Stop Waiting for the "Right Time" to Figure Out What's Next

Editor's Note: This post was originally published in July 2023 and updated in December 2025 with insights specific to entrepreneurs who wait years to figure out what's next with their businesses.

Are you waiting for the "right time" to figure out what's next with your business?

Waiting until you have more money saved. Waiting until the market is better. Waiting until you feel ready. Waiting until you have it all figured out. Waiting until you're absolutely certain.

Here's the truth: that moment never comes.

And while you wait, years pass. You stay stuck in a business that doesn't fit who you are anymore. You fantasise about change but never move toward it. You tell yourself, "maybe next year" — and then the same thoughts are still there five years later.

The "right time" doesn't exist. There's only now, or five years from now, when you wish you'd started today.

What Entrepreneurs Are Really Waiting For

Let's be honest about what you're actually waiting for:

Waiting for certainty. You want to KNOW the decision is right before you make it. You want a guarantee that whatever you choose — staying and redesigning, or exiting strategically — won't be a mistake.

Waiting to feel ready. You think there's a version of you in the future who will have the courage, clarity, and confidence you don't have now. You're waiting to become her before you start.

Waiting for permission. You're waiting for someone — your partner, your team, your accountant, the universe — to tell you it's okay to want something different from what you built.

Waiting for financial perfection. You tell yourself you need six more months of revenue, or need to hit a certain number, or need to have X amount saved before you can even consider making a change.

Waiting for the business to stabilise. There's always something — a launch, a busy season, a team transition, a market shift. You tell yourself you'll figure it out "once things calm down." But they never do.

The problem isn't that you're not ready. It's that you're using "waiting" as a way to avoid making a decision.

Why Entrepreneurs Wait (And Why It Doesn't Work)

You're Waiting for a Guarantee That Doesn't Exist

You want certainty before you decide. You want to KNOW whether staying or leaving is the "right" choice.

But here's what nobody tells you: you won't get certainty until AFTER you make the decision. Clarity comes from taking action, not from waiting.

You can't think your way into confidence. You have to decide your way into it.

You're Waiting to Have It All Figured Out

You think you need a complete plan before you start exploring your options. You think you need to know exactly what you'd do if you left before you can even admit you want to leave.

But that's backwards. You don't need the full plan to start the conversation. You just need to admit where you are now.

You're Waiting for External Permission

You're waiting for your partner to say, "Yes, you should do this." You're waiting for your accountant to tell you it's financially viable. You're waiting for market conditions to be perfect.

But the only permission you need is your own. And you won't give it to yourself while you're waiting for everyone else to go first.

The Cost of Waiting

While you wait for the "right time," here's what's actually happening:

Years pass. You've been stuck in this same place for how long now? Six months? Two years? Five years? That's time you won't get back.

Your resentment grows. The longer you stay without addressing what you want, the more you resent the business, your team, your clients, and yourself.

Decision fatigue sets in. You've thought about this so many times that you're exhausted from the loop. And still no closer to clarity.

Opportunities disappear. The longer you wait, the fewer options you have. Market conditions change. Your energy decreases. Exits become harder.

You lose trust in yourself. Every time you tell yourself, "I'll figure this out soon", and don't, you erode your confidence in your own ability to make decisions.

The "right time" isn't coming. It's already here. You're just not seeing it.

What "Stop Waiting" Actually Means

Stopping the waiting doesn't mean:

❌ Making a rash decision tomorrow

❌ Quitting your business impulsively

❌ Having it all figured out before you start

❌ Being 100% certain before you move forward

Stopping the waiting means:

✅ Getting honest about where you are NOW

✅ Starting the conversation about what you actually want

✅ Exploring your options (stay and redesign, or exit strategically)

✅ Making decisions from clarity, not from avoidance

✅ Moving forward even when you don't have all the answers yet

You don't need to have it figured out. You just need to stop pretending you don't know something's off.

How to Stop Waiting and Start Getting Clear

1. Admit Where You Actually Are

Stop sugarcoating it. Stop telling yourself "it's fine" or "I just need a holiday" or "maybe next quarter."

Get honest: Do you want to be doing this in 10 years? If the answer is anything other than "yes," then waiting isn't solving the problem.

This is exactly what we explore in the Redesign Programme — getting brutally honest about where you are so you can figure out what's next.

2. Stop Waiting for Certainty Before You Explore

You don't need to know the answer before you start the conversation. In fact, you CAN'T know the answer until you explore it.

Book a free clarity call. Spend 50 minutes getting honest about what's really going on. You'll walk away knowing whether this is temporary burnout or something deeper — and whether coaching could help you figure out what's next.

You don't need to commit to anything. You just need to stop avoiding the conversation.

3. Challenge Your "Waiting For" Stories

Every time you catch yourself thinking "I'll figure this out when..." ask yourself:

What am I really waiting for? Certainty? Permission? The perfect plan?

Will that thing ever actually arrive? Or am I using it as an excuse to stay stuck?

What would become possible if I started exploring NOW instead of waiting?

If you struggle with this alone, the Redesign Programme gives you a thinking partner who helps you see what you can't see when you're inside your own head.

4. Start Small, But Start Now

You don't have to make the big decision today. But you can:

• Admit how you really feel (to yourself, or to a coach)

• Book a clarity call to talk it through

• Start exploring what you actually want (not what you think you should want)

• Map out your options without committing to any of them yet

Small steps forward beat years of waiting every single time.

Real Talk: When Entrepreneurs Finally Stop Waiting

I've worked with entrepreneurs who waited years to have the conversation they needed to have. And when they finally stopped waiting and started exploring, here's what happened:

• They got clarity faster than they expected. Once they stopped avoiding the conversation, the answer often became obvious within weeks.

• They realised they'd been gaslighting themselves. They'd convinced themselves they "should" stay, when really they'd outgrown the business years ago.

• Some stayed and redesigned their role. They realised they didn't need to leave — they just needed a completely different relationship with their business.

• Some transitioned out strategically. They discovered that staying wasn't serving anyone, and they built a clear exit plan.

• But all of them said the same thing: "I wish I'd done this three years ago."

Don't be the person who looks back in five years and says the same thing.

The Difference Between Waiting and Wisdom

There's a difference between:

• Waiting because you're scared (staying stuck for years)

• Taking time to explore thoughtfully (actively working toward clarity)

Waiting = avoiding the conversation, hoping the feeling goes away, staying in limbo indefinitely

Thoughtful exploration = getting support, mapping out options, actively working toward a decision

One keeps you stuck. The other moves you forward.

The Redesign Programme helps you move from waiting to exploring — so you can make a decision you feel confident in, instead of staying stuck in indecision for years.

You Don't Need Permission to Want Something Different

You've been waiting for someone to tell you it's okay to want something different from what you built.

Here's your permission: You're allowed to want what you want.

You're allowed to have built something successful AND want something different now.

You're allowed to explore whether staying or leaving is right for you.

You're allowed to get support in figuring it out.

You're allowed to stop waiting.

Stop Waiting. Start Exploring.

The "right time" isn't coming. There's only now, or five years from now, when you wish you'd started today.

Book a free 50-minute clarity call. No sales pitch. No pressure. Just an honest conversation about where you are and what's next.

Or if you're ready to stop waiting and start getting clear, learn more about the Redesign Programme — the 6-month coaching journey for entrepreneurs who've built something successful and need to figure out what comes next.

The question isn't whether you'll eventually figure this out. The question is: will you start now, or in five years when you wish you'd started today?

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