Remoter’s Life: Sherri DeWolf

Meet Sherri DeWolf, Owner/Consultant at Deeply Creative, living in Ontario, Canada. This is how she makes remote work, work for her.

Sherri, can you tell us a bit about yourself?

I am what some call a #teacherprenuer. I left an 18 year teaching career to start my business nearly 5 years ago. I love hats (and wear many of them — both literally and figuratively). I’m a deep-feeling, water-loving, mermaid at heart (thus the play on my biz name, Deeply Creative) who loves playing with words, inspiring others, creating and making things look pretty!
I also love to travel and explore new places!

Can you tell us more about your current job?

I help small businesses market their businesses… with HEART! I work primarily in small biz Social Media Management, Website Builds, Logo Creation, Email Marketing, Creative Consulting/Coaching (Yes, people pay to pick my brain and help them get started on their own projects!), Event Planning (I was part of the original @keywestmermaidfestival crew and am now bringing an event to the shores of my own home with @mermaids_and_mariners on the St. Clair!)

Do you have a dedicated space to work?

Generally, anywhere there’s a good wifi signal works for me! From home, I work at a space/table in my living room in front of a big picture window facing the water. This way I can catch the sunsets and all of the ships that pass by. I live along the St. Clair River which is an international divide between the US (Michigan) and Canada (Ontario). Coffee shops and my dock are also favourites!

What does your typical workday look like?

I tend to be a night Creative who often “burns the midnight oil”, so it’s not uncommon to see 2am before I put myself to bed. My day doesn’t usually start until mid-morning, when I wake up and check my accounts on my phone and work on community engagement for an hour while still cozy in bed. Then, I’m up taking care of domestic duties until I begin any work after lunch. My workday is very organic, so some days I’m scheduling social media content and creating graphics, while others, I’m working on a website, email campaign or on a video consult. I have a lot of free time since most of my tasks can be scheduled in advance and I schedule a month’s worth of content for each client at a time. If I want to enjoy the day, I do! There’s always the evening when all the world is quiet to happily plug away at projects.

What tools do you use to stay productive?

I still use a traditional planner that I write tasks down in and love to check off. I also use several different social media schedulers to help organize and deliver client content. I keep notes and content calendars in a binder divided by client and I still prefer real notes over storing everything digitally.

What is your current workspace setup?

A MacBook Air on a table in my living room with my Alexa and two furry helpurrs (Oscar and Shamus) nearby.

What’s your favourite unplugged activity?

I love walking along the water, going to the beach, boating, paddle boating and spending time on my dock. Music and dance are great ways to unwind and time spent with family and good friends is always good for the soul.

What do you like most about working remotely?

I love living life on my own terms. I decide where and when I’m going to work and whether I’m just going to take the day and enjoy it! My favourite thing is knowing I can work from anywhere and that I’m not limited by my location since I can take my work wherever I go. Prior to COVID, I was able to work remotely from my island home away from home, Key West. You can check out my adventures there at @sherri_in_paradise.

Thank you Sherri!


Deeply Creative ~ Creative Consulting Services


Sherri in Paradise


Mermaids & Mariners on the St. Clair


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