Do you Think like an Employee or a like a Boss?

Mantis sitting on a rock, thinking with a cigarette in his mouth.
Mantis sitting on a rock, thinking with a cigarette in his mouth.

Do you think like an Employee or like a Boss?

Let’s talk about mindset. Before you begin anything, mindset is key. I recently took a course in Internet Business Mastery and the first week alone was spent on mindset. The great Michael Jordan once said, ‘I take two shots. Once in my mind, and once in reality.’ Talk to any professional athlete,  and they will tell you how crucial it is to get into the game. Mental game. Get into the mindset of battle. Visualize the movements. Visualize where the ball is, and where it will go. When you actually get on the field, it’s just mechanics because you’ve already done it before. In your mind. I’m sure I almost state the obvious when I say, thinking like an employee is vastly different than thinking like a boss of a corporation. Your own corporation.

In the Beginning

If you grew up in North America, and diligently went to school, trying hard to get good grades and play the game of the grade school and college system, chances are, like me, you spent about 15 years in the school system getting trained and groomed as an employee, to someday get a good job and work for a large, prestigious company with a promising career path. By now, it would seem that it is widely accepted that the school system was originally designed to support the industrial revolution. It was designed to churn out workers to support our companies. And by and large, it’s done a great job of it throughout the ages. But times have changed. I know I’m telling you nothing know when I say, what worked for the industrial revolution does not apply anymore. We are in the height of the Information age. I know for certain that I’m not alone when I want more than just to work for someone else all my life. I remember getting to about 90k / year, and thinking, there’s gotta more to life than this. Getting more money wasn’t the answer. Sure it’s satisfying for a little while, but soon the novelty of making that additional $120 every paycheque wears off, and you start to once again grow fidgety. In fact, it’ll get to the point where it doesn’t even matter how much more money you  make because a sizeable chunk of it gets withheld in taxes anyway. There’s gotta be something else out there. That was going through my mind on a daily basis. How long could I keep up this charade?


Paradigm Shift

I remember the day after I took that leap of faith and landed my first contract, I was asked: “What are your (business) hours?” Inside I thought, “what do you mean what are my hours? Aren’t they the same as your hours?.. what a silly question. Then it dawned on me. He’s asking me because I get to set my hours of operation. I’ve never gotten to before because I’d always played by someone else’s rules. Now.. I’m on the opposite side of the table. I get to make the rules. That was the first example of many that I had to get used to. As an employee, I didn’t much care about what ‘the client’ thought. I had no client. I had an employer. I had a babysitter, in the form of a manager. Like every exam I ever took in school, I learned what the rules were, and played by them to win the end-game. But now, if I screwed up, it was my own name on the line. I began to think like a company. I start noticing what customer service was like wherever I went. And I got clues as to how I could apply those to my profession. Overnight, I was in the customer service, accounting, business development, strategic leadership departments of my own one-man company. I started using phrases like:

‘Thank you for your business,’ when I signed on a new contract.

‘My pleasure,’ instead of ‘no problem’ when answering even a simple question.

‘How can I be of assistance,’ instead of ‘what’s up,’ when asked a question.

I got on a schedule of invoicing, and never again submitted my time late. I thought in terms of business expenses and tax impacts upon making every purchase. I started dressing better at work…. being more professional in my interactions. Every single little thing that I did, I did on behalf of my company. I daresay, I thought of doing none of this as an employee. I had absolutely no reason to bother.

Moving from Employee to Boss is more than mechanics. It’s, as illustrated above, an entire mindset shift. I can’t stress the importance of this enough. Where are you in this space? Few of us think of the intricacies and even bother to consider this when thinking about making the leap as an employee. Furthermore, I would say that without this mindset, you’ll never make the leap.. or at least find it really hard to do.


Quiz: Do you Think like an Employee or Boss

Here’s an acid test that can help you determine where in the mindset spectrum you are between Employee and Boss… Ultimately, it could help you gauge how ready you are to make that leap of faith to join the rest of us in Atlantis (100 points if you understand the allusion):

Answer True or False to the following:

  1. You do only what is asked of you — You do whatever needs to be done to get the job done.
  2. Your job title defines you. It either makes you extremely proud and you do more because you’re the ‘senior manager’, or frustrates you because you’re only a pawn in your organization. — You have no ‘job title’ even though you were engaged to fill a particular position. You’re paid to add value to the company, and you will add value
  3. Most of your income is spent on your monthly living expenses, and maybe 5% or less goes to a small retirement fund.
  4. You’re super worried about the economy, and that the top competition of your employer just cut 25% of their workforce this quarter.
  5. You prefer to ask for permission before trying anything, rather than taking a gunshot approach: doing it, and asking for forgiveness later.
  6. If your company laid you off right now, you would be screwed because you’d have to live off a line of credit until the next gig comes around.


…In the wise words of Warren Buffett, ‘Employees say Yes’ Entrepreneurs say No’.. meaning entrepreneurs don’t let things distract them from their main focus. But employees are paid to say yes. (at least good employees are) Yes, to the role that they were hired for. Yes to executing the company’s vision. I was a great employee.. until I took the proverbial blue pill.  I was conditioned for 30 years of my life to follow someone else’s rules, I didn’t recognize what it looked like to set the rules. Now, I set the rules. I can’t wait for you to do that too. So, I ask you. Do you think like an employee or a boss?


  • Cat, you have an excellent point here, I remember I went to this mindset switch couple of years ago, although I remained an employee (I’m a consultant too). But this small mindset tweak was obvious for my manager’s manager’s manager 🙂 and I was rewarded with 30% pay raise, I got to choose what responsibilities I wanted to do next and a lot of flexibility in my working conditions. It was like being my own boss already, so I chose to remain an employee. But things always get better, I’m preparing to quit this perfect job soon because I’ll reach financial freedom 🙂

    • Cat Lam

      Reply Reply June 22, 2016

      Yes!! Totally agree!! That’s so amazing how you have such a great gig. But you’re totally right. Financial freedom is so important. Freedom to do what you want, when you want it, for how long you want. Rock on!

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