Work from home in your pajamas: the dream, or nightmare?

May 11, 2021

by Kenneth Holland

'There's been this quest to 'work from home in your pajamas' for years. Now that people have to...they're not digging it...'

There’s two sayings on the internet (because…y’know…there’s none of that online)…

‘It’s Not What You Know. It’s Who You Know’


‘All working from home did was get me smelly pajamas’

(The second gets debated...whatever...)

For those who have sought out business freedom there’s been this quest to ‘work from home on your own terms’ … ‘work in your skivvies whenever you want with no alarm clock’.

Let me just give you some Kenster wisdom that might help you:

Successful people don’t work in their pajamas.

Successful people don’t work whenever they want.

Successful people have an alarm clock.

Successful people don’t need an alarm clock.

Working from Home Should Be the OPTION...Not the Goal...

You think the chubby fat guy in his underoos in Mom’s basement who makes millions exists? You know…’Underground secret finally exposed…this guy never comes out of hiding to reveal his secrets blah blah…’!

No. They have an office (that’s above sea level) and they work bloody hard.

I drank that Koolaid for far too long…

…until I started going to events and hung out with real millionaire marketers. I didn’t pester them with inane questions of tactics, new traffic sources and their ‘secrets. I just LISTENED. Even if all they talked about was their lunch or their newest car (which was most of the time).

What are you absorbing?

You might think ‘well, you’re not going to get anything out of that’. There’s something funny about humans. We can absorb a mere ‘vibe’ without ‘learning’ anything.

Like the saying goes: ‘Just being around them made me better’.

And it did. And it DOES.

Oh, and I committed to working my fucking ass off.

Working From Home is Great…When You Don’t

Two interesting things happened when I started working from home:

1. I loved it when I started NOT doing it

2. I stopped wearing pajamas when I realized they made me miserable

Having the OPTION of doing it was all I needed to feel free. And yes, I do work from home. But I became disciplined enough to treat it with not only the commitment it requires, but learned what NOT to do as well. And I leave the house…a lot.

Yes, there are people that do work from home and are successful. But…

a. They are the EXCEPTION
b. They have great family support

Don’t be the exception. The odds are against you.

Even the 'Solopreneur' needs a cheerleader...

One of the worst things that can happen to someone getting in to home-based business (and this goes for telecommuters as well) is having an unsupportive spouse or partner.

I’ve even know people that have built successful business(s) from home where the partner would say ‘great…don’t want to know about the business…just bring in the money.’

Your partner has got be fully invested in your vision.


Being a ‘lone wolf’ is not going to get you far. It’s just not. We are built to interact…to feed off one another.

So, if you do want to work from home…

– Throw the pajamas away

– Go surround yourself with the people you KNOW you need to surround yourself with. And do it a lot.