22 Things I Didn’t Know Until I Worked For Myself

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Since leaving my 9 to 5 day job, you can read more about that day (here), I have had to adjust to working from home.  As a result there are certain things that I didn’t realize would happen until I was actually, well, working from home.

Here are a few of them in no specific order:

The week and weekend blur into one – there is no ‘weekend’ or ‘working week’
You forget what day it is because you don’t have the Monday or Friday on/off routine
The dreaded Sunday night back-to-work-in-the-morning feeling disappears
You never really have a day off
You can work in pajamas 
You stop watching the clock waiting for ‘lunch/home time’
It’s a feast or famine income
The UPS and FeDex drivers know you well
The UPS and FeDex drivers are curious to know what you do for a living
Your subway metro card cost drops dramatically
There is no such thing as a public holiday weekend
You understand what ‘hustle’ means
You can work anywhere in the world as long as you have wifi and a laptop
You don’t get that TGIF feeling
The space behind your chair is neat for possible video Skype calls…
…but you have conference calls looking like something the cat dragged in
The quiet: You can go all day without saying one word
You can sleep in…
…but you have to be self disciplined
You learn that uncertainty is a part of doing what you want for a living
You can go days without any physical adult interaction
Working on your birthday is not mandatory.  Mine is today so I’ll do a half day ; -)

.  .  .

I really enjoy working from home and running my own business. It gives me a sense of freedom and independence that I have never had before and I am thriving from it. Of course, there are still stresses – especially financially. This is especially prevalent at the moment with the Covid-19 outbreak we are enduring. I am only a small business so financially it is going to be demanding, but I have heard about COVID Small Business Assistance that could be critical. It’s my next job to take a look and sort it out.

Feel free to add to this list if you’re in the same boat!


  1. Simona M says:

    Happy birthday, have a great one, and all these ring true, the delivery men one made me laugh, and I always greet them looking like something the cat dragged in, I guess that will make them wonder, what I do. I guess they think I drink all day, ha!

    • Karen says:

      yea the delivery men definitely know me well. We often have little chats with the regular ones that I’ve known for years. OMG I laughed out loud at the drink all day thing….

  2. DT says:

    Happy birthday Karen! I wish you many more productive and stylish years ahead.

    • Karen says:

      Thank you so much for that. Esp the productive wishes!

  3. DISOWNED says:

    I love this list! It’s been just over a month since I’ve traded in the 9-to-5 for my laptop life, and I can totally sympathise with these realizations. The very first one I noticed was the lack of weekends! Everything I do, even just running to the supermarket, has its potential to be a part of my work day. But, because of my NYC-Workaholic attitude, I actually love it!

    <3 dani

    • Karen says:

      ahhh a newbie!! I know right the lack of weekends – it all just merges into one giant day almost. Congrats : )

  4. DEESIGNGEEK says:

    Aww its my birthday today and it’s my dream to work from home / freelance. Great post!

    • Karen says:

      OMG twins!!! LOLOL enjoy you day and I hope your dream comes true one day too : ))

  5. Anonymous says:

    Your blog like fashion has become part of my religion. You inspire me in ways you can’t imagine (sitting at my desk becoming misty eyed as I type these words) Every time you mention the freedom of being your own boss it tells me to just go for it, yet I feel somewhat unsure because of my own insecurities and the financial uncertainly long-term. As you see these are small excuses but, what has me trapped in the world to which I don’t belong (Hospitality/Restaurant Industry) gaining no growth; not challenged and lastly only able to show my creativity via my OOTD and Make-up application.
    Keep doing what you do and Enjoy the day beautiful!!!

    Emily 😉

    • Karen says:

      Oh God this made me really feel this. Do you blog at least? to me blogging was my outlet. I need it to release/escape/vent like a diary that was therapeutic I suppose if it make me feel better about not having to only think about ‘that day job.’ Maybe consider saving up like for a good 6 months or so – enough for you to consider taking some time off if you can and see? Its scary though and not something to jump into until you have some sort of savings in place first to feel better about the ‘leap of faith’

    • Karen says:

      Thank you!!!

  6. Romantic Tea says:

    HAPPY BIRTHDAY ! I wish you a lot of happiness !

    Thanks for sharing this 🙂

    • Karen says:

      ahhh thank you and same back to you

  7. Lady Bug says:

    23. You can spend two weeks on vacation with your best friend (either in NY or UK) without having to suck up to the boss or “calling in sick” HAPPY BIRTHDAY my darling. I wish I could drink a cocktail with you today but I know you’re in good hands. Have a ball xxxxxxxxx

    • Karen says:

      You are so right! Same with spending time with Mum and Pete – no more 1 week only trips! I miss you and hope we meet up soon.

    • Karen says:

      I know right? it all merges together

  8. Lynda D'Souza says:

    I can relate to it all Karen. I think I missed the corporate fancy dinners the most initially. Definitely don’t miss the horrible Monday feeling. Thanks for sharing this, made me feel soooo much better. Happy Birthday to you !!

  9. Erica C. says:

    Happy Birthday Beautiful! 🙂

    • Karen says:

      Thank you E : )

  10. PinkCheetahVintage says:

    Your online friends become your co-workers 🙂
    Happy B-day!

    • Karen says:

      I laughed out loud when I read this but it’s true!

  11. Anonymous says:

    Happy Birthday Karen!! You’ve been such a great inspiration to me since 2011.. I check your site daily for inspirations. You are a friend in my head, My kids know you by name.. I think of you when I shop. Although I have a 9-5 job.. I see life as a mixed bag, nothing is totally perfect. That little filling of accomplishment, even the gut to even take the risk to switch career.. to me, is priceless. Enjoy your day beautiful!

    • Karen says:

      WOW can’t tell you how nice it is to read this. I’m going to remember this comment for a long time. Enjoy your day too.

      Karen x

  12. ngawina says:

    Happy Birthday Karen!!! Always been a huge fan of yours, you’re such an inspiration to me and I so love his post!! Have a marvelous day!!!

  13. BougieHippie says:

    Here’s another one: I use the gym as a reason to get out the house and on slow day I use it as one of my faux accomplishments of the day.

    Happy Bday!!!!

    • Karen says:

      Yes that should be on the list.

  14. Christine Williams says:

    I’m also working from home today, in my pj’s, wondering if I’ll be exposed to any sunshine or human interaction. So much uncertainty! Happy Birthday!

    • Karen says:

      LOL I know exactly what you mean. Thx love

  15. Zoé says:

    Really nice list! I remember the days without saying one word, sometimes, the first outloud word after a long silent period was sounding so weird, like it wasn’t not my voice! It’s children that changed things for me, daycare then school, and the 9-5 is back.
    happy birthday! I love your blog, by the way…

  16. Mimi says:

    Wishing you Happy birthday, one date behind. Got good reasons though! Yesterday was out hiking in beautiful British Columbia to celebrate my birthday too! 😉
    Been following your blog for a good 6 years now. Started when I was living in France, then the past 3 years from Uganda. And now… Canada 🙂 It’s pretty much a daily standard “stop” on your blog to check it out!
    Love what you share with us!! Keep it up 🙂
    Best Wishes for many more years to come. Happy Birthday!

  17. Maggie A says:

    Happy Happy Birthday! You independent self made inspirational woman! <3 Thank You for doing what you do. You’ve inspired many (like myself)

    Maggie A

  18. antonia says:

    happy belated birthday karen! still waiting for the day i run into you on the train/in bk/in the city!

  19. Show Must Go On says:

    Happy bday! What did u do before, at your 9-5 office job?

  20. Roz says:

    Happy birthday Karen. Great list! Unfortunately, my refrigerator seems to never be far enough away!

  21. PuffyNYC says:

    Hope you had a great birthday. I have one: You must constantly remind friends and family WITH 9-5 outside the home careers, that you do INDEED in fact WORK during the day just as they do and that you are not available to be the emergency errand runner nor lunchtime phone chat buddy for them.

  22. Dee Gray says:

    I turn 50 day and I feel it is never too late…..one day I will read your list and say ..”she was right”

  23. the style potato says:

    it is refreshing to see a blogger that so humble and so down to earth. thank you for being such an inspiration and for being so true to yourself. happy birthday and i wish you all the best!! and i hope to be my own boss one day, i’m still working on achieving that!!

  24. Eduarda Loureiro says:

    You have to remind yourself, on those lonely days, that you are doing what you love and it will pay off, eventually, in ways you could have not imagined.