Yesterday morning, I was trying to decide whether to put a paywall on a Substack article.
That was it. One article, one paywall. A decision that should have taken me around 3 seconds.
Several hours later, I’d mentally created a new publication, reconsidered my entire paid subscription model, reorganised my digital-product vault, planned a future workshop, questioned whether I should build a new brand, wondered how it might connect to my future books, and briefly contemplated my whole life’s choices.
All while reading an article by a popular male creator telling me that success is simple.
Marvellous.
By the end of all this mental self-worth juggling, I hadn’t just lost sight of my original decision. I’d started questioning whether there was any point writing at all.
This is something I’ve noticed in myself over the last few years, and the more I speak to other women of a certain age, the more I see it everywhere.
We have ambition. Buckets of it.
We want to write books, start businesses, travel, make more money, get healthier, create meaningful work, become visible again and do something with all the experience we’ve gathered over the last five decades.
But instead of just choosing and making the next move, we second guess ourselves and try to design the entire future.
Then we become so overwhelmed by the complexity of everything we might do that we struggle to do the one thing sitting directly in front of us.
Ambition Isn’t Always Loud
When we picture an ambitious person, we often imagine someone striding confidently towards a clearly defined goal, making decisive moves and telling anyone who will listen where they’re heading.
I think a lot of women experience ambition differently.
We tangle it up with responsibility, self-doubt, other people’s expectations and the desire to make the right decision for everyone involved.
We don’t simply think, “I want to write a book,” and then go write the thing.
We think about the subject, the audience, the title, the publishing model, whether it fits our existing brand, how we’ll promote it, what people will think, whether we’re qualified, whether it could become a series, whether we should build a course around it and whether anyone will still be reading books by the time we finally finish the bloody thing.
The original desire becomes buried beneath forty-seven unanswered questions.
From the outside, this looks like a lack of confidence, discipline or commitment.
And maybe it is all of those things, but more often than not, it’s actually just the fear of getting it wrong.
Strategy = Clarity (Ummm…)
If we research enough, plan far enough ahead and account for every possible outcome, perhaps we can avoid wasting time, losing money or looking foolish.
This becomes particularly seductive after 50 because we’re increasingly aware that time matters.
We don’t want to spend three years building the wrong business, or write a book nobody buys, or launch something, change our minds six months later and hear someone say, “I knew that wouldn’t work.”
We want our next move to count, so we place it under so much pressure that moving becomes almost impossible.
I recognise this in myself.
I currently have 3,000 boxes of Travel Challenge Cards to sell. That is the job directly in front of me.
At the same time, I can see possibilities everywhere. Books I want to write, ecommerce brands I could create, a bigger movement for women over 50, journals, card decks and a purpose-led business that could support communities around the world.
I’m excited by all of it, but excitement quickly turns into complexity when I start trying to make every future possibility fit into one perfect master plan.
Then I’m standing at the bottom of an imaginary staircase, worrying about the design of the fiftieth step while repeatedly tripping over the first one.
The Audacity of Keeping It Simple
There’s audacity in deciding that your idea is good enough, your experience valuable enough and your message worth repeating without constantly questioning whether you should be doing something else.
And dare I say it, men seem better at this than women.
I realise that’s a sweeping generalisation, and there are obviously plenty of overthinking men and wonderfully decisive women.
But I’ve noticed that many successful male creators are willing to simplify their work almost ruthlessly.
They choose one subject, repeat the same core ideas, make bold statements, sell something and keep going.
Meanwhile, we’re still wondering whether our message is inclusive enough, nuanced enough, useful enough, original enough and perfectly aligned with everything we may want to create between now and 2032.
We care deeply about getting things right. We consider context, consequences and other people. Those are strengths, but they’re also a subtle form of procrastination when every small decision is forced to carry the weight of our entire future.
IMHO, men are also often more comfortable assuming their ideas deserve attention.
Women tend to gather more qualifications, do more research and wait until they can defend every sentence in a court of law before confidently sharing an opinion online.
Then a man with half the experience publishes his version, calls it “The Only Strategy You’ll Ever Need” and sells a million copies.
I’m exaggerating, but only slightly.
Complexity Is a Great Hiding Place
There’s another reason we do this.
Planning makes us feel productive without us having to face the possibility of rejection.
As long as I’m working on the strategy for my book, nobody can refuse to buy it.
As long as I’m refining the concept for a new product, it cannot fail.
As long as I’m deciding whether my article should be free or paid, I don’t have to publish it and discover how many people really care.
Complexity protects the dream from reality.
But reality is the only thing that can give us the information we need!
No amount of thinking will tell us whether our concepts resonate. Whether our ideas could become products, books or businesses.
We have to start, create, share and notice what happens.
Action = Clarity
We all know this one by now right?
You do something, no matter how small. You receive information and you adjust your course based on what works and what doesn’t.
We do it so naturally in life, and yet when it comes to growing a business or an online presence we expect ourselves to be instant strategic experts.
And if we’re not, surely we’re behind the eight ball.
This is simply not the case.
We don’t have to know whether an idea will become a book before writing the first essay.
We don’t have to decide whether a business will become a global brand before selling the first product.
We don’t have to understand exactly who we’re becoming before taking one step away from a life that no longer fits.
And we don’t need to make every idea work.
Some will go nowhere. Some will lead somewhere you never expected. A few may become far bigger than imagined, but we’ll never discover which ones if we insist on seeing the whole staircase before lifting our foot.
Throw Out the Crystal Ball
Women over 50 don’t need a lecture about thinking bigger.
Many of us are already thinking so big that we’ve created seventeen possible futures and a colour-coded spreadsheet for each one.
Perhaps the braver move is to make things smaller.
Choose the idea that matters today, and give it enough time to show you what it could become.
Let it be imperfect, incomplete and unrelated to the empire you may or may not build five years from now.
My current job is to sell my Travel Challenge Cards, keep writing and allow the strongest ideas to earn their way into my future.
I don’t need to build every version of that future today.
Neither do you.
Your ambition doesn’t need another strategy, another spreadsheet or another six hours disappearing down a research rabbit hole.
It needs you to stop staring into an imaginary crystal ball and just and take the first step.
Ready to Stop Overthinking and Get Started?
I wrote this article because I’m spectacularly good at telling myself to stop overthinking, and considerably less good at actually doing it. 😂
So I created something to help.
For paid subscribers, I’ve turned the idea behind this article into The BOLD Action System & 90 Day Journal.
A simple four-step framework for choosing one idea, giving it a proper 90-day shot and stopping yourself from reopening the decision every time another shiny possibility wanders past.
B — Back one idea
Choose something worth exploring without needing to know whether it’s the right thing.
O — Only ninety days
Give it enough time to find out what happens without turning it into a lifetime commitment.
L — Lock it in
Park the other possibilities and stop making the same decision over and over again.
D — Do the thing
Take action, get real information back and adjust from there.
It comes with a printable BOLD Commitment Sheet & 90 Day Tracking Journal, so you can choose your idea, set your 90-day window, decide what you’ll do first, track your progress, and safely park all your other brilliant ideas until review day.
Download The BOLD Action System + Commitment Sheet
🎒 This download is for paid subscribers
Paid subscribers get every downloadable resource I create, plus full access to The Backpack, my growing library of courses, guides, workbooks and tools for building more freedom, travelling more and making the most of life after 50.
Inside you’ll find:
All subscriber-only downloads and resources
My courses and guides on funding your freedom and building portable income
Resources for becoming a nomad and travelling smarter
New tools, guides and resources added regularly
Become a paid subscriber to download The Bold Action System and get instant access to everything in The Backpack.
