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Why I started the same business three times

I've been thinking about how the businesses we see have the shadows of false starts behind them. We don't see the shambles of ventures collapsed under the weight of circumstance, indecision, or poor judgement. And #realtalk, I've struggled with all three.


Leaning into my digital communication knowledge, I decided to launch my freelance career, the third iteration of a business I have started over and over (and over!) since January 2020. Yes, 2020 was bananas. But because it was bananas I think it's a great example of how rough it is to start something in any year, and, coincidentally, how easy it could be if we changed the way we look at small business.


Date: January 2020

Greatest strength: Confidence

Biggest hurdle: Childcare

I decided to take the freelancing plunge in January 2020. I was in the latter half of maternity leave and trying to piece together a back-to-work plan that would accommodate a toddler, a husband living most of the month in another city, and, you know, fulfillment. I'd worked as a freelance writer for a long time and decided it was time to launch a more comprehensive business. I reached out to contacts and got some projects underway. Childcare was up and running by February. In mid-March 2020 the Covid-19 pandemic hit North America. For me that meant no childcare, no grandparents, and no partner. My husband was not only stranded in another city but involved in bringing PPE to Canada from Asia. I was incredibly proud of him, but also incredibly alone. I was consumed by baby care and the anxieties the pandemic brought to so many people. My business went on the shelf so I could simply handle the day-to-day.

I went to a really negative headspace after this happened, blaming myself for not being able to make it all work. I knew running a business is hard so why wasn't I just working harder? Clearly, I couldn't control a lot of what was happening. In order to get back in the saddle with some confidence on my side, I had look at the real picture. Being hard on myself wasn't being more realistic, it was draining. Being honest about what had blocked success allowed me to make better choices later.


Date: Summer 2020

Greatest strength: Support network

Greatest hurdle: Confidence, direction

Some of my support network was back in place by late spring and I turned back to freelance work. I wasn't nearly as confident as my first try. I also had less childcare time than I'd originally planned and, as a result, became obsessed with optimizing the hours I put into working. I stressed to no end about filling my day with tasks that paid and became frustrated when I couldn't piece together enough. I resented the time away from my family that I couldn't bill, and so didn't put any work into planning or figuring out what my business was at its core. When people asked, "What do you do?" I didn't have a clear answer. When my husband was laid off in July, our financial situation got serious. I decided to take a full-time job with a predictable paycheck. A total lack of confidence made it easy for me to use the new job as an excuse to put the business back on the shelf.


I don't know that I would have had it in me to start again if it wasn't for the supportive voices of my partner and some key family and friends. Though I was overwhelmed, they'd check in on my progress and ask real questions. They helped me pick through the layers of self-doubt. They helped me realize I was discouraged not because the dream was impossible but because I was drowning in fear and pessimism. So when circumstance turned to my favour I was ready.


Date: Fall 2020

Greatest strength: Direction, support network

Biggest Hurdle: Perfectionism, timidity

In August 2020, Metro Vancouver saw the start of a second wave of Covid-19 cases. I was working closely with young children at the time and it was no longer safe to keep my son's high-risk grandparents, our source of childcare, in our bubble. Additionally, my husband found a safe job and we decided it would be best if I tried to work from home, since my skills transferred to the virtual workplace.


This time circumstance forced me to take the business off the shelf and put it right in the centre of my desk. I literally found a second-hand desk and stopped working on my bed. I started being more intentional with what I was doing. I started noticing my downward spirals and turned to affirmations to halt the process. I'd repeat phrases like the following over and over until I was calm, even if I didn't immediately believe them:


"I am successful."

"I am smart."

"I deserve the support I receive from others."

I talked to anyone and everyone who was a business owner about how they managed their day and outlook. I received invaluable advice about identifying values instead of actions (why you do what you do instead of what) and a list of practical tasks for getting started. Two of the best tips were these:

"Just get started."

"Done is better than perfect."

From there, everything has clicked. I have both a clear idea of what my business is and the flexibility to assess new opportunities. I know what my skills are and, more importantly, why I want to share them with people who need them. The "to-learn" list is still longer than the "learned," but it's an inspiring place to be.


I think if we could be honest about our missteps and celebrate the journey over the arrival we'd see many more people giving it a try. You've heard all about my false starts. I'd love to hear yours.


Where are you at in your journey?

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