How to Ditch the Cubicle

hustle and flow

If I had an FAQ, ranked number one (just above “How do you stay so casual?”) would be variations of “How do I work full-time from home?” Often it’s from someone who’s tired of his 9 to 5 or someone who wants the flexibility of staying home with kids, with various other reasons in between.

Some thoughts from your self-employed pal. Take it all with a grain of salt; I’m currently wearing sweats.

+ Don’t quit, but start now. Unless you don’t need the income, quitting on Friday and starting something new on Monday is ill-advised. Jim has a career, but also really enjoys graphic design, and would like to do that for himself and work from home full-time. But instead of yelling “I quit” and doing the pelvic thrust dance in front of his boss, he starts working on graphic design on the side.

Jim works 9 to 5, comes home, has dinner with the family, and works on graphic design from 7 to midnight. On Saturdays, he brings his laptop to a coffee shop and spends the morning working. Each week, he’s putting in roughly 30 hours. Jim banks that money, because freelancers need a hefty emergency fund, and once he’s ready, he makes the leap from working for someone else to working for himself.

+ Weigh all the monetary pros and cons. Now that I no longer work full time out of the home, I’ve said goodbye to twenty hours of commuting time each month, I’m spending less on gas, and the phrase “business casual” is no longer part of my vocabulary. But at the same time, my utilities have gone up (I’m home all day, using the electricity and blasting Pandora and keeping myself warm) and I have to shell out my own money for computers and pens and neon sticky notes.

How to Ditch the Cubicle: work full-time from home

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+ Consider the children. “But the children love the books!” – that nun from Elf, right? This one applies if you have kiddos: I will be super real about how easy it is to work at home with three kids — it’s basically impossible. Your mileage may vary, however. Maybe you have just one docile child or maybe you can totally focus when throw pillows are whipping past your head at impressive speeds, but for me – if I have eight hours of work time scheduled for a day, those are eight hours where I am not in charge of caring for my kids.

If you’re looking to just work a couple of hours a day, naptime + the hour after bedtime can suffice, but if you’re putting in a full day, consider childcare arrangements or creative work hours. Example: at one point I worked from 5am to 8am, 12pm – 1pm, and then 7:30pm to 10pm. Kind of hellish, but totally doable.

+ Does it have staying power? I’d apply this one to blogging or even direct sales efforts (which I’m seeing a lot of in my FB feeds these days). Even if I was raking in crazy amounts of cash for one blog, I would never put all my eggs in this one basket. Are blogs even going to be cool in two years? Will podcasts have replaced them? Many people are quitting all of that in exchange for secure traditional jobs, not vice versa. I totally sounds like a naysayer, but I guess my point is — keep the long-term in mind.

+ Is it a job or a hobby? One of the coolest things someone can do, IMO, is to pursue a passion. But passions don’t always mean careers. The formula goes beyond do you love it? to also include and is there demand? Or what if it’s a little bit of both? You hand-weave really pretty baskets, and you sell enough to make a hobby you love free for you. That’s incredible! There are people who spend crazy amounts of money on their hobbies, and you get to do yours for free. Maybe even for free + a couple of tacos at the local taco truck. There’s nothing wrong with grinding it out at a 9 to 5 and pursuing a hobby after hours.

+ Go balls to the wall. (That’s an aviation reference, not a body part one … Mom.) If all of the dots connect, give yourself the green light and be all in. It’s a little scary, but most cool things are. There are times where I quietly coach myself and say “If you fail super, super miserably, you can bounce back.”

+ Shake some hands; hug some bodies. Get your LinkedIn profile up to date; put a portfolio together; shoot some emails to people in your field. Shoot some emails to people who aren’t even in your field. I have a casual text thread going with a couple of entrepreneurs in my ‘hood, and our lines of work never cross, but it’s nice to have friendly support.

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  • Reply Lindsay January 26, 2015 at 1:15 pm


    My plan for 2015 is to ditch my cubicle at some point so… I guess my overzealous hand-shaking and body-hugging is now an appropriate business move.

    Do you have some practical tips for networking in a way that isn’t a) creepy and b) annoying to potential connections? (I’m imagining myself as an annoying gnat flying around.)

    Thanks so much for this Roo!

    • Reply Roo January 26, 2015 at 2:29 pm

      I say getting your LinkedIn profile up to date and connecting with people is a good start. Are there any groups in your area that you could join? For example, my area has a “Young Professionals” group, IDK if they consider me young; meetup.com usually has some decent options, too. Facebook, surprisingly, isn’t always a cesspool, and you can often find groups related to your line of work; great for networking, swapping ideas, etc. Aaaand finally, I’d encourage sending people a little note via email, doing a follow on social, that sort of thing. Woooooooo wall of text!

    • Reply Rebecca January 26, 2015 at 11:18 pm

      As a person in a position of power–it’s really, truly, not annoying to reach out to people that would be able to network on your behalf. I’ve had people in my organization come up and talk to me and ask me how I got into my part of the field. This is a good point to say, hey, I’m actually transitioning to “x” and I know you may have a contact. Do you have anyone that you would feel comfortable connecting me with? Personally, I love connecting two people in my network, and it’s easy enough to do for me (quick email to both parties once I’ve been able to confirm with my contact via text). Just make sure that the person you’re talking to is dependable–you don’t want to nag at someone to connect you thus ruining your relationship. :-)

      • Reply Lindsay Durrenberger January 27, 2015 at 8:43 am

        Oh thanks for this. I am always so self-conscious when I reach out to people, especially people who are potential mentors/networking connections. :)

  • Reply Heather Laura Clarke January 26, 2015 at 1:24 pm

    Great post, Roo — and love the new site design. I work from home (with two kids) and this is all totally true.

    For the last couple of years, I’ve been in work-early-mornings/at-naptime/after-the-kids-are-asleep mode, but I recently got full-day out-of-the-home childcare for one full day a week. IT. IS. GLORIOUS. It feels really good to have a solid eight (QUIET) hours each week to work without interruption, along with the other not-so-quiet work hours.

    • Reply Roo January 26, 2015 at 1:31 pm

      That’s amazing! I think the childcare aspect is worth a post on its own, maybe, since there are so many different ways to do it. And I loooooove quiet work hours!

      • Reply Lindsay January 26, 2015 at 1:41 pm

        YES -> Would love a follow up on this. I’ve been trying to work during early hours/nap time (MY 2 YEAR OLD STILL NAPS FOR 4 HOURS IN THE AFTERNOON AND IT IS GLORIOUS)/at night but as I take on more work I’d love to hear how other people manage it.

  • Reply Meg January 26, 2015 at 1:33 pm

    Can I admit that I love my office? Granted, I work for myself…but being in a real office, with at least one other person sitting in the same room so I HAVE to actually do work instead of play Candy Crush all day works so well for me. BUT I got deliberately knocked up…again…for the third time. So this fall we’re doing the real-office gig 2 days a week, and the home office/homeschooling/rodeo gig the rest of the time. Any advice on how to organize/prioritize/buy pretty desk things?

    • Reply Lindsay January 26, 2015 at 1:47 pm

      HA! This is so funny! I love the different perspectives. I find I’m more productive at my house for some reason. I keep getting distracted by coworkers/crap going on around me that I’ll look down and be like “CRAP it’s 4pm and I’ve literally done nothing all day!” But it’s cool that you get a mix going. I also like that. Keeps things fresh and it’s always nice to change scenery.

    • Reply Roo January 26, 2015 at 2:33 pm

      At some point, I think I’ll end up in an office again, but I have looked into coworking spaces, also. One of the people I work with on a day-to-day basis lives about 20 minutes away, so we’ve considered meeting there once a week to work together (and see other humans).

      I have a teeny tiny home office! I’ll have to give you a tour. :)

  • Reply Heidi January 26, 2015 at 2:32 pm

    Great post, Roo! Can I plug another blogger I follow? If you’re wanting out of the cubicle, check out Mr. Money Mustache. Roo, he is your brother in spirit. His focus is on the money part of the equation, and the philosophy is so incredibly freeing…it’s totally empowering for those of us finding the practice of Biting the Tongue at work to be slowly crushing our spirits and draining the joy from our families. Definitely worth the read.

    • Reply Roo January 26, 2015 at 8:38 pm

      Thanks for the rec, Heidi! I’ll def check him out. :)

  • Reply Nina January 26, 2015 at 4:08 pm

    Such good points. I negotiated a work-from-home-full-time-while-caring-for-my-newborn situation when working out my maternity leave with my employers. This was my first baby and at the time I thought to myself, “Hey, you can totally do sales and focus on spreadsheets and help customers troubleshoot over the phone when there is a teeny tiny baby in your arms.” This ended up being impossible. In order to be successful at working from home while caring for kiddos it’s important to have a job where you can actually set your own hours. I did NOT have this kind of job, and while I am extremely appreciative of my male employers for letting me set my own maternity leave terms, I really wish one of us had the foresight to realize I simply didn’t have the kind of job that works in a work-from-home setting.

    • Reply Roo January 26, 2015 at 8:49 pm

      Oh man, that’s totally hard. What are you doing now, Nina?

      • Reply Nina January 27, 2015 at 8:57 am

        Well that newborn will be 6 months old next week and my last day of work from home mom-ing is this Friday. I ended up quitting (though we did part amicably so my reference from them is intact) and will be staying at home with my babers for the foreseeable future. Is it weird to say that I’ll miss the spreadsheets?

        Also, before deciding on staying at home and surviving on a single income (my husband’s) rather than putting my baby in daycare I read pretty much every article on The Centsible Life, which I found through your site. So, thanks for that!

        • Reply Roo January 27, 2015 at 10:51 am

          Ha! Oh I’m glad. Have fun staying at home and enjoying the baby time!

  • Reply Courtney January 26, 2015 at 6:08 pm

    We added baby #3 to our family about 2 weeks ago and I would LOVE to make the transition to working from home soon. For now, I’m using this maternity leave to multitask–getting in as many baby snuggles as possible while also working on my hand-shaking and body hugging :)

    • Reply Lindsay January 26, 2015 at 6:34 pm

      #2 for us is on his/her way in June and we would love for me to transition to working from home by the time that happens. Good vibes to us moms fighting the good fight!

      • Reply Courtney January 26, 2015 at 9:08 pm

        Congrats Lindsey, and good luck!

        • Reply Lindsay Durrenberger January 27, 2015 at 8:44 am

          Thanks, you too!

    • Reply Roo January 26, 2015 at 8:50 pm

      Congrats on baby #3, Courtney! And good luck on all the body hugging. :)

  • Reply Kate January 26, 2015 at 11:12 pm

    THIS POST > Cheetos! :-) Leaving my 8-5 is something I think about daily. “Don’t quit, but start now” is exactly what I needed to hear today. Thanks!

    • Reply Lindsay Durrenberger January 27, 2015 at 8:45 am

      Also “Quitter” by Jon Acuff is a great book resource if you’re thinking of switching things up. He essentially says the same thing. :)

    • Reply Roo January 27, 2015 at 8:53 am

      You’re welcome, Kate! Lots of luck to you!

  • Reply Katie S. January 27, 2015 at 3:54 pm

    LOL, “maybe you can totally focus when throw pillows are whipping past your head at impressive speeds”… Roo you never fail to entertain me! Thank you for making important information fun to read!

    I had my hours cut way back last year as an Office Manager, and while job hunting I filled my spare time with anything anybody would pay me for (planting flowers for seniors, making Shutterfly albums for busy mom friends, etc.) and have since decided that I would like to have my own Personal Assistant business versus going back to the corporate admin world. The transition has been a bit crazy, and I’m always learning along the way, but it’s posts like this that remind me to keep chugging along and that I’m not alone in my endeavors. Thank you for the fun – and information – you provide us readers. =)

    • Reply Lindsay Durrenberger January 28, 2015 at 4:53 pm

      Hey Katie! I’m a 9-5er right now, but with baby #2 on the way with no paid maternity leave options I’ve been doing some virtual assistance work on the side to try and save up some money. Would love to pick your brain if you have any insights/connections!

      • Reply Katie S. January 29, 2015 at 2:46 pm

        Hi Lindsay! Congrats on baby #2! I haven’t actually done much Virtual Assisting because I’ve had people who need in-person help more, but I’ve wanted to get more into it. From what I’ve gathered so far Elance.com and Odesk.com seem to be the most legit sites for VA’s, but I’ve been hesitant due to the low hourly rates we compete with overseas and I need to build up my profile. So, I’ve actually been brainstorming ways I can approach local small businesses and see if there is any work that they need done that could be done virtually or for small periods of time once a week. I’d love to keep in contact and share ideas, so add me on Google+ or email if you’d like: kmsoule at gmail dot com =)

    • Reply Roo February 1, 2015 at 8:28 am

      Look at you hustling! So impressive. I feel like so many people would just feel completely disheartened in that scenario and you just found ways to make extra income. Very cool. Good luck to you, Katie! :D

      • Reply Katie S. February 2, 2015 at 2:44 pm

        Thanks Roo! I did, and still occasionally do, feel disheartened about the scenario, but my hesitancy to go back out there and hunt for something new showed me that something definitely wasn’t feeling right about the direction I was headed. I still have random income and don’t turn down many opportunities, but I’m starting to get to the point of feeling more confident in my abilities and how I want to spend my time so that it can work for me instead of me working for “it.”

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