Sample Chapter

Sample Chapter — What Work Looks Like Now

This chapter comes late in the book, after the diagnosis and the long process of understanding what it meant.

It’s about work—not in the sense of career advice, but in the sense of fit. For most of my adult life, work felt like something I endured rather than something I chose. After the autism diagnosis, I began to understand why certain roles drained me while others didn’t—and why I kept leaving jobs even when I was doing the work well.

This excerpt shows how my understanding of work shifted from “necessary misery” to a set of puzzles I choose to engage with, and what that looks like in practice.

The full chapter goes on to describe specific workplaces and projects. Those sections are intentionally omitted here.

For most adults, work occupies a huge share of waking life—commute, email, meetings, projects, then doing it again tomorrow.

When work feels miserable, it's hard for life not to feel miserable.

For a long stretch, that's where I lived. My days felt like:

Wake up.
Go to a job I didn't like.
Come home.
Repeat.

One of my only real escapes was the weekend, when I could get high and disappear into a different world where work didn't matter so much, at least for a little while.

It was especially hard because I was the primary breadwinner. I had a wife and two daughters depending on my income. Quitting wasn't a neutral choice; it would affect them immediately. So with the exception of Safenet, I stayed, even when I hated it.

At the time, my internal story was simple:

"I hate work, but I have to keep doing it."
I didn't yet have any language for "fit" or "wiring"; I just assumed this was what adulthood felt like.

After the diagnosis, and especially as I aged into my fifties and sixties, that story got more complicated. I started to see that I wasn't just "unhappy with work." I was repeatedly trying to do work in ways that didn't fit how my brain is wired.

This chapter is about how my view of work has changed—from "necessary misery" to "puzzles I choose to engage with"—and what it actually looks like now.

What Work Used to Mean

Back in 2002, during career counseling, I was asked a question:

"What is work to you?"

I didn't just answer in the session. I went home, opened a document, and wrote it out in detail. My list included:

• Work is how I earn money to provide for my family.

• Work is where I make my contribution to society.

• Work is where I create things I can point to and say, "I did that."

• Work is where I demonstrate my abilities and learn new skills.

• Work represents my status in life.

• Work is where I expend most of my effort.

• Work is something I should enjoy and like doing.

I even wrote that work was "the place where I get to engage with people in a political manner." Looking back, I think I wrote that because I assumed that's what successful professionals did—that "playing the game" was simply part of adult working life, even though I never felt naturally equipped for it.

Alongside that, I listed characteristics of an ideal job: long-term focus, problem solving, design and architecture, cross-functional work, constant learning, independence, working with smart people, seeing the whole product, being a kind of "authoritative source" in the middle of complex systems.

If you strip away the noise, the picture that emerges is:

• I wanted work to matter.

• I wanted it to be intellectually demanding.

• I wanted to build things that actually did something in the world.

• I wanted to be recognized as competent.

• I assumed politics came with the territory.

What I didn't yet understand was that the "status" and "politics" parts of that list were going to clash head-on with the way my brain works.

Getting an MBA, in theory, prepared me to move toward those director and VP roles—the places where strategy and "leadership" live on the org chart. But in reality, those jobs are built on politics: alliances, subtext, reading the room, subtle signaling. As my career unfolded, it became obvious I was never going to be comfortable in that arena. Much later, the autism frame gave that mismatch a name and an explanation.

When Restlessness Was a Signal

Looking back now, certain patterns jump off the page. I didn't leave jobs because I couldn't do the work. I left when the conditions that made the job livable stopped being met, frustration built up, and it became clear nothing was going to change.

The times when work felt truly "too hard" were usually when I was stuck in a political situation I had no realistic way to influence or win.

Usually, I'd be working long hours, the conditions that made the job tolerable would erode, I'd start quietly looking, and if nothing improved, I'd leave.

I grew restless—sometimes to the point of quitting—when:

• There was nothing to hyperfocus on.
  If a role didn't offer at least one complex, meaningful problem to sink into—designing a feature, working through a data model, architecting an interface, managing a genuinely complex program—I felt like the engine was idling. Busy, but not engaged.

• It wasn't clear what came next.
  If I couldn't see any upcoming work that felt interesting or important, my motivation disappeared. "Busywork now, mystery later" never sat well with me.

• The organization pushed death-march projects.
  Sometimes executives made promises—usually tied to their own incentives—that translated into nights and weekends for the product team. Features were committed to impossible dates. I watched teams burn themselves out for schedules and scope that were never realistic. In more than one case, the leaders who set those schedules were eventually removed.

• Leadership stopped caring about the end customer.
  In some companies, the focus shifted from solving real problems to shipping something—anything—that could be sold. Corners were cut. Technical debt piled up. People were told to be proud of products no one actually wanted.

• The work didn't feel meaningful.
  At one company, I was assigned to a meandering side product that wasn't strategically important. It bothered me less only because I was in business school at the time; I could tell myself the job was just a bridge while I finished the MBA.

• The culture turned toxic.
  Micromanagement, poor leadership, and politics with no rational basis were huge red flags. At a couple of companies, including Corporate Personnel Systems (after BrianT was fired) and later Advanced Systems Lab (after BruceR was fired), I watched the environment degrade in slow motion. My journals from that time read less like personal reflections and more like system logs. I was documenting failures in leadership and structure the same way an engineer documents failure modes—things others ignored but I couldn't.

• The company looked doomed.
  In a few places, it became obvious that the business wasn't headed anywhere sustainable—startups burning cash with no real product-market fit, small software companies going sideways. Once I concluded that liquidation or shutdown was likely, it was hard for me to keep investing my energy. Continuing to build systems I believed would be scrapped felt dishonest.

• The work diverged from what customers actually wanted.
  I've been in situations where customers were promised things that weren't true and systems were built that didn't match real user needs. That violated something deep in me. If we're building on a lie, my work starts to feel like complicity.

Because of all this, I was often looking for my next job almost as soon as I started the current one—sometimes within a month.

At the time, I treated that pattern as a character flaw: I told myself I was impatient, not a "team player," a quitter, unable to "tough it out" like everyone else.

In reality, it was often an alarm system:
There is nowhere to put your hyperfocus here.
Or the thing they want you to build doesn't make sense.
Or the system itself is heading for a wall.

Once that internal alarm stayed red long enough, my brain wanted out—even if I couldn't always articulate the reasons cleanly at the time.

From Career Ladder to Puzzle Board

For years, I compared myself to a standard template:

• Get promoted.

• Manage more people.

• Become "a leader."

• Make more money.

It's what most of the corporate world seems to reward—and what I saw modeled around me.

My actual career looked nothing like that. I moved across roles:

• software engineer

• process engineer

• project manager

• program manager

• product manager

• systems analyst

I often started strong—especially when there was a clear problem to solve—and then ran into the same walls: politics, loss of meaningful puzzles, cultures that rewarded spin over substance.

The story I told myself was: you failed at building a career.

After my diagnosis, and especially after I shifted into contracting, that story started to change.

As a consultant, I'm not climbing anyone's ladder. I'm brought in to solve problems:

• untangle a gnarly legacy system

• straighten out a broken workflow

• help a team get serious about Agile/Kanban

• bring clarity to an overloaded product organization

Most of my engagements have been part-time but long-running—anywhere from 14-30 hours a week per client, sometimes two clients at once. Working 60-65 hours a week doesn't bother me if I'm in the zone and the puzzles are real.

The metric shifted from "Am I progressing up the org chart?" to "Am I helping untangle real problems in a way that makes sense to me?"

Now that I'm in my early sixties, something else has changed:
I don't have to work in the way I once did. The financial urgency is lower. If a situation became truly miserable, I could walk away and stay home.

And yet I still want to work—because the right kind of work gives my brain the puzzles it craves. The treadmill version of work has mostly fallen away. What remains is the problem-solving version.

The rest of this chapter gets more specific about what ‘fit’ looks like for me in real workplaces, and why documentation and detail became central. I’m leaving that portion out of the public excerpt.