Deborah Simmons
Founder and Director
May 18, 2020

Interview with Deborah, a remote entrepreneur changing perceptions about remote work

Deborah has traveled the world sharing her research about the pros of remote work. See how she is helping companies and clients understand the importance of location independence.

How did you get started with remote work?

This interview was conducted before the COVID-19 outbreak, so the answers convey travels and events that happened prior to lockdowns and travel changes.

I started my own consumer insight business almost seven years ago, so in a sense, I've been working remotely (part-time) since then, but I feel like my true 'remote' journey started three years ago when I spent just over a year living as a digital nomad with Remote Year.

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What are you working on?

I'm currently working on a couple of client research projects - one for a charity and one for a global TV network (so the work I do can vary quite a bit, but it's what keeps it interesting for me).

As well as that, I am continuing to work on what I'm most passionate about at the moment —and that's becoming a remote work consultant and advocate.

I've experienced—and am still experiencing, first hand—what it can be like when a project ends up being awarded to someone else—not because I'm not capable of getting the job done—but because the client doesn't feel comfortable with me working remotely.

Early on in my foray into remote working, it became very apparent that this is a real issue faced by remote workers—and digital nomads in particular. With this in mind, I spent much of my Remote Year experience conducting a longitudinal research study into the digital nomad movement and the trials and tribulations of remote working.

The purpose of it was to help people to understand the lifestyle, the motivations, the benefits, and the challenges so that businesses designing for this audience have some solid insights to design around.

It's aimed at start-ups, developers, coworking and coliving spaces, and travel companies like Remote Year. I've also today been invited to be a keynote speaker at a conference focusing on trends in urban design in Helsinki later in the year.

Since returning, I've continued my work in this area and am now about to launch a series of workshops to support businesses making the transition from a traditional office-based model to a distributed (remote) model.

There is still so much hesitation and misperception around remote working, and I am committed to being a force for change. It's something I believe in so strongly—for the benefit of the business and the individual.

There, I'll get off my soapbox now.

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How do you stay on task?

By design, I generally enjoy my work, which means that it's not too difficult to stay on task. That said, when it's one of those times that my attention span is short, rather than force myself and not be very productive, I'll go away and come back to the task when I am ready to.

I may also give myself a deadline with a reward, i.e., work on this task solidly for an hour, and then I can do something I really want to do, ahem, Netflix hehehe!

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What do you like about remote work?

Having the freedom and flexibility to work where and when I am at my most productive. It helps me to enjoy my work more, which is good for me and great for my clients. Unfortunately, they don't always see it that way, though, but that will change, I have no doubt.

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What do you not like about remote work?

That the word 'remote' has too many negative associations which colour people's perceptions and judgments... and that there's a minority out there who abuse it and give the rest of us a bad reputation.

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What tools do you use to stay productive?

  1. A Roost laptop stand and separate keyboard so I can work comfortably for long periods.
  2. Noise-canceling headphones so I can listen to music or to my interviews without disturbing coworkers, and so I can block out noise that's distracting me
  3. When I'm in the analysis stage of a project, I also love to have some magic whiteboard sheets that stick to the wall or window using static and are reusable. I find these useful to jot down my thoughts or ideas as they pop into my head as I'll be percolating away regardless of whether or not I'm actually working at the time. My windows at home always have at least one or two sheets with random thoughts scribbled on them. One of the projects I'm working on at the moment is health-related, and I made some notes about it causing 'relationship issues' on my whiteboard. My boyfriend came round and was trying to decipher my notes, and he thought I'd been writing stuff about him.

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Where do you conduct your work?

Ah, well, there is no simple answer to that question. Sometimes I work at home in London, sometimes at cafes or coworking spaces, sometimes from wherever I happen to be nomadding at the time... and then there are clients who prefer me to work in-house with them.

I try to build as much flexibility into contracts as possible, but there's still a lot of work to be done to build enough trust with clients that the work will still get done to the same standard if I am not sitting at a desk in their office.

When I started writing these responses, I was sitting on a train heading back to London from Glasgow, and as I finish them, I am on a yoga retreat in Costa Rica. Tough, I know.

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What about your space helps you to be productive?

It totally depends on my workstate at the time (see my conference paper on digital nomad workstates for more info). I've worked in so many different workspaces around the world, but the ones that always stand out in a positive way, are the ones that really understand the needs of their clients.

Generally, for me, this means:

  • Lots of natural light
  • Comfortable chairs and comfy areas
  • Clearly defined social and quiet working areas
  • A genuine desire to build a community by hosting relevant events
  • A steady supply of health (and less healthy) snacks and drinks so that I don't have to lose my flow when I'm working on projects that require deep focus.
  • I don't need to make too many calls but... DECENT CALLROOMS, folks! Whether you're using them or sitting near them, if they're not fit for purpose then everyone suffers.

I also tend to gravitate towards workspaces that demonstrate they care about sustainability.

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What does your workday routine look like?

The truth is, it varies. When I'm at home, it always starts with fresh coffee and responding to the most urgent emails. I find I get started almost as soon as I wake up, and then I get around to showering and getting dressed at around 10.30, and then continuing with work.

If I'm going to be at home all day and can afford a bit of distraction, then I'll go for a walk or a swim on Hampstead Heath at lunchtime, or go to a cafe for lunch and to work for a couple of hours.

There's a dog pond on Hampstead Heath close to where I live, so sometimes I go there to dog stalk.

It's amazing what a cuddle with a furry friend can do for your day!

Otherwise, I go stir crazy and bounce off the walls (one of the most prevalent challenges for remote / home workers). If I'm traveling and in a different time zone, then it does depend more on my clients' needs. I NEVER have the TV on when I work, but I often listen to music or a podcast.

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How do you decide priorities?

Generally, if there's something I'm putting off or I have an uncomfortable feeling about something in the pit of my stomach, then that's the thing I'll tackle first.

It's never as bad as you expect it's going to be. Otherwise, it really depends on my deadlines and sometimes what I'm in the mood to do. Some days I feel really creative and can spend hours focused on a single task. Other days my attention span can be really short, so I'll do all my organising, emails, and other quick tasks that are still productive.

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How do you avoid burnout?

Such a good question. I'm not sure there's a one-size-fits-all answer for this.

As a small business owner, I'm aware of the tendency to relax a bit when I've got a lot of work commissioned and then go crazy on new business development when things are quiet.

I know this is not the best approach, though, because really I should be drumming up new business when I'm already busy. As an intermittent nomad, when I'm traveling, I always plan to carve out some time purely for work and some time purely for play. It doesn't always work out as planned, though as it can be really hard to switch off. My workflow fluctuates, so I do try to ensure that I give myself time to relax when I can.

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What are you looking to achieve in the next five years?

To firmly establish myself as a credible remote work consultant and to focus the majority of my projects on the future of work and urban design.

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What advice would you give to a new freelancer?

  1. Always have at least four months' worth of income in the bank.
  2. If you're not OK with living like a prince/ss one month and a pauper the next, it may not be for you.
  3. Try to have multiple streams of income (or passive income) if you are concerned about your workflow.
  4. Make sure you're doing it for the 'right' reasons (for you).
  5. Give it a chance, and if it's not for you, don't feel you've failed if you decide to go back to working for a company—there's absolutely no shame in that.

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What did we forget to ask Deborah Simmons?

At RemoteHabits we're always trying to improve our interviews, what question should we have asked Deborah Simmons?


Deborah Simmons

Deborah Simmons is founder and director of Camino Insight; a consumer insight consultancy that focuses on helping businesses to transition from traditional office-based structures to a more distributed set up.

Deborah’s foray into the future of work began in 2017 when she lived and worked for a year as a digital nomad in Europe, Latin America, and the US; conducting research into the movement as she traveled. Now, based back in London but traveling intermittently, she presents her research at conferences, coworking, and coliving spaces across the globe and conducts research into related business challenges.

Deborah’s background in qualitative and UX research means she always puts the user at the heart of every project, giving her a unique perspective and ability to generate fresh, vital insight.

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