Podcast 13: Taking Risks That Pay Off

Posted by: Penny Rackley   |   Comments Off on Podcast 13: Taking Risks That Pay Off   |  Posted on: Sep 02, 2016

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Are you stuck doing the same old things and getting the same old results?

You probably already know what you need to do to be more gratified in your relationships, to have better health, to make more money, but maybe just can’t find the courage or the wherewithal to make it happen?

If fear or apathy are holding you back from the life you want, then this is your show. Together, with some introspection and private writing, we’re going to pinpoint the right risks for YOU, and avoid the awful poison of regret.

Taking Risks: I’m here to tell you, other than trying those weird new Oreo flavors, I’m not much of a risk taker myself. No skydiving, not a racecar driver, no baccarat tables. I’m going to be the first one out of the lake and into the boat when a lighting storm starts.

BUT at the same time, I acknowledge that in order to get some of the things we really want for ourselves — enriching experiences and relationships and financial opportunities — we have to be willing to take some risks.

We don’t want to look up in five or ten or twenty years and say, If only I’d have tried this.…If I’d only found the courage or the energy to try that. So today, if you think you’re ready to take a little leap and make some positive changes, then stick with me. We’re going take this time to define:

– what risks are genuinely worth our effort
– specifically how we’re going to get started
– and when it’s time to get up off the couch and really GO FOR IT

Risk is Scary

Of all people, I acknowledge that risk can be uncomfortable. Fear — of course — is the main thing holding us back from success. Fear of:

being wrong
being different
thinking for ourselves
disappointing ourselves or other people
revealing ourselves
judgement or disapproval
being hurt
being vulnerable

Sometimes we’re even afraid of success and the changes that might come with it. However, I don’t know where you’re at, but — I’m 50! I’ve already come to the day when I’m regretting risks I didn’t take, and opportunities that I didn’t have the guts to pursue.

But if I don’t get past my fears and take some risks, I’m going to AN OLD LADY WITH A WHOLE LOT OF REGRET. I don’t want that, and I don’t think you do either.

A Little Confidence

Before we set our brave new goals, let’s build our courage with some positive truth about taking risks. If you’d like a worksheet to write on, THE LINK IS HERE.

For now, let go of the idea of your goals and the future and fears, and just think about your life. What are some of the risks you’ve taken that have really paid off in a big way?

(Here I tell a personal story about a time I took a risk that paid off. I made a friend!)

The point of this exercise is for you to remember a time in your life when you’ve had the courage to take a risk and then benefitted from it. Maybe you…

Invested a 1000 in a stock you believe in
Summoned the courage to ask for a raise
Submitted a portfolio of your work

Now’s the time for you to write out the chances you’ve taken. The ones that kind of make you feel like you won at life!

Risks That DON’T Pay Off

Let’s identify the kind of risks that we don’t want to include in our writing — the kind that usually don’t pay off. When we take scary risks to fulfill our OWN life goals, we see immediate gains in confidence and life satisfaction, even if things don’t turn out exactly as planned.

But when we take risks, stick our necks out, for someone ELSE’s goals, the risk seldom pays off. Risks like…

…taking the bar exam because your dad wants you to be a lawyer.
…putting your finances on the line to open a boutique with your sister because it’s fulfilling HER dream.
…quitting a job that fulfills you, and retiring early because your kids say its time.

As I’m sure you can imagine, these are the kinds of risks that aren’t necessarily going to pay off for you. So as you write out your goals and the risks they will require, make sure that it’s truly YOUR GOALS you are striving for. If you’re going to all this planning and trouble and anxiety, we want it to benefit your dream.

Time To Write It Out

Spend time now writing out some of your goals and the risks you’re willing to take to make sure they happen. If you’re using the worksheet, write them on the bottom half of the first page.

What I wrote on my worksheet: One of my life goals is to be a published author. I can write all I want to my little heart’s content, but if I’m going to be published, I have to send my work out for others to judge — either by submitting it to publishers or publishing it myself. That’s my big risk. I have to risk the reader’s rejection or boredom.


What have you been holding back on? What needs to get done for you to live a gratified life? Maybe it’s:

pursuing love again
regaining your health
starting a new business
quitting smoking
starting a new family
pursuing a leadership position at work
earning your Masters degree
choosing to retire

Think through and write about a few choices that are relevant to you. You’ve got your physical health to consider, your financial health, your career, maybe your children…what’s important and urgent enough to YOU that you feel you MUST make it happen?

Go to page two of your handout if you’re using one, and choose and write down one goal and the associated risk that you are willing to take. One that will gratify you and grow your life. The one I’m writing down is: Publish a book. Think about yours, commit to it within yourself, and write it down.

Count the Cost

We want to be honest with ourselves here, to be trustworthy and forthcoming with the truth. So let’s get it out there, on paper. What are the potential costs of taking your risk?

With mine, I might look like a complete fool if I publish something that’s not worth reading. I might damage my reputation as a coach. I could embarrass my family, my children. I could waste a lot of time working on something that has no real value. These are potential outcomes, and they are worth considering. But are they worth ditching my entire dream?

What about yours? Think it through, and write down the potential costs of taking your risk.

Pursuing love again – If you’re rejected, you might feel hurt or unworthy.

Regaining your health – There could be discomfort, soreness when you go back to exercise. You might miss your favorite, fatty foods.

Starting a new business – You risk financial instability. You could go bankrupt, or not be able to afford the life you are accustomed to.

Quitting smoking – There might be nicotine withdrawal. And if you fail, you’ll still be a smoker.

You get the idea. Here, we are counting the potential costs of taking our risk. In this exercise, be your own best counselor and best friend. Tell the full truth!

But What About The Benefits?

I really hope you’ll spend some time thinking through all the benefits that could come into your life if your risk pays off. What might getting clean, or succeeding in school, or making peace with your family mean to your future self? Imagine it fully, and spend time in that vision.

For me, if I publish a book successfully, and there is some interest in it — really just SOME interest — I would be so excited, because I love writing, and it could open up other opportunities to write. I love thinking about that! Think about your goal, and the exciting, encouraging, fun things that could happen for you if this works out.

Taking Risks Is Good For Us

Taking risks isn’t just going to increase our chances of getting what we want. Even just trying — finding courage to take our risk — helps us see ourselves in a more positive light, teaches self-confidence and builds the belief that we can handle whatever life throws at us.

Knowing you *can* take a risk, and accept the consequences of that risk, and not let fear rule you makes you (and me!) a more confident person overall.

Swinging The Bat

When I was doing research for this podcast, I read that Reggie Jackson hit more home runs than almost any other player in the history of baseball, but he’s also logged more strikeouts than anyone else in baseball history.

That’s a whole lot of trying and failing — publicly trying and failing! But is that what we remember about Reggie Jackson? No! It’s the home runs. You know, the absolute fact is, if I don’t publish a book, If I don’t even TRY, then there is ZERO CHANCE of success.

Hear that again: There’s no chance of success if we don’t try. If we’re going to score, we’ve gotta swing that bat.

Using Regret

For most of us non-risk takers, the idea losing hurts more than the idea of winning feels good. We’ll do just about anything to avoid short-term pain. So we keep things the same. We wallow in the status quo. We keep things the way they are rather than possibly make our circumstances worse. We say,

“I’m going to STAY in this terrible job that I hate and that’s boring, because things could always be worse.”

But people who study risk say that for most of us there comes a point, usually in mid-life, we stop feeling regret about what we’ve done that hasn’t worked and INSTEAD have MORE regrets about what we haven’t done, what we haven’t had the courage to pursue.

Don’t you look back at pictures of yourself when you were younger and think, “Why didn’t I have confidence then? Why didn’t I take chances then? Why didn’t I believe in myself then?” And don’t you think we’ll look back to NOW when we’re 80 or 90 and say the same thing?

For instance, I didn’t know until I was 40 that I love to dance. Now I look back at middle school and high school and genuinely regret not having pursued gymnastics or drill team in my youth. But that time has passed.

What held me back then? Shyness. I was fearful of people making fun of me, looking stupid, being awkward.


When I think of what’s holding me back from my goals now, it’s the same kind of thing. So, I go to Zumba, I go to hip-hop dance classes, I enjoy myself now so that I don’t look back when I’m 80 or 90 and think, “You know, when I was 50, I was healthy enough to dance. I should have done it then!”

I don’t want to have that regret. What about YOU?

Saying Goodbye to a “Lost Possible Self”

Sometimes we’re afraid to take a chance on a new life direction because we are still clinging to an old goal that doesn’t suit us anymore. And these old, outmoded goals suck the energy out of us, keep us stuck and rob us of enthusiasm for a real future.

(Here I tell a story about a “lost possible self”.)

Those who are able to say goodbye to an old image of “happily ever after” are better able to reengage in life with goals that reflect the truth about what’s possible today. By doing this and by being flexible in our thinking, we become happier and more successful in accomplishing our goals.

If we can accept and release our “lost possible self”, we are happier and better able to go for what IS realistic and possible — a new and exciting, attainable goal. There is a difference in quitting and being realistic. If you need help determining what’s possible and what might need to be set aside, call me. I’d love to coach with you about that.

Action Time

You’ve had time to decide what action you’re going to take. Look at the goals and risks you’ve listed. Maybe it’s:

pursuing love again – making that call or text
being healthy – getting that scary long-overdue mole check or colonoscopy or mammogram
starting a new business – quitting your current job, applying for a loan
quitting smoking – telling your family, throwing your cigarettes away

When are you going to start? Write that down too, and commit to that date.

I’d love hear from you about this! Email me at pennyrackley@mac.com about your risk and when you you’re going to take it. And if you’d like me to hold you accountable for that, let me know and I’ll email you in a couple of weeks to check on your progress.

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