My good friend Shawn Kanungo (check him out, he’s a professional speaker who has lots of great videos about the latest innovations and disruptions happening in the world) was once asked at an event what advice he had for a group of employees. He came back with something really startling – he said to do something the next day to get yourself fired.

Of course, he did not mean to do something inappropriate like hacking into the servers or stealing money from the company. What he meant was to do something risky at your workplace that people normally ask permission for from their boss or from management and rather than asking for permission, ask for forgiveness (after the fact).

His words always stuck with me (I mean he’s that kind of impactful speaker) but it is also the sort of unconventional advice that gets people to pause and reflect on some of the things that we have been doing. I have no evidence of the sort but I have this intuition that a lot of people (employees more so but may be applicable to entrepreneurs, consultants, freelancers, artists, etc.) can take more of a proactive approach and to take on a few more risks than we should.

Now I’m certainly not a huge risk taker myself but I have taken a few risks in my life that I wanted to share including the lessons that I learned from some of those risks that I have taken.

Assessing the risk vs. the reward

The risk vs. reward is a common balance often found in investments. Stocks with a high risk often have a high reward associated with it (say something like penny stocks which have a very high risk but if you buy 100 penny stocks for a few dollars and the stock goes up to a few dollars, you have made quite a bit of return). Of course, the risk vs. reward discussion is difficult to assess for things like a job opportunity or moving to a few different places. How do you know what the risk is of moving to Vancouver vs. moving to Toronto? And what is the reward for either place? Hard to say but it is at least one angle to consider as you are comparing different things.

Worst case scenario are not as bad as you think they are

Sadly, I have to admit that I’m a bit of a want-repreneur. I want to be an entrepreneur – wouldn’t it be nice to have my own business and not have to answer to other. Yet there’s a part of me that is extremely risk-averse – what would happen if I quit and I couldn’t keep up with everything? Food, mortgage, basic expenses. But often times, the ‘worst case scenario’ is really not that bad. It’s certainly not un-recoverable – so what if you quit your job making six figures today to start your own business. You probably have some savings in the bank, you could live for a few months trying to make your dream come true and if nothing works out, you could always go back in to the same or similar job, maybe with a pay cut but at least you would be able to get back on your feet if things didn’t work out.

Tim Ferriss has an excellent TED video where he outlines his fear exercise. He lists out his top fears and then, addressing each of the fears, figures out what is the worst case scenario and what he could do if that worst case scenario happened. Maybe one of his fears is that he spends a year writing a book and the book does not get picked up by any publisher. In that case, he could self publish, or he could use the book as content for his blog, or he could use the content and combine it with some other material to make different books. Another worst case scenario could be that he suddenly gets into a lawsuit and loses all of his assets and money. Well, he could get a job and build up his assets from there. In most of these fear scenarios that you lay out, the worst case won’t happen OR the worst case is truly the worst case scenario that could happen and you will realize that after addressing the fear, it really will not turn out that bad. Fear should not stop you from doing the things that you want to do – in fact, I would argue that fear can help give you the direction that you need to do the right things – often the things that make us uncomfortable are the things that we should be doing.

Is it possible to revert the situation even after you have made a choice?

Are you thinking about moving to two different locations, say moving to Hong Kong or Japan. Even if you move to Hong Kong and decide that you should have moved to Japan, what’s to stop you? Think about how you might be able to change your choice in the future and again, do not let your fear stop you from making a decision in the first place.

Is it possible to test out the scenario before making the decision

Say you have to choose between two jobs and once you take one job offer, you ‘burn the bridge’ on the other offer. Before you have to make the choice, see if you can simulate the jobs that you are deciding between. Employers and people can tell you everything there is to doing some work but until you do it, you will never get a true and full understanding of what it means to you. If you are able to simulate those jobs in a different way, maybe you are able to get a sense of how you will feel about the job in the long term.

Seek out others who have taken the path you are thinking about taking

Sometimes you can get information that you otherwise would not have learned about through your research. Other times you will gain valuable networking contacts that you may be able to use. Those contacts that you get in touch with will never have the exact same situation and they can never tell you what the best choice is for you but the best thing you can get is more information that helps you understand the criteria to make a better decision.

Enthusiasm and positivity is key

No matter what, having incredible enthusiasm and a positive attitude can take you far. Any time I take a new job or a new project, I get an instant pang of regret that I should not have taken the job or project. It’s a weird intuitive feeling – something that I’m sure not all of you feel. But through switching jobs a few times in my life and taking on many, many new projects, I’ve recognized that it is a natural feeling. It does not mean to instantly quit or to switch to another project. It just means that you have to dig a little deeper to make sure that this is not just a spur of the moment feeling.

Sometimes you have to take the leap

You may not have all the facts, you may not have the pros and cons list down but you have a pretty good idea (say 80% of the information) of how a specific choice will turn out. Often times, your current pain needs to be strong enough where you will at least entertain different options but if you know you are going to get there, why not take the leap now?

Let me end with a story of how I took a risk and how it turned out. When I graduated from university, I was looking for work and it was the worst time – it was during the recession and very few employers were hiring. It was a bad situation made worse by the fact that there were many layoffs during the recession and these same people that were laid off with many years of experience were looking for work and lowering their standards so that they could find something, anything. As a new graduate with limited career experience (though I did have some co-op experience), it was tough finding a job. I sent out dozens of cover letters and resumes every day in the hopes that something would bite but for a few months, I was stuck thinking about all the jobs that I could be good for but never heard back from. Finally, I heard back about a phone interview from the Government of Alberta. A few months into my job search, I realized that I would not be able to find work in my home town so I ventured out to other cities to see what I could find and this turned out to be a fruitful strategy. The phone interview went well, and the GoA wanted to fly me down for an in-person interview and to see where I would be working. Things went well and I received a job offer. But I then had a decision to make. Stay in my home town? Move to a different city for work?

I ended up moving to the different city for work for a few reasons:

  • I was going to work there for a few years to get some work experience and then find a job and move back
  • It was only a short flight away from my home town so it was not too far of a move
  • Wages in Alberta were quite high compared to the starting wages of other jobs I had looked at

Without moving to Alberta, I wouldn’t have had the opportunity to work at Deloitte and now at EY, my current company. And I have now been here for almost 10 years. I’m not even sure (and you can never be sure) that your choices will lead you in a good direction but I think if you work hard, are positive, and enthusiastic about your work, it will lead you to places that you may not have even thought about.