I remember sitting in my car in the parking lot of a glass-and-steel office building in Austin back in 2019. It was a Tuesday. I had just signed an offer letter for a Senior Product Lead role that paid exactly $142,500 a year plus a signing bonus that felt like winning a small lottery. This was it. This was the number I had written on a sticky note three years earlier. I thought the moment I hit it, some internal alarm would go off and I’d finally feel ‘settled.’ Like I had officially made it to the finish line of adulthood.
I felt nothing. Actually, that’s a lie. I felt a vague sense of dread because I realized I now had to actually do the job. But the euphoria? The life-changing shift in my baseline happiness? It didn’t happen. I sat there eating a mediocre turkey sandwich from the deli across the street and realized I was the exact same person I was ten minutes ago, just with a higher tax bracket and a more expensive commute. It was a total scam.
The day I finally ‘made it’ and why it sucked
We call this the Arrival Fallacy. It’s that psychological trap where you convince yourself that ‘once I get [X], then I’ll be happy.’ Once I get the promotion. Once I hit six figures. Once I lead a team of ten. We treat our careers like a mountain climb, assuming there’s a plateau at the top where the air is clear and the stress disappears. But the mountain is a treadmill. You’re just running faster to stay in the same place emotionally.
I spent fourteen months in that $142k role. During that time, I tracked my ‘Sunday Scaries’ on a scale of 1 to 10 in a private spreadsheet. You’d think with the extra money, the score would go down. It didn’t. When I was making $65k, my average Sunday dread was a 4. At the ‘dream job,’ it averaged an 8.2. I was literally paying for my own misery with a slightly nicer car payment. What I mean is—actually, let me put it differently. I wasn’t just miserable; I was confused. I had followed the script perfectly, and the ending was a cliffhanger that led nowhere.
Success is like drinking salt water; the more you get, the thirstier you become, and eventually, it just makes you sick.
I know people will disagree with this, especially if you’re currently struggling to pay rent. Money matters. Obviously. Not worrying about groceries is a massive leap in quality of life. But once you hit that ‘comfort’ threshold—which for me was around $85k in a mid-sized city—the returns on happiness become almost invisible. Chasing a promotion is like trying to catch the horizon; you run until your lungs burn, but the line just stays exactly the same distance away. It’s exhausting.
The LinkedIn industrial complex is lying to you
I’ve developed a visceral hatred for LinkedIn. I don’t just mean I find it annoying; I actively think it’s a net negative for human sanity. Every time I log on, I see people ‘humbled and honored’ to announce they’ve moved from ‘Junior Widget Maker’ to ‘Senior Widget Strategist.’ It’s a giant circle-jerk of performative ambition. We’re all pretending that these corporate milestones are the highlights of our lives because we don’t want to admit that we’re bored out of our minds.
The Arrival Fallacy thrives on LinkedIn. It feeds you the idea that your identity is your title. I fell for it hard. I used to spend my Saturday mornings tweaking my resume instead of, I don’t know, going for a walk or talking to my wife. I thought I was ‘investing in myself.’ I wasn’t. I was just sharpening the tools I used to build someone else’s dream.
I have a take that most career coaches would hate: Most of your coworkers don’t actually like you. They like the utility you provide. The moment you leave that job, 95% of those ‘work friends’ will stop texting you within three weeks. I’ve seen it happen to me, and I’ve done it to others. It’s brutal, but it’s true. When you realize your professional ‘arrival’ is built on such a flimsy social foundation, the goal starts to look a lot less shiny. Total lie.
My 18-month spreadsheet of misery
I’m a data person by nature, so when I started feeling like my career was a dead end despite the raises, I started tracking everything. I tracked my sleep, my mood, my caffeine intake, and how many times I checked Slack after 8:00 PM. Here is what I found over an 18-month period across two different ‘high-level’ roles:
- Correlations: My salary went up 22%, but my self-reported ‘daily joy’ score dropped from a 6.5 to a 4.1.
- Sleep: I lost an average of 55 minutes of sleep per night due to ‘pre-processing’ the next day’s meetings.
- The ‘Worth It’ Metric: I calculated that after taxes and the cost of ‘convenience’ (Uber Eats because I was too tired to cook, therapy to deal with the job, etc.), my actual take-home hourly rate was lower than when I was a freelancer.
- Software: I realized I spent 4 hours a day in Jira. I hate Jira. I think Jira is where creativity goes to die in a pile of digital sticky notes.
I used to think that ‘grinding’ was a badge of honor. I was completely wrong. It’s just a lack of boundaries disguised as work ethic. I remember one specific night, at 11:45 PM, I was arguing with a guy named Dave from the London office about the hex code of a button. A button. I was 32 years old, making great money, and I was losing sleep over a shade of blue. That was the moment I realized I had arrived at a destination I never actually wanted to visit.
What I actually prioritize now (and why my mom is disappointed)
I quit that job. I didn’t have a ‘vision’ or a ‘startup idea.’ I just took a lower-paying role at a company that actually lets me turn my computer off at 5:00 PM. My mom still asks when I’m going to ‘get back on track’ to becoming a VP. She doesn’t get it. She thinks I’m failing because I’m not climbing. But I’ve finally stopped looking at the ladder.
Instead of career goals, I have ‘life’ requirements. This might sound lazy, but I don’t care. I prioritize things that actually move the needle on my day-to-day existence:
- The ‘No-Alarm’ Test: Can I wake up without an alarm at least three days a week? If not, the job is too demanding.
- The Hobby Buffer: I refuse to take a job that doesn’t leave me with enough mental energy to work on my shitty woodworking projects for at least an hour an evening.
- Physical Proximity: I will never commute more than 15 minutes again. I don’t care if the job pays $300k. Life is too short to spend it in a Toyota Camry on I-35.
I also stopped using Notion for my personal life. I know everyone loves it, but I refuse to use it. It’s a bloated mess that makes me feel like I’m at work when I’m just trying to make a grocery list. I use a physical notebook now. It doesn’t sync, it doesn’t have ‘templates,’ and it’s perfect.
I might be wrong about this—maybe some people genuinely find deep, soul-level fulfillment in hitting a KPI or getting a C-suite title. Maybe I’m just not ‘wired’ for the corporate climb. But I suspect more people feel like I do than they’re willing to admit on their ‘humbled and honored’ posts. We’re all just terrified that if we stop running, we’ll have to face the fact that we don’t know who we are without our job titles.
Anyway, I digress. The point is that the ‘arrival’ is a myth. There is no finish line. There is only the quality of your Tuesday morning. If your Tuesday morning sucks, the title on your email signature isn’t going to fix it. Trust me. I checked the data.
What did you do last Saturday that didn’t involve a screen or a ‘professional development’ goal? If you can’t remember, you’re probably chasing a horizon that doesn’t exist.
Stop climbing. Just walk.