Why I wouldn't delay solopreneurship (or other dreams) because you’re single

A reality check about waiting on "ideals"

Morning beach walks in Maine

I shared this quote from a mentor in last week’s newsletter: “Solopreneurship is not only a business model, it’s also a lifestyle.” And it applies to entrepreneurship at large. It’s the unconventional path—or what some call “the pathless path.”

Paul Millerd

has made the latter more approachable through his book, ‘The Pathless Path: Imagining a New Story For Work and Life’. In it, he shares his story of leaving a prestigious career in Corporate America as a burnt-out consultant to pursue an unconventional path forged through “painstaking experiments, living in different countries and the goodwill of people from around the world.”

I bought Paul’s book months ago but I only got around to reading it in June during a family vacation in Maine. We spent an incredible week at a beach house but as the only singleton among my three siblings, their wonderful partners, and babies, I had to contend with the odd bout of anxiety about when I’ll finally meet “the one.” So it felt like fate when I read this particular passage in Paul’s book—and how he subsequently met the love of his life, Angie: 

“I was also 33 years old, single, and had recently declared to my friends that I was giving up on dating and shifting to the “cool uncle” phase of my life.”

Being 33 myself, currently single, tired of online dating, and having mastered the “cool aunt” gig, I read Paul’s words over and over again. He explained how “releasing his grip on the future” made space for the right things—and people—to emerge. And it made me realize that in my quest to make my solopreneur career a success, I may have been gripping onto the future too hard. I spent the bulk of the past two years working overtime—nights and weekends—with no sense of boundaries. I told myself “I had to” in order to get things off the ground and to be frank, I still think those excessive hours were necessary. I learned a tremendous amount in a remarkably short amount of time and I don’t regret it. But I also realize I’d blindly succumbed to a “workaholic” persona that I’ve now let go of to prioritize making space for the type of partnership and family I want to have.

Most of us operate on a spectrum and over the past couple of years, I’d moved more toward the “controlling, neurotic” edge of mine. Paul’s story inspired me to loosen my grip and embrace the art of living in the present. It feels good to be back to my fun-loving, easy-going nature—the one that led me overseas for the better part of my 20s to experience new ways of living and think deeply about that which is the norm back home. I feel like myself again.

Reality check

I’ve had many moments over the past two years where I wished I had a partner, particularly someone more experienced with entrepreneurship who could’ve helped me find my way as an entrepreneur. But had I waited for that opportunity, I would still be champing at the bit to leave my 9-5 with no end in sight, wondering what could have been. That said, I’ll be honest, anytime I see someone shouting out their partner for being their biggest supporter, I feel like I’m missing out on a pertinent part of success. 

A couple of months ago, I sighed and said to one of my closest childhood friends, “I could do so much more if I had a partner.” But she was quick to correct me by saying, “You don’t need to do more, Ali. You’re already doing so much. You don’t even realize it.” That’s when it finally clicked for me. It’s not about finding the right partner to do more, but that things would be that much easier and more fulfilling. 

But even then, I have to give myself a reality check. Because as much as I like to think having a partner would provide me with everything from a soundboard to a proofreader (I keep joking with friends that I'm going to add “proofreader” to my Hinge requirements), let’s face it, solopreneurship is hard. Full stop. And even the best significant other can’t be everything for you—and you wouldn’t want to put that pressure on them.

So if there’s one thing you take from my experience, I hope it’s this: “I’ll do it once I have a partner to support me,” is one of the most limiting mindsets you can take on. It’s also unrealistic to wait on an “ideal” that doesn’t exist.

When it comes to chasing dreams, sometimes you need to get the ball rolling on your own. That includes building a business. It can be terrifying and taxing—at least it has been for me. But it’s been even more rewarding to eliminate the “what could have been” scenario from my past. And I’ve been able to leverage a mix of partnerships with family, friends, and peers to satisfy different needs I’ve had along the way. In other words, sometimes you need to take a leap of faith and get on the pathless path before you identify partners—romantic or otherwise—to walk it with. You just have to believe the right partnerships will blossom for each season.

And in the spirit of empowering you to follow your heart down pathless paths that beckon, I’ll leave you with my favourite Paulo Coelho quote:

“The journey is not about becoming anything, but to unbecoming who you are not.”

Thanks for reading and have a wonder-full week,

Alexandra

From Montreal with love, sunshine & encouragement to “enjoy the ride”

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