So many people walk through life carrying a quiet feeling that they’re somehow falling short. Even when things look successful from the outside, there can still be an internal pressure saying “do more,” “be better,” or “you should be further ahead by now.” In this episode, Andrew and Catherine unpack why that feeling exists, where it often comes from, and how to begin healing it from the inside out.

They explore how childhood conditioning, comparison, perfectionism, achievement culture, and societal expectations shape the way we see ourselves. From parenting and relationships to careers, money, and personal growth, the conversation dives into the many ways “not enough” can show up in everyday life.

Andrew and Catherine also share how they’ve challenged traditional ideas of success in their own lives by redefining what fulfillment actually means for them. They explain why external achievement can never permanently fix internal self-worth and why true confidence has to be built from within.

If you’ve ever felt like you were constantly trying to prove yourself, earn approval, or chase a version of success that doesn’t actually make you happy, this episode will help you pause, reflect, and reconnect with who you truly are underneath the pressure.

• Why feeling “not good enough” is a universal human experience
• How perfectionism and comparison fuel self-worth struggles
• The connection between childhood praise, criticism, and adult anxiety
• Why achievement only creates temporary relief
• How societal expectations shape the goals we chase
• The danger of tying your worth to productivity or performance
• How to separate self-worth from external success
• Why learning to receive compliments matters
• The importance of resting without guilt
• How to stop auditioning for love and approval
• Questions to ask yourself if you constantly feel behind
• What it means to build your life from the inside out

• The Layers of Life framework
• Five Year You Coaching
• Previous Five Year You podcast episodes on personal growth, identity, and emotional healing

If this episode resonated with you, share it with someone who may need the reminder that their worth is not something they have to earn.

For coaching and resources designed to help you create the next version of yourself, visit: Five Year You Coaching

Hosts: Andrew Dewar & Catherine Collins

In this episode of Five Year You, we get real about failure, setbacks, and those moments when life just… derails. If you’ve ever asked, “Why is this happening to me?”—this conversation will help you reframe the tough moments and find meaning, strength, and even humor in the mess.

👇 Scroll for tools, timestamps, and links!

✨ What You'll Learn in This Episode:

• Why setbacks are a natural part of the growth journey
• The importance of mindset: victim vs. curiosity
• Practical coping skills for when you’re in the middle of a setback
• The power of contrast days
• How reframing failure helps you become the person you're meant to be
• Parenting wisdom: why we shouldn’t shield kids from failure
• How to process big feelings—without getting stuck
• Fanny pack of coping tools (yes, we said that)

✅ Helpful Tools & Resources:

📱 Opal App – Reduce Screen Time & Reclaim Life

🎧 Audible Free Trial – Personal Development on the Go

🍳 Instant Pot – Save Time, Eat Well

💬 Favorite Quotes:

🌟 Glimmers of the Week:

Catherine: Finally making a long-put-off doctor appointment thanks to a little loving push.

Andrew: Wearing yellow for the first time and loving the way it feels.

📲 Stay Connected:

🌐 Website: https://fiveyearyou.com

📸 Instagram: https://instagram.com/fiveyearyou

📧 Email: hello@fiveyearyou.com

⚠️ Disclaimer:

This content is for informational purposes only and not intended as a substitute for professional mental health or medical advice. Some links may be affiliate links. As an Amazon Associate, we may earn from qualifying purchases.

💬 Your Turn:

What’s a setback that taught you something valuable?

Drop it in the comments—we’d love to hear your story.

🔔 Don’t forget to subscribe and tap the bell for weekly inspiration.

🎧 Available wherever you get your podcasts.

#FiveYearYou #OvercomingSetbacks #MentalHealthTools #PersonalGrowth #CopingSkills #LifeLessons #SelfImprovement #Resilience #Podcast #AndrewDewar #CatherineCollins

5 Year You Coaching https://fiveyearyou.com/coaching/

If you’ve been feeling like someone else’s success makes you uncomfortable… like you’re comparing more than you want to admit… like certain people just trigger something in you—this episode is for you.

Because here’s the truth:

Jealousy isn’t something to be ashamed of.

And more importantly… it’s not a flaw—it’s feedback.

💭 What This Episode Covers

• Why jealousy isn’t a “bad” emotion—it’s information
• What your jealousy is actually trying to show you
• How to stop suppressing or projecting jealous feelings
• The hidden beliefs that keep you stuck in comparison
• Signs someone else might be jealous of you
• How to handle jealousy (yours and others’) in a healthy way

🚨 Why Jealousy Happens

1. It Reveals Your Desires
2. When you feel jealous, you’re reacting to what someone represents.
3. It’s not about them—it’s about what you want.
4. 👉 Result: You get clarity on what matters to you
5. Learned Beliefs Create Resistance
6. If you believe “rich people are greedy” or “happy people are just lucky,”
7. your brain will block you from becoming those things.
8. 👉 Result: You stay stuck wanting what you’ve labeled as “bad”
9. Suppression Turns Into Projection
10. Ignoring jealousy doesn’t make it disappear.
11. It shows up later as criticism, resentment, or passive aggression.
12. 👉 Result: You push away what you secretly admire
13. Comparison Without Awareness
14. You compare your life to others without asking why.
15. You feel frustrated—but don’t explore the root.
16. 👉 Result: You stay in the loop instead of growing from it

😞 The Emotional Cost of Jealousy

When you believe “they have something I don’t,” it creates:

• insecurity
• frustration
• quiet resentment

And the worst part?

👉 You miss the opportunity to turn that feeling into growth

⚠️ The Hidden Danger

Unchecked jealousy can quietly shape how you see others—and yourself.

Examples:

• Dismissing successful people instead of learning from them
• Making backhanded comments to feel better
• Judging lifestyles you secretly want
• Avoiding growth because it conflicts with your beliefs

👉 You block yourself from becoming the very thing you desire

🔑 The Truth You Need to Hear

There are no “bad” emotions

There is only information

Jealousy doesn’t mean you’re a bad person

It means you’re an honest one

What you feel is pointing you somewhere

Not holding you back

👉 You just have to be willing to look at it

🔄 What Jealousy Actually Means

It means something inside you is waking up

It means you’re noticing what you want

It means you’re ready for more

This isn’t something to hide from

It’s something to learn from

👉 It’s the beginning—not the end

🛠️ How to Shift Out of the “Jealousy” Mindset

1. Name It Without Shame
2. Instead of avoiding it, say: “I feel jealous.”
3. That honesty is where growth begins.
4. Get Curious
5. Ask yourself:
6. What exactly am I jealous of?
7. What does this person represent to me?
8. Challenge Your Beliefs
9. Notice your automatic thoughts:
10. “Rich people are…”
11. “Happy people are…”
12. Rewrite what no longer serves you.
13. Shift From Comparison → Possibility
14. Instead of “Why them?” ask:
15. “What would it look like for me to have this too?”
16. Watch Your Words
17. Avoid criticizing or minimizing others.
18. What you say about them often reveals how you feel about yourself.

💡 Key Takeaway

Jealousy isn’t your enemy

It’s your internal compass

It shows you what you want

And where you’re holding yourself back

👉 Use it as direction—not judgment

✨ Glimmers from This Episode

• Realizing emotions are guidance—not something to fear
• Catching your thoughts and choosing a new perspective
• Letting yourself want more without guilt
• Seeing growth as something available to you too

💬 Final Thought

The things that trigger you…

are often the things meant for you.

Pay attention to what stirs something inside you.

It might just be pointing you toward your next chapter.

If this episode resonated with you, share it with someone who needs this reminder 💫

If you’ve been feeling like things finally start going well… and then somehow fall apart… like you can’t stay consistent even when you want to… like you get anxious the moment life feels calm—this episode is for you.

Because here’s the truth:

You’re not randomly messing things up.

And more importantly… you’re not broken.

💭 What This Episode Covers

• Why you sabotage good things (even when you don’t mean to)
• The concept of a “happiness ceiling”
• How your past shapes your comfort zone
• Why calm and peace can feel uncomfortable
• Signs you’re subconsciously self-sabotaging
• How to start shifting your internal “thermostat”

🚨 Why Self-Sabotage Happens

1. Your “Familiarity Thermostat”
2. Your mind and body are wired to return to what feels normal—even if it’s stressful or chaotic.
3. 👉 Result: When life gets better than your baseline, you unconsciously pull yourself back.
4. Worthiness Wounds
5. Sometimes, deep down, you don’t believe you deserve good things.
6. 👉 Result: You disrupt what’s going well to match how you feel about yourself.
7. Addiction to Stress
8. If you grew up around chaos or instability, calm can feel unsafe or unfamiliar.
9. 👉 Result: You recreate tension because it feels more “normal.”
10. Fear of the Unknown
11. Success, peace, or happiness at a new level can feel unpredictable.
12. 👉 Result: You retreat back to what you know—even if it’s not what you want.

😞 The Emotional Cost of Self-Sabotage

When you believe “this won’t last” or “something bad is coming,” it creates:

• anxiety
• overthinking
• self-doubt

And the worst part?

👉 You end up proving your own fears right.

⚠️ The Hidden Danger

Self-sabotage doesn’t always look obvious—it often feels justified.

Examples:

• Picking a fight during a great moment
• “Losing motivation” right when things take off
• Creating problems that weren’t there before

👉 You don’t realize you’re choosing discomfort—you think you’re reacting to reality.

🔑 The Truth You Need to Hear

• You are not behind
• You are not broken
• You are not incapable

What you’re experiencing is conditioning.

And that can change.

👉 You are allowed to feel safe in good things.

🔄 What Self-Sabotage Actually Means

It doesn’t mean you’re failing.

It means:

• You’re growing
• You’re stretching beyond your old identity
• You’re entering unfamiliar territory

👉 It’s the beginning—not the end

🛠️ How to Shift Out of the “Self-Sabotage” Mindset

1. Notice the Pattern
2. Start catching the moment things feel “too good.”
3. Ask yourself:
4. Is something actually wrong—or just unfamiliar?
5. Name It in Real Time
6. Say it: “This is my thermostat kicking in.”
7. Labeling it helps you create space instead of reacting.
8. Sit With the Discomfort
9. Let things be good without interfering.
10. Practice staying in the calm—even when it feels strange.
11. Normalize Good
12. If something positive happens—don’t rush past it.
13. Let it sit. Feel it. Get used to it.
14. Raise Your Baseline Gradually
15. You don’t need to jump from survival mode to perfect peace overnight.
16. Small shifts create lasting change.

💡 Key Takeaway

You’re not sabotaging your life on purpose.

You’re regulating back to what feels safe.

But safe doesn’t have to mean stressful.

👉 You can teach your system that good things are safe to keep.

✨ Glimmers from This Episode

• Learning that calm is something you can grow into
• Realizing awareness is the first step to change
• Finding peace in small, steady progress
• Letting yourself enjoy when things are going right

💬 Final Thought

Maybe things aren’t falling apart.

Maybe they’re finally coming together in a way you’re not used to yet.

And maybe…

this time…

you don’t have to ruin it.

If this episode resonated with you, share it with someone who needs this reminder 💫

If you’ve been feeling like you’re behind… like everyone else is ahead… like you should be further along by now—this episode is for you.

Because here’s the truth:

Almost everyone feels this way at some point.

And more importantly… it’s not actually true.

• Why the feeling of being “behind” is so common
• The hidden pressure of comparison culture
• How timelines are created (and why they’re not real)
• The emotional toll of constantly feeling “not enough”
• How to reconnect with your own path
• Practical ways to shift out of the “behind” mindset

You’re constantly measuring your life against other people’s highlight reels.

• Social media shows curated success
• You don’t see the trade-offs or struggles
• You compare your reality to someone else’s best moments

👉 Result: You always feel like you’re losing

You’ve been taught there’s a “right time” for everything:

• Career milestones
• Marriage / kids
• Buying a house
• Financial success

But those timelines?

They’re learned—not real.

You’ve been conditioned to measure success by:

• Money
• Titles
• Status
• Possessions

But none of these guarantee fulfillment.

When you believe you’re behind, it creates:

• Anxiety
• Pressure
• Rushed decisions
• Self-doubt
• Low self-worth

And the worst part?

👉 That “catching up” feeling never goes away

There will always be someone “ahead” if you play that game.

When you feel behind…

You start making decisions that aren’t actually right for you.

Examples:

• Staying in careers you don’t want
• Rushing relationships
• Buying things to “keep up”
• Following paths that aren’t aligned

👉 You stop living your life—and start living a timeline.

• You are not behind
• There is no universal timeline
• Life is not linear
• People peak, pivot, restart, and reinvent constantly

👉 You’re not late. You’re just on your own path.

This feeling isn’t a failure.

It’s a signal:

• You’re becoming more self-aware
• You want something different
• You’re ready for growth
• You’re outgrowing your current situation

👉 It’s the beginning—not the end

Ask yourself:

• What does success look like for me?
• What do I actually want?

Not what looks good.

Not what impresses others.

What feels right.

Don’t compare one area of your life to someone else’s whole life.

Look at:

• Your growth
• Your experiences
• Your strengths

👉 When you zoom out, you’ll realize you’re doing better than you think.

Most timelines are:

• Socially constructed
• Arbitrary
• Not aligned with your life

👉 You don’t have to follow them.

Progress isn’t about how fast you go.

It’s about:

• Consistency
• Alignment
• Intentional steps forward

Ask yourself:

• What actually matters to me right now?
• What feels aligned?
• What do I want—not what’s expected?

You’re not behind.

You’re just:

• Becoming aware
• Questioning old patterns
• Starting to choose your own path

👉 And that’s where everything changes.

• Finding joy in small wins (like thrifting wins or a sunny walk)
• Reconnecting with community (like a book club)
• Appreciating simple moments you once overlooked

Your life isn’t on a clock.

It’s on a path.

And you’re still on it.

If this episode resonated with you, share it with someone who needs this reminder 💫

You’ve done the work.

You’ve built the habits.

You’ve pushed through the discomfort.

So why does it still feel like you’re not fully that person yet?

In this episode, we break down the final (and often hardest) step of personal growth:

taking full ownership of who you’ve become.

Because becoming the new version of you isn’t about doing more —

it’s about deciding you already are that person.

1. Why you’ll never “feel ready” to become your next version
2. The gap between doing vs. being
3. Why the “messy middle” feels so uncomfortable
4. Fear of success and identity shifts
5. How to stop waiting for permission
6. Letting go of your old story
7. How to fully embody your new identity

You don’t wait until you feel confident.

You decide, today, that this is who you are.

There’s a gap between:

1. Doing the habits
2. Being the person

That gap feels uncomfortable because your brain is catching up to your actions.

When you say:

1. “I’m trying to be disciplined”
2. “I’m trying to be confident”

You reinforce that you’re not there yet.

Instead:

1. “I follow through”
2. “I take care of my health”

If you’re waiting for validation…

You’ll stay stuck.

Ownership happens when you decide:

“This is who I am now.”

Every time you say:

1. “I’ve always been like this…”
2. “I’m just not that kind of person…”

You reinforce the old version.

Let it go.

Ask yourself:

1. What would future me do here?
2. What would the version of me I’m becoming choose?

Small decisions = identity reinforcement.

There is no final version of you.

There are seasons of:

1. Becoming
2. Being
3. Expanding again

And learning to sit in the “being” phase is just as important.

You’ll notice:

1. You trust your decisions faster
2. You stop over-explaining yourself
3. You recover quicker from setbacks
4. You feel more calm and grounded
5. It starts to feel… normal

That’s when it clicks.

What would it look like to fully own this version of me?

If you’re stuck in the gap and want support:

👉 https://www.fiveyearyou.com/coaching

We work with you 2:1 to help you:

1. Break through identity blocks
2. Build confidence
3. Fully step into your next level

You don’t need another breakthrough.

You don’t need more proof.

You just need to own who you’ve already become.

If you loved this episode, share it with someone who’s in their “messy middle” right now 💫

If you’ve been doing the work, making changes, and still asking yourself…

“What if I’m wrong?”

This episode is for you.

Because one of the hardest parts of growth isn’t starting —

it’s staying on the path when doubt shows up.

👉 Coaching: https://www.fiveyearyou.com/coaching

1. Why doubt shows up when you’re actually growing
2. The myth of certainty (and why you’ll never feel 100% sure)
3. The difference between being off track vs. uncomfortable
4. How to recognize real signs of alignment
5. Why you don’t need external validation to stay on your path
6. How to build self-trust without constant reassurance

You don’t get certainty first…

You get clarity after you take action.

Growth removes predictability — and your brain will resist that.

That doesn’t mean you’re doing it wrong.

It means you’re doing something new.

Even when things aren’t perfect, there’s an internal steadiness.

You’re not forcing everything — opportunities, people, and ideas start to align.

Even if others don’t understand your choices, you know they’re right for you.

Your actions feel aligned with who you’re becoming.

You feel resistance — but it doesn’t stop you.

Small habits start sticking. You show up more often as your future self.

Being on the right path does NOT mean:

1. You feel confident all the time
2. You have certainty
3. You see immediate results
4. Other people understand your decisions
5. It’s easy

Discomfort is part of alignment — not proof you’re off track.

Most people don’t lack direction…

They lack tolerance for uncertainty.

Small daily actions build confidence in who you’re becoming

Every time you seek reassurance, you weaken your own voice

You don’t need proof yet — just momentum

Focus on effort, consistency, and how things feel

1. What felt aligned today?
2. Where did I trust myself?
3. What small step did I take forward?
4. What nudges or signs did I notice?

You don’t need full certainty to be on the right path.

You just need:

➡️ A direction that feels aligned

➡️ The courage to keep going

➡️ And the willingness to trust yourself

Catherine:

First garage sale + thrifting day of the season 🛍️

Andrew:

Finding small signs of alignment (like his “dime moments”)

If this episode helped you, share it with someone who’s questioning their path right now 💫