Why Thinking Like A Boss Can Help You Grow Your Business

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Thinking like a boss when you run your business is a challenge, but is vital to success. Here's how to do it and grow your business as a result.

January will mark two years of self-employment for me, and I have to say, it’s been quite a journey. At this point, I don’t think I could ever go back to working for someone else but sometimes I still struggle to think like a boss.

I’ve had the opportunity a time or two to go back to a full-time office type job and work for someone else, and I admit, I have been seriously tempted. But, at the end of the day, I want to pursue my own work and my own dreams and no office job can do that for me. I’m not alone. The Pew Research Center reported that three in ten people are now self-employed, so I know many others are considering taking the leap too.

One of the challenges to self-employment as I said though is getting into that boss mindset. When you quit your job and start your business, you will likely make your money by providing a service or a product. And, when you provide these things it can feel like the client or the customer is your boss.

The client as a boss


The biggest mistake I made in the early days of my business was viewing my clients as my boss. It actually took an e-mail from a client to snap me out of that mindset. It was last year around the holidays, and I e-mailed a client to ask if it was okay if I take some time off for Christmas and not send in a post. This particular client liked newsworthy posts so everything had to be written quickly as the financial news came out (it couldn’t be written ahead of time.)

Well, my client wrote back and said, “Cat, you don’t have to ask me permission to take off for the holidays. You don’t work for me. You decide when you write and when you don’t write.”

That e-mail really hit home for me because he was right. In trying to be a super-writer and please all my clients, I forgot that I am actually the boss, not them. I can say when I’m taking time off at any time. That’s why I became self-employed, after all. However, when you’re in the trenches and you’re trying to support a young family, it’s hard to say no to work and hard to get into the boss mindset.

The Characteristics of a Boss


In order to help you get into the boss mindset as well, here are some characteristics of a boss:

  1. A boss makes their own schedule.
  2. A boss decides who to hire.
  3. A boss decides who to fire.
  4. A boss decides which customers and clients to work with.
  5. A boss does whatever it takes to make their business succeed.

You can practice this mindset every single day as different things come up in your business. For example, any time you decide to take a day off (like I did for Thanksgiving Day) remind yourself you can do that because you are the boss. 

If a potential new client offers to hire you at a rate you can’t accept, feel free to pass on the opportunity because you are the boss.

If you hired someone to do work on your website, graphic design work or virtual assistant tasks but they aren’t reliable or are doing a terrible job feel free to fire them because (yep you guessed it!) you are the boss.

I truly believe that over time, with enough self assurance and enough of repeating this over and over again, you too will come to realize that you are the owner of your business and you call the shots.

Thinking like a boss when you run your business is a challenge, but is vital to success. Here's how to do it and grow your business as a result.

It Does Get Better


I realize that many of you may be reading this and thinking that you can’t say no to opportunities and clients because you need to make a living. I’ve been there, and I totally get it. However, I want you to know it does get better. I’ve literally increased my income to about twelve times what it was when I got some of my first freelancing jobs ever in 2011.

There will be times when you have to take on work you don’t want to just to pay the bills, but always in the back of your mind know what you want as your end goal which should be to only do the work you love and work that will project your business to where you want it to be. Remember that money isn’t everything, and that by saying no to work you hate or which is below your rate, you’re freeing yourself to say ‘yes’ to the work you most enjoy. With that goal and a boss mindset, your potential is truly limitless so go after it!


Have you quit your job to work for yourself? Have you ever ‘fired’ a client? Did you find it hard to get into the “boss mindset”? What other challenges have you faced in making the mental shift?

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Catherine Alford is the go to personal finance expert for parents who want to better their finances and take on a more active financial role in their families.


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