Choose Your Business Carefully

How to Choose Your Business Carefully

There’s a video floating around on YouTube right now where a guy, let’s call him “Terry”, is showing off his fancy Bentley. Or rather, he’s taking us, the viewers, with him as he buys his new Bentley.

If you get through that, you learn that he has his own company where he shows off what a “cool” place it is to work. He’s got beer, video games, ping pong and it looks like it’s a party place instead of a workspace.

If you stick with him further, he starts to claim how having what he calls a “real business” – a business with an office (and a lease he has to pay), employees, and all that – is better than any other kind of business out there.

That’s where he lost me.

You see, for a split second on my own business journey, I wanted to be like Terry.

When we first started our business, we moved to the Seattle area and we lived in Kirkland. There was an office space downtown that was vacant and I pictured having my own business there. I pictured having a crew of 20-something’s all typing away on their Macbooks doing work for our clients.

I also pictured myself being Mr. Cool Boss and throwing pizza parties and telling everyone to take Fridays off.

I’m going to circle back to this but long story short, I didn’t do that and I’m sooooo grateful I didn’t.


The first step towards freedom is coming up with a way to make money on your own without the help of a full time job. So, you need to think about what kind of business you’ll run.

To do this, you need to look at what’s out there. You have to look at what’s required to make each business run.

Here are some questions to consider:

  • Will you need to be in one geographic location?
  • Will you need a dedicated workspace – a shop or office?
  • Will you have to buy equipment?
  • Will you have to have employees? If so, do they need to be local?
  • Where will you get new business? How will you drive new sales?

With that in mind, the following are three big tips to help you further evaluate the right kind of business for you.


When you first start a new business, your odds of making it a success from the get-go are increased if it’s based on what you already know, or at least, can learn quickly.

To get started, think about the following:

  • What did you study in school?
  • Do you have any certifications?
  • What are your main responsibilities at your current job?
  • What other specific experience do you have from past jobs?
  • Are you a member of a club and if so, what kind of club?
  • What are your talents?
  • What do other people ask you for help with?

As you’re looking to start a new business, think about what skills you may already have but take for granted.

Just this last summer, I discovered my cousin is awesome at making kitchen tables – all handcrafted by him. He’s amazing actually, but kind of just does it for fun. I told him he could start a nice little side hustle doing it. It could even turn into a full time thing.

The point is, you’ve got to evaluate what you already know and can do because it might give you a HUGE head start.

With my own skill set, I didn’t have the inclination or the desire to secure an office space or to hire employees let alone deal with all the challenges employees bring with them – sick days, office politics, etc.

No thank you.

My skill set allowed me to start something that I could work on from anywhere. And that actually leads me to the next tip.


You’ve got to remember your values when it comes to deciding what business to start. You could work super hard in some business only to find, years later, that it’s just not for you.

When you start with your values in mind, you’re going to be much happier and much more successful from the very start.

If you’re unclear on your values, fill in the following:

I’m happiest when…

Here are some common values:

  • Connecting with others
  • Independence
  • Mobility
  • Financial Stability
  • Healthy Living/Well-being

Another way to think of your values is to view them as your highest priorities.

Let’s go back to our friend Terry. Terry seems to think that being Mr. Cool Boss is what constitutes a real business. It’s clearly his priority, or one of his values, to be “a somebody” – to have all the worker bees look up to him as the bossman.

If you personally decide that you want to have an office and throw pizza parties and be Mr. Cool Boss, awesome. Good for you. I’m not here to talk you out of it.

Personally, it wasn’t for me.

I wanted to leave the corporate life behind forever. My own values as they related to my the kind of business I wanted to have included:

From the very beginning, I was happy with my business.


Because it was based on my own values.

Now, keep in mind, what I listed above are MY values. They may not be yours. If the boss thing gets you excited, then go for it!

I might sound a bit judgy about our friend Terry, but the fact remains that nobody can or should judge your values. That’s a personal thing.


The final point to remember when deciding what business to start is to remember your vision. This is the big reason WHY you’re starting your business.

In other words, you’re starting your business SO THAT you can do (fill in the blank with your own personal vision).

In my own case, my wife and I worked hard on our business SO THAT we could move “somewhere tropical”. It ended up being Cozumel, Mexico and we loved it.

After 4 ½ combined years there, we wanted something different and Edinburgh, Scotland quickly became our new destination of choice. We’re here now and we’re having a blast.


If you’re like Terry and buying a Bentley, and commuting to an office, and dealing with employees everyday gets you going, awesome. Go for it! Really.

If not, remember what I shared above. It will help you as you think about what kind of business to start.

If you do, your chances of having a successful business go up as does your own personal happiness. Which, in the end, is kind of what it’s all about.