Highlights from #imakealiving Chicago and Looking Back on the Year!

FreshBooks was on the road last month! We hosted our final #imakealiving event of 2017 in 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. In November, we hosted our seventh #imakealiving event in Chicago. Here’s how it all went down!

Highlights from #imakealiving Chicago

The inspiring panel included Amanda Elliot (Founder and head writer of the popular blog Windy City Cosmo – where entrepreneurs can explore a variety of Chicago’s tech spaces, start-ups and events), Leah Jones (VP of Health Care Engagement for Olson Engage, and is trying to find a name for her as-of-yet unrecorded health policy podcast), Billy Yost (a rockstar who’s band The Kickback just released a new album called Weddings and Funerals), John Siuntres (The current reporter at CBS Radio Chicago, and hosted The Word Balloon Pop Culture Podcast for over 12 years), and Caitlin Rosberg (A regular at Ladies’ Night at Graham Cracker Comics in the Loop, editor of the Ladies’ Night Anthology, and serves as treasurer on the board of Chicago Nerd Social Club.) The event was moderated by Saul Colt, North America’s best word of mouth marketer.


What an inspiring time we had visiting your city, Chicago! The Second City venue could not have been a more gracious 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 insights, sparking meaningful discussions throughout.

Amanda weighed in on the topic of starting a small business. Her sentiments were this: there are many great reasons to become an entrepreneur, despite the challenges ahead. It’s well worth the journey to get to that place.

She felt that becoming a small business owner empowers you to do many things: create your own projects, have a voice in the world, build upon your skillset, and actually make a difference.


Our panelists discussed the topic of what success looks and feels like to them, and the role passion plays in this success. Measuring and defining success often varies from person to person.

Caitlin had a very realistic take on the matter. She believed success doesn’t have to be this romanticized thing — it can be simple. Passion doesn’t always equate to the ‘butterfly feeling’ of following something unique. Success can simply be finding the right client fit for you, having a job you enjoy doing, and even just being able to feed your dog!

Her advice overall? Never undervalue your time. Always remember that time is money, and that at the end of the day, the amount of time spent working translates into paying the bills.

And finally, the group discussed the notion of patience. Patience is certainly a virtue, and our dedicated panel could not have related to this more.

John explained that patience should be viewed as ‘luck meeting preparation.’ He went on to say that while someone may be hopeful to land a job, they still have to be working on other things in the interim. If you get too caught up in the headspace of ‘what’s next,’ rather than focusing on being productive in the ‘now,’ you will likely end up worse for wear.

Looking Back on the Year of #imakealiving

We were very fortunate to have run 7 amazing events in 7 great cities this year: Los Angeles, New York City, Toronto, Portland, OR, Austin, Boston and Chicago. It was wonderful taking #IMakeaLiving to so many different places. We are grateful to all of our host cities and venues, and look forward to revisiting them in the new year!

Our panelists in each city had their own insights on life as a small business owner, however we noticed a few common themes across the board.


Suffering from imposter syndrome was a topic that came up in every conversation. It was intriguing to hear each panelist’s take on their experience with it.

Lindsay Wolff Logsdon (from Portland) flipped the understanding of imposter syndrome on its head. She felt that while it’s important to be confident in what you do, you also must appreciate that there’s a lot to learn. The goal must always be to continue to grow, and to have that appetite for learning.

Leah Jones (from Chicago) explained that imposter syndrome is overwhelmingly real. She admitted that for a period of time, she felt she was the least qualified or knowledgeable person in the room. It was only after getting involved in stand-up comedy that her confidence began to boost. Putting herself in front that audience challenged her to gain a thicker skin under the spotlight.


The comparison of small business life verses full-time employment came up in many conversations across each city. The overall consensus was that security doesn’t truly exist.

Chrystie Vachon (from Austin) explained that security is over-rated: the reality is, anyone could get laid off at anytime. Meaning the security people believe they have as an employee may be more of an illusion.

Jackie Lam (from LA) explained that if she could give advice to her younger self, she would not worry so much about security. Security can be an impermanent. At the end of the day, you could fail just as easily as you could succeed.

Finally, our panel conversations always touched upon that link between small businesses and following your passion.

Rick Turcozy (from Portland) went on to discuss the importance of having a sturdy business model behind your passion. He explained that hobbies, in essence, aren’t paid. So we must be honest with ourselves about whether we can make money from our passions.

CC Chapman (from Boston) felt that having passion for what you do is important, but that it cannot be the only driving force. Skill and drive must also be motivating factors.


about the author

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.