Side Hustle & Flow Interview Series: Michael Bungay Stanier

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The Side Hustle and Flow Interview Series is designed to inspire hard-working corporate employees to either start a side hustle if they are interested in eventually starting a business, or to keep going with their existing side hustle through the inevitable challenge of limited time and energy.

So far we have profiled Chandoo, Willie Jackson, Dan Schawbel, Laurie Gay, Carmen Sognonvi, Desiree Adaway , Gwen Morrison, Jenny Blake , Glen Southern , Alexandra Levit and Eleanor Mayrhofer.

Today I am profiling Michael Bungay Stanier, who is an author, speaker and business person. He wrote Do More Great Work, as well as partnered with Seth Godin to create End Malaria, a book with contributions from authors like Dan Pink, Tom Peters and Sir Ken Robinson (and yours truly) that to date has raised over $300,000 for charity.

He is a dear friend, and a hysterical human being, as you will find out shortly. I hope you enjoy the interview.

1. What was your former day job?

In 2001 I was living in Boston and working as an Unhappy Change Management Consultant. Meaning, I was unhappy not that I managed unhappy change. Although come to think of it, that’s also true.

My wife and I had gone to a pub, written down the name of 3 cities each on a beer coaster, and on revealing them to each other decided to move to Toronto, a city I’d never been to before. (My other two options were Berlin and Leeds. Also cities I’d never visited.)

I lined up another job – also a change management consultant – and we booked our tickets to fly on September 11th. For obvious reasons, that plan then fell through and when we did arrive in Toronto, my job had vanished.

I spent the next six months continuing what was now a tradition of being an unhappy change management consultant, but this time working in-house for a non-profit life insurance company (yes, I know that sounds contradictory) that was rebranding. It’s fair to say I made little to no impact, and (luckily) three days after the Canadian equivalent of the Green Card arrived, I was fired.

2. What was your side hustle?

What I was working on as a side hustle when I was at the life insurance company, was a coaching practice. I was doing my certification training, and attempting to refine my “who do I coach?” approach from “anyone with a pulse and a wallet. Or just a wallet.”

I started out charging $250 a month for 4 x 1 hour calls. Or free. A lot of free. This, by the way, is not a sustainable business model.

But I actually had a second phase side hustle. For the first year out, I found a job creating branding models for a research company for 2 days a week. They paid me just enough to cover living costs for my wife and me, which weren’t huge – we had and have no kids, no car, no house. So we only had to fund my drinking problem. (I’m kidding.)

What that meant is that I spent that first year doing a lot of experiments about what I might do, lots of small gigs drawing on my past history: facilitation, training design, creativity and innovation, strategic planning. When someone called me to say, “Can you do this?” I’d pretty much say “Yes” and then “How do you spell that exactly?”

3. When did you start working on it?

The key thing I started working on as soon as I moved to Toronto was building some relationships. I had lukewarm introductions to about 3 people, and I used that as a starting point and just went and drank a bagaziliion cups of coffee to meet people.

Lots of bad coffee.

Lots of people I only needed to meet once.

But “working on the side hustle” isn’t just about the technical expertise, I think. It’s about building the reservoirs you need of emotional, financial, relationship and technical resources you can draw upon. Because you’re going to need them more than you might think.

4. Did you tell your employer you were working on a side project? Why or why not?

My employer was proving to be largely indifferent to the work I was doing for them. They would have been supremely indifferent to what I was doing on the side.

5. How did you know when it was time to quit your day job?

As my boss uttered the words, “you’re fired” I resolved then and there to quit my day job. It was an amazing synchronicity of timing.

With the year long 2-days-a-week job, I had enough money saved and enough strong next-steps and leads to be able to step away from that safety net

6. What scared you about that decision?

For phase one … well, everything. I knew no-one in Toronto. Or in Canada.

For phase two … much less. I had a sense of resilience and “we can make this work”. It really helped that I’d sat with the question, “How much is enough?” so that I knew a minimum number I had to earn for us not to become reliant on my busking skills. Which don’t exist.

7. How did it turn out?

It was a disaster. My wife left me. I lost more than half my body weight. After the leg amputation I developed a nasty rash and…

No, just kidding. It’s been very very good. I spent the first three years really doing almost anything that came my way. It was very much a grab bag of whatever.

Then, someone sent me a photocopied page from Milton Glaser’s book Art is Work, and it proved to be a moment of clarity and inspiration. Box of Crayons started to evolve to where we are now: helping people and organizations do less Good Work and more Great Work.

We got more and more courageous about standing for something (and therefore saying No to other things), and that focus has continued to serve us well

8. What are you doing now?

We’re still helping people and organizations do more Great Work. Our money engine is four training programs I’ve created, and we have a faculty of external program leaders (and many internal leaders within organizations) who deliver them. And I write books, give speeches, run some workshops, create conferences … basically, create cool stuff that inspires me and I hope others and contributes to people doing more Great Work.

9. What advice would you give for others who are working on a side hustle now that you have a bit of distance?

Here are three pieces of advice:

1. Treat everyone else’s sage advice with deep suspicion. It’s probably only partially true, and it may not be true for you.

2. Build a number of reserves – not just money, but relationships, support, self-care, learning, technical – that you will be able to draw upon when you’re working on your side hustle.

3. Whatever your business plan is, it’s going to be wrong. Likely, completely wrong. So you have permission and freedom to iterate. Fast prototyping and testing things out, so you can have reality slap your ideas around a bit to see what will really flourish

3.5. Build a mastermind group. I’ve been in one for 7 years, and it’s been a powerful place to build insight and trust and courage and humility. Jen Louden is part of mine, and she created a “how to” product here, if you’re curious:

10. How can people find you, or hire you?

Option 1: Come to Pam’s fantastic Body of Work Live conference in October to experience the Full Force of My Magnetic Personality. I’ve got the pleasure of doing the opening keynote, which is flattering and will be great fun. {Editorial from Pam: I read Michael’s answers to these questions while on the plane, and I was laughing so hard that I got dirty looks from passengers around me. This confirms I made the right choice to have Michael go first in the lineup.}

Option 2: Sign up for the Great Work MBA ( which is a free and virtual conference I’m curating (a fancy word for “running”). 25 amazing speakers – yes, Pam is one of them – and I’d love you to come along.

And finally – jump onto and make sure you check out (a code word for “pillage”) as much of the free stuff as you’d like.

Tweet Michael at @boxofcrayons

Feel free to take all three options, of course.


Thank you so much Michael for sharing your story! As long as I have known you, I did not know the sordid details of your side hustle journey, so learning more about it makes me appreciate your current success even more.

I suggest your next side hustle be a stand up comedy business.

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10 Responses to “Side Hustle & Flow Interview Series: Michael Bungay Stanier”

  1. […] Pam Slim’s Body of Work is a powerful and transformative new book that shows us how to take a look at how we are greater than the sum of our parts. Pam demonstrates how to find the connections among diverse accomplishments, sell your story, and continually reinvent and relaunch your brand. (As part of her “side hustle and flow” series, I sat down with Pam and shared my own experiences of how I got from there to here.) […]

  2. Anita says:

    I find the Side Hustle & Flow series incredibly inspiring. Keep it up! And thank you 🙂

  3. I love these stories. I wrote a story on my own side hustle that led to personal success and positive impact on my community. Many people have told me it helped them:

  4. […] My interview with Pam Slim is part of her “side hustle and flow” series, telling the story of how I get from There to Here. It’s one of the more funny things I’ve written – I think you’ll enjoy it. […]

  5. Marc Cobe says:

    A dream becomes a goal when action is taken toward its achievement.

  6. Vonnie says:

    Great interview! Love the synchronicity of timing. Whether your pushed or pulled, it’s all part of your where you were born to go. Looking forward to meeting you at Body of Work.

  7. Brian Shea says:

    Fantastic interview. Hysterical writing. and lots of great lessons here. a big takeaway for me:

    “Lots of bad coffee.

    Lots of people I only needed to meet once.”

    Thanks for sharing this Michael and Pam!

  8. faisal says:

    So that is excellent timing for you when your boss fired you.

  9. Sonia says:

    Okay, I’m even more excited now to be attending Body of Work in a few weeks! Can’t wait to meet Michael!

  10. Matt Schmidt says:

    “As my boss uttered the words, “you’re fired” I resolved then and there to quit my day job. It was an amazing synchronicity of timing.” That’s hysterical.
    So true about building reserves more than just the financial kind.