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Ten Things No One Tells You About Working for Yourself

May 11, 2015

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It’s funny really, when I quit my corporate job with my windowless office, I assumed a lot of things. I imagined a life that felt like summer vacation everyday and to be honest, my life sort of feels like that (I use “sort of” loosely, because that’s exactly what it’s like.) I remember those first few weeks, going to bed at night and not having to set an alarm and the way it made me feel like the next day was Christmas, as if Santa would appear in the morning, hit the snooze for me and tell me to rest my head because I now worked for the best boss in the world: me. While I can admit that the transition was easier than filling up an entire shopping cart at Target in ten minutes flat, there were a lot of things that no one ever prepared me for. I kind of wish there was a version of  “What to Expect when you are Expecting” for corporate babes to read when they leap into full fledged entrepreneurship, but alas, there is no book and so this blog post will have to suffice.

The first days were filled with Real Housewives marathons, minutes spent questioning how I would fill each hour and painkillers (whoops, did I mention I had just undergone an extensive foot surgery? No? I left that out, well that explains the painkillers.) While I hopped around the house on one leg, I was filled with so much happiness and freedom that I missed the opportunity to really think about what this new life would look like. So here we go, an honest list of what it’s really like to be your own boss.

1.)  You learn to talk to anything: dogs, oranges, the elderly next door neighbor. You learn to welcome any interaction outside of your own human existence because gone are the days of eating lunch with colleagues or office chatter. Suddenly you are five again, creating invisible friends and treating your dogs like the guy from HR.

2.)  You might gain five (or ten) pounds: wait, what? This isn’t part of the diet plan? Well, you go from running around all day (sometimes in high heels) to a life that includes yoga pants (that never go to yoga) and a sedentary lifestyle that lives next to your kitchen. Friends, heed my warning, start working out again, you now have time for it and you’ll thank me later.

3.)  You quit that 9-5 job so that you could work less, be with friends more, and chase those dreams, right? Well, get ready to work from 7-9… wait, that’s 14 hours, yup. Us entrepreneurs, we have an extra chromosome of hustle in us that forces us to become workaholics. The best part is that you’ll likely rather work 80 hours for yourself than 40 for someone else but now is your chance to mentally prepare.

4.)  Life will feel like one big date from match.com. Suddenly you have no work friends, no reason to put on real pants, and you begin to question who the hell are your friends or if you even have any. Welcome to the phase of life where every interaction feels like an awkward set up from eharmony. Don’t say I didn’t warn you but I encourage you to nail down friendships before making this leap so you don’t keep talking to oranges (refer back to #1.)

5.)  You imagination wanders to jet setting, hanging with celebrities, toasting champagne whenever anything awesome happens but the truth is you are now hosting company parties: population one. Get used to celebrating successes with a two minute dance party alone in bed (if you’re like me and work in bed) and crying through failures with a bottle of wine at 11AM alone. This is the life you chose, remember that one when you worked alone and no one cared about your blog that only your mom reads.

6.)  Speaking of office parties, suddenly you are stripped of vacation time, employee of the month titles, and holiday parties. Woops, you did that to yourself but fret not. You can throw a random “work party” on a Wednesday evening with or without friends and sleep off your hangover that those two glasses of wine left you with on Thursday. Work will wait for you, don’t worry.

7.)  “What exactly do you do?” used to be a question you could answer with some long acronym or title that you created to sound impressive but suddenly you are defending your career to the dentist while they drill through your teeth. You become someone who speaks in paragraphs, not sentences in order to explain what the hell your dreams are and how competent you are at chasing them.

8.)  Your laundry will be a hilarious mix of spandex and cotton. Really, you will be so happy to ditch your uniform that you will forget (intentionally) that real clothes exist and suddenly your stack of yoga pants will be so high it tips over. Enjoy the elastic reality that you have whatever dress code you want and most days bras are optional (thank god.)

9.)  You’ll want to quit (more than once.) Somewhere along the way you will question everything: the house, the job, the career change, the dreams. You will lay in a pile of tears all alone in your yoga pants and think that you can’t possibly go on. You will daydream of working at Walmart and how little responsibility you will have until you come to and remember that you are doing what you love.

10.) Speaking of what you love, you are blessed my dear friend, to have the guts and gusto to do what makes you happy. Remember on those tough days that this is all worth it. Put your happiness first, laugh when your friends think you live a glamorous life, and be grateful that this whole reality is yours and you have created it for yourself. Designing a life you love isn’t for the faint of heart but you, darling, are doing it and doing it well!

 

 

 

 

 

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  1. Jessica

    May 11th, 2015 at 4:15 pm

    haha- I can totally relate to all of these! I’m pretty sure my dogs don’t understand when I talk to them, but it make me feel better all the same!

  2. EricaJ

    May 12th, 2015 at 1:10 pm

    Yessss! This. Every single one. I think I shouted “preach” after reading each one. Good thing there’s no one around to hear me….except my oranges. Thanks for making feel a little less alone in this lil crazy dream chasing thing.

  3. Halley Razz Gray

    May 19th, 2015 at 4:14 am

    Hahaha, LOVE all this! You’re so right on all of these.

  4. Cara Chace

    July 14th, 2015 at 7:27 pm

    So spot on!!

  5. Jessica Flannigan

    July 14th, 2015 at 7:39 pm

    Nails it! Totally nails it. I am three years in and still feel like a big fat fraud most days. I question my existence and work every single day even though if I truly look back, I have come a long way in terms of my career, my readership and my income, but it still feels like a joke some days.

  6. Robbyn Juleson Hodgs

    July 14th, 2015 at 8:58 pm

    Thank you so much!! I really needed to be reminded that I am not the only one that struggles with entrepreneurship. I’ve wanted to throw in the towel so many times, but I can’t do that to myself. I truly love what I do!

  7. Jessica Golden

    July 14th, 2015 at 9:06 pm

    on the money!!!

  8. Adrienne Vernon

    July 14th, 2015 at 9:29 pm

    TRUTH! I can’t even tell you how true some of these are (but my dog could haha). Thank you for writing this. It helps us entrepreneurs not to feel so alone. 🙂

  9. Sarah Le Donne

    July 14th, 2015 at 10:05 pm

    Such an honest and refreshing post, so much appreciated! (And it’s SO true!) 🙂

  10. Berni Xiong

    July 15th, 2015 at 12:11 am

    OMG this couldn’t have come to me at a better time! Thank you! <3

  11. Stephanie

    July 15th, 2015 at 5:28 pm

    Brilliant, I can relate …

  12. Claire Riley

    July 15th, 2015 at 6:08 pm

    This is excellent! So right!!

  13. Mary Beth at MBZ Interiors

    July 15th, 2015 at 7:08 pm

    Thanks for the confidence boost. The one thing I have found out after being fired as a paralegal and opening my own biz is that there are so many women out there doing their own thing and not kissing any bosses’ B.U.T.T. (as I had done stupidly for 20-some year). Good for all of you, good for all of us, We Rock!

  14. Kirsty

    July 15th, 2015 at 7:45 pm

    Love it! So very true!! I feel like I have less time and then I realise the flexibility I have for my kids 🙂 Living the yoga pant theme unfortunately though and can sometimes weep for social interaction! 🙂 Great blog!

  15. Mishelle Handy

    July 15th, 2015 at 11:15 pm

    Love it!!

  16. jennifer

    July 15th, 2015 at 11:36 pm

    Some many thoughts, this is so my life. I’ve learned to try to make as many online friends as I can because they are really the only people I talk to on a daily-ish basis to keep my sanity!

  17. Tyler Sailsbery

    July 16th, 2015 at 3:30 am

    Written on my 30th Birthday which is rather funny because I am not sure that with my entrepreneurship life I will ever have to fully grow up. This was an amazing list though yoga pants really haven’t worked out for me.

  18. Shaina

    July 16th, 2015 at 3:40 am

    YES! I adore the realness of this, and I’m glad I’m not the only one talking to random things. 🙂

  19. Kim McAllister

    July 16th, 2015 at 1:18 pm

    How true! Nice to have our experience articulated in such a humorous way! We are our own support group!

  20. Sarah Jurg

    July 16th, 2015 at 3:39 pm

    Haha! Adorable and spot on!

  21. Debbie Bellaby Illustration

    July 16th, 2015 at 5:29 pm

    half right, – we don’t all work in our pants ;) but i do talk to the cat – a lot

  22. Lauren MacMoyle

    July 16th, 2015 at 7:05 pm

    This is SO accurate! I am GLAD I’m not the only one!

  23. Adelia Lorena Carrillo

    July 16th, 2015 at 8:31 pm

    I literally giggled the whole time reading this. This is spot on to my life. It ain’t as glamorous as people think. hahaha! Great article!

  24. Kusjka

    July 17th, 2015 at 11:07 am

    Excellent!

  25. Leanne Steyn-Begley

    July 17th, 2015 at 12:53 pm

    Ha-Ha. I can totally relate. It’s too funny though – “extra chromosome of hustle” – happily addicted with no hope of any cure 🙂

  26. Aileen

    July 17th, 2015 at 3:43 pm

    SO needed this reminder now.
    I’m one year in and half the time not sure what the heck I’m doing.
    But loving it…
    Thanks!!
    Xx

  27. Link Love - Week 30The Surly Housewife

    July 29th, 2015 at 5:18 am

    […] 10 Things No One Tells you About Working for Yourself Spot on. […]

  28. Penny Love Crownover

    August 1st, 2015 at 6:35 pm

    I’m a new realtor and just quit my “corporate job” on June 8th. THIS BLOG IS SO ME. I love the honesty about all of this and #10 is absoutely the best. I do enjoy my new career (even if I am almost 59) and working for me. I will have to say talking to oranges isn’t so bad (ha). I do catch myself turning up the radio and dancing around the house for my “coffee breaks” and singing at the top of my lungs, then remember, oh wait, I need to get back to work and walk over to the kitchen table and smile. 🙂

  29. Sally Beck

    August 11th, 2015 at 1:07 pm

    Thank you! You have completely nailed it & so glad there are other people out there that feel the same as u do some days! Put a smile on my face xo

  30. Morgan McIntire

    September 2nd, 2015 at 12:42 pm

    I feel like I should start investing in yoga pants so by the time my two-year plan kicks in and I start working from home, I’ll be good and ready.

  31. Clara Griffith

    September 2nd, 2015 at 12:47 pm

    Uhm, did we just become best friends?

  32. Lauren Schwarz

    September 2nd, 2015 at 1:05 pm

    Yup! #8 is me all the way…and also its piled high. Somehow I can never get it done :/

  33. Gabrielle Halle

    September 2nd, 2015 at 1:18 pm

    ahaha LOVED this!! Number 7 and 9, my favorite. Walmart bagging job with no responsibility? Soo many days I start browsing the internet for applications 😉 This was so great and encouraging and just made me sit and laugh (from my home office that sits between my bedroom and my kitchen).

  34. Cinnamon Ruvolo Wolfe

    September 2nd, 2015 at 1:24 pm

    yep yep and yep. Some days I absolutely love and some days I just want to go back to someone else being in charge.

  35. Crystal Bolin

    September 2nd, 2015 at 1:27 pm

    This was so on point!! Thank you so much for speaking the truth!! I left corporate America too! Needed this!!

  36. Kayla Satrom

    September 2nd, 2015 at 1:35 pm

    100% truth!!

  37. Elizabeth Muscara Haase

    September 2nd, 2015 at 2:01 pm

    This. All of it! I should make an employee of the month plaque for myself.

  38. Susie Marie

    September 2nd, 2015 at 2:02 pm

    This is hilarious and all so true!

  39. Emily Bolt

    September 2nd, 2015 at 2:19 pm

    This is too good.

  40. Kathryn Elizabeth Gillespie

    September 2nd, 2015 at 5:54 pm

    I love this so much! So. Very. True.

  41. Brittany Barnhart

    September 4th, 2015 at 8:13 pm

    This was a great read. Relatable and so true! Thanks for the laughs! 🙂

  42. Amy Lynn McCorkle

    September 10th, 2015 at 2:49 am

    Exactly my life..

  43. Maggie Skarich Joos

    October 6th, 2015 at 1:19 pm

    I needed these reminders today. Thanks Jenna!

  44. Gretchen Lynn Robards

    October 6th, 2015 at 1:47 pm

    I love you and I love this because this is totally my life.

  45. Hannah Stonehouse Hudson

    October 6th, 2015 at 11:19 pm

    I go to the grocery store for social skill re-engagement 😉

  46. Chelsea Burkholder

    October 7th, 2015 at 9:41 pm

    Yes, yes, and yes. I am also in a world of strethcy pants, networking coffee blind dates, and conversations with all inanimate objects in my house. And the neighborhood cat. I love you for writing this, it’s spot on!

  47. Laura Veariel

    October 13th, 2015 at 3:48 am

    O my gosh! God bless you! I LITERALLY just did this (quit my big corporate job to get happy etc.) but you describe it so cute!

  48. Ariadne Kapsali

    October 27th, 2015 at 11:44 am

    absolutely LOVE this. I have just joined the work-from-home crew and have started ticking the list quite nicely! Thank you for sharing xx

  49. Hayli De Jong

    October 27th, 2015 at 12:12 pm

    Ahhh I love this. I am a teacher by day so over the last summer I got a glimpse of what it WILL BE like to work for myself haha. Some days it was quite boring since I hadn’t yet started to really get clients or make money, but now I KNOW I could stay busy all day and love it.

  50. Bethanne Arthur

    November 12th, 2015 at 2:58 pm

    Just amazing Jenna! I am speechless – love this post so much!

  51. Jessica Roy

    November 18th, 2015 at 10:48 pm

    Hahhaha! #1 is so me with my elderly neighbor

  52. This Domesticated Diva

    November 18th, 2015 at 11:15 pm

    Ummm…YES! I mean, at this point I’m still a wannabe entepreneur because I’m saying yes to too many things that consume too much of my time. But even so….this is spot on! Thank you for your brutal (and hilarious) honesty.

  53. Kaylie Sirek

    November 19th, 2015 at 12:04 am

    YESSSSS!

  54. Candra Cain-Clark

    November 19th, 2015 at 12:05 am

    I just cried my ass off I needed this thank you

  55. Ana Ulloa

    November 19th, 2015 at 3:24 am

    SOOOOOOOOO TRUE !! thank youuuu for your wordssss…. I really needed them today !!!

  56. Joshua Grasso

    November 19th, 2015 at 4:47 am

    nice writeup. Trying to get the courage to go be my own boss myself soon.

  57. Emma Weise

    November 19th, 2015 at 5:31 am

    This is classic! Thanks

  58. Anna Mess Bartell

    November 19th, 2015 at 1:38 pm

    oh my gosh I love this so much! Thank you for sharing! Number 7 & 9 are the story of my life!

  59. Rosaleen Michele Merritt

    November 19th, 2015 at 3:56 pm

    This is Perfect & so spot on! Thank you for saying it while the rest of us are thinking & living it as well!

  60. Jade Pearse

    November 19th, 2015 at 4:21 pm

    Love this!

  61. Kaitlyn Kessler

    November 19th, 2015 at 4:42 pm

    #1!! #2!! all of these!! Yoga pants that never go to yoga… oh man. Wonderful post!

  62. Michelle Johnson Stoddard

    November 19th, 2015 at 5:15 pm

    Awesome! Completely me. If I didn’t have to go to photo sessions with clients, I’d never get out of my yoga pants.. that don’t yoga 🙂

  63. Audrey Groeschel

    November 19th, 2015 at 5:18 pm

    I think your list is brilliant. I think the hardest thing to make sure to do is give yourself kudos. Pat yourself on the back and tell yourself you’re doing a good job. There is no one there to say atta girl so you have to. I read somewhere that you should do your own performance reviews to see how you’re doing too. I haven’t yet but I figure I won’t get written up for wearing inappropriate attire to the office. Thanks for writing this.

  64. Jessica Lail

    November 19th, 2015 at 5:46 pm

    hahaha This is the most perfect blog post. I absolutely love it! I work full time from home for my full time corporate job and for my two side businesses. It can feel really lonely being this busy at your own house. Some days I’m on my computer for 15 hours and my eyes are blurry and I look at how dark it is and look at the clock and I haven’t even thought about dinner and it’s close to 10pm. It’s a scary way to live but I know eventually it will change and I won’t have to juggle so much and can leave the house wearing something besides yoga pants and feel great about it! Sharing this with all the other dreams out there!!

  65. Mel Cunningham

    November 19th, 2015 at 5:47 pm

    Totally on the money… Or talking to apples! Thank you Jenna for such a humourous piece on the real life we lead and the things that have the capacity to slay our determination when things just aren’t happening/happy/or even enjoyable… I have found some wonderful other entrepreneurs to bounce ideas with…. Or even find awake at 4am… That’s social media for you when waking to cold frets and sweats! So proud if anyone daring to take the plunge!

  66. Heather Elizabeth

    November 19th, 2015 at 6:06 pm

    Oh god I love this! I’ve just took the plunge and I have had a few days questioning my decision and hey presto! Little wake up, lovely read 🙂

  67. Justin House

    November 19th, 2015 at 7:25 pm

    I’ve been self-employed, as a web designer, for 19 years. I’m actively applying for jobs now though because I miss the socializing, structure and of course the consistent pay checks. They did a study on entrepreneurs which shows that most are unhappy, namely due to the social factors, or lack thereof. They say we lack touch, even as simple as getting a pat on the back. While I’m going back to work, I’m certainly holding out for a jammin’ job. Thanks for the article, it definitely resonated with me. Peace.

  68. Radhika Basuthakur

    November 19th, 2015 at 7:45 pm

    Haha, gosh this was so funny and SO relatable!

  69. Nettie Ervin

    November 19th, 2015 at 8:38 pm

    I needed this at just this moment. Thanks and I’m adjusting to oranges!

  70. Allison Hailman

    November 19th, 2015 at 10:11 pm

    Awesome and totally true!

  71. Tiyana Robinson

    November 19th, 2015 at 10:25 pm

    This is THEE truth! Ugh. I go days without even going outside! And oh God the yoga pants and oversized tee shirts (>_<) You are so right about weight gain. I've definitely joined a gym (plus it gives me a reason to leave the house!)

  72. Graham Graham

    November 19th, 2015 at 10:28 pm

    I was nodding my head in agreement with every point!

  73. Cathy Field

    November 19th, 2015 at 11:05 pm

    So true! The Fed Ex man just drops his boxes and runs in case I catch him in conversation, six pair of yoga pants fell of the shelf yesterday. Six!

  74. Donna Triska

    November 20th, 2015 at 11:00 am

    I’m a bit over 50 and do group physical activities during “working hours” I get asked if I retired early. I haven’t taken a full day off in weeks. I love my job.

  75. Taylor Manning

    November 20th, 2015 at 11:23 am

    Amazing article! So spot on! Glad I am not alone 😉

  76. Gleeful Grandiva

    November 20th, 2015 at 11:39 am

    What an inspiration! I love this post, it’s funny and so very, very true. Thank you. 🙂

  77. Forever Fab Fit

    November 20th, 2015 at 1:06 pm

    So funny & true!!

  78. Cristina Blanco

    November 20th, 2015 at 1:44 pm

    Perfection!

  79. Dana Rae Bello

    November 20th, 2015 at 2:19 pm

    This is so right on!!! I quit my corporate job 6 months ago & everything you said is true. But it’s the best thing I ever did. And who doesn’t love to work in yoga pants?! Thanks for sharing!

    ReinventingRaeNYC.blogspot.com

  80. Dana Rae

    November 20th, 2015 at 2:26 pm

    Looking forward to following your blog!

  81. Comaru Masahiro

    November 21st, 2015 at 11:52 pm

    (。-_-。)

  82. Shelly Lorts

    November 30th, 2015 at 10:03 pm

    Lol! I just read this after wandering around Walmart for a couple of hours looking for props…and daydeaming about working there and having work friends again. I laughed out loud when you called that out precisely.

  83. Amanda Gahler

    January 31st, 2016 at 12:35 am

    “I encourage you to nail down friendships before making the leap” – best chunk of advice I wish I had read a year and a half ago when I quit my full time job! I will pass this nugget along to anyone who is thinking of making the change! Thanks for a wonderful post.

  84. Anna Elizabeth Marinello

    June 15th, 2016 at 6:10 am

    Love this (:

  85. Christina Adinolfi Carroll

    June 22nd, 2016 at 5:20 am

    awesome and so true!!!!

  86. Alicia

    July 29th, 2016 at 10:29 pm

    I so so needed to read this today, especially #10. I can resonate with so many of the other numbers you wrote. It sometimes feels like a “minor ducats at a thankless job” to coin a line from the 90s movie, “Clueless.” Haha and yes, I am wearing yoga pants and a cotton Tshirt right now since I just got back from the gym. I’m sipping on coffee midday, missing companionship and ready to jump back into editing photos. Thank you for sharing this post–it helps to know that I’m not the only one feeling the way that I do and to know that there are others out there in stretchy pants day in and day out too! Haha 😀

  87. Katie Iacobelli

    August 1st, 2016 at 7:26 pm

    Great post and 100% accurate!! Just started a blog and have been stuck in the “my mom is the only one that reads it” phase. Thank you for the encouragement! I needed to read this today! 🙂

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