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TGIF: Solopreneurs, It’s Time to Step Outside of Your Comfort Zone

The truth is, when you go into business for yourself, nothing is really “comfortable.”

Everything is completely new terrain. There are unexpected potholes galore and if you’re constantly focusing on dodging them, you’re never going to have time to do anything else. So instead, I’ve learned it’s best to embrace them. Take it one pothole at a time, even the darkest ones probably share an important lesson.

(Note: these are usually the smallest, most unexpected ones — like when you trip over a crack in the sidewalk and nearly fall face first in front of a group of strangers. But what do you do when this happens? You laugh at yourself and you keep on moving forward… and maybe pick up your speed a bit to get away from the crowd as quickly as possible.)

You’ve just got to trust the process, and keep pushing full speed ahead.

This sums up my first five (almost six…eek) months of self-employment. There were weeks when I doubted taking such a huge risk, but my emotions were quickly calmed by some reassuring message that came along the next day — like a client saying I bring an entirely different approach to social media than she had ever considered before, or a card from a reader in the mail thanking me for the inspiration to “go at it alone.”

It is so all worth it.

Anyway, there has been a lot going on this week, so let’s get to that.

Highlights This Week

What I’m Writing:

I was starting to feel like I was on hiatus from The Reply because I hadn’t authored any posts in a while. (That’s not to say I wasn’t getting sh*t done behind the scenes though.) We’ve had so many fantastic posts from contributors lately, and I am loving it. I did get back to my regular routine this week, however, sharing my best tips for how millennials can blog their way to their dream career on Monday, as well as today’s post on why you need to pay yourself first.

What I’m Reading:

My favourite read this week was “The Small, Happy Life” by New York Times editor David Brooks. It’s the perfect read for you to check out as you head into your weekend. Brooks asked readers to send in their personal essays describing their purpose in life and how they found it. Here’s a glimpse:

“I expected most contributors would follow the commencement-speech clichés of our high-achieving culture: dream big; set ambitious goals; try to change the world. In fact, a surprising number of people found their purpose by going the other way, by pursuing the small, happy life.”

As someone who tends to focus on those big ambitious goals, this post really resonated. It’s not always the big accomplishments that bring us a sense of achievement. Small successes go a long way too. And it’s important we give them the credit they deserve, pausing to recognize the results of our labours before we move on to the next big target. Tracking your weekly reflections is a helpful starting point.

What I’ve Learned:

I’ve written before about how solopreneurship is a constant balancing act, and I continue to learn more strategic ways of juggling the different hats in my new wardrobe. As business picks up, I’ve had to adjust and find some new routines. This has probably been my busiest week of self-employment yet, which has meant a lot of late nights and early mornings. I’m looking towards taking off up north this weekend for a couple of days to unwind. Because I know I need to take the time to unwind.

What I’ve experimented with:

I had so much fun collaborating on a video shoot for a client this week. I love when small business owners are interested in experimenting with fresh ways to share their brand story. And this one is going to be good.


Shooting a VLOG episode for a client.

I’ve also been working hard with my amazing web designer to launch not one but TWO brand new websites. My business has evolved quickly in the initial months of going at it full-time, and I want my website(s) to reflect these changes. My new Web of Words site ( will give you a much better glimpse at the services I offer solopreneurs and small business owners. And then will be more focused on my freelance writing for publication. I can’t wait to show you the new looks. In the meantime, here’s a quick sneak peek:


How has your week been? Any big plans for the weekend ahead? Go ahead and fill me in below!


Charlotte Ottaway

Charlotte is the founder of Web of Words. She helps solopreneurs and small business owners create real human connections online through blogging and social media. Her work has been published in Maclean's, Canadian Business, Zoomer, The Globe and Mail, The Huffington Post Canada and other Canadian publications. Better known by family and friends as Carly, she currently resides in Newmarket with her husband and fur-babe. To learn more, check out her portfolio at and follow her on Twitter @charlottaway.

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