The Real Story of My Entrepreneurial Journey: PART 3 – The Messy Middles of Collaboration

If I counted the number of hours spent contributing over the last six years to projects and collaborations that didn’t amount to any direct benefits, I would probably cry.

(Thankfully, this task would be impossible so you can hold the tissues!)

Also thankfully, of course, none of this time was lost. It wasn’t directly useful to an objective eye in the present, but it certainly wasn’t lost. Each micro-moment led to the next, and to the next, and to the next, and now to today, ultimately contributing to the point of view I now feel so grateful to hold.

I’m not necessarily a full extrovert (I turn into a mess without enough alone time to recharge) but I’ve always found myself right in the thick of whatever community projects are taking place around me. Need a hand on the event committee? Sure! Need a free snowboarding instructor for the silent auction? Sign me up! Need a standing bike energy micro-generator demo for the Eco Fair? I’m sure we can figure it out! (True story! The bike we built never did work… because, you know, non-engineer over here.)

This tendency to jump right in where ever I’m needed is a blessing and a curse.

A curse because it can pull me in too many directions and slow down progress of each individual part. At the same time, my desire to stick my hands in everything has been a blessing because it has brought tremendous diversity to my experience.

In University, this is probably how I ended up becoming Vice President of the student social enterprise club. (And how my LinkedIn profile is now enticing enough to be invited back by the same organization to share my story on an alumni panel in front of 400 people at the same annual student competition where we presented seven years ago.)

Even while so far outside of ‘my true crew’ at my first job in finance, it’s also how I found myself on the ‘Gen Y’ engagement committee, organizing speed mentoring events for young female professionals to meet more experienced female bankers. And on the social committee planning holiday parties and goodbye drinks when people left (even though no one planned anything for me when I left – which still stings a bit today if I’m honest).

With that kind of track record, it’s no wonder that I’ve been drawn to several collaborations over the past six years (no less than three co-founder teams and many more informal teams and collaborations).

Some failed tremendously and others are going strong today.

I’ve written many times about the topic of building effective collaborations as a changemaker but today I want to share one of the elements of collaboration that I find the most challenging.

While often quick to raise my hand to help out, the opposite doesn’t come naturally at all.

That is – asking for help. Do you feel the same?

I so naturally block out these moments that I struggle to even come up with an example! (I guess this is the shadow side of an optimistic, problem-solving, can-do attitude.)

It seems like the typical entrepreneur, myself included, has a combination of:

  1. an unusually high threshold for letting others give their support, and
  2. a preference to always be in some kind of control of the outcome


Neither ‘wanting to be in control’ nor ‘repelling helping hands’ lends itself well to collaborations!

It’s clear social entrepreneurs recognize the value of working together and overall the changemaker community does a pretty great job of it. 

I believe if there is one skill that dramatically increases each of our abilities to create change, it would be learning how to be more effective collaborators. When it comes to learning to work with people and build strong relationships, it’s a lifetime endeavor!

Yes, it might feel easier working in a vacuum. When you don’t need to ‘run anything by anyone else’ or ‘discuss the pros and cons of your next step’ or ‘get and give feedback at every turn’ then you don’t run the risk of going at frustratingly turtle speed.

But there isn’t a day that goes by where I’m not truly inspired and charged up by the people I work with.

Despite the (sometimes hair-pulling) messy middles on the way, the end results of working collaboratively are straight-up magical. The push and pull of constructive discussion, the brainstorming that leads to the next collision of ideas, and the sheer increase in productive hours are tremendous payoffs that are impossible when running solo. 

When it comes to collaborations, to me thoughtful design is finding the points of leverage where your contribution can be most effective. 

This has two components:

1. Leaning on Your Team

Coming together with a diverse mix of skills and experience, glued together by shared vision and values, yields iron-strong outputs. Every element is stress tested against multiple points-of-view instead of just one.

This ‘stronger together’ approach has paid off for me in many ways. One of the most recent examples was when a member of Captivate (a program I built with Change Creator and my longtime partner-in-impact, Solène, to help impact entrepreneurs put story at the heart of their marketing) said a big part of the reason he joined and felt motivated to craft his story was because of our eclectic backgrounds and the collective benefit of having us all on board to support him.

In the last year, I’ve also made a more conscious effort to gather not just functional teams for executing projects, but also a team of personal moral support. I invested more than ever before in a small mastermind of amazing female entrepreneurs and started working more regularly with a private coach.

Committing to these supports felt uncomfortable – being of the ‘receiving help’ variety it felt selfish and like a waste of time that could be better spent ‘producing’ – but the space it opened up for personal awareness and growth has been invaluable.

2. Leaning on Your Strengths

In school, you’re taught to work on improving your skills and knowledge in areas where you lack. In entrepreneurship, this framing can really drain you and drag you down.
I can’t tell you how many conversations I’ve had with entrepreneurs who feel like they need to endure the pain of muddling through tasks or activities that fall far outside their zone of genius. (Just because… why? If you have an answer to this, I’d love to hear it!)

It’s like all these years of schooling imprinted a feeling that our contribution is only as valuable as our greatest weakness. It’s just not true! The only bound to our contribution is how high we allow our greatest strengths to shine.

Learning to trade in control and perfectionism for the messy magic of collaboration is one of my greatest joys so far in my entrepreneurial journey. I look forward to continuing growing into this and becoming better at leaning on my teams and on my strengths. I can’t wait to see what else is possible when each of us changemakers finds our greatest points of leverage to contribute to a better world, together.

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