Meet Dana Doswell: Her own boss and founder of an entirely remote company. Learn how she’s building two businesses from the comforts of coffee shops and her own kitchen.

Fast facts about Dana

• She’s been working remotely for one and half years
• Dana spends half her time in Latin America and half her time in Canada
• Her second business project, Dozzy Inc, stemmed from a desire to learn Spanish to fully immerse herself in the language

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Before we dive in, can you tell us a bit more about yourself?

I always knew I wanted to run my own company and initially went to university for accounting and finance with the goal of starting my own accounting practice. Once I started in the real world I realized that remote working was really important to me, and needed to change careers to have this. So, I completely switched careers and went to work in sales at a tech startup in Toronto. While I was working there, I started a digital consulting firm on the side called Sidepart. About a year and a half ago I stopped working at the tech startup and started working full-time at my digital consulting firm with my business partner. Since then, I’ve worked remotely in Latin America, India, and Canada. 

While building the Sidepart business here in Toronto, I started learning spanish and really wanted to fully immerse myself in the language so I moved to Latin America for a few months – splitting my time between  Mexico and Argentina. That’s where I began a second project called Dozzy Inc that teaches Latin American companies how to expand their businesses digitally in North America. 

What’s in your tech stack?

Slack, Zoom, G Suite, Zapier, Toggle for time tracking, Dialpad voice system which allows you to text off phone for different phone numbers. What might be unique to my tech stack is we use WhatsApp for international communication. It’s really great for creating smaller employee groups.

What’s your biggest challenge working remotely?

Habit building, 100%. Here’s a great, albeit harsh example of what I mean by that: The day I quit my full-time job, I gave my notice on a Friday and started working full time on my business the following Monday. I woke up that morning and got so overwhelmed by how much I had to do (and didn’t know how to) that  I cried and went back to bed. I had no habits, no routine, and no way of prioritizing my time. One thing to do before getting into remote work is to ask yourself what your habits are? Do you have a work space? Do you have a quiet place where you know you can be focused? It’s so important to create habits that facilitate your own personal productivity. 

What’s the biggest advantage of working remotely?

I’m a bit biased, but for me it’s the travel component. When you get exposed to different cultures, you can see problems in a whole new light. In different countries, people live in a completely different way. They address problems in different ways and you can learn from those different approaches and apply them to business problems.

People talk about flexibility, but what remote work really does is it really makes you feel like the  company trusts you more. When you’re just in an office to be seen, regardless of whether or not you’re actually productive at that time, there’s a lack of trust.  I remember a time working in accounting where I was literally told to sit at my desk, and do whatever I wanted until the executives left. I could be watching Netflix, just so long as they saw me staying there after the execs were leaving. Giving people the ability to work remotely makes employees feel trusted, empowered, and in the end you’ll get better results from that.

Another advantage is the potential long term impact on your physical health when suddenly that 45 minute commute there and back to the office is now spent exercising instead. For me, that commute was the difference between me being able to do yoga twice a week and not. I’ve personally seen the physical and mental benefits of that change for the long term.

Where do you actually work?

Right now I’m in Canada and am moving back to Mexico soon for 6 months. Because my position is primarily sales and workshop facilitation, I need a quiet space. About 60% of the time I work from home and  use the kitchen table because I’m messy and need lots of space! If I’m going writing or content, I go to a cafe because the noise helps me go into total concentration mode. I’ve also discovered on meetup, a group that comes together and does the pomodoro technique. It’s sort of networking and working all in one.

How do you start your work day?

I’ve iterated on this over the past year, but Monday to Friday I get up between 5:30 and 6:00am meditate for 20 minutes and I have a journal I write in, where I identify 3 things I need to do to move the needle that day. Then I usually read for 30 minutes – and this is one of my favourite times of the day. For the first hour or so of the day, I’m technology free in order to focus on prepping a good mindset for the day. After the hour, I cook breakfast or workout. Then, I dive into work. I start with the number one thing that needs to get done, then work my way through the other two. Before I got into this routine, I read a lot about what different leaders’ routines were and figured hey, if it works for them, maybe it’ll work for me.

Would you ever go back to working on site?

Yes. But the way that I would do that is if I was able to build more of a community. What I mean by that is, I don’t work well in really long stretches. There’s this stigma around startups and ping pong tables and that’s not what I mean by community. What I mean is talking about meditation and integrating mindfulness into the way we work. I like co-working spaces for that reason, but I also believe in having your own space. If I were to go back to an office, it would be built around having that type of open community.

What’s one piece of advice can you give to someone who is about to go fully remote?

I have two micro pieces:

1. Develop a morning routine. 100%. Build the habit.
2. Find somebody, and this person does not need to be in your company, who is also working remotely. Have a bi-weekly or monthly call about remote work. Or meetup to work together, where you can support each other. This is a must-have that will keep you sane and also productive.

Do you feel like being remote hinders your career growth in any way?

I did when I was at the other startup. I find that when you get together a group in a large setting, you do miss out on social interaction. Now that I’m responsible for setting the culture and tone, that comes from the top. There’s a difference between talking and showing. I’m always trying to think about this, so this is something my team isn’t feeling as remote workers.

On the topic of loneliness, do you ever feel lonely or isolated working remotely? If so, how do you combat it?

Yes, and this was actually the biggest thing I struggled with for the first month. My advice would be to find multiple people that you can socialize with after work. It’s easy to just stay in your house all day. Create your morning routine, and say to yourself every week I’m going to make social plans after work hours on Wednesdays, or Thursdays – whatever is best for you. 

How do you build a remote culture?

I think it’s important to still have a similar schedule as if you were at an office. I always do two one-on-one calls each week. One is dedicated to “How are you doing mentally, and what other areas you want to work on in the business?” And the other call is to discuss operational and work stuff. It’s important to have both. Having mental health support and work conversations are tangible strategies that will help employees stay engaged and healthy. 

Final thoughts?

1. The ability to work remotely  has been crazy for my career growth because of the perspectives I’ve gained from traveling. Use that to your advantage. If you have the opportunity to travel and experience different cultures, take the opportunity. 
2. Figure out how to structure your days. I use a daily planner, bestself.co. I’m obsessed with it. It’s based on productivity and habit creation. I structured my day around that. Also, read the book Atomic Habits by James Clear. Get excited and then use the book to help keep yourself in line.

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Learn more from remote leaders like Dana:

• Remote Leaders: Why GitLab’s Head of Remote “unchained from a life of commuting”
• Katie Womersley, VP of Engineering at Buffer, on managing an entirely remote team

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