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Why are we so afraid of rejection?

What would you do if you absolutely had to find $5,000 today? Not next month. Not eventually. Today.

Would you take on extra work, find new clients, sell something, negotiate, or ask for help? Or would the thought of putting yourself out there feel so overwhelming that you'd rather stay exactly where you are?

That's the uncomfortable question Erin Skye Kelly puts to Jen in this episode of Naked Money Meetings. And while the conversation starts with $5,000 in debt, it quickly becomes about something much bigger: the fear of rejection, people-pleasing, and the ways we hold ourselves back before anyone else even gets the chance.

Because sometimes the biggest obstacle between us and the life we want isn't money, opportunity, or even ability. It's us deciding we're not going to try.

How does people-pleasing hold you back?

Erin makes an interesting distinction: people-pleasing isn't necessarily about being kind. It's often about managing other people's reactions so we can feel safe.

Think about it. How often have you:

• Said yes when every part of you wanted to say no?

• Avoided asking for a raise because you didn't want to make things awkward?

• Undercharged for your work because you worried about what someone might think?

• Stayed quiet rather than risk disappointing someone?

• Put everyone else's needs ahead of your own?

Sound familiar?

People-pleasing can look generous from the outside, but it can come at a pretty significant personal cost. You end up managing everyone else's comfort while quietly abandoning your own needs.

And eventually, that resentment, exhaustion, and frustration start showing up in all areas of your life, including your finances.

What does fear of rejection have to do with money?

Quite a lot, actually.

When Erin challenges Jen to find $5,000, the issue isn't simply coming up with the money. It's the discomfort of doing what might be required to earn it.

Putting yourself out there. Finding clients. Making offers. Asking for opportunities. Hearing no.

Erin connects this hesitation to two deeply rooted human fears: not being enough and not being loved.

This is where financial transformation becomes about more than budgets and debt repayment. As Erin explores in her bestselling books, Get the Hell Out of Debt and Naked Money Meetings, changing your relationship with money can also mean changing the beliefs and behaviours that influence your decisions.

Sometimes building wealth requires you to become comfortable being seen, asking for more, and risking rejection.

7 ways to stop rejecting yourself

One of the most interesting parts of this conversation is Erin's practical advice for getting out of your own way.

Here are seven ideas worth thinking about:

1. Let someone tell you no. Stop deciding on someone else's behalf that they'll reject you. Make the ask and let them answer.

2. Stop arguing against your own desires. Allow yourself to acknowledge what you actually want before explaining why it isn't possible.

3. Believe yourself the first time. If you're exhausted, you're exhausted. If something doesn't feel right, pay attention.

4. Practice disappointing people in small ways. Saying no doesn't require a lengthy explanation or a 14-page legal brief.

5. Stop editing yourself before entering the room. Don't decide you're too ambitious, too inexperienced, too old, or not qualified before you've even tried.

6. Separate rejection from your worth. Someone declining your offer doesn't mean you're not valuable.

7. Catch the little ways you betray yourself. Accept a compliment without minimizing it. Share your opinion without immediately softening it. Let yourself want what you want.

These small shifts can create much bigger changes over time.

How can you become more comfortable hearing no?

Here's a challenge from Erin that might make you a little uncomfortable.

Think about one thing you've been avoiding because you're afraid of rejection.

Maybe it's applying for a job, asking for a raise, pitching a new client, starting a business, or finally having that conversation you've been putting off.

Now do it.

The goal isn't to collect yeses. It's to become someone who can survive no without deciding it means something terrible about you.

Because you might get rejected. That's part of it. But you might also find the opportunity, client, relationship, or next chapter you've been waiting for.

And you'll never know if you keep rejecting yourself before you even try.

Key Takeaways

• Fear of rejection can prevent you from pursuing financial, professional, and personal opportunities.

• People-pleasing often comes from trying to manage other people's reactions.

• You cannot build confidence by rejecting yourself before anyone else gets the chance.

• Someone saying no does not determine your worth.

• Learning to set boundaries means accepting that other people may occasionally be disappointed.

• You are allowed to want more without immediately talking yourself out of it.

• Success often requires becoming comfortable with discomfort.

  Ready to Stop Getting in Your Own Way?

  What would change if you stopped worrying about hearing no and started focusing on what might happen if someone said yes?

  In this episode of Naked Money Meetings, Erin and Keri continue their conversation with Jen and explore the connection between people-pleasing, self-worth, rejection, and financial transformation.

  It's honest, uncomfortable in all the right ways, and full of ideas that might have you looking at your own excuses a little differently.

  Listen to the full episode of Naked Money Meetings and find out what happens when you stop rejecting yourself.

  Listen on Apple : https://podcasts.apple.com/ca/podcast/jen-get-rejected-get-rich/id1462338073?i=1000793393297

Resource Links 

• Erin Skye Kelly’s Book: Get the Hell Out of Debt
• Erin Skye Kelly’s Book: Naked Money Meetings  

Helpful external resources

• Consumer Financial Protection Bureau: Financial Well-Being  - Explore your financial well-being and identify opportunities to improve your relationship with money.

• CFPB: Your Money, Your Goals  - Practical resources for setting financial goals and managing debt.

• American Psychological Association: Building Your Resilience  - Strategies for developing resilience when facing difficult situations.

To continue the conversation, join us online: Naked Money Meetings Facebook Group