In 2017, I was in the middle of career-planning with my manager. I worked at a media-tech startup in my hometown of Toronto, and this was one of our usual 1-1 checkins. But this time was different. She asked me what my career goals were, and she wouldn’t accept my generic answer of wanting to ‘make an impact.’ She pushed me. She refused to let up until I gave an authentic answer. 

Suddenly, I blurted out: “I want to detach my earning power from my physical location and literal hours worked.” 

With that one statement, I started on the journey of remote entrepreneurship. Shortly after that meeting, an up-and-coming startup founder in Toronto cornered me at an event, saying he loved my writing and asked “could I pay you to write for me?” I said yes, and my business – ghost writing and freelance journalism for tech startups and venture investors – was born. 

I ran my business as a side-hustle until January 2019, when I went full-time. Over the years of being part-time, I got to ease into the mental hardships of both entrepreneurship and remote work. I got lucky in the sense that I could anticipate and plan for any mental health issues before they became a challenge, while I still had a full-time salary and employer benefits. 

Now, I’m full-time remote and have learned a lot about taking care of myself, in particular finding 9 ways that work for me when it comes to protecting my mental health.

1 – I celebrate myself

In 2018, I started a habit of a small celebration every time I closed a client. 

At first, it was a latte from Starbucks, but I was already drinking a lot of coffee and didn’t need the extra caffeine.

Then I decided to upgrade it to a bottle of wine or scotch, but I realized that encouraged a lot more drinking than I wanted to do. 

Now, I buy myself a book every time I close a client. It fits with an intention I have to read 24 books in 2020, but more specifically it’s a gift that keeps on giving. I have a fiction book and a business book on the go at any one time so I can learn and expand my mind in multiple ways. It also feels fantastic to tie a form of self-care (buying and reading books) in with the success of my business. 

2 – I write to build community

One of the biggest issues with remote work is that you can end up feeling very isolated. As a writer, my first instinct is to write. 

So I started Remotely Inclined, a newsletter all about remote entrepreneurship. 

I built myself a platform to share my story to not feel alone. But perhaps more importantly, it’s a platform to connect with other people. I now interview other remote entrepreneurs (I call it Remotely Inclined Chats) and have connected with people from multiple different countries. 

3 – I focus on my professional development

If I was an employee working in an office, chances are there would be some form of professional development available to me, whether mentorship, internal workshops, or a budget I can spend for education. 

As an entrepreneur, no one is handling my professional development for me. And since I work remotely, no one is around to ‘catch’ me and recommend a certain path. 

So I focus on that for myself:

  • I regularly check in with mentors.
  • I read everything I can relating to my work (content writing, building a business, and remote work). 
  • I take courses (like Growclass). 

4 – I help others where I can

I’ve been very fortunate that my business has done well enough for me to live comfortably. While it’s not pulling in millions (yet!), I am in a position of privilege. So I give back: 

5 – I meditate

The simple act of breathing deeply and intentionally helps me find peace in my day. 

As an entrepreneur, lots can happen in a given day. But the ~15 minutes I take out to mediate really help me. I personally like The Deepak Chopra Center’s 21 Day Abundance Meditation.

6 – I avoid video calls

It sounds counterintuitive, but I’ve found that video calls are actually worse for my mental health in the long run. 

In particular, video calls:

  • Force you to be at your desk, not moving. 
  • Force you to be prepped and ready. 
  • Create anxiety about what my apartment looks like. 

On the flip side, phone calls: 

  • Allow me to walk around, pace, and feel comfortable. 
  • Wear what I want. 
  • Not worry about what my apartment looks like. 

7 – I compare apples to apples

Before I chose to focus on my remote business instead of looking for another job, I asked myself three questions:

  1. What upside do I want more – the security and growth of employment or the opportunity of entrepreneurship?
  2. Which downside am I more willing to tolerate – the politics of the workplace or the major swings of entrepreneurship?
  3. Which environment do I want – the pre-built, comfortable office environment or the build-everything-yourself environment of remote work?

All three questions made it clear that I wanted remote entrepreneurship. So I made the choice very consciously, which is something I remind myself of on the bad days. Yes, the bad days of entrepreneurship suck and the bad days of remote work also suck, but I made the conscious choice that I was more equipped to handle those bad days than to handle the bad days of being an employee. 

Comparing apples to apples helped me through the bad times.

8 – I start every day the same way

Remote work and entrepreneurship are the two work styles that carry the most uncertainty. Each day could be totally different from the previous and the next – and that’s something you just have to deal with. You can’t escape it no matter who you are. 

So what I do instead is choosing to start every day in the same way. For me, that’s:

  1. Making coffee (or buying coffee, if I’m travelling). 
  2. Sending myself my “Daily Priorities” email. 

In the Daily Priorities email, I have four categories: Run the business, Grow the business, Client work, and Personal tasks. Under each heading, I put the key things I need to accomplish that day. As I accomplish them, I cross things off the list. 

With this method, if I get pulled into a random direction or face an emergency, I can handle it then immediately get back on track by looking at one email. I also activate my own drive and motivation to complete things for the satisfaction of crossing something off the list. 

9 – I workout

Mental health and physical health are intricately connected. Not only is working out a way to keep my body in shape, but it’s also a break from the hecticness of the day. 

I don’t use my phone when I work out, so it’s a no-tech time. Instead, I use the time to focus exclusively on what I need and doing my best right in the moment. It helps me stay present, it helps me connect with my mind and body in a different way than deep work or meditation. 

Mental health is ongoing

I’m always learning, and sometimes things still knock the wind out of me. When that happens, I turn to friends and family for additional support or journal to write out what I’m feeling instead of having it on my chest. 

What I’ve learned over my years of being a remote entrepreneur is that the tactics for success are the same, but your foundation starts differently. 

In an office, you are provided an environment that you must work at to make your own. With remote work and remote entrepreneurship, you’re presented with a completely blank slate and you have to experiment and try new things until you find what works for you. However, I think that’s what makes remote work so powerful: everything is blank to start, so you have a choice. 


  • Stefan Palios

    Journalist and entrepreneur passionate about the people behind tech

    Stefan is an entrepreneur who has founded three businesses (one failure, one success, and his current one). He writes about diversity, innovation, and entrepreneur journeys, among other things. He's the founder of PulseBlueprint Publishing, an digital publisher focused on helping people solve workplace challenges.