The Fastest Way to Fund Your Freedom (Even If You’re 60+ and Starting Over)

A smart and simple strategy you can use today to get unstuck and move forward

I received an email this weekend from a lady starting over at age 61.

Mentioning no names, she wrote;

“I’m in dire straits financially. Any suggestions to cut to the chase, stop spinning and make some real money?”

First of all — YES. And you’re not alone.

I hear from so many people in their 50s and 60s who are talented and capable, but stuck.

They’ve got skills and decades of experience, but they don’t know where to start in this noisy online world. And they don’t have time to faff around with funnels or spend months building a blog or audience that might (eventually) pay off.

So let's cut to the chase. If you need money coming in quickly, want to feel more confident, and just need enough space to breathe and figure out your next move, freelancing is the fastest path forward.

And before you roll your eyes, I’m not talking about fighting with AI for copywriting gigs, learning to code, or chasing clients on LinkedIn. I’m talking about starting with what you already know how to do.

Why Freelancing Works (Especially If You’re 50+)

If you’re over 50, you’ve done a lot. You’ve worked in offices, raised kids, navigated relationships, coordinated holidays, planned parties, handled deadlines, and probably been the go-to person for sorting things out when nobody else would.

All of that is useful.

You might not call yourself a “freelancer,” but if you’ve ever:

• Written reports, newsletters, or blog posts

• Planned events or managed diaries

• Helped a friend tidy up their CV or LinkedIn profile

• Made simple graphics for a fundraiser or small business

• Organised a system to keep things running smoothly

Then you have billable skills.

People are looking for reliable, grown-up humans who can get things done without drama. That’s where we shine. We’re not flakey. We don’t ghost clients. And most of us are pretty damn good at figuring things out on the fly.

“But I Don’t Know What I’m Good At!”

If your brain just screamed “I don’t have any useful skills!” — take a breath.

I hear this all the time, especially from my female friends who’ve been juggling life roles without recognising how much value they’ve built up along the way.

Here’s a quick exercise I’ve shared with many friends:

• Write down five things people have paid you for in the past.

• Write down five things people often ask you for help with.

• Write down five things you genuinely enjoy doing that come easily to you.

Somewhere in there is your starting point.

If you're still stuck, scroll through listings on Upwork or Fiverr for ten minutes. You’ll start seeing tasks and think, “Hang on, I could do that.” From virtual assistance to content editing to customer support or slide deck formatting, the scope is broad.

And the bar isn’t as high as you might think. The hardest part is often just showing up and writing a half-decent pitch.

Your 5-Day Freelancer Kickstart

Here's how you could get started and be earning in the next few days:

Day 1 – Pick your starter skill

What could you confidently offer today?

Examples:

• Admin (inbox, calendar, research)

• Writing (bios, emails, blog posts)

• Editing and proofreading

• Event or travel planning

• Canva or PowerPoint formatting

• Customer support

• Social media management

Spend some time browsing jobs and profiles on Upwork & Fiverr for ideas.

Day 2 – Set up your freelance profile

Choose one platform: Upwork, Fiverr, Freelancer, Writers Access etc.

Keep your bio focused but simple:

• Upload a professional photo

• Create a short intro

• Write a clear description of what you do and most importantly how & who you can help

Example:

“I help small business owners write clear, friendly blog posts that sound like a real human wrote them. I’m fast, reliable, and easy to work with.”

Day 3 – Find 5 Easy-Fit Jobs

Browse the listings and start looking for small gigs.

• A $75 blog post here.

• A $50 editing job there.

• Maybe a $200 project for someone who needs help tidying their website copy.

Save five that seem doable.

Focus on what they need, not just what the title says.

Day 4 – Write 5 custom pitches

The reason so many fail on platforms like Upwork is that they write generic, irrelevant pitches.

Create a bespoke and specific pitch. Respond directly to the project that's being advertised and why you have the skills and temperament to do it confidently.

Example:

“Hi Sarah, I’ve read your brief and I’d love to help. I’ve worked on similar pieces for [a travel brand/an art blog/etc.], and I can turn this around within 3 days. Let me know if you’d like a quick sample or want to jump on a call.”

One of the best pitches I ever received included the line;

“Let me do a free sample. If you like it, pay me. If not, no worries.”

He still works with me to this day.

Day 5 – Apply, Respond, and Repeat

Hit send. (Don't start thinking about all the reasons it might not work, back yourself!)

Reply quickly if someone bites and be clear, kind, and easy to work with.

Don’t get any responses? Keep pitching. Don’t give up after five and think ‘oh this isn’t going to work for me.’

You might get a job from one pitch, it may take you 20, or even 50. Keep going! All the naysayers who’ll tell you it’s too competitive online now, or it’s too hard, are simply the ones who gave up too easily.

That’s not you, right? You have more tenacity than that!

Freelancing isn’t magic or overnight riches, but it’s honest work that pays real money and builds your confidence at the same time.

And once you’ve done a couple of jobs, you'll start to get feedback and reviews, which helps you get the next jobs more easily and that's when it starts to snowball.

Freelancing Doesn’t Mean Tech Wizardry

Let's bust that myth right now.

Freelancing does not require coding, complex funnels, or any Silicon Valley sorcery.

In fact, some of the most in-demand freelance gigs are low-tech, high-trust.

Jobs like:

• Customer support (via email or chat)

• Inbox or calendar management

• Proofreading content before it goes live

• Formatting blog posts or ebooks in Google Docs

• Research and spreadsheet work

• Personal assistance for coaches or course creators

• Blog or article writing for small businesses, coaches, or travel sites

• Basic graphic design using Canva (great for social posts, ebooks, or presentations)

• Project support like planning events, research, or outreach

• Client management for small teams who need someone steady in the background

These aren’t high-stakes, high-tech roles. They’re human, task-based, and the kinds of things you’ve probably already done a version of in your life.

How to Earn Your First $1,000

Let’s keep this grounded. You’re not aiming for six figures this week, instead aim for your first $1k and grow from there.

Here’s how that could look:

• 10 x $100 blog post packages

• 4 clients @ $250 for 10 hours of VA support

• 20 hours @ $50/hr editing/proofing

• 10 x $100 Canva slide decks

• 2 x $500 website audits or SEO reviews

That’s your first $1,000. And it’s entirely doable within a few weeks if you’re consistent.

And once you’ve got cash flow coming in, you’ve got breathing room. You can reinvest, save, or start growing something else on the side, like a digital product, a journal, or a simple Substack newsletter like this one.

Freelancing Can Be More Than a Stepping Stone

Some people start freelancing and end up building a business around it. They niche down, hire others and grow their services.

Others keep it light and simple with just a handful of great clients and a bit of extra income each month (that gives them enough to travel the world and work on the go).

You don’t have to scale or go big, but you can if you want to.

And that's what I love about the freelance path. It’s flexible, meets you where you are, and giv you options without locking you into anything.

And it’s one of the most realistic ways to start making money from your laptop quickly, without having to build a whole empire from scratch.

If You’re In A Pinch, Start Here

I know what it’s like to feel out of time, low on options, and buried under advice that only makes things harder, when all you really want is a way to earn real money doing something useful, without sacrificing your dignity or your peace of mind.

Freelancing is the quiet, unfancy, deeply practical answer to that.

It won’t make you rich overnight, but it can make you solvent which gives you space to breathe, think clearly, and make decisions from a place of calm instead of panic.

And from that steadier place, you can start to rebuild, whether that means growing your freelance work, launching something of your own, or simply feeling like yourself again.

You don’t need a master plan. Just a bit of breathing room and the courage to take the next right step.

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