Roundup: Advice I’d Give Myself in Year 1 of My Business

Hindsight is 20/20... Why seven entrepreneurs started their own businesses—and what they’d tell themselves if they could take a quick jaunt back in time to their first year in business.

At FreshBooks, we know that the best advice comes from people who’ve been there. That’s why we asked a variety of successful small business owners in communications to share their sob stories, successes and tips for fellow entrepreneurs.

Over the next few months, we’ll check in with them on important topics like cash flow, bad projects, distractions, marketing, customer service and more.

Paul Russell, Marketing Writing and Communications

  • Years in business: 25

What I Do:

“I’m a writer and communications consultant specializing in both corporate communications and marketing. I have extensive experience working in the human resources (internal communications) and financial services (external communications) areas.”

Why I Got Started:

“I was a lawyer from ages 28 to 32. When I was 33, I quit my job and my wife and I backpacked around the world for a year. It was one of the hardest things I’ve ever done, but also the most rewarding. When we came back to Toronto, I’d had a taste of freedom plus the confidence of knowing I could overcome a lot of obstacles. That’s when I started freelancing.

“Running your own business gives you the absolute freedom to make your own decisions, and I love the direct relationship of doing good work and getting paid for it. Other than commission sales work, working for yourself is the only way to get that.”

Advice You’d Give Yourself in Your First Year of Business

“Probably to ‘get out there’ and show your face at events, because most of my work has come from happen-chance. I met an older cousin by fluke at a holiday party and he listened to what I was doing and the said he knew someone at a firm who he thought could use my help. That ‘by chance’ conversation turned into about $1.5 million in income for me over the course of my career so far.

“Also, a photographer friend gave me Working Alone: Words of Wisdom for the Self-Employed by Murray Felsher and that book changed my life. It’s old (1994) but it’s a total pep talk about the value of your work and to make sure you charge for it. I highly recommend it.”

Jennifer Matthews, Writer and Editor

  • Years in business: 23

What I Do:

Communications strategy, including project planning and communications audits. Plus, writing and editing of:

  • Internal communications like training materials, conference scripts and change communications
  • External communications like magazines, annual reports, brochures, books, fundraising documents, executive speeches and presentations and websites

Why I Got Started:

“The penny dropped for me when I saw what my corporate communications team was paying a freelance writer we’d hired for a particular project. Not long afterward an opportunity to freelance came my way, and I began doing magazine writing and editing after-hours. I have loved being my own boss and wouldn’t trade it for anything.

A key highlight for me? The variety of projects I’ve been able to work on, and the truly interesting clients I’ve had the opportunity to meet and work with. Not so great? The challenge of managing work flow and cash flow. It can be either feast or famine in this business, and I’ve been fortunate to have a partner with a steady paycheck and benefits to help even things out!”


Advice You’d Give Yourself in Your First Year of Business

“When I first graduated from university and started job hunting, one of my strategies was to open the Yellow Pages (oh, how networking has changed!) and cold-call freelance writers and editors. Several were more than willing to speak with me, and several told me to start freelancing right away. I wasn’t comfortable doing that, and I’m glad I didn’t.

“Working on a corporate communications team for a few years gave me an inside perspective on the people who would eventually become some of my freelance clients. I had a much better understanding of the politics and culture they have to deal with – and that makes me a better supplier for them. Plus, it gave me a steady source of income and benefits to fall back on while I got my freelance business (slowly) off the ground.”

Suzanne Colmer, Image and Style Consultant

  • Years in business: 10

What I Do:

We help women and men shop smarter and teach them how to love all of the clothes in their closet.

Why I Got Started:

“For the freedom to undertake big bold dreams and make them real. I love the blank canvas of entrepreneurship. I am not a paint by numbers type of gal.”

Advice You’d Give Yourself in Your First Year of Business

“You are not an island! Surround yourself with entrepreneurs that inspire and push you. There is nothing more valuable than a tribe of people that you can bounce ideas off of. And look at your numbers. Every day. I underestimated how important bookkeeping truly was/is.”

Andrew Campbell & Jess Campbell, Workshop Training, Speaking, Writing, Project Management

  • Years in business: 8

What We Do:

“Andrew’s focus is on training and skill development in communications; Jess does project management and freelance writing.”

Why We Got Started:

“A lot of it had to do with passion and flexibility together. The passion comes down to focusing on doing the things we have liked about past jobs and working hard to build business around those things. We also have a dairy and grain farm that doesn’t always go well with a traditional 9-5 job, so we wanted something that included the ability to get work done on our time (like evenings or weekends). Being able to do that and build a business around the things we really look forward to doing is exciting.”

Advice You’d Give Yourself in Your First Year of Business

“Don’t get too niche too fast. There were things I really wanted to do, but those jobs weren’t flying in. I should have taken a few other opportunities early on, but learned pretty quickly that other jobs like part-time contracts or longer-term projects that don’t fit what you really want to be doing are just a stepping stone to get you where you need to be (including cash-flow positive!)”

Stacey Stein, Copywriter, Communications Consultant, Journalist

  • Years in business: 5.5

What I Do:

“I provide copywriting and content marketing services to clients in a wide range of industries. I am also a freelance journalist and have been published in some of the country’s top newspapers and magazines.”

Why I Got Started:

“I’ve always wanted to experience the satisfaction of creating something from the ground up and being my own boss. I also enjoy the flexibility of creating my own schedule. As a bonus, I get to do the work I love!”

Advice You’d Give Yourself in Your First Year of Business

“There will be ebbs and flows to the business cycle and that’s okay! Actually, I still need to remind myself to heed this advice even though I’m more than five years in!”

Tim Dolan, Digital Strategy Consultant & Trainer

  • Years in business: 4.5

What I Do:

“Kickframe is a new type of consulting and training firm built to serve the need that organizations have for a specialized digital strategy partner that is independent, agile and experienced. Kickframe helps organizations become better digital marketers.”

Why I Got Started:

“I love having greater control over who I work with, what I work on and how I approach helping clients. Working independently allows me to have more freedom over these things, particularly how I allocate my time, that working in a larger agency or consultancy would not offer.”


Advice You’d Give Yourself in Your First Year of Business

“The two most important factors for your success are your reputation and your network. If people don’t know you or want to work with you, everything else is a waste of time. I wish I appreciated the importance of networking earlier in my career – the majority of my clients come from word-of-mouth and the more mouths the better.”

Joshua Speers, Graphic Designer

  • Years in business: 5

What I Do:

“Graphic design, web design, branding, design/marketing consulting.”

Why I Got Started:

“I started my own business because I wanted to make a bigger difference in the way we experience the world, and working for another company wouldn’t allow me to do that. I’m still in the game because I’m building my dream, and helping other businesses succeed along the way.”

Advice You’d Give Yourself in Your First Year of Business

“Have more faith in your choices and your ability to succeed as a business owner.”

about the author

Freelance Contributor Heather Hudson is an accomplished freelance writer and journalist based in Toronto. She writes for a number of publishing, corporate and agency clients who depend on her to deliver high-quality, on-brand content and journalism with a fresh perspective. Learn more about her work at .