The Ultimate Guide to Working At Home In Your Underwear

Three No-Nonsense Productivity Tips

So there I was, sitting in my underwear, feeling like a complete fool.

No, this isn’t the start of some cheesy movie. It’s the result of an experiment I tried during the early days of my entrepreneurial journey, when working from home was my only option.

I saw tons of Facebook ads promising, “Make six figures working from home in your underwear! Buy my course so I can show you how!”

So, like any open-minded novice entrepreneur, I bought into the hype and tried it. (Not buying their courses. I just tried working from home in nothing but my skivvies.)

The problem is, it didn’t work. I got less done, and felt more ridiculous.

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Why Your Work-From-Home Attire Matters

The promise that we can make oodles of money online in our underwear feels alluring. But it doesn’t work in practice. It turns out, what we wear matters more than we think.

Appropriate attire tells your mind, “It’s work time.” When we put on football pads and a helmet, we expect to play football. When we put on nice pants and a collared shirt or blouse, we expect to do business.

Changing context affects our psychology, more than we know. Human beings are not good at switching contexts. I’m sorry (not sorry) to turn to  “hard science” here, but we are wired for context

Doing the same thing, at the same time, in the same place, boosts your brain’s processing speed like none other. It’s like the “muscle memory” you developed when you learned to ride a bike as a child.

This is one reason professional athletes have pre-game rituals. More specifically, it’s why baseball players have their pre-batting rituals. It simply sets their brain in the right mode.

Ichiro Suzuki pointed his bat at the pitcher and adjusted his sleeve. Nomar Garciapara unstrapped and restrapped his gloves, and tapped his helmet. I put on business casual before a sales call. It just works.

Discipline will take you from ordinary to extraordinary. Check out this podcast with former Navy SEAL Brad McLeod to learn more!

How To Sober Up Your Productivity

The key to success isn’t to work in exotic places, wearing unusual clothes. Do you think Tom Brady just played in his 10th Super Bowl because he’s wearing a Tampa Bay uniform, instead of a New England one?

The trick is to do what Brady does whether he’s in uniform or not – develop a consistent context for work, and psychologically prime yourself for success. Here are a few tips to get started.

  1. Get Up At a Normal Time

When the pandemic hit, it suddenly became easy to sleep in later than usual. People lost commutes, and the need for proper workplace grooming.

I saw plenty of tweets saying something like, “I just woke minutes before my first Zoom call!” And then there are memes with the man who looks professional (from the neck up) on screen, while wearing no pants off-screen.

I chuckle when I see them, as you do. But the odds are that person isn’t going to build a thriving, seven-figure business anytime soon. 

I’m not trying to sound like a crotchety curmudgeon here; I want to offer best practices to see you achieve your dream. Dressing appropriately for business is just one of those things.

So, treat your workdays like … workdays! Act as though nothing’s changed over the last year. With so many of us working from home, we need structure more than ever.

Get up at the same time every workday. This will pre-program your brain to hit the ground running.

  1. Create a Dedicated Workspace

This tip refers to the earlier one about context. Your brain prefers to do the same thing at the same time, and the same place. Entrepreneurs thrive on this exotic thing called structure.

When you do this, your mind will develop shortcuts that make your thinking faster and clearer, even if you’re not consciously aware of it. Over time, this becomes a way of “automating” yourself, just like with any other activity.

If you can, invest in a nice desk with good lighting, and only work in that space. When work is done, move away from that space. That way, when you walk up to the desk in the morning, you’re in “go” mode every time.

Wear Nice Clothes… Even On The Phone

Something I’ve noticed in the past few months is that I actually dress nicer when I can’t be seen.

During our live streams at Offline Sharks, I tend to dress casual, to connect with the audience. It's a style that conveys my personality.

However, when I hop on a sales call, teach a voice-only webinar, or even just need to bust out a ton of work… I dress up. This puts me in the zone, just like a uniform does for a soldier.

It makes sense, too. Think about it: Would you rather go on a sales call with a Fortune 500 CEO dressed in your pajamas, or your Sunday best? How do you think those outfits would affect your confidence?

If you’ve been working in your sweatpants, or even less than your sweatpants for the length of the pandemic, then it’s time to get back to normal. I’m all about progress, but this is one tradition we need to recover.

Tomorrow morning, get up early. Step into your dedicated workspace rocking business casual. And watch your productivity soar.

For more secrets that the so-called gurus won’t tell you about making seven figures online, check out my podcast!

About the Author
Tom is the host of What's the Secret podcast and co-founder of Offlinesharks.com

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