#39 - What If I'm Not Good Enough

I've been having a ton of self-doubt recently regarding a lot of things I’m trying and doing. I think the same self-doubt applies to trying something new or taking a chance on yourself and is the reason we hold ourselves back so often. Here’s how I’m getting myself out of it and 5 tips if you’re feeling the same way.

What If I'm Not Good Enough? 5 Ways to Beat Self-Doubt and Keep Going

From Guyset Podcast - A Guy's Guide to What Should Be Talked About

Ever had one of those weeks where everything feels off? Where every mistake feels magnified, every criticism cuts deep, and that voice in your head keeps asking: "What if I'm just not good enough?"

You're not alone. Self-doubt affects everyone, especially guys in their 20s navigating new jobs, relationships, and life transitions. This feeling can paralyze you from taking risks, applying for jobs, asking someone out, or pursuing your goals.

Here's how to recognize self-doubt for what it is—and more importantly, how to overcome it.

Why Self-Doubt Hits Guys in Their 20s So Hard

Your 20s are full of firsts:

• Starting a new job or career

• Living independently

• Navigating serious relationships

• Taking on real responsibilities

• Figuring out who you are as an adult

Each new experience carries the risk of failure, which feeds that inner voice saying "you're not good enough." And when you mess up (which everyone does), that voice gets louder.

The Psychology Behind Self-Doubt

Catastrophizing: This is when your brain takes one negative thought and spirals it into the worst possible outcome. Instead of "I made a mistake at work," it becomes "I'm terrible at my job, I'll get fired, my life is ruined."

Cognitive Dissonance: Your brain actually convinces you that avoiding risk is "protection." If you don't apply for that job, you can't get rejected. If you don't ask her out, she can't say no. It feels safer to stay where you are than risk failure.

The 97% Rule: Research shows that 97% of the things we worry about never actually happen as badly as we think they will. Your brain is literally overestimating the danger.

5 Strategies to Overcome Self-Doubt

1. Play Out the Worst-Case Scenario

What to do: Write down or talk through what you're afraid will happen. Be specific.

Example: "I'll apply for this job, they'll reject me immediately, waste my time, and I'll feel like a failure."

Then ask: "Okay, that happened. Now what?"

Reality check: Even if the worst happens, you've proven to yourself that you can try. You've learned something. You've taken action instead of staying stuck.

2. Remember: Lean In, Try, Fail, Feel, Stand Up Again

This is the cycle of growth:

• Lean in: Decide you're going to take the risk

• Try: Actually do the thing you're scared of

• Fail: Accept that failure is likely and normal

• Feel: Allow yourself to experience disappointment

• Stand up again: Get back up and try again

You don't have to be perfect. You just have to keep going.

3. Give Yourself Grace

You're probably new to most things in your life right now. It's your first time:

• In this type of job

• Living in this city

• Being this independent

• Navigating adult relationships

Cut yourself some slack. You're not supposed to get everything right immediately. Making mistakes doesn't mean you're not good enough—it means you're learning.

4. Look at People You Admire

Think of someone you look up to. Ask yourself:

• What risks did they take to get where they are?

• How many times do you think they got rejected?

• Did they always play it safe?

Everyone you admire has faced rejection and failure multiple times. The difference? They kept going despite the setbacks.

5. Ask: What Would You Tell a Friend?

If your best friend came to you with your exact problems, what would you say?

"I'm not happy at my job, but I'll probably get rejected by every place I apply."

You'd probably say: "Why not just try? You'll never know unless you apply. The worst they can say is no."

Treat yourself with the same kindness you'd show a friend.

When Self-Doubt Keeps You Stuck

Self-doubt often holds us back from:

Job Applications: "I don't have enough experience, why even try?" Dating: "They're out of my league, they'll just reject me" Starting Projects: "People will think I'm weird for trying this" Sending Important Emails: "They probably won't even respond"

But here's the truth: The fear of never trying is worse than the fear of failing.

The Reality About Failure

• Failure is data, not a death sentence

• Every rejection teaches you something

• Each "no" gets you closer to a "yes"

• Failure means you're pushing your boundaries

• Success without any failure usually means you're not taking enough risks

Questions to Combat Self-Doubt

When that voice starts up, ask yourself:

1. Is this thought helpful or harmful?

2. What evidence do I have that this is actually true?

3. What would happen if I tried anyway?

4. Am I catastrophizing right now?

5. What's the best-case scenario if I go for it?

Building Resilience Over Time

The more you practice:

• Taking risks despite fear

• Bouncing back from failure

• Challenging negative self-talk

• Trying again after setbacks

The stronger your resilience becomes. You're literally training your brain to handle uncertainty and rejection better.

The Truth About "Not Being Good Enough"

Here's what nobody tells you: Everyone feels like they're not good enough sometimes. The difference between people who succeed and those who don't isn't that successful people never doubt themselves—it's that they do it anyway.

Your worth isn't determined by:

• How quickly you pick things up

• How many times you get rejected

• Whether you make mistakes

• What other people think of your efforts

Final Thoughts: You're Stronger Than You Think

That voice telling you "you're not good enough" isn't protecting you—it's holding you back. The only way to prove it wrong is to keep trying, keep failing, and keep getting back up.

Remember: You'd rather live with the discomfort of growth than the regret of never trying.

The wave of self-doubt will hit again. That's normal. But each time you ride it out, you get stronger. Each time you stand back up, you prove to yourself that you can handle whatever comes next.

You are enough. You've always been enough. Now go prove it to yourself.

For more honest conversations about navigating your 20s, mental health, and personal growth, listen to Guyset - A Guy's Guide to What Should Be Talked About. Available on Apple Podcasts, Spotify, and all major platforms. Send your questions to advice@guyset.com

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