[tcbawo]

  * This might sound trite, but you will make the most money when your company has lots of money.  If your company is struggling or its industry is going through a cyclical slowdown, you will typically make less than at a flush firm or in a booming industry, even if you are a top performer.  Tactically switching industries midway through my career led me to significantly higher comp longer term (several multiples).  
  * Become indispensable in the key areas that are most highly correlated with company success.  I mean improving the company's bottom line, not working more hours than anyone else.  Be focused and direct.  These priorities are often broadcast by ownership/the executive team, but sometimes the message gets lost in translation by middle management.  Do these things with visibility and measure the difference you've contributed.  If your job isn't in the critical path or your job doesn't have enough transparency, move on. 
  * If you don't have equity, it's not your company.  Don't make the mistake of sacrificing your mental or physical health for your company's sake.  It's never worth it.  Having 'moral' equity instead of real equity is an awful feeling.  Instead of holding out, moving on was always the right call for me.

[austin-cheney]

Be careful about that second point. I have seen people posit themselves into positions of critical design decisions only to position the business around their core strengths. That is toxic. It will buy you increased job security for a time, but if your strengths are out of alignment with common sense it’s only a matter of time before you and your team are crushed by tech debt. An example is imposing all business logic goes in Kubernetes because you good at Kubernetes. Be aware that you will likely encounter this at least once in your career.

[screwturner68]

The second point hasn't really helped me much, I opened a new line of business basically doubling my groups revenue. I spent almost three years trying to convince my boss to stop leaving all sort of money on the floor and actually pick it up. It took a while but then he finally got it and ran with it, the only problem is I am the only one with the skill set to actually do the work, the rest of the group is still living in 2008 and being told what a great job they are doing (IMHO they are ripe to be off shored). Now the wok is spinning up and I'm still the only person that has the skill set but there are no rewards for that skill set aside from management telling me I have to teach everyone what I know (and that's not going to happen)

[austin-cheney]

Incidentally becoming the single point of failure isn't the problem. The problem is an ethics violation of intentionally positioning yourself before the cost and maintenance considerations of the application.

If, in your example, you become the single point of failure because nobody else wants to engage in modern practices to increase the durability of the application then its a management problem. The way to think about that is: that by changing direction are you reducing time and cost of delivery? If so you have become that single point of failure by pushing for greater ethical considerations.

Beware though, everybody especially people who are ethically wrong, will claim their way is better. The differentiator is measurements: speed of delivery, speed of refactor, degree of risk, speed of labor, quantity of dependencies, compile time, load time, and so on.

[philomath_mn]

The first bullet reminds me of the "cones" from _The Clipper Ship Strategy _ -- it's a great read that not many people have heard of.

[jselysianeagle]

> Tactically switching industries midway through my career led me to significantly higher comp longer term (several multiples).

Out of curiosity, which industry did you switch from (and to)?

[tcbawo]

I worked in telecom for a number of years. After years of outsourcing and cost cutting, I left and took a job at a company that might be considered fintech now. This coincided with the early days of electronic trading. This led to a software career in finance, which was an unanticipated but lucrative career turn.

[philomath_mn]

I've had a similar experience transitioning from defense to fintech. The work is interesting and I found non-dog-eat-dog companies that still pay very well.

[keplerdos]

Would you mind recommending a few companies from your experience? May look into that path myself.

[cableshaft]

These are great pieces of advice, and something I wish I had followed earlier in life. I probably should be following one of them now even.

[tcbawo]

I had never considered sunk cost fallacy https://en.m.wikipedia.org/wiki/Sunk_cost on the long term time horizon of my career. In multiple cases, I stayed on longer than I should have. Early in my career I suffered from short term thinking, rather than guiding my job in the direction I wanted. Will growth allow me to follow the career track of my manager or other senior IC? Do I even want that? Am I gaining valuable experience, or am I beginning to stagnate?

[robin-redbreast]

Where is this from?