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.
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.
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.
You quit that 9-5 job so that you could work less
You know… 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.
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.)
Your world: population one
Your 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.
No one celebrates anymore
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.
“What exactly do you do?” becomes your nemesis
Yeah, hardest question ever. It 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.
You’ll never wear real clothes
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.)
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.
It’s totally worth it
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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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!
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.
Hahaha, LOVE all this! You’re so right on all of these.
So spot on!!
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.
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!
on the money!!!
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. 🙂
Such an honest and refreshing post, so much appreciated! (And it’s SO true!) 🙂
OMG this couldn’t have come to me at a better time! Thank you! <3
Brilliant, I can relate …
This is excellent! So right!!
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!
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!
Love it!!
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!
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.
YES! I adore the realness of this, and I’m glad I’m not the only one talking to random things. 🙂
How true! Nice to have our experience articulated in such a humorous way! We are our own support group!
Haha! Adorable and spot on!
half right, – we don’t all work in our pants ;) but i do talk to the cat – a lot
This is SO accurate! I am GLAD I’m not the only one!
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!
Excellent!
Ha-Ha. I can totally relate. It’s too funny though – “extra chromosome of hustle” – happily addicted with no hope of any cure 🙂
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
[…] 10 Things No One Tells you About Working for Yourself Spot on. […]
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. 🙂
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
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.
Uhm, did we just become best friends?
Yes yes yes to all of these! I swear I talk to any animal or object that will “listen!” I heard a great quote that said “Owning a Small Business: working 70 hours a week for yourself so you can avoid working 40 hours a week for someone else” and I feel like that couldn’t be more true!! 🙂 Thanks for this wonderful post and ALL your wonderful posts!!
Yup! #8 is me all the way…and also its piled high. Somehow I can never get it done :/
Amen! Love all of these! So true!
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).
yep yep and yep. Some days I absolutely love and some days I just want to go back to someone else being in charge.
This was so on point!! Thank you so much for speaking the truth!! I left corporate America too! Needed this!!
This was awesome!! So on point! Needed this!!
Ps. Can I ask what Facebook comment Plugin you use? Thanks!
100% truth!!
This. All of it! I should make an employee of the month plaque for myself.
This is hilarious and all so true!
This is too good.
I love this so much! So. Very. True.
This was a great read. Relatable and so true! Thanks for the laughs! 🙂
Exactly my life..
I needed these reminders today. Thanks Jenna!
I love you and I love this because this is totally my life.
I go to the grocery store for social skill re-engagement 😉
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!
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!
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
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.
Just amazing Jenna! I am speechless – love this post so much!
Hahhaha! #1 is so me with my elderly neighbor
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.
I love this list – I’m a stay at home daycare provider and I can relate to nearly all of this! : )
YESSSSS!
I just cried my ass off I needed this thank you
SOOOOOOOOO TRUE !! thank youuuu for your wordssss…. I really needed them today !!!
nice writeup. Trying to get the courage to go be my own boss myself soon.
This is classic! Thanks
Thank you this is wonderful and much needed lots of love and light , I was just about to leave everything and get back to a job , its quite funny how every time i think of giving up , so artist or inspiration magically pops up and tells me to go on .
thank you so much 🙂
oh my gosh I love this so much! Thank you for sharing! Number 7 & 9 are the story of my life!
This is Perfect & so spot on! Thank you for saying it while the rest of us are thinking & living it as well!
Love this!
#1!! #2!! all of these!! Yoga pants that never go to yoga… oh man. Wonderful post!
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 🙂
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.
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!!
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!
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 🙂
This is SO TRUE. Especially the part about yoga pants and talking to your dogs.
Thank you for the laugh.
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.
Haha, gosh this was so funny and SO relatable!
I needed this at just this moment. Thanks and I’m adjusting to oranges!
Awesome and totally true!
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!)
I was nodding my head in agreement with every point!
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!
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.
Amazing article! So spot on! Glad I am not alone 😉
What an inspiration! I love this post, it’s funny and so very, very true. Thank you. 🙂
So funny & true!!
Perfection!
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
Looking forward to following your blog!
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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.
“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.
Love this (:
awesome and so true!!!!
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 😀
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! 🙂
Sometimes I feel completely stupid to want to get that life back. Several years ago I was a stay-at-home mom and had the opportunity to just got for it. Unfortunately, I was in a marriage that wasn’t supportive and in the end didn’t work. Now I am back in corporate America and, while I work for an amazing company, the desk jockey life aint for me. I working to be able to make the jump back to self employment responsibility (did I mention my two littles) and you have been a huge encouragement. So thanks. Remind me I said thank you when I’m in the tear crumpled bottle of wine time.
[…] think Jenna Kutcher‘s blog about the Ten Things No One Tells You About Working for Yourself, is a good place to start in analyzing if your personality type is cut out for this kind of a […]
This post is so perfect – full of truth and humor! Thank you for sharing this!
Every single one of these is so true. Reaching out from my desk to yours and waving hello!
love the web design & this post is great
Mel x
mediamarmalade.com
Omgah, Amen! I’m having such an awkward relationship with my start up. but I know if I just keep going (just keep swimming) that it’ll outweighs the blah moments. #10 is what makes it worth it. Absolutely blessed.
This is amazing. I can relate 100%. You’re one in a million, Jenna! Thanks for being you and inspiring us women who need a friend that understands this journey through entrepreneurship!
So true and funny! Thanks for that.
Thank you so much for sharing this! Ironically tomorrow is my last day at my corporate job, and I am moving into full time entrepreneurship! I am looking forward to the challenges, and am thankful for my two rescue dogs (new coworkers), who will be there to celebrate the good, bad, and crazy with me!
Hey Jenna!
I recently quit my job to go full time with the Nutrition Consulting business I co-founded with a fellow classmate from college! I found your blog to be delightful and somehow re-assuring. I know things wont be picture perfect but everyday feel’s like a gift I gave to myself!
Yes!!
Haha I prefer bananas 😉 Oh and my French Bulldog Frank loves to hear all about my day, so I’m lucky! I’m still making that move into more freelance but I have a photographic dayjob so I’m okay with the progress and I already have no colleagues to chat to in the “office” as my office is my car, in between appointments to photograph properties!
Great blog and I’m glad I’ve found you, thank Facebook and your emails 🙂
Girl, I LOVE this. #preach
As a recent jumper into the entrepreneur thing, some days the high is real and other days it’s a marathon just to sit down and write for an hour. (thank God for yoga pants, amen to that sista!)
Thanks for all your real, raw encouragement and examples. You make this whole boss babe thing a lot more fun. 🙂 May God bless your yoga pants right off!
So grateful to be my own boss, but this list nails it on the head when it comes to what it really looks like to work for yourself. Thanks for sharing!
(also, thinking I need to invest in a dog….you know, so I have someone to talk to. 🙂 )
Ahh yes! It was so good to read this, a way to reassure myself that the annoying ups and downs are pretty normal 🙂
This is SO true! #1 and #4 especially- not having work friends is the worst! I actually considered getting a JOB at one point (gasp!) just to make friends in a way that didn’t feel like a blind date!!! :0
This is so unbelievably true!! I am a silversmith and live in a town of 7 so interactions are limited to begin with!!
You might have just saved my life with this post. I drove my daughter to dance after a seemingly productive day with one hitch i’ll have to work out Monday or tomorrow if I feel like it. But we stopped by Starbucks and it was buzzing in there. Nothing came together right, I dropped my daughter’s snack box we had just bought on the floor. I began to cry so I couldn’t even wish the man who was so kindly trying to help us a Merry Christmas like he did for us and we hustled out. I cried all the way home. I pulled myself together a little and sat down on the couch to catch up with some of your e-mails and navigated to this post. I work at home and I’m lonely sometimes. I’ve had a hard time admitting it, because I love what I do, but this is a bi-product I didn’t expect or plan for. Somehow just knowing I’m not alone helps! Your website, writing, and podcast are fantastic. Thank you!
Jenna! THANK YOU for dropping this TRUTH – so relatable and I feel a lot less crazy 😉
Thank you for sharing:)
This is so me!!! Thank you thank you for putting this down and for sharing your story! I’m so happy now I am not the only one wearing elastic pants every day to work! It is so easy for me to be hard on myself and criticize this “lazy” look… Hearing your words made me feel good with myself, and made me cut me some slack! Knowing that I am not alone means the world! xx
I love you Jenna Kutcher. I’d gladly have you as my +1 in a party of 2. I’ve been working from home for the past 6.5 years and totally agree with everything you’ve written about working for or by yourself. One thing you forgot to mention is that your house will get really organized. Because all of that water cooler time is now spend reorganizing the junk drawer for the third time. Sometimes distractions come in that flavor. Keep doing what you’re doing and I’ll keep following.
All so true and so funny. I went from being a taciturn city person staring at the sidewalks with headphones on avoiding all eye contact, to a person who compliments strangers on their shoes and makes inane comments about weather to literally any human being within ear shot. Totes worth it though 😀
SO funny… and true! Glad you could empathize with me girl!
Jenna! I love this so much and 100% relate to all of this! Especially, the pants, bra and talking to animals part. And, I really needed a good laugh so thank you!!
🙂
Thank you so much Jenna for all that you share. You are such a blessing. It can be a lonely road sometimes and can feel pretty overwhelming. It’s lovely people like you, and your honesy, that keep my going on the hard days 🙂
Never have I read something and related to it THIS much. 🖤 Love it all.
This is great! Thank you for sharing. I am not at the point where I can quit my corporate job but looking forward to the day where I can cry in bed alone during the day!
I am currently in the stage of getting ready to work for a party of 1 and boy is it intimidating! I don’t have a single friend or family member who has gone the entrepreneur route so I am SO THANKFUL that I found you! Your emails and blog posts have felt like the friend I have needed to tell me all the dirty deets and to also tell me I CAN do this 🙂
if this is what it’s like than I can’t wait to reach that point! Thanks girl, I have recently become obsessed with your blog and podcast! Big fan! Keep rockin it! Your such an inspiration!
This is everything! Thank you for being so real <3
This sums up everything I’ve been experiencing after quitting my job! Such a realistic and relatable article. Made me feel happy and more confident 🙂
Currently struggling with #9. I didn’t think that quoting would actually be something I’d consider but managing a home, kids, work on my business and soon to be homeschooling a high school student. Oh and I tend to forget I’m married and desperately miss lounging around with my husband. I know I’ll get over this hurdle and I’m slowly feeling another wave of motivation but DAMN! No one told me about this!
I actually laughed out loud, I swear! Especially the ‘two minute dance party’ oh my god… SO true! I do this ALL the time when someone great happens. And then something bad happens and I just wanna quit. 🙂 You are SO right with this stuff!! 🙂
Hiya Jenna,
Just want to tell you that I LOVE the way you write as it’s so funny and interesting and I think you are a great teacher too. I adore the way you paint neat pictures with your words and only pray I can be as good as you one day….I have only just started on the journey of being an Entrepreneur…and you are the lucky one to be my guide!! Love Debra x
I’m in my yoga pants now 🤭
You really made my day. I thought I was all alone in this venture too 😅
Thank you so oh sooo much for this article 😊
I just laughed my but off (that are currently hugged by yoga pants, thank you very much)!
I love this! I’ve recently had to take time off my Medical Degree and currently not working to fill in the time so I can totally relate ! Spending time On your own, living in yoga pants, talking to myself 😂🙌🏼 I don’t have my own business…YET but am enjoying this time off to really hone in the details of how I want my future endeavour to look like and think about how it is going to sit next to being a fully liscenced Dr! I am soooo glad I stumbled across your work! ❤️❤️🙌🏼 Jenna you’re amazing and inspirational!
❤️❤️💗💗 Thank you! You hit the head on the nail! I’ve been self employed now for 20 years but had a “home based business” for 16 of those years. It is sooo worth it!! Sweatshirts and lulu lemon leggings and all! Keep it up Jenna! Xo Val
I needed this! I’m wanting to step out and start my own gig, but it’s hard to really do it. This helps give so much perspective with raw, super funny, honesty. Thank you!
This literally came at the right time for me……I work from home after working in a windowless office like you and have been struggling with the loneliness. I too have considered a career in Kmart to gain friends!! I feel like I have lost the ability to relate to other humans and worry about my communication skills. Thank you Jenna for making me feel like I am not alone… thank goodness for my cat who rarely leaves my side – am off to buy an orange or two xxx Ps…, you are going to make an amazing mummy xxxx
I can totally relate to this ……I am at home after working in a windowless office like you and have been struggling with the loneliness. I too have considered a career in Kmart to gain friends!! I feel like I have lost the ability to relate to other humans and worry about my communication skills. Thank you Jenna for making me feel like I am not alone… thank goodness for my cat who rarely leaves my side – am off to buy an orange or two xxx Ps…, you are going to make an amazing mummy xxxx
Thank you for this post! I know that it is over three years old, but it hit the spot for me today! I started working for myself (quite by myself) three months ago, and I am experiencing all of this. I’ve read others’ warnings before, but this set was full of humor and positivity, both of which I appreciate tremendously! You’ve got a new fan in me, Jenna!
[…] this although [I believe] doing these things would probably increase probability of your success. Here is an interesting post about working for […]
You had me laughing out loud! This is so accurate… I was planning to start my dream business, but getting laid off pushed me to start chasing that sooner than I planned. It’s been one of the best things to ever happen to me!