A Major Crossroads in My Solopreneur Journey

As I celebrate this newsletter's second birthday 🎈

We’re just over a week into the latest Write of Passage cohort (the very course where this newsletter was born two years ago when I was a student). This time I’m working as an Editor providing student feedback. Stay tuned for lessons learned in the coming weeks.

Today marks this newsletter’s second birthday. We’re officially in toddler territory, but thankfully there’s nothing “terrible” about it.

But I am at a crossroads.

Back when I sent my first edition to a whopping six subscribers on October 12th, 2021, I had a clear idea of what my newsletter would be about. Or so I thought. I started writing exclusively about courses but by my third edition, I was veering inward. I began writing about my journey.

Until now, that “journey” has been navigating entrepreneurship as a one-woman show. But as I’ve shared in previous posts, the allure of solo-ing hasn’t translated to fulfillment. Without backup dancers or the ability to duet with others, I’m left performing everything myself. And while that can be a fun challenge, it can also be very lonely.

Hence I’m at a crossroads.

Two Ways to Go

I spent the latter half of my summer pondering what the hell I should do. Oddly enough, my surroundings had me back and forth like a ping-pong ball sailing through the air with the lightest of ease. I’d leave Montreal for the Laurentians (i.e., the country) and find myself thinking “I should stick with self-employment,” as I floated in the lake surrounded by trees and rolling hills.

But the minute I was back in Montreal, anxiety would hit my stomach like a baseball bat, emitting panicked thoughts in a hellish home run. “I need to find a job,” I’d think.

Professional Perspective

It was hard to reconcile these opposing feelings. (Your guess is as good as mine which one was the angel versus the devil.) And since I couldn’t decide what to do, I decided to call in reinforcements. I went to see a therapist who specializes in anxiety and burnout (the two things I’d found myself struggling with), and sure enough, she helped me put things in perspective.

By validating my reluctance to make a decision given the gravity of each option—and their polarity—my therapist helped me realize the decision didn’t have to be all-or-nothing. I could find a part-time job to fulfill my desire to be part of a team again while continuing to do my solopreneurship stuff in tandem. (Funnily enough, a friend had given me similar advice earlier this summer but hearing it from my therapist registered differently. That’s the power of professionals, right?)

But back to ditching the all-or-nothing mindset. Initially, back in August, getting a part-time job seemed like the obvious answer to my dilemma. But fast forward a couple of months and having given myself more time to reflect, I’ve realized I want something different.

Now, I want to find a full-time job.

The Road I’m Choosing

I’m going to make the transition from solopreneur to teammate or cofounder within a great company. And the best part is I feel calm, grounded, and excited about it.

I’ve realized that after two great—and gruelling—years of working independently, I’ve learned a ton and exercised as much freedom as I could. I’m grateful I had the guts to chase my dream of self-employment. It’s something I knew deep down I had to do.

And I did it.

But while I’d anticipated being completely fulfilled on the solopreneur path, I’ve discovered it doesn’t suit me. The leadership aspect and continuous learning are straight up my alley, but the lack of teammates to collaborate with, get feedback from, and socialize with is something I’ve found myself increasingly missing since I left my 9-5.

So now I’m keen to find the best of both worlds.

I’m setting the intention to manifest a great role where I can continue operating in my “zone of genius” within an entrepreneurial, innovative team—a team that strives for excellence with the aim to be the best at what they do.

I can’t imagine anything less after freelancing with companies like Maven, Write of Passage, and Actionworks.

Conveying My Value

What’s really cool about writing this newsletter (and there are many things) is the responses I get each week. Case in point, back in August when I shared I was going to look for a part-time role, I included details on the type of work I was looking for.

I got a lot of wonderful messages—people forwarding relevant job ads, offering connections and words of encouragement.

But the one that really blew my mind was from a reader named Trevor Bragdon. Trevor specializes in pitching and he suggested I reframe what I do to better convey the value as follows:

“It sounds like you are great at figuring out solutions to important problems and enjoy working with founders/CEOs, and they enjoy working with you because you think like them.

What if you positioned yourself as:

I work with founders/CEO and their companies in two ways. 

1. Help Founders and CEOs create courses and talks to become thought leaders in their industry

2. Help companies take the skills of their best employees and turn them into training and best practices. We all have employees we wish we could clone. I work with your best employees to understand how they do the job, and what makes them excellent, and then turn it into training to help other employees get to their level. 

Or something like that. Basically, change the framing of the value associated with each. Helping a founder become a thought leader could be worth 5 or 6 figures to them. Helping a company replicate the skills of its best employees is enormously valuable.”

Whether you read my initial version or not, I can assure you Trevor’s version is much better. Because if there’s one thing I’ve learned about marketing these past couple of years, it’s that you sell people on outcomes.

Another big takeaway from this exchange is when you open up about your journey, you invite in all kinds of support. And on that note, I’ll continue sharing my journey once I land a full-time gig. In the meantime, stay tuned for updates on my quest.

Thanks for reading and have a wonder-full week,

Alexandra

P.S. I’m happy to announce my Montreal-devised plan to pursue a full-time opportunity has passed the “lake litmus test”. I was up there a couple of weekends ago, and for the first time in a long time, I felt at peace.

Early autumn morning at the lake (photo taken September 30th)

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