The Freelance Life: Leaving the Home Office for the Real Office

When I was first offered the position, a long-term freelance gig writing health-related content for a big-name Manhattan institution, I hesitated. A steady paycheck would be nirvana but could I handle this one daunting specification? “Writers are required to attend in-person weekly staff meetings,” among other on-site requirements.

On-site? You mean out of the “comfort” of my office, by which I mean the small table I sit at, alone, in my bedroom? And I’d have to be somewhere at a certain time — 9 AM Mondays, to be exact . This would add a whole new layer to my morning routine, something called “caring what the hell I look like when I leave the house.”

After much deliberation I decided, after nine years of working from home, that it would be good for me to break out of my hermit-like routine and get out amongst the people. Today was the first day in the office, and from the minute I walked out the door I realized why people get that jealous look in their eyes when I tell them I work from home.

The shocks, surprises and reminders came in rapid succession. All are manageable, but only if you are prepared for them. So here are 13 tips to help you transition from home office to the  corporate life

  1. You need to wear shoes. And you have to keep them on all day. This is non-negotiable. As such, you will have to walk in shoes. Possibly for long distances. This will be an affront to your soft, widened-over-time feet. So throw a Band-aid in your bag. If you decide to wear heels, pack a whole box
  2. How you smell now matters. And you definitely want to do something about that hair (keeping in mind that borrowing your daughter’s scrunchie is fashion suicide, and that “fashion suicide” is a thing you should care about). Lipstick is a good idea too.
  3. Decide which of your two “Suitable for the Workplace” outfits you will wear. Hint: The wool suit will kill you in any month between May and October. And make sure the day’s high is over 70 before daring to bare your legs. Also, it might be time to stop being so cheap and spend some cash on work duds.
  4. You have little control over your commute. You’re used to your “drive time” taking as long as it takes to walk from your bed to your desk. Now, however, you are at the mercy of forces you cannot control: mass transit and/or traffic. So even if you leave 15 minutes early, as I did, expect you will be late, as I was. Instead, on your first day, leave an hour early so you can accurately figure out how long your commute really will take.
  5. You’re a worker now! It’s rush hour, and at some point you’ll find yourself one in the mass of people moving in one direction, filtering into various office buildings. Your pace will naturally join that of the crowd. You’ll look around and soak it in — the energy, the sense of purpose — and feel energized. (You’ll also spy the young women in flip-flops and have an “aha!” moment.)
  6. The assumption is you’re a possible terrorist. Enter most New York City office buildings and you’ll be stopped before you hit the elevators. You have to sign in. You might have to show ID. You might even have your bag searched. If you haven’t worked corporate since before 9\11, as I haven’t, this will be a somewhat creepy shock. The world has gone crazy, and in doing so has added an extra 10 minutes to your commute.
  7. Social Media is no longer considered “work.” Once you arrive for your on-site work day, you cannot fall into your normal routine. Meaning, you cannot spend the first hour scanning Facebook and Twitter, not even under the guise that “being socially aware is key to my marketing strategy.” All the client would see is a contractor who is completely ignoring them, while on their dime. Not smart.
  8. Meetings! They will remind you of why you left the corporate workforce. When you’re used to working alone, and working fast, sitting in a room with 12 people staring at a Powerpoint makes “Freelance You” think: “What a waste of time. This is killing my hourly rate!” But here’s the bonus: Like a real job, you’re now being paid to just sit there. So relax back in that swivel chair. And chuckle over the fact that you’re being paid to sit. But then remember to…
  9. Stay awake! Loud, gaping yawns are a statement unto themselves. Learn to stifle them.
  10. You’re on another schedule now. If it’s 10:30 and you’re hungry for lunch, suck it up. Your kid waits for lunch period at school, and you’ll do the same in the workplace. Same goes with quitting time. You leave when everyone else leaves. This will drive you insane at first, this lack of control over your own time. But remember: Steady Paycheck.
  11. “Lunch” is a thing. It’s a specific portion of your day, devoted solely to taking a break and grabbing a bite. It’s something you do separate from working. You might even leave the building, go shopping and eat something you did not prepare. And it might be really yummy.
  12. The unmentionables. You cannot do any of the gross things you do while sitting alone in your home office. You know what I’m talking about. Figure out how to manage it.
  13. Which leads to… You will have to use a public restroom, which is a reminder of the most overlooked perk of working from home: a private loo. Consider this when deciding how much fiber to have in your breakfast and how many cups of coffee to consume.

But even after all of these shockers, my day in corporate America was an invigorating experience. Bouncing ideas off of others, hearing others voice their experiences — it’s a third dimension that is all-too-often lacking in most solopreneur enterprises. So if you have the opportunity, get out of the office. Only do it in a pair of comfortable shoes.


  1. As someone who has very recently made the transition back from freelance to the in-office world, and now shares an bathroom with about a dozen dudes as well as women (!!), I so related to this! But that steady paycheck though…. 🙂

    • Yup, a check that comes every two weeks?! I am giddy at the concept. I’m curious to see at the end of this how I feel about work-from-home vs. something more collaborative. Hmm… stay tuned…

      • For me, I’m extroverted enough that being alone all the time (and I was bad about scheduling lunch dates/in-person interviews, etc.) actually became MORE exhausting than being in an office. Here’s hoping you find your perfect balance!

  2. You captured it all, Cynthia. It took me two hours to get in this am; looking at mass transit, travel mugs, and iPods now. Good to see you today–and every week for 2014!

    • Great seeing you too Jen! It was so great to see a familiar face. And we get to do it all again tomorrow!

  3. I put on shoes, wear office-appropriate clothes, spray on perfume, and sometimes even put on makeup, to work at home. I use it all to mentally prepared for the work day. But, the whole spending the first hour checking FB, Twitter et al? That would be tough to cut out. And sharing a bathroom? The worst. At least for you it’s only once a week, so you get the best of both worlds.

    • I put on makeup everyday regardless of where I’m working, mostly because I get depressed looking at myself in the mirror otherwise. But I have to admit that getting dressed up felt very good. I’ve been too frumpy for too long.

  4. You guys are shaming me! Makeup — alone at home?! For a Skype session, yes. Perfume, always.

    Cynthia, follow the savvy practicality of our friend Salley Shannon, (who recently saved me from a bad heel blister) — cut strips of moleskin (what dancers use on their toes) and carry them, bandage size, in your purse. Bandaids slide right off, but moleskin (soft fabric w/ adhesive back) won’t.

    I would also add (not that you need this) — keeping a fresh manicure and pedicure in sandal season! The most depressing part of joining the commuting herds is people who have no basic understanding of good grooming. You see a lot of things you wish you did not have to.

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