Before You Kill Your Day Job, Ask Yourself Tough Questions

Clay Collins rants about the stupidity that traps us. On his my story page, Clay describes himself as a Professional Day Job Killer.

In contrast, Hugh MacLeod from Gaping Void tells you not to quit your day job.

I won’t tell you who is right… I don’t know… but…

Before You Kill Your Day Job, Ask Yourself Tough Questions

I once wrote that getting a job isn’t the best way to earn money and that might sound hypocritical coming from a man who has a job. No doubt, generating passive income is a better way to earn money than working for a paycheck. It allows you to create new ideas and grow businesses with more of your time.

If you are thinking about killing your day job, do this exercise first. It is an exercise you should do whenever you consider making major life altering decisions.

This isn’t some magical exercise, this is hard core critical thinking abut yourself and your future.

Imagine what life would be like if you didn’t have a job. Imagine what is possible for you, with your talents, with your work ethic, and with your energy levels.

Don’t waste your time fantasizing about beating Tiger Woods in the British Open, winning millions and retiring to a desert island, unless you have some reason to believe you could actually do that. And even so, think about the end result. Is it what you want? Do you really want the attention? Do you really want to live on a desert island?

Write down in detail what you’ve imagined. If you can, describe it like a novel.

Then dig into into it. Start asking probing questions about this potential future you are planning for yourself. Write the questions down. Answer them in writing.

Here’s an example:

A friend told me he wanted to quit his blue collar job and go to college and become an architect. Sounds noble, right? Here’s the problem, we as a society put higher value on architects than plumbers, but that doesn’t tell you a thing about what you want.

It may be your ego pushing for status. Only you know.

To find out, I asked him these questions:

  • Have you talked to any Architects about their lives? What did you learn?
  • What do they do all day?
  • What kind of people will you work with?
  • What does their work feel like?
  • What is the first year like?
  • How much you can you expect to earn? At one year? five years? ten years?
  • How much does the school cost?
  • Do you have the money? If not, how will you get it? Debt?
  • If debt, how long will it take you to pay it back?
  • What will your future income be minus your debt payments?
  • How many years will the schooling take from your life?
  • What will you do to pay your bills while you are in school?
  • Do you like school?
  • Have you ever succeeded in school?
  • Why will it be different this time?
  • Do you believe you have what it takes to complete the program? Why?
  • How long is the typical internship? Do you believe internships will be available when you finish?
  • Will you need to relocate to find employment? Are you willing to move there?
  • Once you finish your internship, what will you do? Start a private practice or get a job?
  • Are you sure this is the future you want for yourself?

If you’re thinking about quitting your day job, ask yourself a similar set of questions.

  • What would my life be like without a job?
  • What would I do all day?
  • Who would I spend time with?
  • How much money would I need to entertain/educate/grow myself during those added free hours?
  • What business or income stream would generate that money?
  • What plan do have to create that business?
  • Do you believe you have what it takes to create that business?
  • How will you get the money to create that business?
  • What will you do if you fail? What’s your backup plan? It is highly likely you will fail multiple times.
  • Is it possible that doing what you love will become a chore when it must generate revenue?
  • Is it possible you’ll end up a slave to different master?
  • Would your new business chew up even more time for less money?
  • Does your family support you?
  • Can you handle the stress of massive change?
  • Can your family?
  • Is quitting your day job something you need to do right now or can it wait until a better time?

Many unemployed and retired people suffer major depression when they no longer have somewhere to go every morning. Is it conditioning? Sure, but it is also about finding meaning and purpose. If you aren’t going to your job everyday you need to find meaning some other way.

Why is Brett Favre playing for the Jets this year? Because football gives him meaning in life. He doesn’t know what to do with himself without football. If you’ve been working in a cubicle, driving a truck, enforcing the law, teaching children, or hammering out configs in VI editor for the last 10 years, what will you do when it ends? Think about that! It’s more important than you might think.

  • Does your plan reinforce meaning in your life?
  • How did you feel last time you were unemployed? Motivated or depressed?

Doing what is right for me

I asked myself these questions (and many more) and as crazy as it sounds, I discovered I want to keep my day job. I discovered that my life is just the way I want it, except for these things:

  • I want more money (everyone does, right? Is my boss reading this? The CEO?)
  • I want more time to learn and discover
  • I want more time to be creative

I find achieving creative flow (being in the zone) incredibly satisfying. This is the state all writers, designers, gamers, and programmers know well. The mental state when time disappears, when you are so absorbed in something that the world seems to stop and there is nothing but the subject at hand. This state is my drug of choice. Achieving this state of mind ensures I learn, grow, create, and earn more money. It also ensures my happiness and my sanity.

I find the zone almost impossible to achieve at home. When I do, it is usually late at night, when everyone is asleep.

I need an office, away from home. Even if I quit my job and created another micro-business, I wouldn’t be any happier. I am an employee and shareholder in a innovative growing company that encourages creativity. It is a company that has helped me grow tremendously. I’d be a fool to walk away from a company like this right now.

Besides, Christine and I already have a small business which generates $250,000 in revenue annually and is growing. We also have multiple income streams. Someday, maybe, I’ll spend more time growing those businesses and income streams, but right now, this is where I need to be. This is right for me.

Now ask, what is right for you?

When I was 13, I wanted to be a rock star because of the perceived benefits I’d gain. Blogging can easily turn into a similar dream, so if your goal is to become a rock star, more is always better, isn’t it?
That’s the trap. More attention, more visitors, more Diggs, more money, more credibility, more about you. But that isn’t how money is made over the long-term. Money is made by offering more of yourself to others, that’s why most rock stars implode, they get too self-absorbed. The smart ones survive because they know the rules.

Napoleon Hill talked about this in Think and Grow Rich. He said that when riches come, they generally come indirectly. People that go directly for the money usually burnout because their heart isn’t in it.
The desire was for the money, not the journey. True wealth comes from ideas that expand freedom.

Being a slave to your ego isn’t freedom, working a job you hate isn’t freedom, but sometimes a job is the right place for someone. Sometimes you need one to get the funds to do what you really want. Sometimes it’s the right place to learn and to grow. You can get an education on the job and get paid for it. Some employers offer their people incredible freedom. It all depends on what you want.

So what do you want?

3 thoughts on “Before You Kill Your Day Job, Ask Yourself Tough Questions”

  1. Lots of good material here. I like how you incorporated your personal ambitions and desires at the end, after challenging people to ask all the right questions in the beginning.

    And really though, I personally feel that most people refuse to ask these questions because they’re afraid of what the answers might be.

    The answers might make implications about the actions they should take that their heart may not want them to take.

    Exercises like this one are the necessary ones where we can merge our hopes with the landscape of reality around us so we can hope to find a way to put those hopes in that landscape. It forces us to acknowledge the truths and make possible modifications if necessary.

    In short, it makes us think things through and act wisely as we work toward what it is we want.

    Great post Steve.

Leave a Reply

Your email address will not be published. Required fields are marked *