When To Leave Your Job

This is the first part of a two part series. In part 2 I’ll cover ‘How To Leave Your Job.’

Quitting your job can be a very uncomfortable experience. The fear and uncertainty associated with leaving a job is enough to drive people into an anxious frenzy. I should know: I quit my job today.

However, these feelings are completely and utterly misplaced. The moment I decided to quit was an important step in reclaiming my life. I am in control and am no longer a slave to the routine. No matter what your situation (quitting outright to start a business, switching professions, or just changing companies) you should find comfort in “going for it.”


Everyone makes excuses. To quote Timothy Ferris, “The timing is never right. Conditions are never perfect. Someday is a disease that will take your dreams to the grave with you.”

In my case, the timing for my departure is both good and bad. The lease for my apartment is going to expire at the end of the month so I’ll no longer be tied to a large payment each month. This is going to allow me to travel without the guilt of paying for a place I’m not spending any time in. However, I couldn’t have picked a worse time to leave a blossoming company. I am on the ground floor of company that is revolutionizing its industry. The company is being called the new Apple in its particular field. It is currently an indie nipping at the heels of all the majors. I am completely serious when I say this company is amazing. After informing some of my co-workers that I was leaving, they called me Stuart Sutcliffe. Sutcliffe was the guy who left the Beatles in 1961 and then died a year later (good thing for him – the 60’s might have been pretty rough to live through).

Quitting is something I want to do and if I don’t embark on this journey now, I might never. What will more time do for me? If I wait longer some other excuse will pop up.

I’ll just invest in the company when it goes public!


  1. Quit when your job is no longer advantageous to you and your goals.
    Don’t lie to yourself. Why are you really holding this job? Do you just want to pay the rent? Are you looking for a career in this industry? Are you extremely passionate about cleaning toilets?

    The majority of people work strictly because they want more money. They tell themselves otherwise. “I love finance. Doing other people’s taxes is exhillerating!” Yes, you need a certain amount of money to maintain and live. No, it’s not as much as you think. If you want more money, fine. For most that is the determining factor of holding a job. But if your goal is to be a musician, why are you working 40 hours a week in a office? If your goal is to own your own business, why do you continue to work a job that doesn’t lead you in that direction? Figure out what your goals are and work towards them. If a job gets in the way of those goals quit and get a different one.

  2. Quit when you are undervalued.
    You should view yourself as a contract worker for hirer. You only work for someone when you are receiving adequate compensation.

    If you are making $10 bucks an hour then analyze why that is. There is a reason. Maybe you need more education. Maybe your job sucks. Maybe you’re trying too hard at work. Relax a little and work according to how you’re getting compensated.

    It is always good to check out what the competition has to offer. Baseball players jump around to the teams that will pay them more money. Look for opportunities to advance your career (if that’s what you want). You have no obligations to a company. They’re making money off of your work and you’re trying to get paid. It’s a two way street. Companies need to give you incentive to stay.

  3. Quit when your gut tells you it’s time.
    This point is related #1, but it goes a little a deeper. If the job you currently hold seems like it is benefiting your present goals, but you are still unhappy, this means it’s time to go.

    For example: Let us assume that your current goal is becoming CEO of your company. You’re slowly working your way up the corporate ladder. You get promotions and pay raises at the appropriate times. You’re putting in the extra hours. On paper, everything is going great. You’re advancing towards your goal and you’re getting paid what you’re worth. But something is wrong. You’re not enjoying the process. This is a red flag that it’s time to quit or take some time off. From an evolutionary standpoint, human beings weren’t designed to sit in offices and work all day. It’s against our nature. Trust your instinct. If it’s time to move on, it’s time to move on. If you’re in a rut, it might be a sign that your goals are shifting.

In conclusion, a job is not something you’re forced to do. A job is something you choose to do – it’s leverage for obtaining your goals.

The Real Life Tony Hawk

What is 3 feet tall, has 4 wheels and scares the shit out of me? A skateboard. Yes – a little recreational board that a lot of 3 year olds can ride.

I never owned a skateboard growing up and it’s obvious. My mom always thought they were too dangerous so she never allowed me to buy one. I had friends who would ride but I stuck to my bike; which is somehow safer? Maybe my mom was just scared of the skater image. I’m not complaining. I was happy enough to get my skateboarding jollies playing Tony Hawk.

The few times I have tried to skateboard have been short and near disastrous. I end up on my ass with a handfull of road rash from the cement. I have a hard time steadying myself and gaining balance. I played sports competitively for a significant portion of my life, but when I’m on a skateboard I’m like an elephant trying to balance on a needle. Not graceful.

Yesterday I came down the stairs and found my roomate’s skateboard staring at me. Mocking my fear. So I said “Fuck off skateboard, you’re hitting the streets.”

I headed outside and cautiously set the board on the ground. Go time. One foot at a time I stood on the board and began to slowly drift down the driveway. But as I neared the edge of the street my balance shifted right and off I went. I slowly stepped on again, pushed off, and then fell off.

Skateboard: 1, Derek: 0.

At that moment I had two options. Either give up or analyze why I suck and correct it. I chose the latter and decided that my problem was a) lack of speed to keep my balance and b) fear. So I literally said, “Screw it,” and pushed off hard. Away down the street I went.

Within five minutes I was doing something I never thought possible. I was riding a skateboard consistently, only intermittently falling off, and actually going somewhere. I tested my new sense of confidence and made it all the way to my bank in one piece. I even waved at a couple girls along the way.

Although this story is, I’ll admit, kind of sad, it does represent something great that is happening in my life. I’m actively questioning my fears and taking steps to overcome them.

Undoubtedly, in the next several months, I’m going to be facing a whole slew of new fears. I’m going to be leaving my job, starting a business, traveling, and writing about my experiences everyday. I look forward to the challenges but the real test is overcoming my fears.

What are you afraid of? Other than heroin, is there anything you’ve always wanted to try but have been too scared to do?

Go out and do it.

Talk To Strangers: They Might Have Candy

Goal: Become a social hero

I am not a hermit but I’m definitely not a social superstar. I want to be though and I think that’s natural. We all would love to be the guy/girl who everyone is excited to talk to. We’re social creatures – people on MySpace acquire friends they’ve never even talked with! The outgoing people in our society tend to be more confident, happier, take action, have high social standing, and make more money.

There are extroverts who can interact with people in almost all settings and there are introverts who are too shy to even talk to themselves. Then there’s the rest of us who I’d describe as social caterpillars. On occasion we try to to morph into butterflies, but we can’t quite produce enough silk to get the cocoon started. Deep, I know, but also very true.

In my mind, I can see several advantages to being a sociable and extroverted person:

  1. People who are social live longer. Studies have shown that people who have strong social ties live longer than isolated people. The other day I was waiting to use a bathroom in a hotel lobby. A girl came and stood next to me. Normally I would have said nothing and stared directly at the door contemplating why the stick figure with the dress has no hair…
    But I remembered my new mission, decided to do something uncomfortable, and actually struck up a conversation with her. The person occupying the bathroom must have been releasing some demons because the conversation went on long enough for her to reveal that she was in school to become a physical therapist. This was awesome (and relevant) for me because I’ve been having back problems lately. I asked her several questions about physical therapy and my back and she gave me some stretches and advice! Since that time, I’ve put her advice to the test and can honestly say I feel better. I am now healthier because I talked to a stranger. Will I live longer? Probably.
  2. People who are social are richer. People who network make more money. In the corporate world, it can lead to bigger and better jobs. In the marketing world, the more people you know, the more people you can try to sell your ideas to. A couple weeks back I was sitting at my desk on Monday and realized that Coachella was that weekend. I hadn’t planned on going this year because I didn’t want to cough up $250 for the tickets. So, I brainstormed a little, and started sending out text messages and emails to some of my friends who might be able to hook me up. Within 10 minutes, I got a response from a friend who works as marketing coordinator for a music magazine. She said she had free tickets for me if I could pass out fliers at the end of the night. Boom! Saving money is making money.
  3. Social people have more exposure to potential partners. Before I met my current girlfriend I was at a party. I was forced into an awkward conversation with a girl I didn’t know. Before I knew it, her and all of her friends were back at my apartment hanging out. One of those friends turned out to be my girlfriend.
  4. Social people have more stories to tell. “Hey remember that one time…” No, I don’t because I wasn’t there. I was sitting at home playing World of Warcraft. Have you ever noticed that coolest old people are the ones who tell stories? If you’re social you can even acquire stories from other people and make them into your own.

The list could easily go on but I’ll stop there. I think I’ve established that the pursuit of a social life is a worthy one and I want to be the biggest most impressive social butterfly around! I want to be confident talking to everyone from hot women to grandma bums.

But it’s hard and not comfortable. It doesn’t come naturally to me.

So, what can I do to change my habits? How can I change my behavior and become socialalbe? I’m not sure really, but I’ll experiment a little and take some baby steps to get there.

My first mission is to say “hello” or “good morning” to everyone I see on the street for a week. No matter what. If I have to go out of my way to say “hi” I’ll do it. If I have to fire off “how are you?” 10 times in a row to ensure everyone gets a greeting I’ll do it.

I’ll post my results one week from now in part 2. Wish me luck.

Beginnings: The First Post

When I was in high school one of my professors told the class to “live uncomfortably.” I paid no attention. I continued to live comfortably. Since that time my life has progressed something like this:

  • I graduated high school with straight A’s and went to community college. I didn’t go away for college because it was safer to live at home and go to community college than to venture out.
  • In community college I changed my course of study twice. I switched from communication studies to music and right back again. My dad and I agreed that it would be extremely difficult to make money as a musician. Best get a “normal” degree.
  • In Fall 2006 I transferred to UCLA. I did the intelligent thing: I interned every quarter to ensure I had a job waiting for me when I graduated.
  • After college, I landed myself a “real job” working 9-6. The paychecks started rolling in on the 1st and 15th. Simple and easy.

This is of course an abridged version of my life over the past several years. There have been intermitent times where I have explored and experimented and lived. I’ve traveled, jumped out of a plane, and I have even got laid a couple times. But overall, its been a pretty typical American life based on comfort and stability.

This life path works for some people but I would argue that the vast majority of us are unhappy in it. We’re all so unhappy that our discontent becomes our new reality. Thus any fleeting moment of joy we experience is false happiness. Our lives are just slightly less shitty for that moment in time.

I have decided that this must change (and it will). The routine and the day to day boredom is toxic. But there is hope with the “live uncomfortably” mindset.

I’m going to live each day forward challenging myself to do certain things that are uncomfortable for me. I have many goals relating to social skills, weight training, music, business and on and on. By forcing myself out of comfort zones and habits, I can grow in all of these areas (i.e. talking to new people, lifting heavier weights, it all applies!).

I hope this blog might inspire you as well. I plan to post daily challenges for everyone to try, but in meantime I will just write 2-3 articles a week documenting my experiences and thoughts.

Push yourself everyday to do things that you don’t necessarily want to, and you can not help but grow!