Rosemary Richings

Showing up consistently and offering valuable resources to your target audience is a valuable way to build trust and relationships.


Rosemary Richings is a copywriter, editor, and content strategist for the web, based in her hometown of Toronto, Canada. However, she is also known for her love of travel, and will sometimes work far away from home. She works with a combination of e-Commerce and retail business owners, eager to use their products to improve the lives of their community. Her work has been featured on sites such as Buffer and Search Engine Journal, and she has worked with clients such as Yellowpages Canada and E-Bay. On an ongoing basis, she also produces content for her blog, Rosie Writing Space, and her podcast, People Behind the Business; both platforms are a source of guidance for independent business owners that need help with “putting themselves out there” without a large budget to work with.

Where did the idea for your company come from?

Back in 2009, I started my own blog, after I participated in an independent theatre festival. The interesting thing about that moment though is that I was so sad for it to come to an end, and I wasn’t sure why. After a day of just resting, I had this really important revelation. The real reason why I felt like I was losing something important wasn’t because of the art of putting on a play. It was because I was realizing the one thing I value the most: knowing that I helped form a community and start a conversation. So, on a whim, I started a blog.

At first, I wrote under a pen name that was just my initials and a nickname my family has used for years. But as time went by, this led to a series of events, that changed the entire direction of my life. What started as a few guest blogging appearances turned into not-for-profit blogging and content marketing experience; this taught me everything I know. Then, when I finished my undergrad, I suddenly found myself with no job, and no actual plan. You know that cliché saying: “life is what happens when you’re busy making other plans”? That’s what turned this into a business. I put up an ad on E-Bay and said that I was a writer for hire, and businesses approached me, expressing an interest in paying for content just like what I was already writing. This opened my eyes to one very simple fact: people need good content to stand out in a crowded marketplace.

They either don’t know how to do it themselves, or they don’t have the resources or time to do it themselves.

What does your typical day look like and how do you make it productive?

I split up my time between working from home and working from my co-working space, and it has been really, really good for me on both a professional and a personal level. Mondays and Tuesdays, I work entirely from home. Wednesdays and Thursdays, I work from my co-working space. Because I invested in the hot desk option, I don’t have to commit to just one desk. There’s even a spot with couches I use for creative work, where I really need to focus and tune everyone out.

On Fridays, I’ll typically only go to the co-working space if I’m recording podcast episodes or I’ve scheduled an important phone call or video-related appearance. Otherwise, I’ll stay home and do quiet but fun work, like podcast edits, emails, and content creation.

I also run really regularly. In between my military brother and my super fit parents, I’ve always been surrounded by people who encourage me to live a healthy lifestyle. And running is my activity of choice, thanks to a cross country coach I had when I was in elementary school who awakened my love of running. I prefer mornings for my run, because it does amazing things for my productivity for the rest of the day.

Another key part of my productivity is just how seriously I take rest. Saturdays and Sundays, I generally don’t answer emails or do any work, unless it’s something urgent like a prospective client asking for a project quote. I also don’t work after a certain time. Once it’s dinner time, it’s time to unplug for the day.

How do you bring ideas to life?

I’m a huge believer in just trying stuff, but I don’t pull the trigger and try stuff out, until I’ve sat down and converted the bigger picture of how it all works into a Trello board. Then, I talk it over with both my significant other and my family. Because they’re the voice of reason in my life. I always get the reassurance I need, if my small, voice of reason inner circle thinks that what I’m doing isn’t a bad idea.

What’s one trend that excites you?

I love the rising popularity of Facebook Groups. The idea of tapping into a niche, global community of people is exciting to me. Because I really love mediums that open up the world to like-minded people. But with all the scandal and etc. that happened with Facebook, it’s hard to know what the future brings. As long as some version of Facebook groups exists in the future, I’ll be totally happy with the way things are.

What is one habit of yours that makes you more productive as an entrepreneur?

I’m great at sticking to routines and schedules. So, once I developed well-organized systems for organizing various projects, I got clients who wanted to work with me more than once. I also figured out very early on what, if I automated it would save me time. I have everything from my weekly schedule, to my invoicing software connected to Zapier, my automation software.

What advice would you give your younger self?

You basically have two choices: be like everyone else and lead a life filled with regrets or listen to that instinct inside of you that wants to create and help people create. And if you pick option two, don’t keep to yourself so much. Because you’re not Emily Dickenson, and you likely never will be, and that’s okay! That was the biggest mistake I made early on…more specifically in my teen years. I naively assumed that being good at writing was all I really needed to survive in this world.

Since I was such a shy, socially awkward person when I was in school, blending in to the background was a bad habit it took me years to overcome.

Tell us something that’s true that almost nobody agrees with you on.

There’s so much more to life than just working. I mean…sure people need to make money, but I grew up in an environment where spending more of your life working than just plain living was celebrated. I think work and peoples’ personal life need to be treated like two, totally separate things.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

Taking time off for a day, a week, or morning is not something I apologize about. As I already mentioned, rest is sacred to me. When I need time off, I just take time off, and I wouldn’t trade that for anything. I think more people need to take that seriously too.

What is one strategy that has helped you grow your business? Please explain how.

The two most important elements of my business’s growth have been:

• My willingness to create custom, accessible content that helps people I want to reach
• And also, what really helps is my willingness to just keep talking to people.

At first, people didn’t really understand why I gave away valuable resources for free, but actually it helps accomplish the two most important elements of any business: relationships and trust. That way, when they do actually pay for my services, they know it’s worth it, and feel like they understand what I’m all about.

I make a big point of making myself present once a week with new content. Sometimes it’s a blog post or podcast interview, and sometimes it’s something like a Facebook live or an answer to a question that someone within my target audience asked online. And I keep things consistent. And it’s so consistent that when I don’t create something new, people wonder what’s going on.

That way, when people need me, they know where and how to find me, and they know they can count on me.

What is one failure you had as an entrepreneur, and how did you overcome it?

I have had a grand total of two terrible client experiences, and they have two thing in common: a missing gap in the communication process and major differences in terms of expectations. Ever since, I do my best to stop that from happening by never working without a contract and never answering emails after my office hours are over. I also have my own PDF I give clients that lays out in deep detail how much things cost, how and when to reach me, and how I typically work. I also use Trello to keep the communication process between myself and clients as clear and transparent as possible.

What is one business idea that you’re willing to give away to our readers?

People are always so down on themselves when they “put themselves out there” and nothing happens, but usually the problem isn’t what they’re doing, it’s the fact they’re not doing that enough. Results take time, and nothing comes instantly.

What is the best $100 you recently spent? What and why?

Getting a co-working hot desk at the Centre for Social Innovation in Toronto. That has been amazing! I work totally alone, and this has allowed me to always have people to talk to, and potentially collaborate with in the future.

What is one piece of software or a web service that helps you be productive? How do you use it?

It’s a tie between Zapier and Trello. Zapier is amazing because it saves me so much time by automating admin tasks I hate doing and could be spending doing other things. Trello helps keep me organized and reminds me of what I need to do right now. It also makes client communication relatively stress free.

What is the one book that you recommend our community should read and why?

“Quiet: The Power of Introverts in A World that Can’t Stop Talking” by Susan Cain. I think it’s a good one, regardless of what you do for a living. It will change your point of view on how people live and work in school environments, in the workplace, and also in their personal lives.

What is your favorite quote?

I always find myself going back to a quote that a great grandmother apparently said a lot: “I ain’t a lonely person.” Because that’s a good goal to strive towards.

Key learnings:

• Showing up consistently and offering valuable resources to your target audience is a valuable way to build trust and relationships.
• Never work with other businesses without having a formal, written legal document like a contract. Always pair your legal document with project management software to keep the communication process transparent, clear, and comfortable.
• Any admin aspect of your business you can automate with software such as Zapier, will save you time. And anything that will save you time, will allow more time for activities that generate revenue, or some sort of PR.