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Writer's pictureChris Moss

8 questions to help you decide what business to start

Updated: Nov 21, 2022


These 8 questions should help you work this out...knowing what business to start or even what job or career to go into is difficult even for the most certain people. When thinking up what I wanted to do, I reverted back to some old questions I asked myself 5 years ago before starting my first business.


Before I jump into this blog - I want to thank the team at Oversubscribed for helping me pull these blogs together and support with my social content creation. If you are interested in raising your profile online, head over to Oversubscribed.



You don't want to make the wrong decision to then spend hours and even years doing something you hate. Sadly a lot of people find themselves in this position.


However it's never too late to decide to make a career change or start a business.


My aim is to spend more days doing things I enjoy than days spent doing things I dislike. That being said, sometimes you have to do things you don't want to, to get to where you want to be.

Now that I understand more about the time and effort that goes into scaling a business, I want to make sure I love what I do. This wasn't something I took into account when starting my first business but wish I had. However don't be fooled into thinking you are going to love everything you do 100% of the time. While running We Are Media is hugely satisfying for me, there are obviously days and tasks I don't enjoy.


These questions allowed me to work out what I value and as a result can now set goals that are aligned with my values. The first time around, I set my goals before I worked out what I valued; as a result I set goals that weren't totally aligned with me, meaning elements of what I was doing didn't feel right.


These 8 questions should allow you to discover what you value the most and therefore give you a clearer understanding of what goals you should set / business you should start.

1. What 5 things do you most value?

- This might be family, opportunity, helping people, success or creating a better world. These values need to be true to you and may be totally different to these examples.


2. In 30 seconds or less, what are your 3 most important goals?

- Writing these within 30 seconds should allow you to not over think it and produce goals that you would like, as opposed to something that comes straight to you. You won't want to stick with these goals, but they will help you understand your current thoughts.


3. What would you do if you won £100 million?

- After you've travelled, spent time with family and friends - once you've decided you need to fill your days with something meaningful and needed a focus in life, what would you spend your time doing?


4. What would you do if you only had 5 years to live?


5. What did you always want to do but held back doing?


6. What makes you feel the very best about yourself?

- This could be anything, it could be when you are socialising, it could be when helping people, it could be after hitting a goal etc etc. The aim of this is to see what makes you feel good. If you can have goals / a business that allows you to feel this some or most of the time then you are more likely to enjoy it when it gets tough (which it will).


7. Imagine you could have one wish. What would you do if you knew you could not fail at it?

- This one wish can only be used on an idea / business / perfect job, that you would attain without failing. This question should remove any fear of failure or lack of knowledge that is holding you back.


8. What is your one major purpose in life?

- Do you have a major purpose in life? If not, what would that purpose be? To help people; to be an international business leader; to be all knowing about property or even a motorbike specialist? If you could have one major purpose you wanted to achieve in life what would it be?


Now that you have answered these questions, look back over them to see what you value in life. You now want to think of an idea that includes these values. For example, if you value travelling then perhaps you could start a business / make goals that incorporate this. These values may change over time, which is also fine.


Also see:

If I can help just one person not make the mistakes I have made then this website will be worth it. See what I am up to now and follow me on Instagram and Linkedin


These questions were developed from a section in Brian Tracy's audiobook worth listening to - see more recommended reading here.

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