9 Pieces of Advice for Your First Year in Business

Hindsight is 20/20... Here's why 9 entrepreneurs started their own small businesses—and what they’d tell themselves if they could take a quick jaunt back in time to their first year in business.

first year in business

According to the Small Business Administration, about 1 in 12 small businesses close every year. So if you’re determined to see your new business succeed, a solid business plan isn’t enough. You’ll need a strong business model, a target market, and the determination to go after new opportunities.

Of course, some of 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 and new small business owners.

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

Feli Oliveros, Finance and Business Writer

What I Do:

“I’m a freelance writer who specializes in long-form content for B2B and financial services companies. My areas of expertise include personal finance, small business finance, human resources, and marketing.”

Why I Got Started:

“I’ve always known that writing would be a part of my career somehow. But after being overworked at my first full-time job and getting fired four months after starting, I wanted to do things my way from that point on.

“Luckily, my short stint at that company taught me some things about how a business should (and shouldn’t) be run, so I used them as a basis for building my new venture and learned everything else on my own. I’m grateful for that experience now because I love the flexibility and freedom that freelancing offers. Plus, the satisfaction that comes from seeing how far you’ve come is like no other.”

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

“Looking back on everything, I wish I had a mentor to guide me through starting a new business. The way my first full-time job crashed and burned around me was very demoralizing, to tell the truth. I loved learning how to create a business plan and operate a business, but part of me was terrified of taking action and failing again. Because of the pressure I put on myself and having to learn everything from scratch, it took a long time to make my business sustainable. Having someone to learn from would’ve saved me a lot of stress and heartache.”

As a small business owner, your first year in business plays a huge role in its success — but at the same time, it’s not always the make-or-break factor. Use your community as a sounding board for your ideas, and your judgment and hard work to build a business you can be proud of. We’ll be here with you every step of the way.



Paul Russell, Marketing Writing and Communications

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 then 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

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 workflow 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.”

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Suzanne Colmer, Image and Style Consultant

What I Do:

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

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 group 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, Training and Project Management

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 a 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 and Journalist

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 and Trainer

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

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.”

Heather Hudson

Written by Heather Hudson, Freelance Contributor

Posted on July 23, 2018