DupƩ Burgess

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Stop trying to plan everything

by Dupe Burgess
Aug 16, 2026
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The best opportunities are often unexpected

Read time: 5 minutes

Some of the biggest changes in my life weren't exactly part of the plan.

I didn't go to medical school expecting to leave medicine.

I didn't move into consulting thinking I'd eventually build a business.

And I definitely didn't start posting on LinkedIn expecting it to lead to some of the opportunities it has.

Looking back, I often spent too much time trying to predict exactly where things will lead. Trying to control things too much, perhaps.

What I now know is that sometimes it's impossible to see or control the route ahead.

But what you can do is consciously make decisions that give you more options later. And I've started to think that actually this is a much more useful way to plan.

 

1. Not every decision needs an obvious return

We're often taught to ask what "return" we'll get from something before we do it. A promotion? A new client? A paid project?

But some of the most useful things I've done had no obvious return at the time. Their value came through later, often in ways I wouldn't have predicted.

I've spoken at events for a lower rate, knowing I'll be in the room with key stakeholders in my industry. I've posted on LinkedIn every day for two years, knowing that opportunity may present itself later.

It's easy to dismiss things, but actually the pay off can come down the line and in bigger ways than anticipated.

Try this: Before dismissing something because there's no immediate payoff, ask whether it could create useful possibilities later.

 

2. Some choices open doors. Others close them

Two opportunities can look equally good on paper but have very different long term consequences.

One might give you a better title or more money today.

Another might expose you to a new industry, teach you something valuable, or introduce you to people you'd never normally meet.

I've become much more interested in the longer term opportunities, and opening doors I wouldn't otherwise have been able to. 

Try this: When weighing up an opportunity, ask: "If I say yes to this, what could become possible later that isn't possible today?"

 

3. You don't need to turn every interest into a plan

I think we're sometimes too quick to create a plan around everything:

- A new interest becomes a side hustle.
- A new skill becomes a business case.
- A conversation needs an outcome or "next step".

But I've definitely learnt that skills and interactions can be valuable without immediately knowing where it's going.

Following something just because it's interesting is a valid approach and can take you into rooms and ideas you couldn't have planned your way into.

Try this: Make time for one thing you're curious about without deciding in advance what it needs to become.

 

4. Optionality only matters if you're willing to use it

Notwthstanding my previous point, there's no point creating options and possibilities if you're too afraid to act on them.

At various points I've had opportunities that didn't fit the plan I had in my head. But some of the best decisions I've made involved changing the plan.

I think that's the real value of optionality:

Not having endless choices, but having enough flexibility to take a different path when a better one comes along.

Try this: Look at something you're currently working towards. Are you committed to the outcome, or just to the plan you originally made?

 

The takeaway

I still think goals and plans are useful.

But increasingly, I don't think the aim is to predict exactly where you'll be in five or ten years.

It's to keep creating enough possibilities that you have choices when the world, your circumstances, or your mind changes.

Sometimes (quite often) the best opportunities are the ones you couldn't have planned for anyway.

Speak soon,

DupƩ

 

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