. Problems require time to think about them before they can be solved. Otherwise, you come up with a bunch of haphazard solutions that lead nowhere.

Spend time thinking, not in meetings.


93 reads

Pretentious, Elitism, and Privilege Can Blind You

There’s a lot of it in tech.

Code tests for devs can quickly turn into racial screening. The dollars on offer can lead to a complete disregard for how normal people live, who don’t drive yellow Porsches funded by the latest farm animal game app. Some of those I met in tech didn’t know how bloody lucky they were.


108 reads

Many of them came from poor upbringings and got into high-paying jobs without seeing the shift from who they were to who’d they become. A high-paying job in tech is a privilege. The point is to use that job to help others who are where you used to be. Call it mentorship. Call it leadership. Whatever.

Open-mindedness can be quickly lost too. One leader said to me, “We don’t touch anything AI or Machine Learning because they’re not mature enough.” This seemed like a naive comment to me. AI is already everywhere. It will be in our coffee shortly. *Waves hello to AI in his coffee cup*


78 reads

Geek culture is cool

Kids at my high school used to get bashed if they were geeks. I managed to survive as a borderline geek.

It’s funny how the world reverses when you age. Geek culture is honored when you work in tech. The nerdier your keyboard, the cooler you are. The more you geek out on Fortnite after work, the louder the cheers at an all-hands or town hall meeting.


82 reads

Staying up late to obsess over one line of code makes you a warrior fighting the roman Battle of Cannae on your own. We all have our chance to be cool at some point in our careers. Don’t wait to be cool. Practice your version of cool. Approval from others is underrated. The quirkier you are the more your avatar is etched into people’s minds.

Memorable equals opportunity


74 reads

The Best Part Isn’t the Money. It’s This.

A high-paying job in tech sounds amazing to a lot of people. Money can buy a lot of things. But money didn’t really motivate me anymore in my career. In fact, it led me to quit my high-paying job .

The best part about working in tech is the people you work with. This applies to any job. They make it all worth it. They cheer you up when you’re having a rough day. They remember your birthday. They invite you to their home for a BBQ to cement the relationship. They refer you for new opportunities because they want to see you excel in your career.


81 reads

I’m about to get married. When I host a small dinner with friends, a lot of the attendees will be people I worked with within tech. My tech colleagues became friends and that’s really the best part.

Now that I have left a high-paying job in tech, there’s one thing that hit me like a Japanese bullet train yesterday: they’ll miss you.


93 reads

A colleague sent me a text: “I miss working with you.” He’s a man’s man. He rarely shows his feelings. He’s afraid to be vulnerable. Emotions rarely overwhelm him.

Hardest lesson: You’ll miss those you work with. Because you’re not going to be working with the same people forever. At some point, you will have to say farewell to them. It sounds easy until you do it.


81 reads

The solution is simple. Don’t say goodbye to people you work with. Say, “I’ll speak to you soon.” Then schedule a time to catch up with them. Staying in touch is how you keep the best part of a high-paying job.


79 reads



Stay-at-home cat momma 🐾


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