Building a Business at 50+ Without Quitting My Day Job: Week 2 Results

Some bad news…

I lost a client this week. Honestly, it stings, especially since they were a good one.

That’s something you probably won’t hear the get-rich-quick gurus admit when talking about building a business in your 50s.

I just want to be straight with you because the truth is it isn't all sunshine, rainbows, and face-melting guitar solos. You'll have bummer days like this.

But because I built my business around multiple income streams, losing one client hurts but doesn't break me.

And, if you ask me, a bad day running a one-person business is WAY better than a good day working at a job I don’t want to be at.

So, enough about me, let's figure out how we can get you another income stream (without having to quit your job and "go all in").

Here’s where I’m at with my new business and how you can apply my lessons to your situation.

Newsletter Business Week 2 Results

Current Stats:

• Income: $0 (but getting close!)

• Zoom Conversations: 2

• Partnership Opportunities: 3

Big Wins:

1. Podcaster reached out after seeing my LinkedIn conversations

2. Found multiple partnership opportunities, including:

   • Bartered services with a coach

   • Started working with a creator (building his newsletter for free)

   • Potential newsletter service partnership

Proof That Just Showing Up Works: It's crazy how opportunities present themselves when you just get involved in a community. Put the right message out there, know your stuff, and start having conversations.

(Did you miss week 1? Tap that 👉️ see why I started building a business at 50).

What I Worked On This Week:

1. Focused on Outbound Marketing

• Shifted from my usual inbound approach (Google Ads guy here!). Inbound is still part of plan just a smaller part for know.

• Why? Faster path to revenue and real-time customer feedback

• Learning "conversational selling" (a fancy way of saying "talk to people about their problems without being pushy")

2. Hired a Coach (By Accident!)

Found him on LinkedIn and worked out a barter deal:

• He teaches me outbound marketing

• I help improve his course

• Steep discount + coaching in exchange for my expertise (win, win)

Why Coaching Matters: Even after years in marketing, I get in my own way. It's like the cobbler's kids having no shoes - when it's your baby, you miss stuff. My coach spotted holes I was blind to (even though I knew better).

What I Learned About Offers

Working with my coach showed me my original offer was too bloated and not focused enough.

Key Insight: put focus on pain points. People respond more to solving immediate problems than to future pleasure. Think bleeding neck versus sore back. If your neck is bleeding, you need help now. But if your back is sore, ehhh, I’ll get to it to it tommorrow.

What's Working Now:

1. Testing Through Action:

• Created a free case study with a creator

• Documenting my entire process in Notion ($)

• Building repeatable systems, I can use to scale, and create courses with.

2. LinkedIn Strategy:

• Daily engagement in relevant conversations

• Focused my posts around my core offer

• Building a presence where potential clients hang out

What I'm Working On Next Week:

1. Content Creation:

• Building 7-14 day social media series

• Focusing on newsletter pain points

• Demonstrating expertise through showing, not telling

2. LinkedIn Engagement:

• Increasing daily conversation time

• Getting my face in front of newsletter-curious people, I can help

• Moving from comments to conversations

3. Process Documentation:

• Creating standard operating procedures

• Building content I can repurpose

• Setting up in case I want to outsource some tasks

💡 Opportunity of the Week: Local Newsletter Business Gold Rush

Between 2005 and 2024:

• 3,200 newspapers closed or merged

• 204 counties became "news deserts."

• 1,562 counties have just one weekly paper

The Opportunity: Start a local newsletter covering:

• Regional sports

• Local news

• Community events

• Basically, anything a newspaper covers

Real Examples:

• The local newsletter “Catskill Crew” makes six figures.

• 6am City is hiring unemployed journalists and is crushing it in local markets across the country.

Those are examples of how far you can take a local newsletter business. You don’t have to hire anyone at first (or ever).

Here’s how….

🤖 AI Tip of the Week

Use this Perplexity.ai ($) prompt to jumpstart your newsletter:

"Give me the news for the past 7 days in [your city, county or state]"

And hell, you don’t even need to do this for local news, you can start a newsletter for an industry your in or hobby you are interested in:

• Job recruiting

• Material Handling

• HR management

• Minnesota Vikings Football

• Underwater basket weaving

• 80’s toy collecting (sing it “monchichi, monchichi, oh so soft and…”) 😉 

• Whatever!

Try this…

"Give me the news for the past 7 days in [your industry or hobby]"

Basically, you are just helping people by saving them time to have to look for the news themselves.

And if you can ad expert insights, unique perspectives and/or just make the news entertaining, even better.

Your Action Steps This Week:

1. Look for one pain point you can solve simply

2. Show up daily where your clients are

3. Document everything you do

Reply with "SIDE GIG" if you want to brainstorm some side business or newsletter ideas.

Next Week Preview:

I'm diving deeper into outbound marketing and testing my new offer.

Stay tuned for more…

• Real conversion numbers

• Actual client feedback

• Complete process breakdowns

Music Memory Lane

Speaking of the news, how about a little Huey Lewis and the News?

I had a hard time picking a song because I like a lot of them. But went with “I Want A New Drug”.

Give it a listen, and when he sings “I Want A New Drug” swap in the word “Job” for “Drug”

Kinda works don’t you think?

Have a good one,

Corey

P.S. Lost a client but gained clarity. Sometimes, setbacks are setups for comebacks. Want more clarity for your future? Reply with “SIDE GIG” and let’s chat.