The 150 Point Rule of Thumb. How to Strategically Approach Career Pivots.
We don't always begin our careers where we'd like them to end up. We're not stuck with jobs where we began them. I walk through paths to move your career in a new direction.
Welcome to the Scarlet Ink newsletter. I'm Dave Anderson, an ex-Amazon Tech Director and GM. Each week I write a newsletter article on tech industry careers, and specific leadership advice.
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It’s easy to get stuck in a specific position or industry.
While software engineers in tech-heavy areas (San Francisco, Seattle, NYC, etc) regularly move from company to company, in the rest of the world it’s extremely common for people to stick to one industry for the majority of their career.
Why do people tend to stick to the same roles and industries? Because it’s significantly easier to get a role when you have done the job before.

When you’re graduating from college, this is the first roadblock everyone runs into. So many positions require at least a few years of experience in your field. It’s tough to find those entry-level positions where they’re ok hiring someone without experience.
But what happens when you want to change roles or industries as an experienced employee?
Let’s say that you graduate from college, and become a quality manager at a tool manufacturer. Are you stuck running quality projects for toolmakers for the rest of your life? What happened to following your passion? What about exploring different types of jobs over your career?
If you now wanted to become a project manager for a tech company, is that a lost cause?
Getting stuck with your first job.
I remember interviewing a candidate for TPM (Technical Program Manager) at Amazon as a bar raiser. They’d spent 20+ years of their career in project management. But all of those years were at automotive companies, running automotive projects. They were passionate about working at a tech company, but it was certainly a stretch for them to get a position.
The reason I remember them is that they opened up a bit at one point of the interview process. They said they had always loved technology, but they had been living in Michigan when they graduated from college, and they ended up working for a local automobile company. And they felt that this decision as a 21-year-old college graduate was haunting them as a 40 something year old.
And if memory serves, they didn’t get the role.
An accidental career path.
How did you get your first job? If you’re like most of us, you got it because they offered you a job.
Oh, certainly there are those graduates from Stanford with 6 outstanding offers from big tech firms, but I think the majority of people take the first job they’re offered. Because getting a job out of college is already a bit of a victory.
You graduate from your University, you apply to several entry-level positions, and you work where you get your job. Yay, your parents are thrilled. You can finally stop being a leech and pay for your own car insurance.
Then you build skills in your field, along with domain expertise. And you build trust with your co-workers. This means that your growth inside your company (based on your local expertise) is likely larger than it would be outside the company. So maybe you stay.
Alternatively, you take a higher paying job in a similar company, but one step up. The modern cool version is a software engineer from OpenAI might take a job at Anthropic. Alternatively, you might be an automotive project manager getting a job at a different automotive company. But in either case, it’s likely the same job in the same field.
How do we go about more drastic job changes? How can we both accept that first entry-level role (where we might not have many options), but also maneuver ourselves through our career into a dream role?
That’s the fun part. Because I’ve seen it happen repeatedly. I’ve worked with many people with insane job histories. And because I’m a curious person, I’ve always asked, “How did that happen??”
Well, to begin, let’s talk about what is typically considered when hiring for a role. I’m going to break down what they look for in what I’ll call the three pillars of hiring. I’ve invented that concept, and it’s pretty awesome - as you’ll see.