Why I Never Work in My Pajamas

It’s a cliché.

Everyone talks about how when you finally quit your day job and start working from home, you’ll be able to do all the things you couldn’t do in a regular 9-to-5.

You can wake up whenever you want. You can choose your own business hours. You can eat a healthy lunch instead of relying on fast food. You can cruise through Facebook without an overbearing boss giving you the stink eye as she passes your desk.

And then there’s the big one…you can work in your pajamas!

Seriously, I’ve see hundreds of social media updates, blog posts, and other messages from new entrepreneurs bragging that they’re working in their pajamas. Watch out, we’ve got a badass over here!

“Pajamas are empowering!” they say. Throw away your suits and heels, and pull on your elastic-waist sweatpants and that free T shirt you got when you signed up for a credit card in college.

Who cares what you look like now that you work from home, right?


When I hear about an entrepreneur working in her pajamas (or worse, seeing a photo of her wearing said pajamas—gah!), I just want to shake her by her shoulders and scream, “Girl, what the hell are you doing???”

Many of my clients work from home, and slowly but surely as they start to relax into self-employment, they’ll notice they’re not getting as much done as they had hoped. Some days they don’t cross a single item off their to-do lists.

The same thing happened to me a few years ago when I started my coaching practice. Wearing pajamas and yoga pants just seemed natural since I didn’t need to dress up for an office anymore.

My blazers and trousers hung abandoned in the closet. They were probably mad at me.

After a while, I noticed my self-esteem was nose-diving, and it was getting harder and harder to accomplish anything. Most days I’d watch Star Trek reruns instead of writing blog posts or courting new clients.

I finally got it together and decided that I was going to dress nice even if it was just for me. Because I’m worth it, dammit! I planned my outfits, put on makeup, and blow dried my hair like I had done in my previous corporate career.

It was a miracle! Giving a damn about my appearance breathed new life into my business, and my productivity skyrocketed.

I actually wanted to do my work because I felt capable. If I could look this good while at home, what else could I do?

That’s what most people don’t realize. Wearing your ratty pajamas doesn’t mean you’ve embraced freedom and non-conformity.

It means you’ve given up.

I took my transformation a step further and began conducting my client calls through Skype or Google Hangouts. Now people would see me every day on video, and I had better look like someone who knows what she’s talking about.

I’ll never go back to wearing pajamas while I work, and I sincerely hope you never wear your lounge clothes while creating and growing your business.

You’re better than that. And your customers deserve better too.

Do you wear your pajamas when you work from home?

This post focuses on Step 2 of the Life Editing Process, Delete Bad Influences. For more about life editing and what it can do for you, click here.

The Secret Formula for Unwavering Daily Motivation

You’re not lazy . . . you just lost your mojo! Here’s how to recharge your batteries for the long haul.


  1. Angelique on April 4, 2015 at 11:01 pm

    You’re so right!! If I take my business seriously, I should dress like I take it seriously, even if I’m not going to see anyone and I’m spending the day weaving, embroidering, and sewing. I get so much more done if I’m dressed. If I’m embarassed by the crappy sweats I’m wearing, I definitely won’t feel like putting myself out there, even by computer. The right mindset makes a huge difference!

  2. Gisele Grenier on April 2, 2015 at 10:38 am

    Although I have two jobs… creative designer for corporate clients and creative designer for consumers, I dress myself as if I’m meeting a client. But… what I wear are my nicest jeans and a nice top and jacket. So it’s corporate casual 🙂

  3. Erika on March 30, 2015 at 7:26 pm

    You are so right, as always, Sage! You’re clothes and appearance really effect how you feel and how you approach the tasks at hand. It’s sort of like wearing costumes. That’s how a lot of actors get “into character” is by going through wardrobe and makeup. 🙂

    • Sage Grayson on March 30, 2015 at 7:59 pm

      I never thought of it that way! Startup entrepreneurs definitely have to “fake it ’til they make it” at the beginning, and sometimes that means acting like they’re more advanced than they are. It’s dressing for the job you want, not the job you have, right?

  4. Ashley on March 30, 2015 at 9:55 am

    This is something I really hadn’t thought about but now that you mentioned it, I agree. You should dress to work and be productive not to lounge around or sleep.

    I was wearing workout clothes or jeans and a t-shirt most days. Since I just started incorporating YouTube videos I decided I just need to dress well, do my makeup and my hair; just so I’m ready to go and film or take pictures.


    • Sage Grayson on March 30, 2015 at 8:05 pm

      Good point, Ashley! It’s easier to do your work when you’re dressed, have makeup on, and are ready for anything. There are fewer obstacles slowing you down. Thanks for commenting! 🙂

  5. Shakyra on March 30, 2015 at 7:40 am

    Absolutely agree!
    I’ve tested it my self and the change in mood and productivity is immense! Specially if I’m wearing my work out clothes. It will make me focus on work more so I can soon after go work out.

    • Sage Grayson on March 30, 2015 at 8:07 pm

      That’s a great idea–wear the clothes you need for whatever you’re doing immediately after work (eg, exercising). It’s focusing on the reward so you’ll finish your work faster. Thanks for commenting, Shakyra. 🙂

  6. Francine from Callaloo Soup on March 30, 2015 at 5:41 am

    Yes! I am in total agreement! For me I think it actually started after I had my son. I felt so much more like a capable mommy when I got showered and dressed every morning. And then when I got back into working on my business it carried over. No one ever sees me, but I feel so much more empowered and serious when I get fully dressed in the morning.

    • Sage Grayson on March 30, 2015 at 8:09 pm

      Good point! Big life changes such as becoming a mom or recovering from an illness or injury can make you slide back into lounge clothes. Even moms (especially moms!) deserve to look and feel their best. Thanks for commenting, Francine. 🙂

  7. Pam @ Hodge Podge Moments on March 30, 2015 at 4:11 am

    I love this! I’m definitely going to remember this when I’m working on turning my blog into a business this summer and no longer working as a teacher. Dressing for success is definitely important no matter where you work!

    • Sage Grayson on March 30, 2015 at 8:10 pm

      Yay! I love hearing when someone’s planning on starting a business. Check out my Startup In 60 group program that’s coming out in a month. It’s a time management course for women who want to start businesses. Thanks for commenting, Pam. 🙂