Highlights from #imakealiving Toronto and Looking Ahead to Portland!

July 25, 2017

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

Small business owners are finding unimagined opportunity in the new economy. But it can also create scary uncertainty – after all, everything is NEW! But one thing is certain, when it comes to small business FreshBooks has your back. Last week, we hosted our third #imakealiving event in our own hometown: Toronto!

Highlights from #imakealiving Toronto

Just under 300 eager beaver small business owners arrived bright eyed at 8 a.m. last Friday morning for the Toronto event at FreshBooks HQ. Our very own CEO, Mike McDerment, was there to give the keynote speech and many keen FreshBooks employees were on hand to help.

Toronto’s inspiring panel included Pay Chen (TV host, writer and producer), Dawn Laing (Director of Communications and Marketing at Nuvango, Geleskins and NOTION), Richard Thomas (a futurist who has worked at Idea Couture and Kinetic Cafe), Chris Hamoen (Co-Founder & CEO at Account HQ), Ben Zifkin (CEO and Founder of Hubba) and Jeremy Bailey (self-proclaimed Famous New Media Artist).

Happiness and Making a Living

Many small business owners start their own business because they believe it will be more fulfilling than working for somebody else. In that regard, they often take a big risk on happiness. They often also believe they’ll have more agency as small business owners: they’ll be more in control of what they earn and being rewarded for their hard work.

But happiness and income can also seem at odds with each other.

Pay Chen discussed entrepreneur’s expectations of happiness. She presented the idea that happiness is not an everyday feeling, but an overall experience – that you can be happy even in moments that are challenging, emotional or even difficult.

Pay also pointed out that while it’s a mistake to think money is the source of happiness, it’s important to acknowledge the importance of money too. It shouldn’t give business owners “the icks” to care about money and to try to grow their income.

Dawn Laing shared that in the early part of her career she had followed the money, but now she finds a balance. She also touched on how putting too much emphasis on passion and happiness can be counter-productive… It’s really okay to keep some of the things you love as hobbies and not try to turn them into sources of income.
As CEO of Hubba, Ben Zifkin presented a different perspective. He prioritizes making others happy, which is something to consider as your small business grows and you add staff.

For Chris Hamoen, self-awareness is huge: You know yourself better than anyone. So know what you really want and own it. But you also have to be patient: Sometimes the fastest way to your goal is to slow down and grow in a slow and steady manner (enjoying the ride along the way!)

Our Keynote Speaker: FreshBooks CEO Mike McDerment

FreshBooks CEO Mike McDerment focused on business courage for his keynote, and shared multiple examples from his own experience.

In one of his stories, Mike talked about his early days running a small design agency and the challenge of figuring out how much to charge clients. He recounted a time he undercharged a client, who went on to profit hugely from his work. It was a hard way to learn the valuable lesson to always charge what you’re worth.

Mike then shared how he exhibited business courage as the CEO of FreshBooks. In earlier years, he had always been known as someone who would never ever take funding. But over time, he realized that to grow you need to bring on advisors, mentors and – yes – investors.

It’s dangerous to become so entrenched in your opinions that you cut of your nose to spite your face. So, yes, be confident in your instinct, but don’t hold onto judgments that are no longer serving you. At the end of it all, allow yourself to evolve and change your perspective over time.

Of course, that’s not to say that what was right for FreshBooks (or any other company) is right for your small business. In fact, there is no right and wrong to growing your business. So, know yourself; figure out what is right for you. If you try to do something that you don’t believe in, you won’t succeed.

Looking Ahead to #imakealiving Portland

Event: #imakealiving powered by FreshBooks
When:  Wed, 16 August 2017, 8:00 AM – 11:30 AM PDT
Where:  The Cleaners at Ace Hotel, 403 SW 10th Avenue, Portland, OR 97205
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 keynote speaker, Saul Colt, 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!

We’ll be announcing our speakers in the next few days but tickets sold out quickly for New York and Toronto, so hurry to grab one for Portland!

RSVP to the #imakealiving event here

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

Portland is the fourth leg of an ongoing series of events that take place in a different city each month. The #imakealiving event will continue on to 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.