Streamline Your Life

The Art of Risk (Part 1)

Taking a professional risk can lead to incredible rewards, but also incredible consequences. It’s scary, exhilarating, and makes all but the bravest of us wish at times that we had never been presented with the option in the first place!

And therein lies the key to making a decision.

How do you know whether taking a risk is a good idea? It isn’t easy! Entire books have been written about this subject. There really is no wrong or right answer, because it is entirely dependent on the situation. But I can help you come to a decision.

First, here are some questions to ask yourself:

1 – If you were to fail, what is the worst that could happen to you?

This is probably the most important thought to consider. If the risk involves robbing a bank, then the worst that could happen is that you go to jail. This is a pretty big “risk” and it’s illegal. So I don’t recommend it. That was easy.

Just about everything short of robbing, stealing, cheating or going on a wild spending spree with no gains possible is worthy of considering.

But if the worst possible result is that you’ll just lose a job and be unemployed for awhile, then what? You can’t find another job. You run out of money. Ok. You have family and friends, right? You can stay with them for a bit. Don’t have any friends? Well, maybe you can go to a temp agency.

No family, friends, or temp agencies in your neck of the woods? You could always file for unemployment. There are quite a few safety nets that can catch you as you fall down the mountain before you hit the bottom. Your odds of ending up on the street might be a lot smaller than you think. That’s what you are really afraid of, right?

2 – Will I truly be happier if I succeed at taking the risk?

This is also important. Many of us fall for the “grass-is-greener” syndrome and are ok for awhile, but eventually realize that things were not as good as they seemed from the other side of the fence. That amazing-looking new managerial position at SuperWidgets is demanding. Maybe we shouldn’t have moved all the way to Cincinnati for a job that is more stressful.

Try to picture yourself there.

3 – Am I afraid of failing if I take this risk?

There is an easy answer to this question. It’s not really a question.


If you weren’t at least somewhat fearful of failing then you wouldn’t be deliberating. You’d just take the risk. Fear is what makes a risk a risk! It is important to acknowledge this.

Some examples of risks that might be worth taking

  • Speaking up at a company meeting when you disagree with everyone else in the room
  • Quitting your job and going into business for yourself
  • Moving to another state or country because you might like it there
  • Taking a week off of work to focus on a project that excites you
  • Taking a week off of work because you are burned out
  • Telling someone that you love them
  • Going against the grain at work by coming up with a better method of solving a problem
  • Complaining about an unfair work situation
  • Taking charge of a work project when nobody else seems to want to
  • Teaching yourself how to do something on your own rather than taking a class

Some examples of risks that are not worth taking

  • Jumping out of a plane with no parachute
  • Eating fistfulls of glass
  • Covering yourself with fish and wandering into grizzly country
  • Jumping down an elevator shaft from the 65th floor
  • Throwing the pilot off the plane in mid-flight
  • Running into a burning building because you forgot your favorite pair of Zubaz
  • Supergluing your eyes shut and drawing fake eyes on the lids to trick people into thinking you are paying attention

Short of absurdities like these, can you think of any others?

In short, just about all risks that don’t hurt others or put your life in danger are at least worth some consideration.

Nothing to Lose

Many people work dead-end jobs in order to pay the bills because they are afraid of ending up financially desecrated. Even though they may be miserable at work, they continue to plod onward. This happens with equal frequency to those who earn $130,000 as to those who earn $17,000 a year.

That’s right. A high-level software engineer can be just as risk-averse on the job as a floor-mopper at Taco-John’s. This is the case even when the turnover rate of a job is high because people like to hold on to what is comfortable.

I have a friend who has actually been a software engineer for almost five years. He continues to work in this job, despite how busy and irritated it can make him because of the good salary it affords him. He could probably earn a lot more and have to work far fewer hours if he only took on freelance projects, because he has a lot of skills. But he will not take that kind of risk because he is content to be where he is, even if he is tired and busy a lot of the time.

Then there are the wage slaves.

You’d think that the people who earned such terrible wages would be more afraid, and rightfully, than those who earned a lot more. But this just isn’t true, as extravagant lifestyles of the wealthy are expensive. The key here is that people are afraid of losing what they have. A rich person is used to their rich lifestyle.

That’s another huge part of the fear aspect of risk. Fear of losing what you have. Even if it sucks.

Staying in a miserable job just to pay the bills is a very common thing. But the minute you find yourself in this situation, you should be looking for a way out. It’s not worth being miserable, ever. If another situation comes along that seems like a risk (such as an opportunity that requires you to relocate, or a chance to try out for Survivor: Season 57), it’s got to be better than what you are doing. Really.

Still Unsure?

Take my Risk Assessment Quiz coming later this week in part 2. The results will straight-up tell you if the risk you are considering is worth taking. But don’t just take my advice. You have to believe in yourself as well.


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