How To Take A Risk


“Scary work pays well.”  

                                    —Darren Hardy

This post was first published in 2019. I’m re-publishing this post right now because of what we’re all facing these days as entrepreneurs. Now, more than ever, we must dig down deep and find ways to exceed, succeed and stand out.

But even more we need to rely on each other, search out new resources and take big risks. This post is about how to take the risks you want to take even when you think you can’t.

I hope you enjoy this post but mostly, I hope you use it to keep moving forward, to keep succeeding in uncertain times and to take the risks that will help you succeed.


As we look back on 2019 one of my favorite months of blogging was June when I wrote about my secret formula for taking risks in my life.

Taking risks are fundamental to success in life and in business. But how do you do it when you’re paralyzed by fear? I will tell you. You don’t burst through you comfort zone. You expand your comfort zone.

Here’s how I expand my comfort zone on a daily basis…

Owning a business, being an entrepreneur, means taking risks. Sometimes you’re taking risks everyday on behalf of your business.

What are the most important risks you have to take in your business? I break those risks down into 3 categories:

  • Asking for help
  • Using your relationship capital
  • Speaking publicly

Asking for Help

Asking for anything is difficult if you’re not in the habit or don’t feel you deserve it. Becoming an entrepreneur is an opportunity to learn how to overcome some of our darkest issues.

Issues like low self-esteem, not feeling deserving, poverty consciousness are all tested when you decide to start a business. And one of the biggest issues is our ability to be good receivers. How much do we feel we deserve to receive?

Entrepreneurs love to help people! Many times that’s why people become entrepreneurs in the first place. But asking for help feels defeating.

It’s not. It’s an instrument of success.

Are you willing to test your power of deserving? Are you ready to expand your comfort zone?

Asking is an important exercise as an entrepreneur. You have to ask for:

  • testimonials
  • feedback
  • ratings and reviews
  • favors
  • opportunities

So how do you ask for what you need your business?

I’ve got a strategy for that.

It’s a strategy I’ve used for a long time with great results. I have over 2500 reviews, case studies and testimonials for my business. I know how to ask for stuff.

My strategy is simple, effective and easy to implement, in three steps.

Step One

Start with your heart. Be authentic and caring. When you come from the heart it gives others permission to do the same. Just be yourself, be honest and forthright.

Don’t send form letters or emails. Don’t beat around the bush. Don’t overdo it. Simply ask the favor. Whether it’s a testimonial, a favor or feedback, just ask. If they say ‘no’ don’t push just let it go and move onto the next person on your list.

Step Two

Be specific. If you’re asking for a review, don’t ever ask, “Hey will you review my product?” Kiss. of. Death. Why? Too broad. People will have to think about what your product is, what it did for them, if they’re still using it, etc, etc.

Same with feedback or a favor. If your favor is too broad or general they’ll get scared that it might be a huge commitment and blow you off.

Ask for one specific thing: feedback on a particular project or product; an introduction to one specific person or entity; a review of a specific product or service.

Be as specific as you possibly can be. This will put people at ease and make them eager to help you.

And where appropriate give them a template to follow. This way all they have to do is follow the template. The template does the thinking for them.

Step Three

Be brief. Cut the fat. Don’t send an overly wordy email. Don’t keep someone on the phone for 30 minutes while you work up the courage to ask your favor.

Being brief will be greatly appreciated by the person on the other end.

If you are heartfelt, specific and brief in your requests people will appreciate that and want to help you out as quickly as possible.

If they can’t help you out they will let you know and you both can move on.

This is a seemingly simple strategy but if you follow these guidelines and not take things personally you will have success most of the time.

Related Post : How To Overcome Fear: Why Scary Work Pays Well
Related Post : How To Use Public Speaking As the #1 Growth Strategy for Your Business
Related Post : How to Get Results with Relationship Capital

Using Relationship Capital

Asking a friend to take you to the airport at 6am.

The bartender sends over a round of drinks on the house.

Your credit card company waives its $35 fee on your late payment.

These are all examples of relationship capital in your personal life. What does relationship capital look like for an entrepreneur?

  • Requesting a pitch meeting with your friend’s company
  • Asking a colleague for a referral to a more successful person or business
  • Using your customer base to launch a new product or service

These are all important examples of using relationship capital and they are all necessary when growing your business. Relationship capital is extremely important for one specific reason:

Relationship Capital collapses the sales cycle.

Each one of these examples of relationship capital, if successful, is going to speed up the time it takes to deliver your product or service to the marketplace. The ultimate goal of any business is getting your goods and services into the right hands.

That’s done in a myriad of ways and asking for help from people you know simple speeds up that process.

So how do you do it successfully without offending anyone or risking not being taken seriously?

I’ve got a strategy for that. 😉 See a pattern here?

Step One

Serve first, request second. Don’t ever hold back your assistance, feedback or knowledge. By being quick to help others you are putting relationship capital in the bank.

By serving first you are letting people know you are always here to help. When people know you are helpful they, in turn, love being helpful back.

Check out Robert Cialdini’s book, Influence: The Psychology of Persuasion. The very first principle is the Principle of Reciprocity. Reciprocity is powerful. Learn to use it. And always give first.

Step Two

Consistency. Being consistent with your word and your actions imbues you with trust. When people trust you they are more willing to help.

Robert Cialdini also talks about consistency as one of the secrets to influence. Consistency instills confidence over time. And it’s this confidence people will remember when you reach out for a favor.

Step Three

Join a mastermind. Business masterminds are the work horses of the entrepreneurial world. Masterminds are uniquely positioned to offer a judgement free zone for asking for any kind of help you may need for your business.

  • Not belonging to a mastermind means you are going to miss out on meeting people who can help connect you to whole new worlds.
  • Not belonging to a mastermind means you’re going to miss out on learning about new business strategies before everyone else.
  • Not belonging to a mastermind means not hearing about opportunities that could scale and grow your business exponentially.

Masterminds are incredible tools of business growth and the very definition of relationship capital.

Speaking Publicly

Public speaking is is incredibly scary for a lot of people. I’m not just talking about getting up in front of hundreds of people at a convention hall. Public speaking can be:

  • A sales pitch for a group of people in a company
  • Speaking to a group of investors
  • Speaking one-on-one trying to sell your product or service
  • Giving a webinar or one-day retreat to a group of 15 people
  • Doing an interview for your book

These are all examples of public speaking and these are all very real possibilities for a successful entrepreneur. If you want to be a successful entrepreneur, you cannot be too afraid of getting up and speaking.

Being afraid is an ok thing to be until it stops you from actually doing the thing you need to do.

And here’s the thing about fears: they are usually held in place by unsupported beliefs you have about yourself:

“I’m not worthy.”

“I’m not good at public speaking.”

“I’ll never make a million dollars in my business.”

These are all unsupported beliefs, meaning they have no basis in truth. Have you ever made a million dollars? No? Then how do you know you can’t?

You’re not good at public speaking? Have you ever stood in front of your parents asking for something? Have you ever stood in front of your class in school to give a report?

Have you ever sat in a therapy session and discussed a vulnerable topic with your therapist describing in painful detail the haunting situation or circumstances?

Those are all examples of public speaking. They’re no match for the ridiculous pictures our minds come up with when we hear the words “public speaking” but they are public speaking in their own rights.

And we can take all those unsupported beliefs and dispel their power with this 7-step process.

This 7-step process won’t just help with public speaking. It will help with all the risks and challenges we’ve discussed so far: asking for assistance, and using your relationship capital.

These 7 steps are a blueprint for overcoming any kind of fear that you can face as an entrepreneur. Being an entrepreneur is not for the faint of heart. Being an entrepreneur means facing your fears every single day.

It’s ok to be afraid but don’t let that fear hold you back from your dreams. The following is how I overcome my fears everyday.

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Step One

Identify a task that scares you. You probably have six or seven tasks in your head and in your heart. Write them all down on a piece of paper, like a brain dump. Just write them all down. Then identify one, just one, to start.

Don’t identify a project as one task. A project is a bunch of tasks. Say for instance, you’re afraid of writing a book even though it’s something you’ve dreamed of doing for a long time. Thinking about the book, it seems like it is one thing – write the book.

But writing a book is many different tasks: coming up with the idea; writing an outline; thinking up chapter names; coming up with a title; writing the first draft of the first chapter, etc.

So if your fear is a book just choose one task related to the book. Maybe that one task is deciding on what the topic of the book will be.

I have clients who’ve avoided writing books for years by just not deciding on a topic. They keep going back and forth. It’s a great way to not move forward. Decide. Let you first scary action card be deciding on a topic to write about.

Now, choose one scary task from your list.

Step Two

At night, just before bed, write the scary task on the front of an index card. Write it at night so that you let it marinate in your heart and head as you sleep.

Writing the task down takes it from being a private affirmation to a public declaration. A public declaration is a motivating factor in getting the task done. If it’s there for the public to see they will hold you accountable.

Step Three

On the back of the card write down what scares you about doing the task. That’s the unsupported belief you have about the task. Once you write it down, it’s outside of you. That’s where you want it. You want to look at the unsupported belief and say it out loud. This way your conscious mind will realize how limiting and untrue it sounds.

We don’t want to burst through your fears. We want to expand your comfort zone by taking baby steps. So this step is confronting your unsupported belief by simply looking at it on paper.

Step Four

Place the card somewhere public. There is no hiding the card until the task is done. You need to put it out there. Pin the scare card somewhere you can see it while you’re walking by.

You can put it up at home, like on the bathroom mirror or near the coffee maker. Or you can put it up at work on your desk. Get creative with where you decide to put it. You can make duplicates and put several up in various places.

This step may be scary in itself but it’s really for you. Seeing it every day will hold you accountable and will nag at you little by little.

Step Five

Take the action. It may take you a week. It may take you a year. It doesn’t matter how long it takes. Be patient and loving with yourself and allow the transformation to happen. One day you will take the action.

Don’t give up. Look at the card every night before bed and every day when you wake. Remind yourself that your fear is an unsupported belief. Saturate and confront yourself everyday with your new knowledge and the task to be done.

I want to make an important distinction. You don’t need to have a positive result or a positive response. Maybe your scary action is asking someone for a favor. Maybe they say ‘no’ to the favor.

It’s still a win because you took the action. You overcame your fear! So it’s not the result we’re looking for, it’s the action.

The action expands your comfort zone. And if you do get a ‘no’ then make another action card and find someone else to ask until you get a ‘yes’!

Step Six

When you have a super scary card, review the other scare cards you’ve already overcome. Look back on all the unsupported beliefs that you’ve confronted. See how much you’ve expanded your comfort zone. Take some time to let that sink in.  

It will give you strength for what’s ahead.

So start small and work up to the ‘big fears.’

Step Seven

Save the scare card when it’s completed. Keep these cards as a diary of what you have confronted and overcome in your life. You can give it to your kids someday or share it with your spouse. Or maybe write a book 😉 maybe teaching people how to overcome their fears.

You’ll be able to look back at this diary and see how much your comfort zone has expanded in your life. Pretty soon you’ll be jumping out of planes and speaking to thousands of people on a stage.

Related Post : How To Overcome Fear: Why Scary Work Pays Well
Related Post : How To Use Public Speaking As the #1 Growth Strategy for Your Business
Related Post : How to Get Results with Relationship Capital

The Wrap Up

When you let go of fear your life and your comfort zone expand. When you can walk through the world without fear you open doors that were once closed to you.

When you let go of fear you can ask for what you want and need. You can use all that relationship capital you’ve saved up. You can speak to anyone, anywhere at anytime and open new doors and new opportunities.

On the eve of a new year and a new decade proclaim to yourself and to the world what you want and what you are willing to do to get it.

Find out what you are truly made of by letting go of all the stuff that doesn’t belong in your DNA: all your fear and unsupported beliefs. And go out there and have your best decade yet.

Want some more great tips on how to ask for testimonials for your business? Click here to find out how to grow your business using testimonials and how to easily get them.

Are you afraid of public speaking?

Are you afraid of asking for assistance for your business?

What risks are you planning on taking in 2020?

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