DCTagged March 17, 2023

 I am a 33 y/o Security Control Assessor, based out of Washington DC, making 420K/year 

About Me:

Current job title: Security Control Assessor (Cyber Security Management)

Current location: DC

Age: 33

Years of Experience: 4

Total Comp: $420,000

Brief description of your current position:

An assessor is within the cyber security framework. There’s 6 steps in cyber security risk management and I work on step 4 which makes sure systems are operating the way they’re supposed to operate and aren’t vulnerable, essentially the preventative portion of cyber security.

How I Got Here


If so, are they applicable to your current position?

I got my  masters in cyber security management and policy.

I also have security +, CISM, AWS, PMP, CISSP, CEH certifications.

Was there an expectation for higher ed?

You don’t need it but it helps your chances a lot more when it comes to landing a cyber roles because they want highly qualified professionals.

How did you pay for degrees/certs?

My companies paid for them.

Jobs leading up to your current position:

I worked as a systems admin and desktop support. At this time I was always networking at every company and reaching out to the security department and learning their certs they got and bootcamps they went to so I could level up myself

I used to go to different meetup groups and met up with many 1st generation African Americans who were making six figures in cyber straight after leaving the continent with no experience, so that’s what prompted me to pursue cyber after my time in desktop support.


What resources were most beneficial on your journey?

Networking dramatically helped me alot and was helpful because many jobs I got I leveraged my network’s referrals and it was a quick path in.

Having as many cyber certs as possible because the more you have the easier it is to be qualified for the niche cyber jobs

Having a clearance is also clutch because it is a long process to get and is very valuable to employers in the DC area. Having that made me very employable and competitive.

How did you begin working multiple jobs?

When COVID happened I was interviewing for a company while working my current job. My current job and company that I was interviewing for both went remote. I figured let me just work both for a while and see how this balances out, eventually I just started adding more jobs and here we are today.

What’s the best way to get multiple tech jobs?

I am always applying weekly and I have my notifications about new jobs from Indeed. I interview with no intention of signing on and if they say it’s in person then it’s always no. But if it’s a yes and the job is flexible and 100% remote I work until I feel like I want more free time back or it becomes overwhelming. Working in the office is always a hard no if you want to work multiple jobs.

What are the benefits of working multiple jobs?

Obviously the money but now I’m in a better position to have financial freedom for things like investments, paying off debts, buying assets like homes etc.

Another benefit is with multiple jobs you have an extremely higher chance to have an employer pay for your education or new skills. You should always be looking out for the next cert or next skill to up level yourself and stay employable.

What are the pitfalls of working multiple remotes?

The lack of balance can be overwhelming, you must make sure you gauge the role before you sign on and if not then, then early on immediately after starting. Since I’m an assessor not an ISSO I make more money with less responsibility and that is the goal. Work less, make more.

If you work for the larger consulting firms don’t add another remote job. They do internal background checks and they check THOROUGHLY. I had to pay them back a signing bonus because they found out I was working another job.

Lastly, taxes are a very different ball game once you make that much money from different streams of income. Make sure you consult with a tax advisor everytime you’re about to onboard with a new company for expert opinion. One year I owed over 10K and I found out that I could have avoided that.

What advice would you give your younger self?

Don’t be afraid to aim high early. Don’t think you’re too young to aim high. There’s no set salary or title  you need to be at by a certain age, go get the most you can get early. When I saw 20 year olds making well over 6 figures (they showed me their checks) that’s what made me realize I had a limited mentality young, now all that has changed.

What’s next?

I  eventually want to work 1 job while keeping the same salary instead of working multiple. I want to get into the cloud because that field seems to be the most optimal to make that kind of money

Overall reflections/thoughts to share/advice:

If you want to get financial freedom sometimes you gotta play the game. Get your certs, get your masters, etc. You’d be surprised how many of these organizations are looking to hire black right now, strike while the iron is hot and get in the game. I don’t think this window will be open much longer due to the economic forecast. Play the game and win.

Find your sweet spot with multiple remote jobs. I was working 5 full times at one time and making over half a million dollars but I ultimately had to quit some because I was sending emails to the wrong people, mixing up names and companies and it was a lot of meeting conflicts. 5 jobs gets overwhelming. 3 jobs was my sweet spot. If you wanna work multiple remotes find your sweet spot and don’t over do it because you will sacrifice your quality of work.

Final Quotes:

When I was working 5 remote jobs and saw all the checks hit my account on the same day for the  first time I felt like I made it. In my head I was screaming “ANYTHING IS POSSIBLE” like I won an NBA Championship!

There was a time I had two meetings at the same time and accidentally went off mute for both. So now both meetings could hear the other. My manager pinged me afterwards and asked to talk. I thought I was in for some bad news but she ended up asking me to give her the game on working multiple jobs!