The One Question That Led This Entrepreneur To Success

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Erin Bury always knew exactly what she was going to do in life, until she didn’t. A passionate upstart journalist-turned-marketer-turned-entrepreneur, Bury rode the roller coaster of business more than once and lived to tell the tale.

Now she is stepping down from Eighty-Eight, the creative agency she built and led for the past six years. On her way to her next challenge (taking on the CEO position at Willful Wills), she chatted with PulseBlueprint about her heroes, breaking her legs (literally), and thinking about the worst thing that could happen.

How do you define success?

Eighty-Eight logo
(Source: Eighty-Eight)

This is a tough one. There are so many ways to define success – your net worth, your career, your personal happiness, your relationships…the list goes on.

I think for me, I define success in two ways: first, having the flexibility to live life the way I want – for me that’s the financial flexibility to travel; having flexibility in my career to work on side projects and have ownership over the types of things I work on; and flexibility in my schedule to design my career/life on my own terms.

The second way I define success is being happy with what you have, instead of constantly coveting what everyone else has. We live in a society where everyone is jealous of someone – but the old adage that there is always someone richer, skinnier, and prettier than you rings true. If you’re always trying to keep up with the Joneses you’ll never be truly happy – so to me, true happiness and success is being content with what you have (while also striving for more, and not being complacent – but because you want to, not because it will get you the next shiny object).

What’s the biggest challenge you’re facing right now?

Willful logo
(Source: Willful)

The biggest challenge I’m facing right now is uncertainty.

I’ve always been someone who had things figured out – I knew from a young age I wanted to go to journalism school and go into a career in marketing, and while I haven’t always known the exact path that would involve, I’ve had a pretty clear plan.

Now I find myself at a crossroads – I’m just finishing up 6 amazing years at Eighty-Eight, and I’m facing a lot of uncertainty around so many things. First and foremost my career, not only because I don’t know what my next move will be, but because I have to figure out what will challenge and excite me, but also around my life situation, since I’d love for 2019 to include living abroad.

I’m excited by the uncertainty – but as someone who has always been a planner – and who plans the big things (my wedding, my career) but also the small things (I’m the person who’s planning get-togethers well in advance and who struggles with spontaneity) – it’s scary.

Which entrepreneur, thinker, or leader inspires your work the most?

Oprah is Bury's inspiration (Source:

I’ve always been inspired by Oprah, and I know that’s cliche because everyone says Oprah, but as someone who’s been retweeted by her in the past (so we’re basically best friends), I think I’m allowed to choose her.

First, she overcame a hard childhood to claw her way into a successful broadcast journalism career – and as a j-school grad who spent a couple years running BetaKit, I identity with where she got her start (although I had a pretty charmed childhood, minus breaking both my legs when I was nine – but that’s a story for another post).

Then she built up an entrepreneurial empire and established an incredible personal brand, bringing that brand into everything from magazines, to her own network. Finally, she’s never been someone who is complacent. She left her show at the height of its popularity to take on a new big challenge – she embodies the idea of just because it’s not broken, doesn’t mean you can’t make it better. I’m someone who has committed to never being complacent in my career and life, and I admire Oprah’s choices to push herself, try new things, and constantly take on new challenges.

What’s the most underrated advice you’ve ever received?

Take the road less traveled

I’m not sure if this is underrated, but it’s definitely the best advice I’ve ever received. When I was considering leaving my first job out of university at a PR agency to go work at a startup, I struggled a lot with whether to take the leap. It was the recession, and most people I talked to thought I was crazy to throw away a secure job for the unknown.

Most people’s parents would tell them to stick with a steady paycheque, but for some reason my mom encouraged me to take the risk. She advised me, when evaluating a decision, to ask “What’s the worst that could happen?” and to always take the risk. So what if the startup didn’t work out and I had to go get a job? If that was the worst that happened, I had to trust that it would be okay regardless. Her advice – to take the risks, and to always remember that even if things don’t work out, if you’re smart and work hard you’ll always have a viable backup plan – have stuck with me and served me well. Now, as I sit her after leaving a job I loved after 6 years to find a new challenge, it’s even more prescient.

What’s your favourite book, speaker, or talk about entrepreneurship?

One of Bury's favourite books, Shoe Dog (Source: Amazon)
(Source: Amazon)

I have a few, and the thread between all of them is showing the journey that comes along with entrepreneurship. Often successful companies can look like an overnight success – but the average company takes 7 years to go from inception to a sale or IPO, and the first couple years are usually just the founder trying to make it work with limited resources, limited awareness, and lots of knowledge gaps.

Favourite books:

Favourite podcast: How I Built This, hosted by Guy Raz (interviews with well-known entrepreneurs).

What’s the most important trait you look for in anyone you work with?

a good employee must be resourceful

The single most important trait is resourcefulness. I remember when I joined a startup a year out of school, a couple months in I asked the founder Sarah Prevette why she hired me, when I was clearly inexperienced and was fumbling my way through learning how to be a Community Manager.

She replied that when she hires people, she doesn’t look for whether they already know the answers – she looks for people who can be resourceful and find the answers without any help. I guess she saw that in me, and now I try to look for that in others.

You can teach people to be better writers, or to perform tasks at your company – but what you can’t teach is that innate sense of “figuring it out” and coming to you with solutions, not problems.

Which of your business responsibilities do you hate the most?

outsource what you're bad at

This is a tough one, as I don’t think there’s anything I hate about running a business that I haven’t already outsourced. I’m a big believer in focusing on the things you do best, and finding experts to do the rest – I know I’m not a finance whiz, so I’ve found great accounting teams to act as a trusted partner.

But I would say the thing I don’t love – and that I would happily avoid in all my future businesses – is applying for grants. Navigating the grant application process – and all the associated paperwork that comes along with it – is extremely time-consuming, and there’s not a lot of visibility into why you do or don’t get accepted. I’m grateful that we have access to grants for hiring, training, and other operational expenses, but I wish the process could be more digital, more streamlined, and easier to navigate as a business owner.

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Photo courtesy Be The Next Her

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