Photo by Terry Boynton / Unsplash

Job Indecision Calculator

What should you do when it comes time to make one of the most important decisions of your life?

What's This All About?

This is about creating access and leverage.

This is about furthering the spirit of Return on Security. If you aren't familiar with what that is, start here.

I want to offer something special to the members who join the Return on Security community. Something that has personally helped me a number of times in my career and something that I think can help you too.

If you subscribe to the Security, Funded newsletter you'll not only get access to the free weekly issues but you'll also get my most popular digital product for free.

Job Indecision Calculator
Calculate the job that’s right for your lifestyle and goals

This digital product is something I normally sell for $20+, and it has helped people from all over the world make better career decisions.

The majority of my career experience has been in the cybersecurity field, and I've used this tool nearly every step of the way.

I want to see other people succeed in cybersecurity careers and their life in general, and I want to be a person who has helped many others get where they want to go. Be it in the form of blog posts, mentoring, or tools just like The Job Indecision Calculator.


What is the product again?

  • This is lifetime access to a Google Sheet template calculator.

Who is this for?

  • This is for someone who likes to prepare and be methodical about big life decisions.

How does it work?

  • The calculator is one part analysis and one part career coach.
  • It uses numbers to help you prioritize what you value based on your phase of life, career goals, and lifestyle.

When do I use it?

  • Use it to compare your current job against another job offer.
  • Use it throughout the interview process so you don't skip talking about anything that's important to you.
  • Use it on your current job to see if the job you have aligns with your career goals and lifestyle (and if you should start looking 👀)

The Story

In 2011, I applied to two different jobs in two different cities doing two different things at the same time. To my surprise, I got job offers from both companies and was left with decision paralysis.

Both jobs were paying roughly the same.

Both jobs were in the cybersecurity field, but at different ends of the spectrum. One was security engineering focused and one was more GRC/IT Audit focused. It was a great problem to have, but the jobs would have taken me in very different career directions 5-10 years in the future.

Both jobs got me closer to my goal of going deeper in cybersecurity, so I couldn't just think about the offers in terms of money.

I needed a way to understand and prioritize what was important to me outside of compensation.

This is when I made this calculator and used decision sciences principles to help me find the right path.

I made this tool to solve my own problem.

The Thought Process

I used a combination of decision science principles and my love for spreadsheets to make this work and pull out what I really needed to know.

Here's a Twitter thread 🧵 that dives deeper into the decision sciences part for anyone interested:

How the sausage was made for Job Indecision Calculator

My Career Journey (so far)

To give you a bit of context I wanted to share my career journey so far.

🎯 Associate IT Consultant at a Public Accounting Firm

🎯 Third-Party Security Assessor at a Very Large US Bank


🎯 Security Engineer at a Regional US Bank

🎯 Senior Security Engineer at a Regional US Bank

🎯 Lead Security Engineer at a Regional US Bank

🎯 Security Engineering Manager at an Online Bank

🎯 Director of Security Engineering at a Very Large Insurance Company

🎯 Head of Data Protection & Cloud Security at a Large US Bank

🎯 Divisional Chief Information Security Officer (DCISO) at a Very Large Bank

🎯 Started my Own Consulting Company

🎯 CISO in Residence at a FinTech Accelerator

🎯 Security Advisor at a Large Private Equity Firm

🎯 Sold my company to a VC firm and stood up an MSP business

⭐️ CISO at a FinTech startup (here today)

I created the Job Indecision Calculator when I needed guidance the most and I've been using it for every major career and life decision ever since.

What's In It For You?

In this tool, you'll learn:

  • How to identify what you value in a job outside of compensation and benefits.
  • How to use decision science principles to assign values to things that are not based on money.
  • How to weight, rank, and score one job vs. another.
  • How to negotiate for what matters to you in the job interview and offer process.
  • What I've learned through my own job moves through different phases of my own life.

You'll also get access to:

  • A catalog with 50+ inputs to consider before making the leap and growing
  • 3 example scenarios from my own life to give you a frame of reference
  • Video walkthroughs of each part of the tool to get the maximum value
  • All future updates and iterations of the tool for free

This calculator helped me move with confidence every step of the way, and I think it can help you too!