7 Ways to Make Decisions When You’re in Uncharted Territory
Some of the hardest decisions I’ve made haven’t been difficult because I lacked experience.
Learning how to make decisions in uncharted territory isn’t about having all the answers. It’s about knowing how to move forward responsibly when experience alone can’t tell you what happens next.
They were difficult because my experience couldn’t tell me exactly what would happen next.
I’ve changed industries. I’ve stepped into leadership roles where I had a great deal to learn. I’ve built businesses. I’ve closed chapters that were no longer right for me and started new ones without knowing exactly where they would lead.
And I’ve learned something important along the way:
“Experience gives you reference points. It doesn’t always give you a map.” — Donna Moulds
That’s the uncomfortable thing about uncharted territory.
You can be intelligent, experienced, capable and incredibly organised and still not know exactly what to do next.
Perhaps you’re considering changing careers after 50.
Maybe you’re questioning whether the way you’ve worked for the past 20 or 30 years is how you want to work for the next ten.
You might be thinking about studying again, building something of your own, changing the way you live, or simply acknowledging that what once worked for you doesn’t fit anymore.
And suddenly, the person who has spent decades making decisions can find themselves second-guessing everything.
So how do you make decisions when you’ve never been here before?
Why Uncertainty Can Feel So Uncomfortable When You’re Experienced
There’s an interesting contradiction that can happen as we become more experienced.
Experience gives us knowledge, pattern recognition, judgement and perspective. We have more evidence of what we’re capable of.
But experience can also make unfamiliar territory surprisingly uncomfortable.
When you’re accustomed to knowing what you’re doing, becoming a beginner again can feel unsettling.
You may find yourself researching endlessly.
Another podcast. Another article. Another Google search. Another conversation.
Is it too late to change careers?
Should I start something of my own?
What should I do next with my life?
What if I make the wrong decision?
Information is valuable. Research matters.
But eventually you can reach a point where you’re no longer gathering information to make a better decision.
You’re gathering information because you’re hoping it will remove the uncertainty.
And sometimes it can’t.
You Don’t Need Certainty. You Need Enough Information for the Next Decision
I have made decisions in my life where I genuinely did not know how things would turn out.
Some worked extraordinarily well.
Some didn’t.
That’s life.
One of the things I’ve come to understand is that commitment and certainty are not the same thing.
“I didn’t always have certainty. What I had was commitment.” — Donna Moulds
You can do your research, consider the risks, seek advice and make the most responsible decision available to you—and still not know the outcome.
That doesn’t necessarily make it a bad decision.
We sometimes judge our past decisions using information we could only have known afterwards.
But that’s an impossible standard.
A better question is:
Given what I know today, what is the most responsible next decision I can make?
Not the next ten decisions.
Not the complete five-year plan.
The next one.
1. Ask Yourself: If I Did Know, What Would It Look Like?
When someone tells me, “I don’t know what I want,” one of the questions I like to ask is:
If you did know, what would it look like?
Then stay with the question.
Don’t immediately dismiss whatever comes up because it seems unrealistic, inconvenient or different from what you’ve done before.
What would you want your working week to look like?
How much autonomy matters to you?
What kind of work do you want to contribute?
How important is flexibility?
Do you still want to lead?
Do you want to build something?
What do you want to learn?
Where do you want to spend your time?
What do you want less of?
Sometimes “I don’t know” genuinely means we don’t know.
But sometimes it means:
I haven’t given myself permission to seriously consider what I do know.
That’s different.
Need Some Space to Work Out What Comes Next?
Sometimes the difficulty isn’t that you have no options. It’s that there’s so much noise around the decision that you can’t hear your own thinking clearly.
That’s one of the reasons I created the 7 Day Resilience Reset.
Over seven days, I’ll guide you through short videos, reflection and practical exercises designed to help you notice the stories and patterns influencing you, reconnect with what matters now and identify one deliberate step forward.
Seven days. Around 20 minutes a day. One deliberate step at a time.
Explore the 7 Day Resilience Reset →
2. Recognise That Your Decision Criteria May Have Changed
The things that mattered to you at 30 don’t automatically have to determine the decisions you make at 50, 55 or 60.
For many years, success might have meant promotion, salary, title, responsibility, a bigger business, a larger team or being the person everyone could depend on.
Those things aren’t inherently wrong.
But you’re allowed to change.
I am still a driven person. I’m still organised. I still have big goals.
I’m simply driven towards different things now.
Balance matters more to me.
Autonomy matters.
Having greater choice over how I use my time matters.
Continuing to learn matters.
Contribution matters—but I’ve learned that my worth isn’t determined by how much I do for everyone else.
“My drive hasn’t disappeared. What I’m driving towards has changed.” — Donna Moulds
That distinction matters when you’re making decisions in a new chapter.
Don’t automatically use an old definition of success to evaluate a future you’re trying to create differently.
3. Listen to Other People Without Handing Them the Decision
Do something you’ve never done before and there’s a reasonable chance somebody around you will question it.
Are you sure?
Why would you do that?
Is that really sensible?
And sometimes:
Are you okay?
Let them ask.
People generally evaluate unfamiliar decisions through the framework they understand.
If everyone around you has followed a conventional career path, an unconventional one may look risky.
If they’ve always worked for an employer, building something independently may seem strange.
If they’ve valued security above autonomy, your priorities may not make sense to them.
That doesn’t automatically make them wrong.
And it doesn’t make you wrong either.
The mature response isn’t to dismiss everybody as negative.
Ask what they’re actually concerned about.
Is there a legitimate risk you’ve overlooked?
Does your decision financially affect your partner or family?
Are there responsibilities you need to account for?
Does the person questioning you have expertise or experience that could reveal something you haven’t considered?
Listen.
Take useful information seriously.
But remember:
“You can listen to other people’s concerns without giving them ownership of your decision.” — Donna Moulds
You’ve been making decisions your entire adult life.
Some will have worked.
Some won’t have.
And I’m betting you’ve taken responsibility for those too.
You don’t suddenly need unanimous approval because you’re choosing something unfamiliar.
4. Ask What Happens If It Doesn’t Work
This is where I think some conversations about reinvention become irresponsible.
We’re often told:
Take the leap.
Follow your dream.
Just go for it.
Sometimes that’s appropriate.
Sometimes it isn’t.
Learning to make decisions responsibly means considering not only what you could gain, but what you can genuinely afford to risk.
If a decision failing would mean you can’t pay your mortgage, feed your family or meet significant responsibilities, that matters.
Perhaps now isn’t the right time.
Or perhaps the idea is right but the execution needs to change.
Could you start while remaining employed?
Could you study part-time?
Could you test the business before depending on it for income?
Could you have ten conversations with people already doing what you’re considering?
Could you build the skill before making the career change?
Could you run a small experiment before making a permanent decision?
Agency isn’t recklessness.
Sometimes the bravest decision isn’t jumping.
It’s building the bridge first.
5. Stop Treating Every Unsuccessful Outcome as a Personal Failure
This is something I think experienced professionals should consider more often.
Projects fail inside organisations every day.
A new initiative doesn’t achieve the expected result.
A strategy needs changing.
A product doesn’t sell.
A project gets cancelled.
An idea that looked good six months ago no longer makes commercial sense.
We assess the evidence, change direction and continue working.
But when it’s our project, suddenly the language changes.
I failed.
There’s an important difference between:
This didn’t work
and
I am a failure.
I’ve built things that worked and things that didn’t.
I’ve made decisions I’m incredibly proud of and others I would approach differently with what I know now.
I don’t need to rewrite those experiences into successes to extract value from them.
They taught me.
They changed me.
And importantly, they gave me information I didn’t have before.
“Backing yourself doesn’t mean every decision will work. It means trusting yourself enough to own the outcome and make another decision.” — Donna Moulds
That’s resilience.
Not endlessly forcing something to work because you once committed to it.
Sometimes resilience means continuing.
Sometimes it means adjusting.
And sometimes it means having the courage to say, this chapter is finished.
6. Don’t Confuse Today’s Results With Tomorrow’s Possibilities
There’s another trap when we’re building something new.
We look at today’s results and use them as evidence of what’s possible tomorrow.
But new skills take time.
New businesses take time.
New careers take time.
New identities take time.
A lack of immediate results doesn’t automatically mean you’ve made the wrong decision.
Equally, determination doesn’t mean ignoring evidence indefinitely.
The better questions are:
What am I learning?
What evidence am I gathering?
What needs to change?
Are the reasons I started still valid?
Am I prepared to keep doing the work required?
There’s a difference between persistence and stubbornness.
Knowing how to make decisions as new information emerges is part of taking responsibility for the direction you choose.
Agency requires us to know when to keep going, when to adjust and when new information means we need to make another decision.
7. Remember That Not Deciding Is Still a Decision
This becomes increasingly important to me as I get older.
There comes a point when you realise you probably have more years behind you than you have in front of you.
I don’t find that depressing.
In some ways, it makes me braver.
Because the questions change.
Instead of only asking:
What if this doesn’t work?
I also ask:
What happens if I don’t try?
Do I want to spend another five years wondering?
Will staying where I am take me closer to the life I want—or simply keep things familiar?
What exactly am I waiting for?
Time doesn’t mean we should become reckless.
Quite the opposite.
It makes how we use our time increasingly valuable.
“There comes a point when you realise you have more years behind you than in front of you. For me, that hasn’t made life smaller. It’s made me braver about how I use what’s ahead.” — Donna Moulds
You Are Allowed to Enter Territory You Haven’t Navigated Before
There will be times when life puts you in uncharted territory without asking your permission.
There will be other times when you deliberately choose to enter it.
Either way, you don’t need to know everything before you move.
I’ve entered unfamiliar industries, taken on roles where I had a great deal to learn, built businesses, changed direction and continued learning throughout my adult life.
The recurring lesson hasn’t been that I always know what I’m doing.
It’s that I trust my ability to learn what I need to learn.
That is a very different kind of confidence.
It isn’t:
I know this will work.
It’s:
Whatever happens, I trust myself to respond to what I learn.
The Next Responsible Decision
If you’re standing in uncharted territory now, you don’t need someone else to hand you the complete map.
Start with the questions you can answer.
What do I actually want?
If I did know what I wanted, what would it look like?
What matters to me in this chapter?
What am I genuinely risking?
Who else is affected by this decision?
What information am I still missing?
What could I test before making a larger commitment?
What is the next responsible step?
Then take it.
Learn from what happens.
And make the next decision from there.
Because you don’t need a map of the entire territory.
You need enough information to make the next responsible decision.
And if you’ve thoroughly considered what happens if it doesn’t work, perhaps there’s one more question worth giving equal consideration:
“And what if it does work?” — Donna Moulds
You Don’t Have to Work Out Your Entire Future Today
If you’re reading this because something in your life or work no longer feels quite right, you don’t need to have the whole answer before you begin.
But you do need somewhere to start.
I created the 7 Day Resilience Reset for exactly that reason.
It’s a practical, self-guided seven-day experience designed to help you step out of the noise, recognise the stories and patterns influencing where you are now, reconnect with what matters to you and begin creating direction.
Each day includes a short video, reflection and practical exercise. Allow around 20 minutes a day.
This isn’t about somebody else telling you what your next chapter should look like.
It’s about creating the space to hear your own answers—and turning what you discover into one deliberate next step.
Seven days. Around 20 minutes a day. One deliberate step at a time.
Explore the 7 Day Resilience Reset →
Is Your Career Part of the Decision?
Sometimes the uncertainty isn’t about whether something needs to change.
It’s about whether you’re prepared to let your career change with you.
If you’ve spent decades building experience, expertise and a professional identity, the idea of changing direction can feel as though you’re throwing all of that away.
You’re not.
Your experience comes with you.
If you’re questioning whether the next chapter of your working life needs to look different from the last one, read Career Change After 50: Why Starting Again Isn’t Starting From Scratch.
It’s about what happens when you stop looking at change as going back to the beginning and start recognising the experience, capability and resilience you’re bringing with you.