The 10 Biggest Problems People Face When Starting an Online Business

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If you’ve ever tried to start an online business and then stopped, stalled, or second-guessed yourself....this post will help you understand why.

Most people don’t fail because they’re lazy, unmotivated, or incapable. They get stuck because they run into the same predictable problems that almost no one talks about clearly.

Below are the 10 most common problems people face when trying to start an online business, especially if you’re mid-career, experienced, and have already tried a few things before.

If several of these hit close to home, that’s normal. It's also fixable.

𝟏. 𝑵𝒐𝒕 𝑲𝒏𝒐𝒘𝒊𝒏𝒈 𝑾𝒉𝒂𝒕 𝑩𝒖𝒔𝒊𝒏𝒆𝒔𝒔 𝒕𝒐 𝑺𝒕𝒂𝒓𝒕

This is the #1 problem. And why this community exists.

Too many ideas. Too many opinions. Too many “proven” models online.

So instead of choosing one, people stay stuck choosing none.

The clarity you're searching for comes from filtering down to what actually fits you. Not by adding more options.

2. 𝑶𝒗𝒆𝒓𝒕𝒉𝒊𝒏𝒌𝒊𝒏𝒈 𝑬𝒗𝒆𝒓𝒚 𝑫𝒆𝒄𝒊𝒔𝒊𝒐𝒏

Research feels productive… but it often becomes a hiding place. And if you're not careful, you might never escape.

People get stuck comparing tools, platforms, niches, and business models instead of making progress. Overthinking creates the illusion of safety. It's killing your business dreams.

3. 𝑳𝒐𝒘 𝑪𝒐𝒏𝒇𝒊𝒅𝒆𝒏𝒄𝒆 𝑭𝒓𝒐𝒎 𝑷𝒂𝒔𝒕 𝑭𝒂𝒊𝒍𝒆𝒅 𝑨𝒕𝒕𝒆𝒎𝒑𝒕𝒔

Many people aren’t starting from zero. They’re starting from disappointment.

Previous side hustles that didn’t work leave scars:

“Maybe I’m just not good at this.”

“I should be further along by now.”

That baggage slows everything down.

4. 𝑭𝒆𝒂𝒓 𝒐𝒇 𝑾𝒂𝒔𝒕𝒊𝒏𝒈 𝑴𝒐𝒓𝒆 𝑻𝒊𝒎𝒆

Time hits differently once you’re in your 40s or 50s.

Every new idea feels like a gamble. People worry they don’t have the runway to “figure it out” anymore.

This fear often leads to total paralysis.

5. 𝑭𝒆𝒂𝒓 𝒐𝒇 𝑾𝒂𝒔𝒕𝒊𝒏𝒈 𝑴𝒐𝒏𝒆𝒚 (𝑨𝒈𝒂𝒊𝒏)

We've all bought them...

Courses

Software

Coaching

Tools

Many people have already spent money trying to get something off the ground and didn’t get results. So now every investment feels risky, even when the real issue wasn’t the tool, but the lack of clarity and execution.

6. 𝑵𝒐𝒕 𝑻𝒓𝒖𝒔𝒕𝒊𝒏𝒈 𝑻𝒉𝒆𝒊𝒓 𝑶𝒘𝒏 𝑱𝒖𝒅𝒈𝒎𝒆𝒏𝒕 𝑨𝒏𝒚𝒎𝒐𝒓𝒆

After enough false starts, people stop trusting themselves.

They rely on YouTubers, influencers, or trends to make decisions for them. Those voices don’t know your skills, goals, or constraints. But they know how to distract you.

You get caught in this trap long enough and confidence disappears. Decision-making suffers.

7. 𝑭𝒆𝒆𝒍𝒊𝒏𝒈 𝑩𝒆𝒉𝒊𝒏𝒅 𝑪𝒐𝒎𝒑𝒂𝒓𝒆𝒅 𝒕𝒐 𝒀𝒐𝒖𝒏𝒈𝒆𝒓 𝑪𝒓𝒆𝒂𝒕𝒐𝒓𝒔

AI. Social media. Automation. Tech stacks.

It’s easy to feel like the game favors people who grew up online. This creates a false belief that experience is a disadvantage when in reality, it’s often the missing ingredient. The younger generation would pay for your real life manual of "what not to do".

8. 𝑴𝒆𝒏𝒕𝒂𝒍 𝑬𝒙𝒉𝒂𝒖𝒔𝒕𝒊𝒐𝒏 𝑭𝒓𝒐𝒎 𝑺𝒕𝒂𝒓𝒕𝒊𝒏𝒈 𝑶𝒗𝒆𝒓 𝑹𝒆𝒑𝒆𝒂𝒕𝒆𝒅𝒍𝒚

New idea. New brand. New direction.

Starting over again and again drains energy fast. Eventually, people stop because they’re tired... not because they’re incapable.

Consistency becomes impossible without a clear path forward.

9. 𝑺𝒕𝒓𝒖𝒈𝒈𝒍𝒊𝒏𝒈 𝒕𝒐 𝑺𝒕𝒂𝒚 𝑪𝒐𝒏𝒔𝒊𝒔𝒕𝒆𝒏𝒕

Motivation comes in waves.

Life, work, family, and stress pull attention away, and without structure, momentum fades.

Most people don’t need more discipline. They need simpler execution.

10. 𝑭𝒆𝒆𝒍𝒊𝒏𝒈 𝑨𝒍𝒐𝒏𝒆 𝒊𝒏 𝒕𝒉𝒆 𝑷𝒓𝒐𝒄𝒆𝒔𝒔

Starting an online business can feel isolating.

No coworkers. No boss. No one to sanity-check decisions.

Without feedback or support, doubts get louder and progress slows.