Highlights from #imakealiving Boston and Looking Ahead to Chicago!

FreshBooks is on the road! Last month, we hosted #imakealiving in Boston. Next up: Chicago!

With great risk comes great reward—and for small business owners everywhere, this couldn’t ring truer! Plenty of heart, soul and labor goes into the creation and maintenance of a small business. And guess what? FreshBooks is here for you every step of that journey. Last week, we hosted our sixth #imakealiving event in Boston. Here’s how it all went down!

Highlights from #imakealiving Boston

The inspiring panel included Amanda O’Brien (Director of Business Development at Flyte New Media, Organizer of Social Media Breakfasts in Portland, Maine), Jeff Cutler (a photographer and writer who focuses on creating inspirational content, and who runs the company Novel Ideas), Chris Brogan (CEO of Owner Media Group and a New York Times bestselling author of nine books), John J. Wall (VP of Marketing at Event Hero and Producer of the highly revered weekly audio program Marketing Over Coffee), C.C. Chapman (co-author of the International bestseller Content Rules, author of Amazing Things Will Happen, and who’s work has appeared on the pages of Rolling Stone and The Wall Street Journal.) The event was moderated by Saul Colt North America’s best word of mouth marketer.


What a wonderful time we had visiting your city, Boston! The Laugh Boston venue could not have been a more accommodating host for our event. This was indeed the place to be if you were in the market for entrepreneurial advice! Throughout the morning, we had a chance to hear from and connect with our speakers, who shared their valuable experiences as small business owners.

Our panelists had some incredible insight, sparking meaningful discussions throughout.

Amanda weighed in on the topic of appearances, explaining that the way you may seem on the outside is not always reflective of what’s going on inside. To others perceiving her in her work, she said she may often seem cool, calm and collected, even when in her own mind she isn’t feeling that way at all.

She added that it’s very important to have at least one go-to person to talk to when you’re having a tough moment or a hard day. In times like these, total and complete honesty will be better and more relieving for you than maintaining composure.


Our panelists discussed the idea that people can have changes of heart in their field. Sometimes people will stick with one job or role forever, and sometimes people will embrace a change-up.

Chris’s sentiment was that it’s in fact crucial to pivot and reinvent yourself in life at times. That on the one hand, you absolutely want to challenge yourself to become better in one area, but that you also need to be constantly evolving and growing. He even used the example of Madonna, as she has reinvented herself many times over in order to stay relevant.

We all learn tough lessons over the course of our lives that we are now grateful for—and this is all too true when it comes to the journey of a small business owner.

Jeff explained he had to learn the hard way in order to really understand his own value. It took him being denied a well-deserved raise at a company to realize that his contribution could be respected far more elsewhere.

He quickly learned that being underappreciated can build resentment. This was the moment that led him to finally move on after finishing one last project at that company—and boy was it ever the right move!

And, finally, our panel touched on a topic that so many of us can relate to in one way or another: failure.

John J Wall explained that there is a lot of failure out there, so it’s important to expect that it may happen to you. This isn’t to say it’ll ever be easy to embrace — but if it can be faced with a strong will, it won’t get you down as much.

Failure is very difficult to go through no matter what, but it’s also a crucial learning experience.

Looking Ahead to #imakealiving Chicago

For the 7th and final city on the #imakealiving tour, we’re heading to Chicago! Our event helps to facilitate and inspire connections between small business owners—and we’re honored to be a part of it all.

Many thanks to Chicago for graciously hosting us next — we can’t wait to try Chicago-style pizza, popcorn and hot dogs shortly after arriving!

Event: #imakealiving powered by FreshBooks
When: Wednesday, November 29th, 9:00AM–12:30PM CST
Where: The Second City, 1616 N Wells Street, Chicago, IL 60614 USA
Details: #imakealiving will host a diverse panel of people from different industries. They’ll share stories about their livelihoods and non-traditional career journeys. Our panelists will then show you how to harness that inspiration and apply it to your own career. Our goal is to motivate and empower you to break out of your comfort zone and take some chances with your career and marketing!
Cost: Free – seeing you thrive is all the payment we need!
We’ll be announcing our speakers in the next few days, so stay tuned.

RSVP to #imakealiving here

Not in Chicago? Don’t Worry, There’s Even More to Come!

This month, #imakealiving wraps up in the city of Chicago for the year. What a great 2017 we had! Want to see FreshBooks come to your city next year? Leave a comment below! And don’t forget to follow @freshbookslive on Twitter!

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FreshBooks is the #1 accounting software in the cloud designed to make billing painless for small businesses and their teams. Today, over 10 million small businesses use FreshBooks to effortlessly send professional looking invoices, organize expenses and track their billable time.