From a $15/hr job, to making six-figures remote: How using constraints helped me change careers, and ditch my old office job forever.
How to use constraints when making a career change
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Have you ever come home from a mind-numbing day of work, and just wanted to scream?
Four years ago, that was my daily reality.
From 9-5, I was making cold calls at $15/hr. Your standard, "bang your head against the wall", office job.
But one day something clicked, and from then on everything was different.
Today, I'm making well into the six figures, working entirely remote, in one of the greatest cities on Earth.
I haven't come home wanting to scream in years.
I started applying Career Constraints to my work.
If you want to ditch your 9-5, spend more time with your family, and upgrade your paycheck, keep reading.
Adding Career Constraints
Twitter limits you to 280 characters, and yet people have used that constraint to write books, promote $100M+ product launches, and lead political revolutions.
Constraints focus our attention. They give us guard rails to work within, by telling us everything that's off limits.
Constraints don’t lessen our world, they focus it.
So how can you use creative constraints to revamp your career?
Start with what you're unwilling to negotiate on.
When I decided I needed to level-up my career, I created four constraints:
CONSTRAINT #1: I will not go back to a University.
This meant I wouldn’t be a Doctor, Lawyer or Engineer. Anything that needed a piece of paper to certify that I was qualified, was off the table.
CONSTRAINT #2: It must be entirely remote.
My ability to travel, whenever I choose, was my biggest concern. Giving an employer power over my salary, location, and time was too much. Location, was off the table.
CONSTRAINT #3: It must, on average, pay six-figures.
This was arbitrary. More of a bragging rights kind of thing. I didn’t need that much money to live, but having the certainty of high wages gives you options.
CONSTRAINT #4: It must be intellectually stimulating.
Okay so I’m traveling and I’m making a lot of money. But without this last constraint, I could find myself in a beautiful villa in Bali— slamming my head against a wall, yet again.
So what’s left?
These constraints immediately rule out thousands of jobs, and that's exactly the point.
After using these four Career Constraints as a filter, here’s what jobs remained:
The point of these constraints was to alleviate the pressure behind such a big decision.
Although some of these jobs might not be a perfect fit, any one of them would be an improvement. No matter what I did, I would be better off.
I ended up choosing Web Developer.
Why do constraints work
Constraints narrow your focus.
Focus helps you reduce friction while making decisions.
Here’s an exercise. (Really try and do it, not just read it)
Name a person
Name a female
Name a young female
Name a young female Latina
Name a young female Latina politician
When you’re asked to name any person, your brain is overloaded with possibilities.
You might search through your memory, and take 5 seconds to answer.
As you progress down, specificity allows you to retrieve an answer with less effort. That’s because, some of the mental sorting has already been done for you.
Finally you reach the last question, and answer with: AOC.
Although she was included in every question before, you almost certainly didn’t name her until the end.
The same applies to our careers.
The answers we’re looking for are right in front of us. We just aren’t using enough specificity to easily find them.
All top performers are already doing this.
Career Constraints tell us what to say “No” to.
They’re a declaration that, lifestyle comes first, then money.
But as an entrepreneur this is suicide right? Not quite.
(Pay special attention to how radical some of these Career Constraints are)
CONSTRAINTS: No emails, less than 4 hours of work per week.
In 2007, Tim started a supplement company. Quickly it generated a few $100K per year, with one downside. It was consuming every minute of his time.
Nearing the breaking point, he identified everything he hated most about his work. What he came up with became his Career Constraints.
Drawing these hard lines forced him to rethink his business. Ultimately outsourcing all the menial tasks he used to be doing.
He now makes $10M+ each year, using these same principals.
CONSTRAINTS: No office, No Full-time Employees.
Pieter began with the end in mind. He wanted the money of an entrepreneur, but none of the headaches.
This forced him to distill his business, Nomad List, from the very start. The company makes over $2,000,000 per year, with no employees.
His business will never make him a Billionaire, but it allows him to live exactly how he wants.
CONSTRAINTS: No meetings, No Deadlines, No Full-time employees.
After trying for years to grow his business, Sahil was exhausted. It just wasn’t going to happen.
So he flipped the model, from “Growth at all costs” to “Freedom at all costs”.
Ironically in doing so, his company Gumroad’s value exploded to over $100M.
Most people use their career to buy the lifestyle they want.
Let me know if this sounds familiar:
Hate job but make good money ↓
Mentally exhausted at home ↓
Need to distract yourself from the terrible day ↓
Spend money (Drinking, Concerts, Self-care) ↓
Feel good enough for another week at terrible job ↓
Return to top ↑
There’s another way.
A way to begin with the end in mind.
And that’s by creating your own Career Constraints.
Here's how, step by step:
Step 1: Determine exactly what pisses you off at your current position!
No opportunity for promotion.
Need to hit a quota for hours.
Boring or meaningless tasks.
Physically demanding work.
Required to be in an office.
Early morning zoom calls.
Always working alone.
Make sure to strip the situation of what’s going on at work—your boss sucks, dispute with management, passed over for promotion— with the actual attributes that annoy you about the job.
Step 2: Envision your perfect day!
This is an important step in creating Career Constraints, yet most people skip it entirely.
When you’re in a position you don’t like, it can feel like your days are playing on a loop.
You end up focusing only on the negatives, instead of envisioning how great your life could be.
Imagine you wake up on the most perfect day.
Where are you?
Who are you with?
What time do you wake up?
What’s the plan for the day?
When do you start working?
How many hours are you working?
Each one of these steps is a constraint in it’s infancy.
If my perfect day is on the beach, but I live in Philadelphia for work. I probably need a job that’s remote.
If my perfect work day starts at 1pm, but I have 6am Zoom meetings. I probably need a job where my team is located in the same time zone.
Step 3: Fill each category!
There are six major categories of Career Constraints.
Using the information you gathered in the reflections above, create one constraint for each category.
Salary: Need a minimum salary?
Location: Need to be somewhere?
Hours: Need to hit an hourly quota?
People: Need to work with other people?
Education: Teach myself, or need schooling?
Time: Need to be doing work at a specific time?
Once you have your constraints, use them to filter.
Your constraints are not your goals, but a way of filtering your life.
The next time you encounter an opportunity, ask yourself:
Is this in line with my constraints, or is money tempting me to make an exception.
This is only the first step in developing a career that is not just about money and prestige.
By using Career Constraints, you start setting hard lines and you begin filtering out opportunities that suck.
Soon you'll be closer to a career that leaves you energized after a long day, rather than one that has you screaming into your pillow.
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