Trying to Leave Corporate (Tech) Life

For the past 33 years, I have looked in the mirror every morning and asked myself: ‘If today were the last day of my life, would I want to do what I am about to do today?’ And whenever the answer has been ‘No’ for too many days in a row, I know I need to change something.

–Steve Jobs

I’m leaving corporate life, or at least trying to. Let me tell you a story about why.

How I Got Here

I had my first professional ‘corporate’ job in the early 90s, while still in my twenties. I’d had jobs before that, of course; in college I worked in a warehouse, drove a cab, made deliveries, waited tables. I’d tried a few desk jobs, but they didn’t stick.

Then I accidentally discovered tech.

That first ‘corporate’ job was testing a DOS (!) software suite called PC Tools, for a company named Central Point Software. I worked on the one pictured below. Remember when software came in boxes?

Because I had some skill with French and German, I was hired to go through the interface and proofread internationalized versions for language errors. I commuted to work, sat in a cubicle near people like me, and was mostly left to my own devices. It was fantastic–the money was easy and plentiful, there was free food, a collegial atmosphere, and I got to work with smart and quirky people making useful things. It tickled the hazy science and technology dreams of my youth. This is it, I thought. This is the life I want.

Though that job was short term, I was in the right place at the right time–tech was booming in the 90s, and jobs seemed to be everywhere. I quickly found a job in technical writing–based largely on the CPS job, my writing skills, and having spent the first few years of college studying electrical engineering. In short–I told a good story about myself, and they bought it. They needed people.

Things really took off after that. What followed was many years of (mainly tech) jobs–filled with commutes, cubicles, great money, and the excitement of working with technology. This is it, I thought. This is the life I want.

People I knew who weren’t in tech were amazed. It was like I lived in a different world. And I suppose I did, but I often felt like an outsider, a pretender. Despite all the comforts and benefits, something felt off. This is it right? I thought. The life I want?

The pattern repeated for years. Startup, layoff. Grad school detour, back to tech. Environmental consulting, another layoff. More tech jobs. Each time I told myself it would be different. Each time I felt like I was living someone else’s life.

In a fit of frustration, I wrote a short book about breaking into technical writing. It did well - better than I expected. I was thrilled. I made plans to write more.

But I didn’t. I was scared, and I needed more money. By then I was married with a young daughter, and the luxury of soul-searching was gone. I needed stability, insurance, and a paycheck that showed up every two weeks.

So I took a job at a large health care company and told myself I’d make it work. And for a while, I did. Eight years, in fact.

But somewhere along the way, the pattern I’d been running from caught up with me again.

Eventually, the commutes felt longer. The cubicles felt more gray and cramped. Though I became a remote worker, I spent more and more time in meetings that could have been emails, and emails that could have been nothing. I worked around layers of bureaucracy, heard “that’s how we do it” so many times it became background noise.

Most days I wasn’t doing work - I was “doing corporate.” Navigating organizational theater. Protecting territory. Justifying decisions that had already been made. Explaining things to people who weren’t really listening.

I began to feel empty again. Like I was going through the motions of what I was supposed to be doing, not what mattered. I felt like a fraud, and I resented it. But mostly I resented myself for accepting it–again.

Today, I’m in the “60+” age category. I have no idea where the time went. To be blunt–I have less time to waste on bullshit. I have resources, but time is no longer a luxury. Now, I think I realize what I struggled throughout my career to be clear about.

Without my realizing it, corporate life had shaped me. “I’m a Senior IT Consultant”, I would say at gatherings, as if I was a job title. The language I used: synergize, operationalize, bandwidth, circle back, move the needle, actionable, drill down, strategic alignment, take it offline. Words that sounded important but meant nothing.

I spent years being valuable in ways that didn’t fit job descriptions. Connecting dots others missed. Explaining complex things clearly. Seeing the human problem underneath the technical one. But corporate life rewards specialists with credentials and titles, not generalists who see connections.

I’d been optimizing for the wrong things. And I was running out of time to fix it.

It’s not just “meetings are annoying” but the deeper waste - the sheer amount of energy that goes into navigating the organization vs. actually solving problems. Corporate life often forces you to serve the technology/process instead of using it to serve humans.

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And so: I’m leaving corporate life, or trying to.

It’s not because I don’t want to work, but because I can’t afford to spend what time I have left navigating organizational theater instead of solving real problems. I’m trying to build a life where my work liberates people instead of just optimizing processes—and I’m figuring it out as I go.

I’m scared, to be honest. Scared I’m too old to start over, or that my runway will run out before I figure this out. Scared I’ll end up back in some corporate job because I couldn’t make anything else work.

But I’m more scared of looking back at 70 or 80 and realizing I spent my last good years serving organizational theater instead of helping people.

What’s Next

This isn’t ‘early retirement’, or ‘I made my money and now I’m free’. Far from it.

I’m not anti-work, either. I just want to spend my time creating things that matter.

And I’m not leaving technology. I still love making things, solving problems, understanding how technology shapes our lives. What’s changing is how I want to spend my time with it: creating things that help people, not just optimizing corporate systems.

There’s a significant gap between the life I want and the life I need. I’m trying to bridge it without compromising back into what I just left.

Where am I today?

I’m trying to be visible again after months of being quiet. I’m looking for work that pays bills without draining my soul. I’m writing to figure this out as I go.

I don’t know what comes next exactly, but I know what I’m NOT doing anymore: work that serves the organization instead of the people. Work that exists to justify itself instead of solving real problems.

I’m building toward writing, making tools, teaching—creating things that help people understand and be more independent. Work that aligns with who I am instead of fitting a job description.

If you’re thinking about this too—about leaving corporate life, about what matters, about how to spend the time you have left, no matter where you are—I’d like to hear from you. Not because I have answers, but because I think we figure this out together, not alone.

I’ll keep writing about what I’m learning. You’re welcome to follow along.

Just be honest with yourself. That opens the door.

–Vernon Howard