“A world where I could make the rules”: Inside Joan Westenberg’s journey to entrepreneurship

When I left my last startup for a month off and a break to breathe, my goal was to find a new tech company where I could go in-house and keep doing the (let’s not kid ourselves) award-winning comms, content, and PR work that I’ve staked my name and built a career on. I wanted to be in-house, because I’ve always loved startups, and my drive to build the new new thing, and be a part of a shared vision that truly matters, has been a core part of my DNA for years.

Eight months later, that hasn’t happened. I’ve written before about the career opportunities drying up as soon as I transitioned. I’ve written about going from a director of communications title at a company that had raised tens of millions — where I had shaped the message, the investor decks, the PR story, the content and every piece of comms that touched the team and the customers — to not even getting interviews at a dog food startup. My career tanked out. Where I used to be sought after for my experience, I found myself being told I lacked the experience I already had.

And it was, to be clear, devastating. It can break you, to look at the career you’ve built and see a flaming wreck where you used to see success. 

It can break you. 

But it didn’t break me.

When I looked at the landscape — and an inbox full of mounting automated rejections, and another week of calls with recruiters who would tell me I wasn’t a “culture fit”, or refer to me as “a transgender” — I took a deep breath, opted out of the crap, and decided the only way to have the life and career I wanted, post transition, was to stop waiting for the gatekeepers to give me permission and build it myself.

Starting Tiny Spells, my self-care startup and community, and Studio Self, a brand, content and comms studio, were my step into a world where I could make the rules; because the rules I was trying to live under weren’t designed to enable or support me.

By building something of my own, I was no longer waiting for incumbent power structures to decide I was worthy, or playing respectability politics with tech founders’ feelings. 

It’s been damn hard; this has not been an easy path.

The prejudice that has prevented me from going in-house has prevented me from closing, or even opening up, conversations with so many companies. People are distracted by who I am, and they’re distracted and apparently disturbed by the fact I am a loud, unapologetic, and at times vocal, transgender woman. I’ve had multiple companies tell me they don’t want to work with me because I’m too controversial or political.

But there have been so many wins.

Being able to talk to, and work with, multiple clients means I’m far more able to cast a wide net and seek out the good people. I’m able to work with a portfolio of tech startups and consulting firms that recognise the strength of my voice and my background in comms. I’ve had success subcontracting through other agencies and consultancies, which know my worth and have used me to transform the way they work with some of their clients, and that’s been a game-changer too.

I am, frankly, at the top of my game, and I am one of the best tech comms minds in the country. I know the craft I’ve chosen, and I know that I am worth gold. If recognising that myself sounds arrogant to you, I’d challenge you to ask if it would still sound arrogant if a (cis) male startup founder said it.

I want to grow my work more. I want to do more, create more, and find ways to be better. I want to make my mark, and be proud of my every day. None of this makes me unique. The point where my story wanders from the beaten path, is the point where I transitioned and became a square peg. I have no regrets about that. I am directionally okay with working out loud, with the complications of my identity, and with making my own way. 

Would I go in-house again? If the Australian tech ecosystem began to reflect the values they espouse at their #IWD breakfast panels, maybe. If a tech company decided the relatively fair compromise of accepting who I am in exchange for my skillset was worth it, maybe. But I don’t intend to wait on that. Not now, not ever.

If I can steer myself, I always will. 

This article is part of SmartCompany‘s special IWD 2020 edition. It was commissioned and guest-edited by Culture Amp’s Aubrey Blanche.

NOW READ: Why the straight, white cis-man’s meritocracy is a fantasy

NOW READ: What it’s like being a trans woman in Australia’s startup ecosystem