Building a Business at 50+ Without Quitting My Day Job: Week 4 Results

You're not going to believe this...

Lost ANOTHER client this week. Had a couple of sleepless nights if I'm being honest (nothing like staring at the ceiling at 3 AM wondering if you're totally screwing up).

I needed to pump the brakes a bit on building the new business to focus on my day gig. Hard to sleep when you're watching a big chunk of your income disappear.

But here's the thing about building side hustles that nobody talks about...

You HAVE to be flexible. Life happens. Your main business/day gig needs attention. Things come up. And sometimes you have to slow down to speed up later.

The beautiful part? Even losing a few clients in one month hurts, but it doesn't wipe me out. Not even close.

Why? Because these side hustles I've built over the years? They're my safety net. They give me options. When one stream dries up, I've got others to lean on.

(Quick side note: This is exactly why I've been preaching about multiple income streams. It's not just fancy internet entrepreneur talk - it's real-world survival strategy.)

Ok, enough preaching, let's get to some teaching. Here's how the week went and what you can learn from it...

Newsletter Business Week 4 Results

• Income: Still at $0 (keeping it real here)

• Leads: 2 new conversations happening

• Meetings: 2 solid talks (and by solid, I mean people who actually showed up)

• Email List: 13 new signups in the past 10 days from the new lead magnet (small wins, but they count)

• Partnership Opportunities: 1 potential collaboration in the works

Quick side note: You might look at these numbers and think "Geez, Corey, that's not much." And you're right. But remember, this is what building looks like - not the highlight reel you see on social media, but the real, sometimes painful, day-to-day grind.

And besides, I had some good wins this week…

Weekly Wins

Missed my $500 in 30 days goal (oof), BUT I'm still in contention for $500 in 45 days.

Here's why I'm actually excited:

• Got a very promising lead in a real estate related niche - they need someone to build and manage their newsletter. We're talking high-dollar niche territory here, folks. Meeting next week and keeping everything crossed.

• Landed a new Google Ads client (more on that in a bit)

• Booked 4 more meetings for next week - 1 for newsletter stuff and 3 for Google ads

Remember when I said things were slow? Yeah, funny how quickly that can change.

What I Worked On This Week

Had to dial back the newsletter hustle this week (because losing clients has a way of reorganizing your priorities). But here's what I managed to get done:

Daily LinkedIn Grind:

• Kept showing up daily (even when motivation was low)

• Shifting focus to B2B (seems like a better fit)

• Had several solid conversations that could lead somewhere

Documentation & Content Creation:

• Created "Newsletter Jumpstart Guide: How To Get Your First 100 Subscribers"

• Pro tip: Went through my Google Drive and found gold - old client instructions, music marketing lead magnets, stuff I'd forgotten I had

• Repackaged it all with new social media strategies I've learned

• Now when someone asks about getting subscribers, I've got something ready to go (Quick side note #2: Cannot stress enough how valuable documenting your work is - it's like building a content library without realizing it)

Getting Back in the Game:

• Did a full inventory of my skills and experience (sometimes you forget what you know until you write it down)

• Started thinking of ways I can package Google Ads, Newsletter, and AI Marketing knowledge together

• Built a network outreach spreadsheet (friends, old clients, partners, past business contacts)

• Set a goal: 3-5 outreach messages per day (should've been doing this all along, but better late than never)

Back to the Hunting Grounds:

• Jumped back on Upwork (more on this in the Opportunity section)

• Sent 6 proposals

• Booked 4 meetings

• Landed 1 new client for Google Ads business

• New goal: 3-5 proposals daily until I rebuild the client base

AI Work:

• Upgraded my AI prompts (the generic ones weren't cutting it)

• Using AI to help with proposals and outreach messages

• Still tweaking my AI newsletter getting started guide to make it more specific

Sometimes it takes losing something to kick your butt into high gear. This week was definitely one of those times.

What I Learned

Had this eye-opening conversation with a newsletter lead. They straight up told me I wasn't explaining the "financial path" well enough. You know, how you actually go from writing stuff to making money. DOH!

This was great insight and it lead to some more ideas I’m really exited about trying.

Here's what else I figured out:

• Upwork has changed more than my hairline since the 80s. They charge for everything now - sending proposals, turning on your job status, probably breathing soon. But here's the thing: as long as they have qualified clients looking for help, I'll play ball.

• AI is a game-changer for proposals. Trained it on all my past work (seriously, ALL of it - projects, testimonials, the works). Now crafting custom proposals takes minutes instead of hours.

• I can still WIN. Getting a new Google Ads client as fast as I did is big. Huge confidence after getting shut out on the newsletter business for the past 4 week.

Next Week's Focus

Time to get serious about network outreach. Building a spreadsheet of everyone I know - friends, old clients, partners, email lists from past ventures. Goal is to reach out to 3-5 people daily. (Yes, I probably should've been doing this all along. Better late than never, right?)

Also on deck:

• Keep rocking LinkedIn and Upwork (because momentum is everything)

• More documentation when I can (because future me will thank present me)

• Close some of these leads (because my bank account would appreciate it)

Opportunity of the Week: Upwork is Still Gold

Lost a client this week and needed to get moving fast. First stop? Upwork.

Here's my quick results from jumping back in:

• 6 proposals sent

• 4 meetings booked

• 1 new client landed

What's Different Now:

• Paid connects ($0.15-$0.90 per proposal)

• Better client quality (so far anyway)

• Stricter platform rules

(Quick side note 3: One good client covers a year of platform fees. Worth the gamble in my book.)

Quick Hack to Get Started: Want to test if Upwork's worth it for you? Spend 30 minutes doing this:

1. List your skills and past wins

2. Search them on Upwork under "Talent" (see what others charge)

3. Search under "Jobs" (check actual demand)

I made a quick video a while back to walking through the exact process - check it out below 👇

You can also check out my earlier post on how Gen Exers can find their worth on Upwork.

AI Tip of the Week: Create Your Upwork Skills Inventory

Here's an AI prompt I developed this week to help inventory my skills and find matching opportunities on Upwork. Feel free to copy, paste, and modify for your needs:

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

What I got back was eye-opening. The AI spotted connections I hadn't considered - like how my time managing engineering documentation could translate to technical writing gigs, or how coordinating team software transitions could be pitched as change management consulting.

Quick example using my background:

Input: "I spent 17 years as a mechanical draftsman, managed new product development, and helped transition our team from 2D to 3D software."

AI spotted these opportunities:
- Technical documentation ($50-75/hr)
- SOP writing ($45-60/hr)
- CAD project management ($65-85/hr)
- Software implementation consulting ($75-100/hr)

(Side note: The 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.

Music Memory Lane

And now making their second appearance here on Redefining Retirement, Middle age Dad Jam Band (here is their first appearance if you missed it).

This song reminds me of the roller skating rink for some reason.

And, did you know it was a cover song? Who knew.

Check it out…

I’d be lying if I said I wasn’t a little jealous of these guys. Having a talented band to jam with in your garage? Good stuff!

Have a good one,

Corey