The Dangers of Playing it Safe


The Dangers of Playing it Safe

You don’t have to go far to hear the dangers of taking risks.  When I was young, I was taught about “stranger danger”.  As I got older, people told me about the threats to travelers.

We’re reminded of them every day in the news.  Turn on the TV and it won’t take long to find dozens of reasons to be afraid and not take any chances.

But what about the dangers of playing it safe?

Look back on your life and think about all the times you took the safe, easy route.  What experiences did you miss?  What awesome people could you have met?

What seemed so scary and risky at the time now seem like missed opportunities.

It’s unusual to hear about that.

You don’t often see headlines in the news such as “Business never started due to fear.” or “Man retires from unsatisfying career and regrets never taking a chance to pursue his dream job.”

We notice the dangers of risk-taking because they are attention-grabbing; they’re often immediate and dramatic.

We take notice of a story about a traveler who was assaulted and robbed or a risk-taking company that goes bankrupt.

The dangers of playing it safe are slower.  They play out over the long-term and are not sudden.  Yet they can be very damaging.

Playing things too safely can mean:

The Natural Tendency to Play it Safe

Nobel Prize-winning psychologist Daniel Kahneman once wrote “For most people, the fear of losing $100 is more intense than the hope of gaining $150.”

In other words, our drive to maintain the status quo is bigger than the motivation to gain.  People naturally prefer avoiding losses to gaining.  We work to keep what we have at the expense of making improvements.

This is why people stay in jobs or relationships they hate.  It’s what keeps you from making positive changes or pursuing your dreams.

But this is no way to live.  You can’t grow as a person if you can’t get past the status quo.  All you’ll do is live a life that is “good enough”.

In order to get past the danger of playing it safe, we have to overcome the tendency to do it.  That means overcoming the fear in our decision-making process keeping us in our comfort zones.

The problem is we often let our fears and emotions get out of hand.  We let them grow a lot larger than they actually are which gives a distorted view of what’s really going on.  That stops us from making tough, risky decisions that could improve our lives.

Whenever you find fear creeping into your decision-making, look at your decision in three steps:

1. What are your fears? – Be specific.

Write down all your fears.  What are you afraid might go wrong?  What’s the worst thing that could happen?

2. How likely are they to actually happen?

Look at each fear you wrote down and analyze them.  Give an honest assessment for each one.  Ask yourself: are they really based in reality or are they completely irrational?

How likely are they to happen?  Try to be as realistic as possible with their likelihood of occurring.  Put a statistic to it, if possible, such as a 10% chance.

3. What’s the best thing that would happen if you did it?

List all the potential positives you would get by making this decision.  Would you be fulfilling a big dream?  Would you be getting out of a relationship or job you can’t stand?  Write everything down.

Take a look at each list.  Do the potential benefits outweigh the drawbacks?

Recently I made a decision that I was afraid of doing: investing money.  I had the opportunity to get back into investing after a long break, but I was afraid of doing it.

I looked at all my fears and analyzed them.  As I did that, I saw that my emotions were clouding my judgment.

My biggest fear was that my investment would fail.  A worst-case scenario was losing everything.

But as I looked closer, I realized the chance of losing everything was low – and even if I did, I wouldn’t actually lose much since I was only investing a little to start with.

My best-case scenario was that I would earn money and implement a new stream of revenue.

It was only after I analyzed my fears that I realized they weren’t that scary after all.  It was just all in my head.

I weighed my options and decided the risk was worth it.  After months of thinking about it, I finally did it.

And I got to do it because I stepped back from my emotions and fear and looked at things logically.

When you think through your emotions and fear, you take away the power they have to keep you from new opportunities .  It will help you see that things that are scary at first aren’t as frightening after all.

I learned a valuable lesson from all those times I played it safe when I was young.  Now that I’m older I try to see each decision as a possibility to improve my life.  I don’t think in terms of maintaining the status quo, I want to make valuable gains.

When you do that, you free yourself to do so much more.
photo credit: Jaybird

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  1. Playing it “safe” will prevent success or turning our dreams into reality. I love your point about writing down our fears, once we identify them we can take steps to overcoming them. Great post!

    • It’s interesting how often identifying fears and taking a good honest look at them makes them have less power. It makes you see that they’re mostly in your head and aren’t as bad as they might seem.

  2. I agree with everything here. There is no such thing as a risk if it’s calculated. That to me is a plan.

    Fear is just a sign that you’re doing something good.

    • I see fear as a good sign too. It means I’m doing something that is pushing my comfort zone – that’s when I grow the most. I’ve spent the last few years working my way towards fear and it’s made a huge positive difference.

  3. I’m constantly battling my own fears of the unknown. I know that in the grand scheme of things, it’s not a big deal, but it’s still hard to take on that risk and be open to change.

    I was just listening to a podcast, Good Life Project, and the person Jonathan was interviewing, Michael, talks about the stories he’s heard from his grandfather. One of the points he made in the interview was that when asked about his biggest regrets in life, his grandfather could only answer with the opportunities he missed, and couldn’t think of the times when he messed up. It’s the risks not taken that stay with us, the mistakes get tossed to the wind.
    Here’s a link to the interview, if you’re interested.

    • That’s an interesting story. It reminds me of that post going around the internet about the Top 5 Regrets of the Dying which talks about something similar. I’ve had conversations like that with older people. Almost all of them said they had a good life, but they just wish they had pursued something they really wanted to do.

      The unknown is scary and unpredictable. But you have to head towards it if you want to change.

  4. There are 2 types of playing it safe:

    On a physical level, I do think that we should play it safe, minimize risk etc to avoid injury, especially as we get older and find that our bodies can’t always do as much as they used to (not talking about anyone in particular there ;-)).

    on a psychological level – you’re absolutely right & I couldn’t agree with you more – push those boundaries and anything’s possible!!

    • Yeah, not all risks are equal. That’s why you have to evaluate them closely to see if your fears are justified. If you’re doing physical that has little positives to it and a lot of potential downsides, it probably isn’t worth it.

  5. If we want to do something a little different, be a bit adventurous, than that means taking a risk. But risks work in two ways. Firstly, the way we always think, which is “what could go wrong?”. Secondly, there’s the positive side, “what could work out better?”

    And as was famously written – “feel the fear, and do it anyway”.

    • Perspective matters a lot when assessing risks. Too often we see it in terms of “what could go wrong?”, but why not see it the other way. What could go right? What could work out better? I’d rather take that positive mindset to risk-taking.

  6. One of my goals in life is when presented with options to go for the one that will be the better story at the senior center when I get older. The safe choice rarely would be worth telling later.

    • That’s how I look at it too. Whenever I try to assess the positives of taking a chance, I always consider if it will make a good story – whether it goes right or not. Like you, I want to look back on things and have good stories to tell.

  7. Great post! I love the point about the tendency to play it safe in particular. Very insightful. I guess, like you say, it isn’t until we broaden our understanding of danger to accomodate more than the ‘what if’ of taking risks and include also the ‘what if’ cost of staying with the status quo. I wonder whether this is the perspective of many high achievers: They see stagnancy as a greater enemy than risk.

    • That’s what I’ve read about successful business owners and highly creative people. They tend to focus more on gains instead of losses. A lot of them take on risks that others won’t do.

  8. “Do something cool but play safe”
    Yo man, this is the whole theory about.
    This is surely a great post!
    If we want to do something differently, be a little adventurous, than that means taking a risk.
    Thanks for this useful share.
    Happy Blogging and Do Something Cool Always 😉

    • I’m glad you love the post, Vivek. Being different and having adventures means taking on risk, that’s for sure. But it can be worth taking on that risk to get where you want to be.

  9. Nice take on loss aversion, Steve!

    This is definitely something I’ve been consciously working on for the last 6 months. I’ll keep working on it.

    My friend who’s a professional day trader and prop trader says he thinks about it every day in order to make better financial decisions.

    • I imagine day traders think about it pretty frequently. There’s a lot you can lose, but also a lot you can gain. It’s a balance you have to keep on top of if you want to succeed.

  10. When you play it safe you’re not actually living your merely existing. You have to get used to taking risks in order to have experiences worth remembering.

    You take little risks without even realizing it. Like buying a car, you sign 5 year loan agreeing to make the payments but who is to say in 3 years you’ll be able to. You assume your financial situation will still be the same or better but there are no guarantees. That’s a risk.

    So why don’t do something big and make it count.


    • There’s a big difference between living and existing. Living life means taking chances and seeing what you’re made of. It’s about putting yourself out there and making mistakes. If all you’re doing is existing, what’s the point of being alive?

  11. I think one of the funniest things to realize is that most of the risks you come up with are completely made up. When you’re dreaming of trying something completely new and different, many of the risks are like “My friends will disown me.” Or “My family will disown me.” In most cases this is just not true. And even if turns out to be the case, it seems to me that you’re better off long term anyway if they’re unable to support your decisions. (Maybe this becomes a more real barrier later in life when friends are harder to come by and family is the only real support system you have.)

    Other things like feeling like you’ll lose your opportunity to get a good job if you do something, infers that you were guaranteed a good job if you went down the route that you didn’t want to in the first place. Which to me is another example of a fake risk.

    Mostly, (at least when you’re young) the worst thing that can happen is that you waste your time, and that’s something you’re guaranteed to do if you play it safe, so the math clearly advocates taking some calculated risks.

    • It’s interesting how often our fears originate in the mind. What seems so scary and frightening at first doesn’t feel that way once you’ve actually done it. It’s important to realize this.

  12. I once took a risk and left my job that was making me miserable. I did not have another job lined up for me and the economy was not that great at that time. But somewhere deep in my heart I knew I could do it and be even in a better position later. In fact, now I am doing better than ever financially and love what I do for living. It was definitely worth while taking a risk!

    • That’s a pretty big risk, I’m glad it paid off for you. I was in a similar situation many years ago. I left a job without another lined up, but in the end it was a good move. I found something else and got out of a job I didn’t like. It’s scary to do, but you can motivate yourself a lot to find another one if you do it.

  13. Playing it safe is the worst thing you could do.

    I think the biggest issue is fear. People are so afraid of doing something that they allow it to paralyse them from doing anything constructive in order to help move them forwards.

    The best way to tell if you’re one of these people is to look at your life and ask yourself whether what you’re doing is constructive and leading you to the right path or a distraction.

    So some examples:

    Reading articles and books on blogging but not actively writing articles and taking part.

    Watching Youtube videos of people dancing Salsa/Tango and not going to class and taking lessons.

    Sitting at the bar with your drink watching other people interact and not taking part yourself.

    We naturally create buffers around ourselves to trick ourselves into believing we’re making progress and to protect our egos from actually going out and doing what needs to be done.

    The minute we learn to see it in our lives, the sooner we can begin to make changes.

    • Your point reminds me a lot of when I would go out to bars with friends. A lot of them wanted to talk to girls there, but would just watch others interact and have fun with them. They thought they were making progress, but, in actuality, they didn’t do anything at all.

      We can trick ourselves into thinking we’re doing something even when we aren’t.

  14. Guilty as charged! LOL!

    I’ve learned a lot over the past few months especially since I started blogging because I am the type of person who likes to play safe as well. Took a hard realization for me to know that this is counter-productive. Successful people are those who does take risks and are not afraid to face the consequences of their actions.

    • When you take it safe, you can end up thrown together with everyone else doing the same things. You have to stand out and get attention. It’s definitely tough and it doesn’t always work, but that’s how you get the big rewards.

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