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.

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.