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How Can I Make Money Online in Midlife? Seven Challenges and Their Solutions

Are you finding yourself wondering, “How can I make money online?” — and you’re in mid-career or beyond?

Great news: you bring so much to the table it’s ridiculous

You’re smart. You know yourself and your strengths. You’re resilient. 

Since 2012, I’ve coached online business owners in our age group.

We’re a powerful group. But that doesn’t mean making money online comes easy for us.

“How can I make money online?” Your midlife challenges are unique

Based on my experience as a business coach, I’m going to take a guess here:

  • You’ve followed all the online advice you can find. 
  • You’ve watched dozens of webinars, hundreds of videos, and read so many blog posts, you’ve lost track.
  • You’ve taken copious notes. You know what you need to do. 

It’s possible that despite all of this, you’re here reading an article about how to make money online in midlife because, well … you haven’t managed to do it so far.

You’re not alone. 

There are seven challenges that hold us back when we’re trying to earn revenue online. I’m going to share the challenges and their solutions in this article.

I’ll examine each stumbling block in detail here in upcoming articles.

Challenge #1: You think your email list is too small

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You haven’t tried to make money online yet, because you keep hearing “you need a bigger email list.”

It’s true, an email list of at least a few hundred people is helpful — but it’s not a requirement.

One massive advantage of building an online business in midlife is your network.

Think about your professional network — the one you didn’t have in the early years of your career. 

You have connections on social media platforms. You know people, and people know you and your work.

That said, it is important to begin growing your email list as soon as you can.

List growth takes time. When you create a lead magnet, your list can grow in the background while you develop an online offer that will generate revenue.

Resource: The Best Lead Magnet Ideas to Build an Email List of People Who Can’t Wait to Work with You

Challenge #2: Your mind is getting in the way

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You may think that success or failure depends on luck, hard work, or whatever is happening in the zeitgeist at the moment.

It’s not true.

You know what’s really driving your success?

That beautiful brain of yours. 

Your thinking can be your biggest asset or your biggest stumbling block. 

If you are:

  • Thinking your idea has to be perfect
  • Thinking someone else has offered your solution and you’re too late
  • Thinking you need to be younger, more tech-savvy, more experienced … more anything
  • Thinking you’re not smart enough, charismatic enough, or outgoing enough

… your beautiful, frightened brain is holding you back.

Unblock your thinking and open the road to success.

Resource: Is Your Mindset Keeping You From Reaching Your Dream?

Challenge #3: Your offer is super boring

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It’s crowded here on the internet. If you want your offer to stand out, you’ve got to invest time and effort into branding it to be unforgettable.

The best online offers for people in midlife:

  • Combine your unique values and strengths — developed over a lifetime
  • Charge a premium for the powerful transformation they deliver
  • Have a unique name, tagline, visual brand
  • Are presented with a framework so they’re easy to explain and remember

If you’re in mid-career and beyond, start by making sure your offer delivers true transformation — not just information.

Make money online in midlife with an offer that changes lives — then do the work to make it memorable. 

Resource: The Offer Accelerator with Pamela Wilson

Challenge #4: You assume you know what your audience needs

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The curse of knowledge isn’t a myth — it’s a real problem that impacts your ability to make money online.

Here’s how:

  • You think you know what your future customers need and you don’t test your theories
  • You create a complicated delivery process that does nothing to improve results
  • You pay thousands of dollars for sophisticated tech that you’re not ready for

When you’re in mid-career and beyond, you’ve developed deep expertise. You have every right to feel proud of that!

But … you must humble yourself about the process of conveying your expertise to others. Skilled adult educators make it look easy. It’s not.

Before you pour time and effort into fancy tech and elaborate solutions, test a simple delivery version first. 

Resource: Minimum Viable Product Examples: Build the Core of Your Online Business This Month

Challenge #5: Your promotions are haphazard

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Once you have a proven offer to sell, you can use it to create consistent cash flow in your business.

But for that to happen, you have to have a plan for how you’ll promote your offer.

If you aren’t making money online, these are the promotion mistakes you might be making:

  • You’re not using a calendar to plan your promotions in advance
  • You don’t know how to harness all your platforms — social media, your website, your email marketing — to promote your offer
  • You aren’t using pricing strategically to motivate prospects to take action

Promotions work best when you go into them with a solid, strategic plan of action. 

Your promotions plan will make the difference between an offer that withers and dies or makes consistent revenue and helps your business grow.

Resource: The 3 Stages of a Stress-Free First-Time Product Launch Plan

Challenge #6: You don’t have systems in place

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Creating systems for all your business tasks may feel like overkill at first. When you’ve only got to remember a handful of things, you can easily keep them in your own brain and do them consistently.

My friend, in an online business, that stage lasts about three months.

Very quickly, you’ll find that you’re juggling:

  • Passwords for multiple platforms
  • Software that has quirks and workarounds you need to know
  • Complex tasks that need to be done consistently

Here’s the thing — if you’re starting every task from scratch and relying on memory, you are leaving money and energy on the table.

That’s where Standard Operating Procedures come in.

When you use SOPs — we affectionately refer to them as “how-to” documents around here — your life becomes so much easier.

You’re not starting each task from scratch. You’ve spent time creating a process that follows all the best practices.

You start by following the process yourself. Before long, you may find a smart person you can hand the task off to so you can work on other business-building efforts that need your attention.

Systems fuel growth!

Resource: How to Prioritize Your To-Do List and Make Massive Progress on Your Big Project

Challenge #7: You have no scaling plan

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Making money online doesn’t look like this:

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It’s usually more like this:

how can i make money online graph 2

It’s more likely you’ll see slow, steady growth that plays out over time.

It takes patience and persistence.

Want to speed up the process?

Don’t assume growth will happen on its own. You need to:

  • Decide how you’ll measure growth: Revenue, time, reach?
  • Set a goal for where you want to be and how much time you want to spend getting there
  • Measure your efforts to gauge what’s working

Growth isn’t inevitable — it’s a project, just like everything else in your business. If you want to scale, plan for it.

Resource: Stop Burnout Before It Starts with This Simple Product Strategy that Grows Your Business

Answers to the 7 challenges to making money online in midlife

How to make money online - plan for success

You bring so much to this task, my friend. Let’s harness your powerful life experience and put it to work growing your business.

Answers to your biggest money-making challenges follow:

How can I grow my email list? 

If your email list is small, focus on building a high-converting lead magnet to attract future customers. Get this in place early on so you can focus on the rest of the money-making tasks while your list grows on autopilot.

Does my money mindset matter?

 If your brain is telling you you’re “not enough,” your business will suffer. Prove it wrong by committing to work smart and grow your business day by day.

Why is no one finding my product or service?

If your offer is not getting attention, nail down the transformation you want to deliver and work on describing it so it’s unforgettable.

Why can’t I sell my product or service?

If your audience isn’t responding to your offer, you may have created a solution prematurely. Be brave enough to test a different idea and humble enough to act on the feedback you receive.

How can I make my cash flow more consistent?

If you’re scrambling for cash flow, you may need to sit down and map out a promotions calendar that keeps your revenue on track and your marketing efforts focused.

Why is online business so hard?

If it all seems too hard and time consuming, you may need to put systems in place that make your everyday tasks easier.

How come I can’t earn more money online?

If you’re stuck at your current earnings level and haven’t been able to get beyond it, it’s time to map out your future goals and turn it into a project you work toward every month.

Wondering, “How can I make money online?” Let’s talk.

If you’re in mid-career, we should talk. 

I specialize in helping people like you to make money online. I help people develop online offers that generate consistent revenue with systems and support — so you’ll never ask this question again.

Follow the link below to get the details on my Offer Accelerator program.

It gives you everything you need to work on all of these challenges and more — and you won’t be alone while you do it.

Learn more about it here: The Offer Accelerator with Pamela Wilson

Pamela Wilson

Pamela Wilson is the Chief Marketing Officer at DCS. She’s the creator of the Offer Accelerator Program. Learn more about Pamela’s content marketing books, and read reviews of the tools used to run this site.
Pamela Wilson coaches people in midlife to build profitable online businesses
I’m Pamela Wilson

In 2010, at the age of 45, I started this site and grew it into a business that offers freedom, flexibility — and consistent revenue.


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