Week 5: What’s Holding You Back? How to Get Unstuck in Midlife

You have an idea.

Maybe it’s been sitting quietly in the back of your mind for years. Maybe it only surfaced recently. Maybe you aren’t even sure you want to pursue it yet, but something about it keeps pulling you back.

Then almost as quickly as you imagine doing it, another part of your brain starts explaining why you can’t.

I don’t have enough time.

I’m not qualified.

It would cost too much.

I wouldn’t even know where to begin.

What if I fail?

What will people think?

Maybe I should just be grateful for the life I already have.

This is where a lot of potentially interesting next chapters end. Not because the idea was wrong, but because we lump every obstacle together and call the whole thing impossible.

This week in Designing Your Next Chapter, I want to do something different.

Instead of telling yourself to be more confident, think positively, or "just go for it," we're going to get much more practical.

What is actually holding you back?

Because once you know that, you can decide what deserves your attention and what doesn't deserve to make the decision for you.

Start With One Possibility

Last week, we explored what your next chapter could look like.

You created possibilities instead of forcing yourself to make a decision. Maybe one involved your career. Maybe you imagined starting something of your own. Maybe it was travel, creativity, volunteering, learning something new, changing your lifestyle, or simply creating more room for yourself.

Choose one of those possibilities now.

Not because you're committing to it.

You're just going to use it as an example.

Complete this sentence:

One thing I would be interested in exploring is ____________.

Now imagine actually doing it.

Not thinking about it. Not talking about doing it someday.

Actually doing it.

What happens next in your head?

Pay attention because that's where Week 5 begins.

Not Every Obstacle Is Fear

I think we're sometimes too quick to label everything a "limiting belief."

There are legitimate reasons why making a change in midlife can be complicated.

You may have a mortgage.

You may need health insurance.

You may have children still at home or aging parents who depend on you.

You may not have enough money to fund the idea you're considering.

You may need training, credentials, technology, or experience you don't currently have.

Those aren't negative thoughts.

They're information.

The problem comes when we treat every obstacle as equally permanent.

Let's say you want to start a business that requires $30,000 and you don't have $30,000.

That's a fact.

But does that mean the business is impossible?

Not necessarily.

The next question becomes whether there's a smaller version you could test, another way to fund it, a different business model, or a reason to postpone the idea.

That's problem-solving.

Now compare that with:

"Nobody will hire someone my age."

Is that a fact?

Probably not.

It may be something you fear. It may even be based on experiences you've had. But unless you've gathered evidence that no employer will hire you, you're predicting the future.

That's an assumption.

And those three categories require completely different responses.

Fact, Problem, or Fear?

When something feels like it's standing between you and what you want, ask yourself:

Is this a fact, a problem to solve, or a fear/assumption?

A fact is objectively true right now.

A problem to solve is real, but there may be options, workarounds, resources, or steps you haven't considered yet.

A fear or assumption predicts something that hasn't actually happened.

Try it with a few common examples.

"I don't have ten hours a week available right now."

Potentially a fact.

"I can't do this because I don't have ten hours a week."

Now we may have a problem to solve.

"I'll never have enough time."

That's probably an assumption.

The words sound similar, but they lead to very different conclusions.

Follow the Fear All the Way Down

Sometimes the first fear isn't the real fear.

You tell yourself:

I'm afraid my business won't work.

Okay.

What happens if it doesn't?

Maybe you lose some money.

And what would that mean?

Maybe you'd feel embarrassed.

And why does that bother you?

Because you imagine other people thinking you were foolish for trying.

Now we've gone from:

"I'm worried the business won't work."

to:

"I'm afraid of being judged if I try something and it doesn't work."

That's a very different problem.

Or perhaps you think you're afraid to change careers.

But when you keep asking what would happen next, you realize the deeper fear isn't starting over.

It's losing the professional identity you've spent 25 years building.

That deserves your attention.

You can't work through a fear you haven't actually identified.

Stop Asking How to Guarantee Success

There's another question I think keeps us stuck:

How do I know this will work?

You don't.

There are very few interesting things in life that come with that guarantee.

So try replacing it with:

If it doesn't work, could I handle what happens next?

Could you change direction?

Could you earn the money back?

Could you find another job?

Could you learn from it?

Could you try a smaller version?

Could you survive someone thinking your idea was ridiculous?

Could you recover?

This doesn't eliminate risk.

It puts risk in perspective.

Sometimes confidence doesn't come from believing everything will work out exactly as planned.

It comes from realizing you trust yourself to respond if it doesn't.

Check the Evidence

When you've been telling yourself something for long enough, it starts to sound like a fact.

"I'm too old."

"I'm not entrepreneurial."

"I'm terrible with technology."

"I don't have the right connections."

"I'm not creative."

"I'm not someone who takes risks."

Instead of immediately replacing those thoughts with positive affirmations you don't believe, examine them.

Ask:

What evidence supports this?

Then ask:

What evidence doesn't support it?

Maybe you've never started a business.

But perhaps you've spent 20 years managing budgets, solving problems, negotiating, leading projects, communicating with difficult people, and meeting deadlines.

That counts.

Maybe you've never considered yourself particularly brave.

But perhaps you've moved across the country, raised children, changed careers, navigated loss, handled difficult relationships, or started over before.

That counts too.

Your goal isn't to convince yourself you're capable of absolutely anything.

It's to create a more accurate assessment of what you're bringing with you.

Ask What Would Make It 10% Easier

Once you've identified a real problem, resist the urge to solve the entire thing at once.

Ask:

What would make this 10% easier?

• Maybe you need information.

• Maybe you need to talk to someone who has already done it.

• Maybe you need a class.

• Maybe you need $500, not $30,000, to test a much smaller version.

• Maybe you need two hours a week.

• Maybe you need to stop doing something else.

• Maybe you need your spouse's support.

• Maybe you simply need to find out whether the idea you keep thinking about is actually something you enjoy.

Ten percent doesn't sound dramatic.

That's the point.

You're trying to make the next step easier, not engineer your entire future in one afternoon.

BONUS EXERCISE: What Is Staying Stuck Costing You?

We've spent most of this week talking about the risks of moving forward.

But there's another side of the equation that we don't talk about nearly enough.

There can also be a cost to doing nothing.

This doesn't mean you should pursue every idea. Sometimes deciding not to do something is absolutely the right decision.

But I want you to compare both sides fairly.

Take the possibility you've been thinking about and ask yourself:

If I don't explore this at all, what happens?

Then consider:

Six months from now:
How will I feel if nothing has changed?

One year from now:
Will I still be thinking about this?

Three years from now:
What might I wish I had at least tried?

Then turn it around.

What might I gain simply by exploring it?

• Maybe you gain a skill.

• Maybe you meet someone.

• Maybe you discover you don't actually want it.

• That's valuable information too.

• Maybe one idea leads to another.

• Maybe you surprise yourself.

• Maybe nothing dramatic happens, but you stop wondering.

We're usually very good at calculating the potential cost of trying.

• Money.

• Time.

• Embarrassment.

• Failure.

• Discomfort.

• Don't forget to calculate the potential cost of never finding out.

You Don't Have to Eliminate Every Obstacle

By the end of this week, I don't expect every fear to disappear. I don't expect your schedule to magically open up or your financial constraints to vanish. I definitely don't expect you to feel 100% ready.

The goal is clarity.

• Which obstacles are real?

• Which problems might be solvable?

• Which fears are predicting a future that hasn't happened?

• Which assumptions have you been carrying around for so long that you stopped questioning them?

You don't need to eliminate every obstacle before moving forward. You need to understand which obstacles deserve to influence your decision and which ones don't deserve to make it for you. That brings us to the final week.

• You've looked at where you are.

• You've rediscovered what you want more of.

• You've identified what matters most.

• You've imagined what your next chapter could look like.

• Now you've looked directly at what's been standing in the way.

In Week 6, we're going to take everything you've learned and answer the question we've deliberately avoided rushing into:

What am I actually going to do next?

Not for the next five years.

Not for the rest of your life.

Just next.