Why 35 Years of Coding Still Leaves Me Regretting Not Pursuing Management

In the opening note, the author states that technology alone cannot change how people work unless you have the ability, authority, and opportunity, and that finding the right position is essential to achieve great ambitions.

The author recounts a 35‑year career as a programmer, realizing that a programmer’s power is limited; no matter how skilled you are, you rarely have the authority to rescue failing products or projects.

He describes a turning point about 20 years ago when his second company was declining, and a five‑year software project for a publishing client ended as the client moved to the emerging internet world. At that time he had been a programmer for 13 years, with roughly nine years in management.

He explains his desire to stop juggling both leadership and coding. In the mid‑80s his first company built a new electronic reporting tool, which he led, handled media interviews, investor relations, and also served as one of three programmers and UI designers. The workload was overwhelming, and after the product launch he fell ill.

In 1994 he faced a career choice between technical management and staying a programmer. He chose programming for its simplicity, later regretting that decision despite participating in many great projects over the next 20 years. He now believes that pursuing roles such as CTO, CIO, or VP of Engineering would have been far better.

He spent a year in the San Francisco Bay Area around 1995, including a stint at Apple when the company seemed on the brink of collapse. He left before Steve Jobs returned, missing the subsequent resurgence of Apple and the internet boom.

Having led major product releases—nine major releases where he wrote the core code without needing later patches—he felt his talent was in high demand. Yet he acknowledges that without senior management authority, his influence remained limited.

He contrasts his own path with his sister’s, who moved into management early, became a vice‑president at a large company, and now has assets roughly ten times his own.

The author emphasizes that many of the worst companies he consulted for suffered from incompetent technical leadership, often led by managers who lacked technical understanding yet made critical decisions.

He shares a specific example of a bank’s engineering VP who claimed he didn’t need technical knowledge, leading to poor procurement decisions and eventual dismissal.

He recounts a personal experience as the second programmer at a startup developing an online store. The lack of technical leadership, a complacent senior programmer, and resistance from founders to hire competent engineers led to the project’s failure and the eventual firing of the original staff.

He reflects that if he had been in a senior management position, he could have steered the company onto a different path, but as a programmer he could only contribute code.

Ultimately, he concludes that without the right authority and opportunity, technology cannot change how people work, and that finding the proper position is key to achieving one’s ambitions.