Ep 136 Career: Overcoming Fear and Insecurity: Why You Need a Plan, Not the Answers

Show notes

Welcome, everybody, to the 136th episode of The Crazy One podcast.

I’m your host, Stephen Gates, and this is the show where we talk about creativity, leadership, design—and whatever else comes up that seems to help creative people navigate this weird, wonderful career path we’re all on.

If you enjoy the show, do me a favor:

• Leave a review

• Tell a friend

• Post about it

• Or go big and buy a billboard—why not?

 

Because what we talk about here only makes an impact if other people hear it. And I like to think it might actually help someone.

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My Most Common Piece of Advice

Today I want to share what’s become my #1 piece of advice.

This is what I tell:

• Leaders at all levels

• People going through transitions

• Creatives trying to start something new

• Anyone facing a challenge and wondering how to move forward

 

This advice applies no matter the goal:

Whether you’re going after a promotion, switching careers, or chasing a new dream.

And here it is:

You need a plan, not the answer.

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The Problem: We Wait for Certainty

Let’s be honest—the beginning of something new is always the hardest part.

As creatives, we’re great at solving problems for others. We break things down, find insights, map out solutions, and go.

But when it comes to our own careers or personal lives? Suddenly, things get fuzzy.

Most people I talk to feel paralyzed because they can’t answer two big questions:

1. Have I figured out enough to get started?

2. How do I even start when it all feels overwhelming?

 

There’s so much unknown. So much uncertainty.

And we convince ourselves:

“I don’t have enough information. I haven’t done enough research. I’m not ready.”

We wait for certainty. But here’s the truth:

You’ll probably never feel 100% ready.

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You Need a Plan, Not the Answer

Let’s reframe the situation.

If you had a client problem or a new design brief, would you have all the answers on day one?

Of course not.

What do you do instead?

You create a plan.

You outline:

• The questions you’ll ask

• The research you’ll do

• The iterations you’ll make

• The steps you’ll take to get clarity

 

Why don’t we treat our careers and lives the same way?

Stop waiting for the “perfect answer” to appear.

Start building a plan. That’s the leadership. That’s the creativity.

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Leadership Is a Plan in Motion

Here’s the thing—great leaders don’t have all the answers.

But they have direction. They say:

“We’re going to go this way. Then we’ll look for this. Then we’ll test that. And adjust as we go.”

Bad leaders are the ones who pretend to have certainty when they don’t. They throw out half-baked answers. People know it’s not real. Trust disappears.

What people want from a leader isn’t all the answers.

They want reassurance that there’s a process.

They want to know you’ve got a plan, and that you’ll figure things out with them.

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Action Beats Insecurity Every Time

Here’s a personal truth:

I’m not the most creative person in the world. I’m not the best designer either.

But one of my superpowers is bias toward action.

Even when things aren’t clear. Even when I’m scared. I jump.

And that’s what’s made the difference.

Because most people get stuck in hesitation. They overthink. They spiral in “what ifs.”

“What if I fail?”

“What if no one listens?”

“What if it all falls apart?”

If I had listened to those thoughts, this podcast never would’ve existed.

I would’ve talked myself out of it like this:

“The world doesn’t need another podcast from a middle-aged white guy. Who’s going to listen to that?”

But I hit record. And here we are.

The fear of starting is always bigger than the reality of doing.

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Get Unstuck by Starting Small

If you feel stuck, here’s what to do:

1. Give yourself permission to start messy

2. Treat your problem like a design challenge

3. Write out a plan—however rough it is

4. Start walking the path

 

Don’t try to solve everything at once. Just commit to figuring it out as you go.

Because honestly, you already have the skills to pivot, adapt, learn, and adjust.

You’ve done it a million times for other people.

Now do it for yourself.

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Don’t Let “What Ifs” Win

I’ve talked to so many creatives stuck in “what if” loops:

• What if I don’t get hired?

• What if my startup fails?

• What if I’m not good enough?

 

Look, if a meteor crashes into your house, we’ll deal with that then.

But don’t let hypothetical fears stop you from trying.

The only real failure is not learning.

The only way to succeed is to begin.

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Crazy vs. Stupid

Here’s the difference:

• Stupid jumps with no plan and no reflection

• Crazy builds a plan, takes a risk, learns, and grows

 

You’re not aiming to be reckless. You’re aiming to be brave.

So the next time you feel stuck, remember:

You need a plan, not the answer.

That shift changes everything.

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Final Thoughts

Give yourself some grace.

Let yourself try.

Build a plan and take the first step.

This approach will:

• Unlock your confidence

• Accelerate your growth

• Help you lead more effectively

• And get you moving toward what you actually want

 

Try it. And let me know if it helps.

Thank you, as always, for listening to the show.

I appreciate you. And I’m grateful for this community.

Until next time – Stay crazy.

Tagged as:
action over perfection bias towards action career transition creative challenges creative confidence creative leadership creative process goal setting leadership advice leadership skills overcoming fear problem starting a project taking risks