Risk Taker vs Risk Averse

Risk Taker vs Risk Averse: Why Taking a Chance on Yourself Can Lead to Great Success

I was speaking with one of my mentees early this morning – he lives in the UK, so it was early for me and late afternoon for him – and he asked me about the risk of leaving a job and coming online, as I did years ago.

The fact is that I’ve always been a risk taker and it’s always worked out well. I could give you several examples, but the one most relevant to you is how I made the decision to resign from my job as a classroom teacher and simultaneously give away all of my real estate clients during a six-month period.

I made a list of the pros and cons. I asked a few people whom I believed were smart and had good common sense. Then I gave myself one week to decide what I would do. I had no children under eighteen; I had enough money to live for at least a year without a paycheck; I knew that I would do whatever it would take to succeed.

Obviously, my choice was the right one for me. And, I was still teaching for eight more months before the school year ended, so I had a cushion of time and money. But once I gave notice to the school district, there was no turning back.

It was more difficult than I had imagined for two reasons” first, because I was not a writer and second, because I thought I needed to do my own tech. But it was also easier and faster than I had imagined because an early Mentor emphasized that the most important word in “Internet Marketing” was marketing.

The Biggest Risk Most Entrepreneurs Avoid: Marketing

There’s another area where risk-taking matters even more than leaving a job or launching a business.

That area is marketing.

In the online world, you can have the best product, the most helpful course, or the most thoughtful content—but if you are not willing to put yourself out there, none of it matters.

And this is where many new entrepreneurs become risk-averse.

They worry:

• What if no one opens my email?

• What if no one buys?

• What if people unsubscribe?

• What if someone criticizes me?

• What if I look inexperienced?

So they delay.

They tweak their website again.
They redesign their logo.
They create more content… but never promote it.

But here’s the truth:

The real risk isn’t marketing.
The real risk is staying invisible.

Every day you hesitate to share your message is a day someone who needs your help never finds you.

Marketing Is an Act of Courage

When I first began building my online business, I realized something important. Success didn’t come from having the perfect product.

It came from being willing to:

• Send the email

• Make the offer

• Talk about my work

• Show up consistently

• Invite people to take the next step

Marketing is simply communication. It’s letting people know:

• Who you help

• How you help them

• Why it matters

• What to do next

But emotionally, it can feel risky because marketing makes you visible. And visibility requires vulnerability.

This is where risk takers have an advantage.

They understand that:

• Some emails won’t perform well

• Some posts won’t get engagement

• Some launches will be smaller than expected

And they keep going anyway.

Because in online business, marketing momentum matters more than marketing perfection.

Small Marketing Risks That Lead to Big Growth

You don’t need to take huge marketing risks. Start with small, consistent ones:

• Send one more email each week

• Share your personal story instead of just tips

• Mention your product more often

• Ask for the sale instead of hoping people will figure it out

• Show your face on video

• Repurpose and promote your content instead of creating something new every day

Each time you do this, you build confidence. And confidence reduces fear.

Over time, marketing stops feeling risky and starts feeling natural.

The Entrepreneur’s Marketing Truth

Here’s what many new online entrepreneurs don’t realize:

You are not just a creator.
You are not just a teacher.
You are not just a service provider.

You are a marketer.

And your willingness to market consistently will determine your results more than almost anything else.

The people who succeed online are not the most talented.

They are the ones who:

• Show up regularly

• Share their message repeatedly

• Make clear offers

• Stay visible even and especially when it feels uncomfortable

Because they understand something powerful:

Marketing isn’t pressure.
Marketing is service.

When you share your work, you give people the opportunity to learn, grow, solve a problem, or move forward in their lives.

And that’s not risky.

That’s responsible.

A New Way to Think About Risk

If you want to grow your online business, shift your thinking:

Instead of asking,
What if my marketing doesn’t work?

Ask,
What happens if no one ever hears my message?

The entrepreneurs who are willing to take that visibility risk—the risk of being seen, heard, and occasionally ignored—are the ones who build sustainable, profitable online businesses.

Because in the world of internet marketing:

Visibility creates opportunity.
Consistency creates trust.
Marketing creates income.

And the biggest risk of all… is not marketing at all.

My decision to leave my teaching job and my real estate side hustle wasn’t reckless: It was intentional.

What I’ve learned over the years is that successful risk takers aren’t gamblers. They don’t jump without thinking. They prepare, they evaluate, and then they move forward before they feel completely ready.

And that last part matters.

If you wait until you feel 100% certain, you’ll almost never move.

Online entrepreneurs face this moment again and again:

• Launch the product or course, or wait until it’s perfect?

• Start the blog or keep researching?

• Raise your prices or stay “safe”?

• Invest in a tool, a coach, or advertising, or hold onto every dollar?

Every meaningful level-up in your business involves risk.

But there’s another kind of risk most people don’t talk about.

The risk of staying where you are.

When I left teaching and real estate, I wasn’t just taking a risk by leaving. I was also recognizing the risk of staying:

• Staying in a career that no longer brought me joy, but also limited my income

• Staying in a structure where my time was controlled

• Staying in a life that depended on someone else’s decisions

For online entrepreneurs, the hidden risks look like this:

• Waiting another year to build your email list

• Posting inconsistently because you’re afraid of being visible

• Never launching because you’re worried no one will buy

• Underpricing because you’re afraid of rejection

Playing it safe can quietly cost you years of growth.

Smart Risk vs. Blind Risk

Over time, I’ve come to see risk-taking as a formula:

Clarity + Cushion + Commitment

Clarity
Know what you’re moving toward. Not just “make money online,” but a clear vision: freedom, flexibility, impact, or a specific income goal.

Cushion
Create a safety net when possible. For me, it was a year of living expenses.
For you, it might be:

• Starting your business part-time

• Building a small emergency fund

• Validating an idea before going all in

Commitment
This is the part many people skip. Once you decide, you stop second-guessing and start executing. You give your energy to making it work instead of worrying about what might go wrong.

In the online world, commitment looks like:

• Publishing consistently

• Building your list every week

• Launching even when you feel nervous

• Improving based on feedback instead of quitting

The Entrepreneur’s Risk Mindset

The most successful online entrepreneurs don’t avoid risk.

They redefine it.

They ask:

• What’s the smallest version of this I can test?

• What will I learn even if it doesn’t work?

• How quickly can I adjust?

Instead of betting everything on one big move, they take many small, intelligent risks.

Write the email.
Publish the post.
Offer the product.
Make the invitation.

Because in online business, action reduces risk more than hesitation ever will.

A Question to Ask Yourself

If you’re feeling risk-averse right now, ask yourself:

What decision am I avoiding because I want certainty?

Then ask a better question:

What is the smallest step I could take this week to move forward anyway?

That’s how risk takers are built—not through one dramatic leap, but through a series of brave, thoughtful actions.

And here’s what I’ve discovered after years of entrepreneurship:

The biggest risk isn’t failing… The biggest risk is never giving yourself the chance to succeed.

What about you? Are you at a point in your life where it would make sense for you to make a more concerted effort with your online business? Are you determined and serious about carving out 15 to 20 hours a week – every week – to build and grow your business exponentially this year?

 

 

I’m bestselling USA Today and Wall Street Journal author Connie Ragen Green. My goal is to help at least a thousand people to reach six-figures and beyond with an online business for time freedom and passive income and to simplify your life by having the confidence to follow your purpose. Come along with me, if you will and let us discover how we may further connect to achieve all of your dreams and goals. Perhaps my “Monthly Mentoring Program” is right for you.