by Glenn Gonda
A Creative Strategy Guaranteed to Crush the $100 Challenge
Before I became a software engineer, I made my living as a recording studio engineer. I have a non-traditional background and I actually used that to my advantage during my job search. Thanks in part to my audio background, I was able to land an engineering role at a music startup.
Recently, I discovered the Breaking Into Startups podcast. It features inspirational stories from people in tech who come from non-traditional backgrounds. I can relate to the stories and have championed the podcast to many people in my network.
Each episode highlights a different person’s journey into the tech industry. Towards the end, the hosts ask each guest a series of “lightning round” questions. It kicks off with, what I call, the $100 challenge:
“Let’s assume you’re starting all over again. You only have $100 and you’re dropped off in a new city. What would you do to get where you are today?”
Guests have provided interesting answers such as driving for Lyft and attending Meetups. One guest even quipped that he’d use the $100 to buy a ticket back to the Bay Area.
After listening to an episode on a flight to Hawai’i, it got my creative juices flowing. When the episode was over, I asked myself what I’d do if I had to start all over. I had another 4 hours to kill before landing in Hilo, so I decided to take the $100 challenge head on.
This challenge isn’t as simple as I thought it’d be. It actually generated even more questions than answers.
I realized that I had to make some assumptions that aren’t made clear during the podcast. It almost feels like I’m solving an algorithm on a whiteboard during an interview. I have to do more discovery around the problem before I try to solve it.
The setup
To start, I’ve defined the following constraints:
- I can bring anything I currently own with me as long as it fits in my backpack and one carry-on sized luggage.
- I can’t sell anything I bring with me.
- I can’t borrow money from anyone, but I can call in one favor from three different people I know.
- I’ve paid my bills for the next 3 months, but I can’t use any of my available credit during the job search.
- I’ve arranged a free place to stay during my job search via Couchsurfing.
- I am given a crispy $100 bill before my departure.
- I am relocating to Portland since it’s the closest metropolitan area where I don’t know anyone.
- I’ll have to make my living in Portland for the next 12 months.
With these constraints defined, I have to be thoughtful about a couple of things. First, I need to be resourceful above all else. Second, everything I bring on this adventure has to serve a purpose.
I’m packing a duffel bag full of clothes including my Telegraph Academy hoody. My goal is to wear it around Portland and leverage the school and its mission as a topic of conversation.
My backpack will hold other money-making essentials. Every day, I plan to carry around my laptop, camera, and a copy of Cracking the Coding Interview.
Now, comes the tricky part. I have to identify my needs and estimate my costs for a three-month long job search. These needs will elevate my budget above $100, but I view it as a necessary investment to put me in a position to succeed.
Arriving in the city
First, I’ll need an affordable and efficient way to get around Portland. Then, I’ll need to rent a desk at a co-working space to give me a place to network and be productive. A music nerd like myself will not be able to function without music, so I’ll need a Spotify subscription. A vast tutorial resource for preparing for code challenges and interviews is critical. Finally, I’ll need a way to edit photos.
After conducting some quick research, my costs will be:
- $100/month for a public transportation pass
- $295/month for a desk at WeWork
- $10/month for a Spotify premium subscription
- $29/month for a Pluralsight subscription
- $10/month for an Adobe Creative Cloud Photography subscription
I’ve already spent more than the $100 I will arrive to Portland with. Based off of this list, I need to generate about $450 every month. Yikes!
After arriving in Portland, the first thing I’ll do is sign up for daily job alerts, but it’s not what you’d expect. I’ll actually sign up for jobs I don’t want because then I’ll know what’s waiting for me the moment I stop hustling. I want the reminder every morning that if I don’t give my best that day, I’ll end up applying to one of those jobs.
Next, I need to think about how to make more money to cover my needs. This is where resources like Nerdwallet can be so valuable.
I recently discovered a bank promotion that would help me fund my expenses during the job search. With a $25 deposit, the bank offers a $250 bonus on new checking accounts. The kicker is that there’s no minimum daily balance or need for direct deposit. This is where my first $25 will go.
Now it’s time to cash in on my favors. I’ll transfer $25 to three of my family members and have them to open a checking account with that promotion. Then, they’ll transfer $275 back to my account and I’ll thank them until they can no longer stand it and hang up on me. With a little effort, I now have $1,000 more than what I arrived with.
Renting a desk in WeWork is my biggest investment, but it’s crucial for several reasons:
- it gives me a primary place with wi-fi to work and offers unlimited access to free coffee.
- it gives me an awesome space to invite people to for meetings.
- I’ll also use their events as networking opportunities.
Even at $295 per month, it’s worth every penny.
Speaking of networking, leveraging the Internet will be important for building strong relationships. Alumni groups, Slack communities, and attending Meetups are all great ways to network. I will also consider volunteering for causes that are important to me such as Code2040.
I can foresee a situation where I burn through money quickly, so having side hustles is also helpful. Side hustles are a great way of bankrolling the job search, but make sure they don’t distract you from the end goal.
Photography is a passion of mine and it’s a skill that can make money. I’ll charge people for LinkedIn headshots and photoshoots. The Adobe Creative Cloud subscription costs $10 every month, but it will make back its money and more. I’ll also organize photo walks around the city to generate more income once I get more familiar with the area.
My second side-hustle comes courtesy of my previous career in the music industry. I’ll advertise my mastering services online to help musicians put out quality music. I’ll rent out a mastering facility for an entire day and complete two albums in that time. Based on past experience, this should net me at least $1,000 after studio fees.
As I stated before, The $100 challenge demands that you be resourceful above all else. I’m convinced that I’ll conquer it, but that won’t stop me from considering new ways to optimize my time and money.
Your turn
Now that you’ve read about my plan, it’s your turn to get your creative juices flowing.
“Let’s assume you’re starting all over again. You only have $100 and you’re dropped off in a new city. What would you do to get where you are today?”