When Working Remotely Doesn’t Work Anymore


You may have seen the recent announcement that I have been promoted to Operations Manager with Outspoken Media and am moving to Troy, NY to join the rest of the team. It’s a great opportunity for which I’m very grateful, and about which I’m very excited, but it doesn’t come without a little trepidation, and a lot of change.

I stumbled into Web writing in September 2008, and have been working from home ever since. I’ve had the dream setup for many writers, and, for the most part, it’s been fantastic! I could sleep late, my dog could spend most of the day lying at my feet, I had a lot of control over my work environment, and my interaction with people was limited to IM, e-mail, and the occasional Skype meeting.

But now I’m giving it all up.

Why would I give up working from home and move nearly a thousand miles to do it? Because working remotely just wasn’t working anymore.

This scenario is one many Web workers will face at some point in their career. When does it makes sense to work remotely and how do you know when working at home just isn’t working anymore?

Let’s take a look.

Why Working Remotely Works

I’m not here to bash the practice of working from home, and tell all you pajama-wearing slackers to get dressed and go back to the office. Telecommuting works just fine for a lot of people and offers a lot of advantages, not just to the remote worker, but to the employer as well.

Employee Benefits

Other than the ones I’ve already mentioned…

  • Tax Deductions – Some companies may cover part of the expenses you incur when telecommuting such as electricity and Internet service. But if they don’t, you can deduct a portion of those costs from your taxes. I’m not an accountant, so check the IRS rules before you start going deduction-happy, and saying I told you it was okay.
  • Saved Money – If you work outside the home, you may grab breakfast or at least coffee on the way to work, and then maybe grab a sandwich for lunch. Add it up. How much are you spending on meals every week? You could save a lot of money working from home and eating at least two meals a day there. I do.
  • Less Spending on Gas – With gas prices being what they are, any opportunity to avoid driving means money saved.
  • More Free Time – I work at least eight hours a day, every weekday, sometimes more. But I still take breaks, and it only takes a few minutes to throw a load of clothes into the washer, clear the sink of dishes, or even vacuum one room. Every task I get done during the week is one less chore that has to be done over the weekend, which means more free time!

Employer Benefits

  • Less Overhead – Every employee in the office contributes to your overhead costs, whether it’s the electricity for their computer, the space for their desk, or the water they use throughout the day. Having an employee work from home reduces those costs for your business, especially if the employee covers the expenses, and then takes tax deductions.
  • More Space – If office space is at a premium, and you’re not ready or able to move into a larger space just yet, having even one employee working from home means the office is less crowded. When people work in too-close quarters, it can wear on their nerves—and their morale. People need space to work and feel comfortable. Whether it’s a full-time remote employee, or everyone takes turns working from home, having enough space for your employees will increase their comfort, thereby increasing their productivity.
  • Access to a Wider Talent Pool – Whether you’re not having any luck hiring locally, or there’s just someone you really want on your team who lives in another city or state, being open to having a telecommuter on staff will allow you to bring a talented person on board without the cost of relocation.

Working as a remote employee of Outspoken Media, I was able to take advantage of many of these benefits. And it worked great while I was managing content creation. It’s easy to write a blog post or an article, and e-mail it in on deadline, or sit in on a meeting via Skype to help create link development strategies for clients.

But the company’s needs changed.

When Working Remotely Stopped Working For Me

Up to now, Rhea and Lisa have been managing both the business and the employees. While they’ve done a fantastic job, it’s difficult to put out fires when you’re trying to speak at a conference, or deal with client budget issues while trying to put together proposals. They wanted to add a middle manager to the team to help streamline communications, improve time management, and let them focus more of their energy on the continued momentum of the business. To create the most seamless transition possible, they decided to promote from within.

They promoted me.

And that’s when working remotely stopped working. I knew to fully accept this new position I needed to be in the office and to work more closely with my team. The thing is, it’s difficult to manage projects, and even more difficult to manage people when you’re not in the office every day. I needed to be there.

This is why I’m giving up the cushy home office, packing up my belongings, and moving my family from South Carolina to New York—to help the company I love working for continue on its path to success, and to put myself in a position where I can continue to grow.

So, what about you? What should you do when working remotely doesn’t feel like it’s working anymore?


  • Think long-term – If your company offers you a chance to move up and take on more responsibility, you need to think about the long-term. Moving itself is never fun, let’s be honest, but if it puts you in a better position now, and will possibly present even more opportunities later, think hard before you turn it down. Also remember that just like office expenses, some relocation expenses may be deductible, if they’re not covered by your company.
  • Consider salary caps – If you’re content with working remotely, and don’t want to uproot yourself or your family, there’s nothing wrong with that, either. Just know that you may reach a point where you can go no further in your current job, which may also mean your salary will reach a cap.
  • Demonstrate value – If you’re not being valued, or you’re not given the chance to grow in your job—whether remotely or in-office—you may need to consider a change. Working remotely does present challenges, but if your current employer is content to let you stay right where you are, and gain a lot of benefit without giving much back, you’re with the wrong company. Telecommuting doesn’t work without respect and consideration on both sides.


  • Consider all staff – Once you’ve identified the need for a middle manager to help grow your business, don’t discount your remote employees. It may take a little time to work out the details, as well as some creative logistics—and yes, possibly some expense—but if you already have someone with the experience and knowledge on your team, use that resource before you try to create a new one from scratch.
  • Consider helping with relocation – If you offer a new position to a telecommuting employee that will require them to relocate, be ready to assist them. Relocation assistance is wonderful, if you’re able to offer it. But helping with house hunting, or being on the lookout for jobs for your employee’s spouse can also go a long way to letting your employee know how much you value them, and making them feel welcome in their new city and workplace. (I can speak from experience and say that this kind of above-and-beyond assistance also reduces the stress of moving quite a bit, and I couldn’t be more grateful for it.)
  • Be prepared to hire new, if necessary – Bear in mind that it may not work out. Your remote employee may not completely fit the bill for the position you’re trying to fill, or they may not be willing or able to move. It’s still the first place to look when it comes time to expand your staff. If it turns out your remote employee(s) need to stay where they are for whatever reason, start interviewing locally.

The main thing is, both employer and employee have to decide what works best for them. If you’re not comfortable hiring someone to telecommute, don’t. If you have trouble turning the TV off and motivating yourself while working at home, stick with the office job. Working remotely doesn’t always work for everyone. But if you do get involved in telecommuting, either as an employee or an employer, it will work best if both parties remain flexible, become champions at communicating, and most of all, recognize when it’s not working anymore so you can fix it and not lose a great employee, or give up a great job in the process.

Your Comments

  • Michael Dorausch

    Congratulations Michelle!

    The move not only says something about your commitment to OSM, it says something about the seriousness of the organization as well.

    All the best to everyone at Outspoken Media.

  • Sully

    Love this – even though working remotely is super easy & cheap these days, it isn’t always the best fit. While technology is making communication easier, it’s still impossible to re-create the organic conversations that occur in the office.

    These types of spontaneous meetings are critical for growing companies like OSM, when a lot of the “corporate DNA” is still being developed.

    I hope you like Troy! The Ruck makes the best wings. In the world. #FACT


    • Michelle Lowery

      Thanks, Sully! Working remotely is fantastic for the right kind of work. But yes, there’s a lot to be said for the camaraderie that can only be built by interacting with your coworkers on a daily basis. I’m really looking forward to getting to know everyone a little better, and being a more integral part of the team.

      And The Ruck…got it! It’s now on the list of places to check out! ;-)

  • Emily Suess

    So happy for you, Michelle, and for everyone at Outspoken Media. Here’s hoping the move and the transition go smoothly!

  • Rhea Drysdale

    This is something the company has wanted for a long time and it finally made sense for Michelle and her family. We’re ecstatic to have them join the office in Troy. This is going to benefit us, the team and clients. Captain Planet style — “let our powers combine! Go Outspoken Media!”

    Michelle, also loved the breakdown. To your point, there are positives and negatives to everything, but we’re proud to have you here and see Outspoken Media growing in this direction. Feel free to move up tomorrow. ;)

    • Lisa Barone

      Does everything have to involve cartoons and super heroes?

      In case you’re wondering, THE ANSWER IS NO!

    • Michelle Lowery

      John and I are both very excited about the move, and I’m very excited to join the rest of the team! Yes, everything has pros and cons, it just becomes a matter of balance. Once the cons outweigh the pros, it’s time for a change. And if I could move up tomorrow, I would!

      Also, yay Captain Planet! You know I’m looking forward to helping with recycling efforts once I’m in the office. ;-)

  • Lily @Merchant Cash Advance

    Best of luck in New York! It sounds like you made a wise career move – and you won’t be upset with living in one of the best cities in the world :)

    • Michelle Lowery

      Thanks, Lily! I agree, this was a really good choice. Also, I’ve visited Troy twice this past year, and loved it! My husband and I are looking forward to getting to know the Capital Region better.

  • yankeerudy

    Working from home can be convenient, but I’ve always said the biggest problem with it is that you live at your office.

    Congrats on the promotion, and good luck in your new (work/home) environment.

    • Michelle Lowery

      Thanks so much!

      Yes, it can become difficult for a lot of people to separate work from home, but I found this was exacerbated by working from the sofa. :-) Once I set up a spare room as an office, and made it pretty much off-limits during non-work hours, it got a lot easier to leave work behind at the end of the day. I highly recommend that for anyone who works from home.

  • Lisa Barone

    If I can be serious for a moment (don’t worry, it’ll pass), your decision to move to Troy to be closer to the team is one of my proudest moments running Outspoken Media. It says a lot about your commitment and, I hope, to what we’ve created here. We’re truly blessed to have the team that we do, both in yourself, Sabre, Danika and the others coming on board. Thank you for believing in what we do and doing what you can to help us do it even better. Our clients (as well as me and Rhea) are really lucky. Really, thanks.

    • Michelle Lowery

      Aw, Lisa, you just made me tear up! It does say a lot about what you’ve created, and continue to strive for, and it’s something I’m grateful and happy to be a part of. I feel blessed to have you and Rhea working so hard to continue to build something we can all be proud of, and be successful in. Not only that, the care and concern you and Rhea have for all of us–both personally and professionally–is readily apparent, and that’s really what I’m most grateful for. Thank you.

  • Nora Chiong

    Mish – FANTASTIC article and you know I can relate! :) So very proud of you and wish you and John all the best in NY. Lisa and Rhea are about to find out what an amazing decision they made in promoting such a talented and organized individual!! You are going to ROCK this!

    • Michelle Lowery

      Ok, first, I SWEAR I did not pay Nora to write this! :-D

      Thanks so much for the support and encouragement, not only now, but always. And we are definitely doing a weekend in NYC! Plan on it!

  • Kathy Lisiewicz

    This does a great job of summing up not just the pros and cons, but why telecommuting does and does not work, depending on circumstances.

    For me, the answer is in the middle. I very much like the interaction of being in an office, but I also really like to be able to work from home one or two days a week. That way I can be on-site regularly to form those relationships and do the work that is best done from the office, but still have those highly productive days with few interruptions and no commute.

    • Lisa Barone

      I’m with you. In my ideal picture, I’d be working in the office 2-3 days a week and working remotely (from a coffee shop) the rest of it. I may actually start taking more “off” days once we get all the new employees in and settled. There’s something to be said for changing up your environment and working where you feel are fewer interruptions.

    • Michelle Lowery

      Thanks so much, Kathy! I think what you’re describing may someday become the norm for a lot of companies. Not only does it offer the best of both worlds as far as office interaction and productivity, but becomes something of a perk for the employees because it give them more flexibility, and more free time. As I said, even just having fewer loads of laundry to do on the weekend helps a lot! :-)

  • Ryan Christensen

    Not to be a debbie downer (I most certainly see *some* value in physical proximity) but I’m curious where specifically you found the struggles to be in working/managing remotely in this case?

    You say that being remote stopped working when you were promoted to the position of managing other staff… could you expand on that? I’ve managed the work of remote people, as well as been remote managed myself (in both large and small organizations — all with great success — over the last many years.) My experiences seem to tell me that if there’s a problem with remote management it’s generally either: a deficiency with the managers skill set (slash ability to manage effectively & communicate with their workers), or the employees inability to do a given job without micro-management.

    I’m certainly not saying either of those is necessarily the case here… I guess I’m just wondering what the conversations were that led to this. You have some truly excellent points in the post, but the actual decision is glossed over with a “I was made a manager of people, ergo I felt I had to move,” without detailing why exactly remote working stopped being an option here, or what work requirements add such value the physical proximity (beyond the ability to run into each other in hallways.)

    On that: other comments mention “the camaraderie that can only be built by interacting with your coworkers on a daily basis” — and I wonder if I’m an edge case… because I seem to find this rather easily with my virtual teams (even when we’re occasionally in the same physical location… it’s not as if we somehow get more productive, or our relationships more friendly.)

    To sum up, I guess I’m saying the vibe the article gives me is “remote work is great, but if you’re made a people manager, you need be in the same physical space,” and that logic doesn’t quite make sense to me…

    Thanks in advance for any insight, and congratulations on the move!

    • Michelle Lowery

      Thank you for your comment, Ryan. It’s always interesting to see other people’s perspectives on things!

      I’m sure you’ll agree that everyone is different. Just as different personalities respond to different management methods, all managers have their own management style, and what works for one person may not work for another. This doesn’t mean any one method is wrong or better. Just different.

      This decision was not made without a lot of discussion, thinking, soul searching, more discussion, and more thinking, both on my part and that of the company. A lot of things led up to it, much more than just the promotion.

      I don’t think that remote management not being the ideal option in one case becomes a black-and-white matter of either the manager’s deficiencies or the employees’ need for micromanaging. On-site employees are managed every day without the need for, or existence of micromanagement. And as you said, there are many successful instances of remote management. I’ve taken part in both remote managing, and being remotely managed as well, also with great success. The past year I’ve worked remotely with Outspoken Media is just one example of that success.

      No remote working situation—no working situation, for that matter—is without its gray areas. I may not have made it clear enough that, in this particular case, based on our experiences prior to this promotion, and where we want things to go, it made sense for me to be in the office in order to be more hands-on, and assist directly not only in the management of employees, but the growth of the company. Something else I didn’t mention at all is my desire to learn more about our industry, and the methods we use to serve our clients, and I feel I can do that better by actually being there. There’s an element of personal growth as well as professional.

      Although my own situation was the impetus for this blog post, it’s my hope that our readers will wonder less about why I made the decision I did, and focus more on the actionable points, and how they may relate to their own situations. It’s always our goal to try to relate to our readers, but we also know it’s going to be impossible to relate to every single person out there because, as I said, everyone is different, and every situation is different.

      Thanks again for your comment. I wish you continued success in your endeavors!

      P.S. Don’t tell Lisa and Rhea, but the real reason I wanted to move to Troy is to have regular access to the Heath Bar lattes at the Daily Grind! ;-)

      • Ryan Christensen

        Thanks for the great reply! I think you’re spot on with:

        …it’s my hope that our readers will wonder less about why I made the decision I did, and focus more on the actionable points, and how they may relate to their own situations.

        I definitely didn’t want to change the topic of conversation too much w/ my inquiries… as what you’re describing is absolutely what people should be taking away from this.

        • Michelle Lowery

          You’re very welcome! Thank you for the thought-provoking questions. I think it’s only natural for people to wonder why someone would make such a big move, and how other businesses are managing their success and growth. Nothing wrong with that. We all have to do what works for us. :-)

          Have a great weekend!

      • Rhea Drysdale

        pssst — we already knew this. ;)

  • Alan Bleiweiss

    What did I do when it didn’t work for me anymore? I packed up and moved 750 miles north. :-) I’m happy to say, that after more than two months here, I’m still pretty excited and happy. so the good news for you is you probably have at least as long as I do to enjoy the honeymoon period of the transition. Since that’s ALL I’ve been here for, I can’t guarantee that either of us won’t be completely miserable after 3 months in the new role. :-)

    Then again – if we are, we’ll have each others shoulder to cry on. #WIN

    • Michelle Lowery

      Good for you, Alan! I’m so happy for you, and so glad you’re happy. I hope things continue to work out for you! I’m confident I’ll still be happy after three months, and beyond, but if you’re not, Troy’s a nice little city! ;-)