How to Be 100% Stoked When Quitting Your Day Job

When I quit my job I knew I was going to be just fine. But as my life is, there is always a grandma, a friend's mom or a football watching uncle who—because they care—worry deeply about my decisions.

For me this time, that person was both my mom and dad.

They thought I was crazy. They consistently would ask, "Are you sure you want to leave such a good job? I mean the benefits, vacation and the culture. Ryland, you're so lucky."

They were right. Everything they said was true. By society's standard I was the luckiest 26 year old on the planet. Why was I leaving?

When I started the job, the value of employer health insurance, a lax vacation policy and a great work culture was massive. I only had a few hundred dollars to my name at the time, and to have a paycheck coming in with those benefits attached was insanely valuable.

But as time went on and my net worth increased those benefits didn't hold as much value. (When you're saving +50% of your paycheck by "time" I mean 2 or so years.)

I wanted freedom of time to create and freedom of location to surf and snowboard outside. I wanted out of cubicle nation, even if the job was A-grade. 

My parents knew and understood why I wanted the things I listed above. Believe me, I told them plenty of times, but those reasons alone never seemed to console their worries about me. 

Communicating to people about financial independence is one of the hardest things for me to do. Add that on to communicating it to my parents and it becomes exponentially harder.

They weren't going to control my decision, but even so I wanted to 1. Get them off my back ;), and 2. Make them feel, at minimum, a bit more at ease about my decision. "How can I bridge this ridiculous gap?" I thought.

That's when I started to dial it in.

I needed to show my mom and dad that this wasn't a rash, childish decision. I had to show them that I had been building massive safety margins to protect myself from any apocalyptic life event that could come my way.

So that I could start peppering these safety margins in to dinner convos and family text threads, I wrote down a list of the safety margins that made me feel so comfortable.

Here's the list that made me feel comfortable taking a leap of faith:

- 1.5 years worth of cash savings
- 7 years worth of investments
- A great resume that can help me get another job whenever need be
- Recommendations from my bosses and coworkers
- And! an invitation to come back to work from the company I was leaving


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I had this perfect text thread that showcased the exact moment my parents let their shoulders drop, but I could find it in both my and my mom's text history. 

Here's my best reenactment of that pivotal text:

Mom: Hey Ry, You know your dad and I love you, but are you sure you don't want to maybe stick out one more year? (Probably like a kissy emoji or something.)

Me: (Deep breath.) I've really thought this one through, mom. I've put away years worth of living expenses, have built a great resume so I can get a future job when needed and have always wanted to do something like this.

Your son is going to use the life you've given him to step away from corporate culture and office life, and explore the world for a bit. He's built the back up plans. I promise you he is going to be okay.

Once my mom and dad started to comprehend all the back up mechanisms I built, I felt them become more at ease. They recognized I wasn't going to end up homeless or jobless, that there was a good chance things would end up better than okay.

Thinking back on it now, this is a great way to test out your leap of faith ideas. If you can convince your worrisome grandma or your Dorito eating uncle that things will be okay, you can be pretty certain you've covered your bases and things will end up A-okay.

Update: It's been 4 months. They've been the most special 4 months of my life. My mom and dad are incredibly stoked for me, and that feels great.


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