There was a time when I would have done almost anything to work at a major law firm.
That was part of the bargain: You work hard in high school, score a 1510 on your SAT, and finish two-hundredths of a point short of valedictorian. You earn a full academic scholarship to an elite college, graduate magna cum laude, and get into a top-ten law school.
Then you try to turn all of that into the thing you were told it was building toward: BigLaw.
During law school, I was lucky to get a chance to work at O’Melveny, one of the largest and most prestigious law firms in the country. The offices were beautiful, and the work was consequential.
Then, one Friday evening, I stayed late to finish a research memo and noticed that the corner offices were still lit.
The Winners
I remember realizing it was the partners still working late.
These were the people who had reached the destination. They had survived the associate years, made partner, earned everything everyone beneath them – me – was working toward.
One of them had photographs from before they became a lawyer. The person in those photographs looked almost unrecognizable. Fit. Happy. Hopeful.
Maybe that comparison was unfair. Time changes everyone. But the contrast stayed with me.
The outline of the real bargain then started to appear. The institution kept score in billable hours, while the rest of life never appeared on the report.
Fork in the Road
I had no objection to hard work – still don’t. Hard work was the one part of the equation I already understood.
But I began to question what the work was for. What if you did everything correctly – worked through school, survived the associate years, finally reached the corner office – and the reward was simply permission to keep overworking at a higher level?
That path seemed inevitable for my trajectory, until suddenly it did not. I had an opportunity to help build a law firm outside the traditional path, and I took it.
Instead of BigLaw, I built a business. I practiced law. I learned operations. I wrote software. I built systems around legal and regulatory requirements.
I eventually helped lead a law firm of more than 200 people and solo-built the SaaS platform that powered much of its $25M in revenue.
It was an unusual career, it was mine, and it did not work out the way I hoped.
Focus on that sentence, because this is not a story where I rejected the conventional path and was rewarded with a clean, triumphant ending.
The application I built still runs today, nearly two decades later, still licensed and in production. Had I built the same thing in almost any other industry, the outcome would have looked very different.
But mortgage servicing is an industry built around one organizing principle: minimize expenses, relentlessly and above almost everything else. The margin pressure is structural and unforgiving, and it flows downhill to its vendors and law firms, making the pie too small for builders to have a real shot at meaningful equity.
So I ended up building as an employee, not an owner – at least for a long time. The value I created was real and lasting. The compensation was not proportionate, however. Not because anyone was being malicious; that’s just how the industry is wired.
When it ended, I had to begin again – not from a setback, but from something closer to the ground being pulled out entirely.
I made the decision to rebuild from scratch and prove my technical chops in new, (hopefully) more rewarding, industries. That meant selling a home my family loved in Southern California, moving everyone to DFW, and betting on myself in a market where nobody knew me yet. My oldest daughter changed schools mid-year, in 7th grade, during Spring Break. I still carry that. A few months before we left, I had my first and only panic attack.
Eventually, I won the bet. It was the right decision and it still nearly broke me.
What Loyalty Taught Me
The second lesson came harder: loyalty can be taken advantage of.
Not always, but often enough that it is dangerous to treat loyalty as a substitute for protecting yourself.
Institutions encourage people to believe that commitment will be remembered and value creation will eventually be recognized. Sometimes that happens. Other times, you happen to build in an environment like mortgage servicing.
It all works until one day it doesn’t, and the other shoe drops.
You then find yourself standing on the side of the road, a virtual job panhandler, trying to explain to strangers where you have been and what you actually did. I know because I’ve been there.
I do not intend to live that way again.
Why I Write Now
That is part of why I am writing. I am not trying to become an influencer. I am trying to build career equity that no employer, institution, or industry can take from me.
For much of my career, much of what I knew and had accomplished was invisible outside the rooms where it happened. I assumed it wouldn’t matter, because the hard work would pay off and speak for itself.
Reality hit harsher, especially once I realized I had to start over. A resume is not enough to explain an unusual career, and neither are job titles nor obvious success.
Lawyer. Database expert. Technology executive. Former managing partner. Builder. Operator.
Every one of them is demonstrably true. Together, they are still insufficient.
So I write about what I know – technology, data, law, architecture, leadership, business economics. The decisions beneath the tools. The things I have built, the mistakes I have seen, the conclusions I earned the hard way.
I am building a public body of work that belongs to me. I have no idea if another shoe will drop, but if it ever does, I do not want to begin again from silence.
The Lights Are Still On
I still believe in hard work. I still believe in commitment. I still believe there are things worth sacrificing for. I’ve been the person in the corner office with the lights on late on a Friday evening, and I’d do it again under the right circumstances.
But I no longer believe hard work speaks for itself. And I no longer believe loyalty excuses leaving your future entirely in someone else’s custody.
Loyalty favors silence, but does not reward it.
So I write. I make silly pop-punk songs. I remain visible.
— Scott
