Career Hacking - How To Get The Career and Money You Want

Career Hacking - How To Get The Career and Money You Want

I was listening to the ChooseFI Podcast while driving to work this morning and specifically picked the episode 088 - Career Hacking The Tech Industry with had one of my favorite FI bloggers, J from Millennial Boss. What she has done with her life is downright amazing, what all of the people in the FI community do is extraordinary: save most of your income, start profitable side hustles, learn to what is important and live a life not dictated by a paycheck. What I was beyond surprised about was that she had a similar strategy to what I was implementing in my own life.

Career Hacking 

I never had a word for my life strategy before hearing her story and the podcast. What career hacking is essentially is to plan and set yourself up for success within your career since in today's working world there is no guide to get to the place of where you want to be in terms of passion and income. 

My Career Hacking Strategy 

Let's start from the beginning: growing up I always had an interest in two things (1) art/all around creativity and (2) making money. I remember around the holidays I would make dozens of crayons drawings on colored construction paper of winter scenes. I would pile all the drawings up behind the couch and carefully construct a fort to hold my handmade inventory. When the family started rolling in, opened up the fort doors and stuck a sign out that said "5 cent drawings". I even had a few buyers. Everyone to this day remembers my little holiday shops. 

As I looked to adulthood, I realized the power, freedom and options that money gives a person. I took up many part time jobs, realizing that I could make some money and I could add the experience to my college resume when the time came. First came working at an ice rink food stand, then came KFC/Taco Bell (it was a two in one, both chicken and tacos), then Subway (which they referred to us as "Sandwich Artists"), then working BOTH at the local library and Subway by the time senior year rolled around. With all these part time jobs I still found time to take honors and AP classes, participate in art scholarship competitions as well as contribute to after school groups and sports. 

When college finally arrived, I continued to work at various part time jobs (which included student work study programs, Bed Bath and Beyond and West Elm) as well as work unpaid internships to try to add as much experience to my resume as possible while having enough money to eat (and not beg my parents for extra cash). 

When college came to an end, I was in a position where many of us end up: struggling to find a job. I had everything on my resume that I thought an employer could want: good grades, work study programs, part time experience, internships in the field I wanted to be in (or so I thought I wanted to be in), as well as fantastic letters of recommendation. All of which got me no where in terms of getting my foot wedged through the corporate door. 

So then I turned to recruiters (which can be a great resource if you know how to use them wisely). I met with about a dozen different recruiting agencies after I graduated to try to find a job, all but one led to a job offer. 

I landed my first big girl career at a Law Firm in Boston. I thought I would be doing some big time money management based on my experience, interview, and what the recruiter said.


My first job was doing billing in actuality. Painful, repetitive, boring billing. Within a month I walked out the door (forgetting my favorite pair of shoes behind but somehow remembering my cactus plant). The 40K I was bringing home wasn't enough nor would this role ever be enough for my pride. After about a month of struggling to find another job, I landed a temporary role at a large bank in Boston processing trades for mutual funds.

I loved my job and seeing all the numbers and guessing the strategy behind the traders' picks, I loved my coworkers who were always down for a post work beer, what I didn't love was that I was making $14 an hour. I waited out 7 months with the promise of being offered a full time roll with benefits, eventually I knew when to put my foot down and took another role from a recruiter as a Hedge Fund Accountant. 

My salary went to 48K, which I was happy with at the time since I could now afford some takeout versus my daily 2 cups of ramen noodles. The work was more prestigious than it actually was, though I was involved with Hedge Funds, it was more like pressing a few buttons and adding some numbers to an excel sheet. Most of my time there was spent researching my next move and how to make more money. 

I knew I couldn't continue down the financial operations route - many of the jobs were being automated and those that needed a human touch were shipped over to India. I loved numbers and money but I didn't like actually working with them. So I turned to my first passion - the arts. I researched various careers that had a creative spin, that would make decent money and have a dynamic career path. I talked to friends, family and friends of those friends and family. What I eventually stumbled on the defining moment of my career so far, UX Design. 

UX (User Experience) is a job that is focused on creating the best way for a person to complete their job: to create a frictionless workflow. I immediately knew this would pay the bills and feed my creativity. What I didn't know was how to become a UX Designer. So at my desk at my Hedge Fund Accounting job, I google for hours, "How To Become a UX Designer". I watched youtube videos, read blogs, talked to friends who were in the field. The field is so new that they are just starting to come out with degrees in UX/UI (User Interface). So I made the decision that was best for me,  to go back to school for my masters in digital media but focus on UX design. 

I finally worked up the nerve to quit my job and dedicate my full efforts for 6 months to building up my portfolio to apply for a UX job. Those six months flew by and I had enough material to add to my website and launch it for the world to see. I worked up the nerve to apply to hundreds (yes hundreds) of UX roles in the Boston area before starting to target ones that would work best with my background, UX Design jobs in the FinTech space. 

Within a month of applying this strategy, I landed my first UX job at a FinTech firm in the Boston Seaport making 65K. I went from 40K, down to $14 and hour to 65K all within 3 years. After working there for about a year, I realized that I had enough traction, experience and was able to do the rest of my masters remotely to gain even more money. When I found a job opening for DOD contractor near where I grew up, I decided that this would be the best option to marry together my love of personal finance (and saving money) as well as working within in a creative field. I am happy to say I have back, living in my parent's home for about 3 months now as well as saving money and planning my next move(s). 

How To Career Hack

Though everyone's journey is different, there's a few key takeaways that anyone can use to their advantage on their journey to either career happiness, financial independence, or changing careers completely.

Know your worth versus having someone tell you your worth.

I knew I was worth more than minimum wage, than $14 an hour, than 40K a year, than 65K a year. And I know I am worth more than 83K a year (what I am currently making now). There are always ways to get more out of your job such as negotiating, seeking out a different company whose wiling to pay you more (especially in this labor market) or investing in yourself or getting a side hustle. Which leaves me to the next point.

Never settle and always research alternatives.

Maybe it's just plain stubbornness or the immigrant Italian mentality I have had instilled that always whispered "never settle". Never settle always led me to explore my options and to research beyond those options. If I didn't deeply understand the ecosystem around me and how to switch careers I would of been stuck at my old job or worse, it probably would of been outsourced while I was there. 

Use your experience now to shape your future. 

I heavily leveraged by past experience to enter a new field. I literally created a "career roadmap" on paper and listed out my point A (where I was), point B (where I wanted to be) and then listed the steps on how to get from A to B and the "alternative roots. What was important was that I used my knowledge in a particular field to transfer into a different role but similar field. Heck, I didn't even need training! And I was training employees with much more experience than me that didn't have the background knowledge I did. 

You're in charge of your own career destiny.

One thing that I always have running in the back of my head is this: "You control your career". You control every aspect such as your performance, your mastery of the job, your relationships within that job and ultimately you steer your career ship through the calm and turbulent times. What matters is how you analyze, react, and then choose what to do. 


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Moving Home #2

Moving Home #2

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