Leadership Isolation: Lonely Doesn’t have to be Alone

Last month, I was invited to take part in a panel for the Women in Tech Regatta titled: ‘A Bird’s Eye View from the Top: How to Avoid Leadership Isolation’. The panel description read: “we’ll hear from a diverse group of CEO’s and startup leaders who will discuss multi-dimensional leadership, building credibility and avoiding isolation.”

When I received the invitation, I was still in NYC co-ordinating travel plans to return home after a 3-month program at NYU and was in the middle of securing a 4-week long pilot with iLead Charter Schools. Needless to say, I was a bit pre-occupied when I initially agreed. However, there was something compelling about the subject matter that I knew I had to take part in — even if it was just to learn from my fellow panelists.

Days leading up to the event, I began to really think about the topic. I sat down to make speaking notes and very abruptly realized that I didn’t have a clue as to where to begin. Instead of thoughtful responses and memorable anecdotes, I sat there with more questions than answers.

I didn’t know it then, but that was my moment of discovery. This feeling alone thing… it’s not something new.

Being an effective leader requires confidence and clarity in your vision and abilities. Your job as a tech CEO is to perpetually sell: sell to prospective investors, sell to users, sell to team mates. So of course, a credible CEO couldn’t ever possibly be uncertain or confused — right?

I don’t know about every other startup founder, but that’s certainly not my reality. The most challenging and lonely part about this entire experience is this battle between keeping your composure and being the strength behind your team with maintaining transparency, asking for help, and being realistic. It’s a constant paradox between a fake-it-until-you-make-it mentality with the Imposter Syndrome.

It’s one thing to put myself through the deep highs and lows of a startup, but I’m also asking incredibly talented people to put their high paying jobs aside or push back the date of their wedding to take this wild ride with me so we can build a company that I don’t know is going to wxist a year fI’m asking them to not only believe in this crazy idea that’s going to transform education, but to also believe in me.

Whether it’s real or not, the pressure and responsibility can be debilitating and dangerously lonely.

I never spent much time thinking about this because I always assumed it was merely a byproduct of the work I signed up for and that it’d go away once I reached a certain level of success.

Nope. Not how that works. The onus is on me.

So, on the day of the panel, I took to the stage and told my truth: I have no idea how to I’m going to deal with this looming depression and I don’t know if I’ll ever be rid of these incessant thoughts about not being ready or enough.

Equipped with a list of responses from my fellow panelists, I took away lessons that I’ll bring with me through every high and low of my founder journey. Namely: lonely doesn’t have to be alone.

This coveted team of talent and unconditionally loving support system I have is here for me. I just have to let them in. And this feeling of loneliness? It’s not foreign to the very people I’m sharing this stage with either.

Experiencing fear and doubt doesn’t make you any less of a strong leader; how you deal with those feelings will, however, define who you are.

How do you deal with feelings of loneliness?



PS. I posted a photo on my Instagram with a caption about this panel and I’d like to share it again here:

“Being a “CEO” is not everything the movies make it out to be. It’s terrifying, exhausting, and sometimes feels impossible. Your 9 to 5 lives in reverse; beginning at 5am and if you’re lucky, ending at 9pm. I live, eat, breathe our business. I wake up and go to sleep thinking about our business. It’s hard as hell.

So without the right team and community, it can also be dangerously lonely.

In spirit of #BellLetsTalk Day, it’s important that this caption that goes with these photos connect the dots and be the catalyst for conversation.

Thank you to the #WiTRegatta for including me on your panel about CEO/Leadership Isolation. I felt like I took away more from my fellow panelists than I contributed so I’m especially grateful for their wisdom and experience during this ever changing, incredibly challenging journey.”

Canadian ed-tech entrepreneur building @get_softserve so that humans have a fighting chance against the robots.