Freelance on Upwork After 50: Earn Extra Income Without Quitting Your Job

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Ok, so you're over 50 and you're wondering…

What is the best way for me to start a business?

Or at the very least, follow your wandering eye and just dip your toe in a money pool outside of your main gig.

Well, I have an idea for you, and it started last month with some success I had on a website called Upwork.

Here's what happened:

I lost a few long-time clients and realized I was getting lazy in my prospecting. My income took a hit, and that familiar "oh shit" feeling started creeping in.

So I decided to return to my old hunting grounds, Upwork, to get the client pipeline flowing again.

The results surprised even me.

And then this week I was thinking about my Gen X readers (that's you) and I realized there was a bigger lesson in this exercise.

I'll get to that but first, some numbers…

Upwork Success: Proof It Works

Ok, so here’s what I got in 30 days on Upwork.

• 12 proposals sent

• 8 meetings booked

• 4 clients landed

• $1,602.60 (and counting) in earnings

• 3 more projects pending

Not bad for something I can’t dedicate a ton of time to - because I still have a business to run and I need write blogs like this for you (which is love doing BTW… thank you for reading).

But enough about me, here's what's really interesting for you:

I believe Gen X professionals have a massive advantage on platforms like Upwork that most aren't taking advantage of.

The Upwork Opportunity Many Gen Xers Are Missing

Most of my friends in their late 40s and 50s are stuck in one of two mindsets:

1. "I'll just keep grinding at my current job until retirement" (even if they're miserable)

2. "I need to start a full business to escape" (which feels overwhelming)

But there's a middle path that offers something crucial: low-risk experimentation.

Upwork lets you leverage skills you already have without quitting your job, investing thousands of dollars, or building complicated marketing funnels.

You control your workload—whether it's a side hustle bringing in an extra $1,000/month or a slow transition into full-time freelancing OR starting a small business.

Why Gen X Has an Unfair Advantage on Upwork

Remember that socket pan story I told you a while back? The one where I redesigned a part that saved my company thousands, but only saw a tiny fraction in my paycheck?

That experience taught me something valuable: your skills are worth far more than what most employers pay you for them.

On Upwork, I've found clients are willing to pay premium rates for three things Gen Xers have in abundance:

1. Deep expertise from decades of real-world experience.

2. Reliability and professionalism because we show up on time, meet deadlines.

3. Problem-solving skills that younger freelancers simply haven't developed yet.

4. Bonus: Honestly, we’re just cooler and easier to work with…

Yep, panache! I had to look that up (I’ll take it).

And if you caught it, that “midwestern” reference is tip too. People will pay premium to work with people closer to home.

My AI-Powered Process for Landing Clients

Here's exactly what I did to land those clients:

1. Brain dumped all my experience, skills, past projects, clients, etc. into a document (this becomes your "knowledge base")

2. Built a great template by improving a script I've used since 2013 (when Upwork was called eLance) using ChatGPT

3. Created a custom GPT to help me create proposals on the fly

4. Copy and pasted the job description into the GPT — like magic, it matched and customized relevant skills and testimonials with the request

5. Edited the output (AI is not perfect yet)

6. Pasted the proposal and waited

Side note: I've turned this into a Custom GPT (aka an AI assistant) that makes this whole process even faster. I'm still working out the bugs, but it's pretty handy.

Common Objections (That Are Holding You Back)

I know what you're thinking, because I thought the same things:

• "I don't have time" → You don't need 40 hours a week. I started with 5-10 hours and still saw results. Just one small project a month is a start.

• "I'm too old for this" → Actually, your age and experience are assets. My clients specifically mentioned wanting someone with deep experience, not just technical skills.

• "The competition is too fierce" → Yes, but most freelancers are terrible at positioning themselves. By focusing on results rather than services, you'll stand out.

• "I don't know how to market myself" → You're already doing it at work! Your profile is just your accomplishments with proof. Start there.

The Big Picture: Building Your "Offensive Retirement Portfolio"

Remember when I talked about building an "offensive retirement portfolio" instead of just saving and hoping for the best?

This is exactly what I meant.

I went from making $25/hour as a cubicle employee to earning $93/hour+ as a freelancer. Now I'm doing $10K-$18K monthly through various income streams.

While Upwork is just one platform, it represents something bigger: taking control of your income instead of waiting for someone else to determine your worth.

The best part? You don't have to quit your job tomorrow. You can test the waters while maintaining your security.

Let’s start that test right now…

AI Tip of the Week: Inventory Your Marketable Skills

Not sure what skills to offer on Upwork? Use this AI prompt with ChatGPT or Claude to help you identify your marketable skills:

You are an experienced career coach and freelance consultant specializing in helping professionals identify marketable skills and find high-paying opportunities on Upwork.

Help me create a comprehensive inventory of my marketable skills and match them with in-demand Upwork categories. Include both obvious and non-obvious applications of my experience.

I have [X] years of experience in [industry/role]. Here are my key experiences and skills: [list your experiences]

Please:
1. Create a categorized list of all potential marketable skills
2. Match these skills with specific Upwork categories and job types
3. Suggest 3-5 specific types of projects I could bid on
4. Recommend hourly rate ranges based on my experience level

Just copy, paste, and fill in the brackets with your information. The AI will help you translate your career experience into marketable freelance offerings.

What I got back was eye-opening. The AI spotted connections I hadn't considered.

Oh and your rate will vary. It doesn’t mean that’s what you get but this is just meant to give you an idea. Also, some rates might seem high, but remember - you're not just selling the skill, you're selling years of experience solving real problems.

Try it yourself and let me know what hidden opportunities you discover. Sometimes our most valuable skills are the ones we take for granted.

Question for you...

I have an Upwork guide I created a few years back called "Proposals That Pop". Some of the information is outdated, but I'd be willing to update it with all the fancy new AI stuff if you're interested.

If so, click the link below and let me know.

If I get a taker or two, I'll build it out.

Click Here to Express Interest in "Proposals That Pop"

Music Of The Week

Did you ever go roller-skating back in the day?

This song takes me right back to when I was about 10 or 12.

I remember playing games like limbo or the one where they rolled the big dice and you had to skate to a corner.

Most of all I remember the music and how I felt.

This song was a big one for slow skate. They’d dim the lights, flip on the disco ball and teen hormones would take over (for better or worse).

It is the first time I remember seeing people my age make out. “What the…Are we allowed to do that?!”

I usually go for something more upbeat in these posts but if you’re reading this on a Sunday morning, it works an “Easy like Sunday morning” mellow selection.

Check it out…

What memories do you have with this tune? Hit reply and let me know.

Talk to you then,

Corey