How My Boss (and CEO) Convinced Me to Quit My Job

By Kyle Milligan / February 16, 2016

Today I quit my job. Well, sort of. The bosses were locked up in reviews and meetings so after a while I decided to just leave and shoot them an email (basically a text message breakup for work). I essentially told them that I loved my team but I wanted to pursue writing full time. I received a phone call from my team lead about 10 seconds after I sent the email from my home. He said,

“I just read your email and I can’t do anything but respect that.”

The decision to quit wasn’t easy. I have been in sales for a couple years and I make good money. As far as I’m concerned, sales is the best field for motivated people looking to make a lot of cash.  Sales organizations usually have grand incentives for high performers and self-starters. The more motivated you are, the better you perform, the more revenues you generate. Pretty basic, right?

But still, I quit my job. Why?

The answer is: “A bunch of reasons.” But it all started one day when something from management backfired in a major way. In a harmless attempt to motivate our team, someone high up the food chain sent out this e-mail:

From: {}{}{}{}{}{}
Sent: Thursday, January 14, 2016 1:52 PM
To: Sales Team SOHO – UN; SDR; Sales Team SMB – UN; Solutions Engineering
Cc: Sales Team {}{}{}{}{}{}
Subject: MASS Market team takes it to THE BANK

Dear Mass Market Teams,

JUST IMAGINE if you had a bank account that credits you with $86,400 every morning? It carries over no balance from day to day…every night the bank deletes whatever amount you failed to use during the day. What would you do?

Obviously draw out every cent, right????

Each of us has such a bank. Its name is time. Every morning, you are granted with 86,400 seconds. Every night, it writes off as lost, and any second you have failed to invest to a good purpose will be lost forever. It carries over no balance….EACH DAY, it opens a new account for you….and each night, it burns the remains of the day. If you FAIL to use the day’s deposits, the loss is yours. There is no drawing against “tomorrow” You MUST live in the present on TODAY’S deposits.

My questions to you: What will you deposit this year? How will you make the most of your time in 2016?

This is your time! Make the most of everyday!!!

I’m excited to see you all off to a great start in 2016!  As we continue to head into the year I want to remind you of our most precious asset. TIME



I stared at my screen for a while after reading this. They were right. I get 86,400 seconds a day.


I felt ashamed. Embarrassed. What was I doing with my life? My talents? All the ambition I preach about. After that email the wheels of thought were set in motion.

Related: Never Get A Real Job By Scott Gerber Review

As I read the email I considered: For everything I’d accomplished, I didn’t really have much to show. I had some degrees that were virtually worthless; they provided no value anymore and came with a mountain of debt. I had made some nice paychecks. I had a couple little cute trophies and prizes (almost all of which I sold), but nothing else.

Here’s where I will differ from the few brave people who stormed out of their corporate cage:

  1. I LOVED MY TEAM. They were all awesome. I came into the office knowing I was going to quit but I couldn’t tell anyone. As I waited for the boss to become available, which never happened, me and my coworkers chatted about our weekends and I felt guilty that I was about to just leave them without a heads up. If you read this, sorry guys.
  2. I LIKED MY COMPANY. It actually was probably the best job I’d ever had. The culture was amazing. The support was great. Everyone I met was special.

But still, and here is my contention: It is a job.

And that’s what I hated about it. I had to go. Or I’d get in trouble. Or I’d lose my job. Then I won’t have any money. Then blah blah blah. Simply put, I don’t want a boss anymore.

I was sitting in Belmont, California and the CEO of the organization was at the front of the room. Someone asked: “If you could give us new-hires one piece of advice, what would it be?”

His response was: “This is going to sound simple but here it is: Do what you want to do. Don’t do what you don’t want to do.

That’s it.

And that was it for me. The final straw.

I was at New Employee Orientation, staying in a fancy hotel, free food, the super bowl was in town, I was getting to go out in San Francisco (all on the company dime) when the CEO unwittingly convinced me to leave his company.

What I did cherish during my few short months with the company were the amazing trips we took. I went to Denver and San Francisco in two months. Each time it came time for all of my new friends and I to part ways, I was sad.

I loved how simple life was while traveling. All I had was a little bit of cash and a couple changes of clothes. I didn’t have to worry with anything else. Life was so basic on the road.

I loved being in a new city. Exploring and meeting new people.

I didn’t want to go back to my desk.

I had a pretty good idea of what I wanted to do and what I didn’t want to do.

After some consideration, I just knew I would rather be poor and ragged, struggling to survive, hustling to support myself, than be comfortable in a big office with a nice view.

And so I left. I quit my job. Obviously not for the traditional reasons. There’s not a nicer position waiting for me. I’m not upset with my company. I’m upset with having a job. Reporting to the same office to do the same shit every day. I just want something more.

I don’t have a plan. Not a real one. I’m going to travel; see friends and family. Try to sell my book when it comes out in April.

I don’t have a safety net. Not a real one. My bills are still around and very real. I have about a grand in the bank but I’ll figure it out. Either way I’m in it now. I’ve “burned the boats.” I guess I’m going to leap and construct my net on the way down. Without a paycheck, desperation will motivate me.

Necessity is the mother of invention, right?

I’ll be writing a lot more with all this free time on my hands so check back or sign up in the box on the right pane to get my posts straight to your email! You can also follow me on Instagram or Twitter if you want to keep up with whatever happens next. Both are @all99kyle

Wish me luck…

About the author

Kyle Milligan

I'm Kyle Milligan. I really enjoy writing. I wrote a couple novels (The Hang-Ups and Hangovers series) and now I blog frequently on a bunch of different websites. I also enjoy lifting heavy things and and writing about it.


Leave a comment: