How to Determine if Risks Are Worth Taking

At a crossroads.You take risks regularly, from backing your car into the street to trying a new restaurant. You only hesitate when your fear of the unknown leads you to focus on the worst that could happen.

I’ve had many coaching conversations start with, “I need to make a decision.” Yet after describing the options, it’s clear my clients want to take a risk but their speculative fear of loss or their guilt around how others might react freezes their brains.

I often ask, “A year from now, what will you most regret not doing?” They always know the answer. The coaching then focuses on the clarifying both what they most want as an end result and exploring all the possible scenarios that could arise with moving toward what they most desire.

Start with the vision, not the action

When you consider any important decision, start with the end in mind. Flesh out a vision of the job, relationship, or lifestyle you want to create. Make sure you aren’t taking a risk because you don’t like what you have now. You need to be clear on what you want instead so there is more of a chance you will achieve something better.

When the picture isn’t clear, the uncertainty overshadows the positive possibilities.

On the other hand, your clear picture of what is possible will help you assess if what you gain from taking the risk is greater than the loss of not doing it.

Here are five guidelines to help you determine if your risk is worth taking

  1. Use a sounding board. You can’t trust your protective brain to make the right choices for you; it is better to talk through options with someone who will not be affected by your choice. Working with a coach is better than family or close friends to help you examine your thoughts without injecting their biases.
  2. Notice how your body reacts, either tensing up or relaxing. As you explain the pros and cons of risking, notice how you feel. Is there tension in your body? Does it represent a fear or doubt you are willing to explore? How badly do you want what the risk will give you? Do you sense friction between your fear and desires? When you talk about the reasons you want to make the decision and why it is important to you now, what uplifts your spirits? Your emotions can help thaw your brain freeze.
    Note – Try the Coin Trick. Assign your options to heads or tails. Flip the coin. The moment you see the result, are you disappointed or relieved? The trick might help you uncover what you really want to do.
  1. Catch your “shoulds.” It’s hard to make a decision when you are attached to other people’s opinions. What do you think they will say if you take the risk? Write these statements down to identify your fear of their judgments. How are your shoulds stopping you from moving toward your dreams? You might not take a leap but you might find smaller steps you can take today to move toward your desired future.
  2. Know your why. When you assess the value of your risk, what type of satisfaction do you gain? Is the reason you give for taking the risk important enough to make a few mistakes along the way, or worth it if you have to admit you did something wrong in the past? Twenty years from now, what would you love to tell people about the risk you took and why you did it? Knowing the purpose for moving forward with a clear vision can give you the courage to face your fears.
  3. Be honest about what could go wrong. Don’t ignore hazards. When you look at possible problems, how would you handle them? When I left my last job to start my business, I knew if I failed, I would find another job. Consider bad outcomes, determine the likelihood they will happen, and what you would do next.

If you decide the risk is worth taking, commit to taking a few steps, even if the steps are small. Enjoy what you learn and all the steps you take on your journey will be worthwhile,

8 thoughts on “How to Determine if Risks Are Worth Taking”

  1. This is excellent information! I just coached a client a couple of days ago who is deep in should I stay or should I go? I’ll be using these techniques in our next session to see how it works for her.

  2. Since my formal retirement – when I sold my business, I have started and failed fir years to accomplish any of my online projects. This procrastination and vacillation is really getting me down. However, I’m going to try Marcia’s advice and see if I can see my way clear.

  3. I love the suggestions above!! I have coached several people who were unhappy with their current situation. In addition to the question, “A year from now, what will you regret not doing” (fantastic question!!) if their vision is move forward toward something new, I encourage doing a “motivational job fit” exercise. From that, build questions for the interview process that address things they would hate to have in a new job (if it’s in the job it would not be a good fit), or they “must have” (if not in the job, it could be a poor fit for them). This includes culture, leadership style, job tasks, will they or will they not have a collaborative team to work with, etc. It is best to work with someone who knows how to build the questions to make them appropriate, and it’s really important to do this work so you don’t “go from the frying pan into the fryer.”

  4. I love the coin toss idea. I used to call this “the waiter” test — if you ask a waiter what you should get, deciding between two dishes, and you’re disappointed with the recommendation they provide, you still know what you should be ordering 🙂

Join the Conversation

Your email address will not be published. Required fields are marked *

Scroll to Top