3 Huge Mistakes Solopreneurs Over 50 Make

How to succeed faster on your solopreneurship journey

Hi, wise adventurer!

Success is never straightforward.

I made many mistakes on my solopreneurship journey. It’s part of the process.

When I work with some solopreneurs, they make exactly the same mistakes. These mistakes are predictable and avoidable, and I will show you exactly how to skip them.

Our greatest strengths - decades of experience, attention to detail, and high standards - can sometimes become our biggest hurdles in the digital world.

We tend to overthink, over-plan, and overcomplicate things that could be simple.

But here's the truth: Your experience is an advantage, not a liability. You don't need to master every new digital tool or spend months perfecting your offer. You just need to avoid these three crucial mistakes that I see solopreneurs over 50 make repeatedly.

In this post, I'll show you exactly what these mistakes are, why they happen, and, most importantly - how to avoid them so you can build your online business faster and with less stress.

Ready to learn from others' mistakes instead of making them yourself?

Let's dive in.

Image by the author using Canva

Not building your email list

Everyone focuses on creating content and driving traffic, but they do not catch the email addresses and get them on an email list.

Huge mistake! Why? Because the email list is your most valuable business asset.

You own an email list, have control over communication with your audience, and make about 90 % of your income from it.

Even with millions of followers on social media, you can lose them overnight. Only a tiny percentage of your followers see your content. The simple truth is that you have no control over your business without an email list.

So stop trying to be popular and start building your business foundation. Likes are not cash, and only monetizing your knowledge will allow you to gain freedom.

Whether you sell an information product or are in e-commerce doesn't matter. Regardless of your niche, you must get people from traffic (whether organic or paid) to your email list.

And once you have an email list, write a newsletter. The worst thing is to build an email list without any communication. But it’s not about just sending offers every day.

You must educate, solve problems, and entertain your audience.

Building an email list on Substack is much easier than building one on the other platforms, as you don't need a lead magnet. The largest factors in growth are:

• writing Notes

• engaging with other creators (likes, comments, shares, and messaging)

I wrote the exact strategy for growing your Substack email list here.

Success Strategy

• Consistent engagement

• Understanding Substack's analytics

• Using opportunities for collaborations

• Tracking what works for your audience

• Becoming familiar with all features in the Substack community

Taking too long to launch your first offer

I get it - you have so much experience, but you are not sure how to package it.

That is completely normal. Most people wait for too long to launch their first offer. They go into analysis paralysis. And they spent too much time and effort on non-important matters.

Why We Delay (And Why It Hurts Us)

The reasons for delay often run deeper than simple procrastination. For solopreneurs over 50, these delays typically stem from:

Perfectionism Born from Experience After decades of professional experience, we've developed high standards. While this attention to detail served us well in our careers, it can become a liability in the fast-moving digital world.

Your first offer doesn't need to capture all your expertise – it just needs to solve one specific problem well.

Fear of Digital Judgment Many of us didn't grow up with social media and online business. The fear of public criticism or digital "permanence" can feel overwhelming.

But here's the truth: most successful online entrepreneurs look back at their first offers with a mixture of embarrassment and pride. It's part of the journey.

The "More Research" Trap "Just one more course." "Just a bit more preparation." Sound familiar? While continuous learning is valuable, avoiding launching can become a comfortable excuse.

The real learning begins when you put your offer out into the world.

The Real Cost of Waiting

Let's talk numbers. If you plan to offer a modest $97 mini-course and delay launching for six months, that's not just six months of lost income. Here's what you're really losing:

• Potential Revenue: $2,910 (assuming just 5 sales per month)

• Market Feedback: 30 clients who could help shape your future offers

• Momentum: 6 months of building confidence and credibility

• Learning Opportunities: Countless insights about what your market actually wants

Your "Good Enough to Launch" Checklist

Instead of aiming for perfection, aim for "good enough to launch." Here's your minimalist launch checklist:

• One Clear Problem: Your offer solves one specific pain point

• Basic Solution Framework: Your step-by-step approach outlined

• Simple Delivery Method: This could be as basic as Zoom calls and PDF worksheets

• Clear Promise: What specific outcome can clients expect?

• Basic Sales Page: Just the essential information

• Price Point: Chosen and stated clearly

• Payment Method: Set up and tested

• Delivery System: Ready to welcome first clients

Your Permission Slip

Consider this your official permission slip to launch before you feel ready. Your decades of experience mean you already have valuable knowledge to share. Your first offer won't be your best offer – and that's exactly as it should be.

Remember that every day you wait is a day someone who needs your expertise is struggling without it.

They don't need your perfect solution.

They need your help now.

Action Steps

1. Take out your calendar right now

2. Block out two weeks for your launch

3. Write down your "good enough" specifications

4. Tell one person about your launch date

5. Start with Day 1 of the launch plan tomorrow

The best time to launch was six months ago. The second best time is now.

Your experience, even imperfectly packaged, is worth more to your ideal clients than your perfected offer that never sees the light of day.

Success Strategy

• Focus on solving one problem well

• Keep your first offer simple

• Set a firm launch date

• Get feedback from actual clients

• Improve based on real experience

Overcomplicating Tech Setup Instead of Starting Simple

One of the biggest roadblocks for solopreneurs over 50 is getting tangled up in technology. I've seen countless aspiring business owners spend months (and thousands of dollars) setting up complex systems before making their first dollars.

Let's break down how to avoid this common trap.

The Technology Overwhelm Spiral

Here's a familiar scenario: You start researching what you need for your online business, and suddenly, you're drowning in options:

• "You need a CRM system!"

• "Set up automated webinar funnels!"

• "Install this course platform!"

• "Get these five automation tools!"

• "Don't forget about project management software!"

Before you know it, you spend more time learning tools than serving clients. This is especially frustrating for our generation, who often prefer focusing on substance over digital bells and whistles.

The Real Truth About Tech Needs

Here's what you actually need to start making money online:

1. A way to communicate with potential clients

2. A way to deliver your service

3. A way to accept payment

That's it. Everything else is optional.

Your Minimalist Tech Stack to Start

Essential Tools (Start Here):

• Email Capturing Platform: You're already on Substack, so that's your newsletter platform sorted.

• Calendar: Google Calendar or Apple Calendar for scheduling

• Payment Processing: PayPal or Stripe

• Video Calls: Zoom (free version to start)

• Document Creation: Google Docs, Microsoft Word or Notion

Success Strategy

• Start with minimal tools

• Add technology only when profitable

• Focus on serving clients first

• Upgrade when you have proof of concept

• Keep your systems simple

Simplicity always wins.

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👉 Tell me in the comments: What mistakes did you make on your solopreneurship journey?

P.S.

Found this helpful?

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