The Real Story of My Entrepreneurial Journey: PART 2 – Too _____ to Give Up (Insert Adjective of Your Choice)

Previously, in Part One of the real story of my entrepreneurial journey…

Fueled by the hardheaded belief that there is no ‘right’ way of doing things, I navigated through the typical business grad career job in the financial industry in my early post-university years. Frustrated by the feeling of ‘living a double life’ I eventually took the leap into entrepreneurship and launched The Sedge from South America thanks to the 6-month runway afforded by Start Up Chile business incubator program. (if you missed the full Part One of my business story, read it HERE)

 

If Part 1 of my journey was a perfect storm, Part 2 was trying on every possible piece of waterproof clothing, being disappointed to find that most contained holes, and somehow weathering the torrential downpour long enough to enjoy the rainbow once the sky cleared.

As someone who used to regularly sleep in until noon on weekends (and still can on occasion) and complained when my dad parked at the far end of the lot, you wouldn’t be wrong to say I’m generally a lazy person.

There are really only two activities in my life where I can confidently say I’m more tenacious than the average bear.

One is snowboarding.

I learned to snowboard when I was 12. Despite having skied since I was little, skiing felt like a giant hassle that I would rather avoid. On the other hand, I couldn’t wait to get out to the mountains to snowboard for as many days as I could squeeze (and find rides for) in a season. It took me a solid two years before I could finally get down the hill without smashing into my knees/tailbone/elbows/face/friend the entire way down – all with giddy anticipation of heading out again the next day. Now, that is staying power!

The illogical perseverance eventually paid off; I became the girl who kept up with the boys, took summersault starts on the hill, and held my own when random teenagers at the top of the gondola challenged me to an impromptu race to the bottom.

The second activity where I’ve demonstrated more staying power than I thought possible is building a business.

We probably had this conversation many times over the past six years, but one day in particular sticks out. Jordan and I were camped out in the backyard one day, soaking up the sun, him with a novel on his lap, me with a podcast paused, both with a cold beer, somehow veering into the topic of my depressing state of affairs in the ‘results’ (code = money) department of entrepreneurship.

I was busy to be sure, and that was part of the problem. How could I be working so hard for so long and still not have a steady stream of customers coming through the virtual door? It didn’t add up.

We’re taught in school that the more effort you put in, the better results you get. Study more, get a higher grade.

Simple.

Except that building a business doesn’t work like that. There are zero rewards for hard work. And outsized results aren’t produced with sheer effort alone. (Just ask the person who accidentally invented the post-it note.)

As any well-meaning friend or family member who cares about your sanity (and maybe your contribution to the household income) Jordan was patiently inquiring to better wrap his head around my unrelenting pursuit of something that didn’t seem to be paying off.

I remember being at a loss for words. For all the ‘lean startup principles’ drilled into my head throughout my six-month crash course in startup land in Chile, I couldn’t quite explain why the experiment needed to keep going. All I could muster was that if I still felt such a pull to put in the time and effort, despite all roads leading to ‘quitsville’, then I simply had to keep going.

That feeling that I didn’t want to stop had to be worth enough to keep going.

This is not to say I blindly charged on taking the same fruitless steps over and over again. To quote my boss from my banking days (speaking to the practice of basing a new annual loan review on last year’s info): “Shit in, Shit out”.

I charged ahead with a blind optimism that the ‘next thing’ would solve everything.

Instead, I learned that entrepreneurship is truly a slow burn.

It’s taking each delicate moment of awareness, insight, and experience, and slowly stockpiling it in a corner of your dimly lit office. This curation is interwoven with moments of standing and staring at your pile of knowledge with a puzzled look, with your hand on your chin in deep thought. Then comes careful rearrangement of the bits and pieces into new designs, over and over again until they start to take some kind of recognizable shape (and the office slowly brightens!). A shape emerges that means something to you and is (miraculously) recognizable and celebrated by some of your favorite people.

I imagine it’s glimpses of this feeling that keeps the entrepreneurial spirit ignited, even in low moments.

There were many low times over the years. Days going in circles with ideas of what do implement next. Endless internet searches looking for information about what actually WORKS when building a business. Getting distracted from true progress (i.e. connecting with potential customers) with pointless website updates, technical wormholes, and webinars on everything from Pinterest to SEO.

I’ll never stop learning, but now I know WHAT to focus on, WHEN. Honing this skill alone is a life-changer.

But it took me a LOT of trial and error to get there; my brain was focused on a strange and wonderful cross-section of activities over the past six years.

That’s in part because I said yes to every opportunity that came my way. If it was remotely social enterprise related, I jumped on it. It was years in a whirlwind of learning anything and everything.

  • I wrote a business plan for a social enterprise cafe.
  • I planned and hosted more events than I can count: fundraisers, community salons, startup weekends, conference presentations, etc, etc.
  • I facilitated social enterprise workshops – many varieties but one that stands out was a series I co-facilitated with a community partner. It ran for several weeks… on Saturdays… in the middle of summer… for zero pay… with a professor who turns out didn’t believe in the economic side of social enterprise one bit (and also felt the need to chastise me for charging for my other work!)
  • I ran live online courses for people across continents, enduring more tech failures than I can count.
  • I re-did websites for other social entrepreneurs.
  • I put in nearly 400 hours sitting with local changemakers, discussing their strategies, and coaching through the challenges.
  • I co-wrote and self-published a book with Solène, another impact strategist who is now a dear friend.
  • I started a side business with Solène where we served 100 entrepreneurs over two years, creating over 20 high-quality trainings and running monthly coaching.
  • I organized volunteers for ‘Humans of Calgary’ (the local version of the famous Humans of New York)
  • I shadowed the production of a short film documentary exhibited at the Canadian Museum for Human Rights.
  • I strategized for my mom’s sleep health business and set up new courses, sales pages, and challenges to help grow her audience.
  • Oh yeah, I even organized a live flash mob in downtown Calgary!

PHEW!

I don’t share this as a laundry list of random activities that filled my days. I share this to give you a full picture of what the messy entrepreneurial journey looks like. But you already knew that, didn’t you? 😉

Some weeks were so jam-packed with commitments that on Friday I couldn’t remember what happened on Monday of the same week.

It all added up to some low periods. One weekend I decided to stay home and ‘catch up’ on work instead of going away to visit family for Thanksgiving. That weekend I distinctly remember feeling a wave of regret but, more often than I’d like to admit, I chose work over family or friends. Not something I’m proud of, for the record.

It all caught up with me in early 2018 when a mysterious chronic sore throat forced me to see the need to streamline and focus to make better decisions for my health. My mysterious illness created a cloud that hung over every decision. It meant weighing each commitment against very real physical pain — instead of my previous self-imposed boundaries that defied space-time laws of physics.

It meant coming to terms with the idea that 2018 was now the ‘Year of Saying No’.

Among many small decisions, some big ones were Solène and I shutting down our changemakers membership community and me leaving my role coaching for the Social Enterprise Accelerator (run by a local organization that I not long before had only ever dreamed of working with).

Even though thoughtful design is what I live for in the social innovation world, it took getting hit over the head to realize that I had neglected to thoughtfully design my own life and business.

I had taken too much on and didn’t make the time to breathe or integrate any of it. What use is that contribution if I’m simply barreling through the motions without the space to follow each beautiful movement through to it’s greatest extent and potential?

Incredibly grateful to add this new learning to my entrepreneurial tool belt, I sliced and diced commitments as best I could to create space for healing.

I resolved to be a more thoughtful designer of my business and life.

In addition to all the practical learning, this is the greatest gift from my years of experimentation and one I hope to keep at the forefront going into the future.

Next week in Part 3 I’ll share what thoughtful design looks like to me now in life and business, and how a few key relationships and collaborations helped me get there.

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