Highlights from #imakealiving Portland, OR and Looking Ahead to Austin!

FreshBooks is on the road! Last week, we hosted #imakealiving in Portland, OR. Next up: Austin!

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 fourth #imakealiving event in Portland. Here’s how it all went down!

Highlights from #imakealiving Portland, OR

The inspiring panel included Lindsay Wolff Logsdon (Head of the Brand Culture Strategy practice at Liquid Agency), Meghan Sinnott (Brand Manager at Nutcase Helmets), Reggie Wideman (a consultant for the Salesforce Customer Success Platform), Rick Turoczy (a staple in the Portland startup community for more than 20 years and founder and editor of the blog, Silicon Florist), Nathan McKee (an artist and illustrator who is inspired by comics, sports, music and other elements of popular culture). The event was moderated by Saul Colt, North America’s best word of mouth marketer.


Wow, Portland – what a time we had together! We couldn’t have chosen a niftier spot for this event than the iconic Cleaners at the Ace Hotel. If you needed tips on how to get some real attention on your small business, this was indeed the place to be. We were in the company of these ambitious thinkers all morning, who shared their valuable experiences with self-employment. (And the delicious shaved ice afterward wasn’t too shabby either!)

All morning, our panelists had some incredible insight, sparking meaningful discussion throughout. Lindsay Wolff Logsdon, on the subject of happiness, reminded us that as we all evolve and change over time, so too can our business endeavors. The key is to focus and have determination in what you do, but to also remain open to new ventures.

#imakealiving As a self-employed professional, you undeniably love what you do. But it’s also worth noting that separating some of your passions from your work helps to keep you levelled. Reggie Wideman’s advice: Keep your little passions on the side. (In fact, he writes poetry when off duty!) Remember to harness a sacred balance between your hobbies and your work.

Do you ever think of your life through the lens of The Wonder Years? What would you tell your younger self, if you could listen to your adult voice? Two pieces of advice Nathan McKee would give himself: plan ahead and never hesitate. Having set goals—but being able to take risks—are cornerstones for success in work and in life.

And, finally, we touched on the topic of imposter syndrome. The panelists agreed that they all experienced self-doubt at least once in their lifetimes. Meghan Sinnott explained that she feels imposter syndrome every day, and has had to teach herself to gain the confidence to develop as a professional.

Looking Ahead to #imakealiving Austin

For the fifth city on the #imakealiving tour, we’re heading to Austin, Texas! Our event helps to facilitate and inspire connections between small business owners—and we’re honored to be a part of it all. Thank you to the Live Music Capital of the World for welcoming us next!

Event: #imakealiving powered by FreshBooks
When: September 13th, 8:00am–11:30am
Where: Stubb’s Bar-B-Q: 801 Red River St, Austin, TX 78701, 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 the #imakealiving event here

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

This is the fifth of an ongoing series of events that take place in a different city each month. Starting in L.A. the #imakealiving event will continue on to Austin, Minneapolis and San Francisco before returning to Los Angeles. Want to see FreshBooks come to your city? Leave a comment below! And don’t forget to follow @freshbookslive on Twitter!

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.