July 3, 2020

How to find the work you were meant to do — what I learned from Chris Guillebeau

Chris Guillebeau is the best selling author of The $100 startup and has developed a brand for himself as someone that can help others find work that they were meant to do and in developing side hustles as a way of life or as a way to supplement your income.

Perhaps the best lesson that I learned from his book is the Joy, Money, Flow framework to finding work that you want to do.

  • Joy is how much you enjoy the work you are doing. If you loathe Monday mornings, you may not be doing work that brings you joy.
  • Money is whether the work you do or want to do can pay the bills. It does not have to make you rich, but it should be able to keep you comfortable.
  • Flow is what happens when you are doing work that is just challenging enough, but not too challenging. It can be what happens when you play video games and you find that hours or days pass as you try to beat a boss or test out different strategies for getting past a certain level.

If the work that you are doing (or want to do) is not hitting all three of these factors, it does not mean that you cannot do the work, but it does mean that you will be missing either one or more of these factors and not getting completely fulfilled from the work.

I also learned the following from his book:

Finding the work you were meant to do is rarely a linear journey.

Long gone are the days where you can find work right out of high school or college and then work there for 50 years until retirement. People bounce around these days and do different things – they may not be satisfied doing one thing for the rest of their life. It’s a good lesson to remember as you are trying to plan out your career – some things cannot be planned.

There’s no right roadmap for everyone.

I often read books trying to find the answers to my problems, especially when it comes to trying to figure out what the right work, job or career is for me. Unfortunately, nobody can provide me with my roadmap, and the same applies to anyone else looking for the exact roadmap for their work. You can see what others do, but what will work for you will be different than what works for the next person.

The leap from side hustle to full time means doing tasks that you may not want to do.

Take a made up example of selling your vegetables from your garden. You may sell to your neighbours, but with abundant vegetables, you decide to set up at a farmer’s market. This means you need to rent a spot, you need someone to sit there and collect cash from customers, you need to make sure that you are reporting your income, etc. There are a lot of business admin tasks that you may not want to do if you want to make it a full time business. That is, these business tasks make something that was fun into something that may be repetitive or onerous for you.

Sometimes life will give you signs that will tell you what you were meant to do.

I honestly think that life will give you signs that will tell you what you were meant to do; however, the point here is that you need to take action. Just as doing stand up and bombing tells you that your material needs work, you may get immediate feedback that your idea for starting a business of solar powered flashlights may not be the best.

Create backup plans to mitigate risks and alleviate fears.

If you are working on a project, and you have a risk, you come up with mitigation plans to minimize the impact or probability of the risk. Why not do the same with the risks that you may be taking for your career or job? See the next point in how to develop some insurance.

Create a career insurance policy.

How do you develop a career insurance policy? Three ways: 1) spend less than what you earn so that you have some money to draw on if you need it. 2) have more than one source of income (if you suddenly lose one source, you are not completely out). 3) network so that you have the right relationships and people when you need them.

Key skills to break out of your job?

Negotiation, technology literacy, writing and speaking, follow up. Writing and speaking will multiply the value that you can bring to any job or work that you do. Technology is a mandatory skill these days whether it is going on the web, selling things online, creating brand awareness, etc. Negotiation and following up are softer skills that are also key to helping you break out of your job. Negotiation is part of selling, persuading people to buy and part of communicating with anyone in the marketplace. Following up is a skill that we can all cultivate and underneath, there is an important skill of persistence.

Every year, resign from your job.

You do not have to actually resign from your job, but I like the idea of evaluating whether or not you want to continue with your job or if you have other better options. This lets you fully commit to your job if you decide that is the best way forward OR to find a better option if that exists and to run with it. If you have a back up plan and a career insurance policy, why not go for it?


What are your thoughts on Chris’ advice for finding the work you were meant to do? What advice would you have if someone asked you how you found the work you were meant to do? Or have you found your calling and if not, what are you doing to find it?

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