Squiggly Careers | Meet Reese Quinn

We recently sat down with Reese Quinn. A founding member of GW, and current Head of Operations at Arcade.

This conversation follows Reese’s winding, non-linear path. We dive into how Reese evaluates opportunity, how they think about their career path and how they’ve come to see that their neurodivergence, just like their generalism, is a total strength.

Hope you enjoy! ❤️ 

Let’s start at the beginning..

Before my life became this constant squiggly and windy road, I had only one horizon.

My heart was set on becoming a professor, and that became my all-encompassing obsession in life. I even got into this top programme, setting myself on a well-trodden path. Little did I know, those dreams were soon to become shattered when the programme got suddenly cancelled.

After all this hard work I had put in to reach this goal I didn't want to just throw it all away, I still really wanted to teach, so I continued with the degree I already had — and landed a teaching job. 

I blinked, and it was suddenly 5 years later. I had evolved into a role that connected teachers and administrators, bridging the gaps between them and helping them both understand and support each other. Eventually, I got itchy feet…

What was your turning point? 

When the pandemic hit. I think this was a time when everyone started to question their lives and whether what they were doing was right for them.

I realised that even though I still enjoyed teaching, it was no longer the right environment for me. There was more potential in my life that I wanted to explore.

Once I decided to leave my teaching job, my path became windy. I started to jump between small businesses, helping them launch and scale in different markets.

I began to make more connections with founders and different people from the startup world, learning this whole new way of life that offered learning opportunities, and a fast pace, which were elements I knew I valued.

I realized, I had finally found my people.

What lessons have you learned along the way?

• I learnt that surrounding yourself with people who truly understand you and how you want to work is so important. After I left my job, the folks I worked with in startups gave me so much support and helped me adapt.

• Another thing that I learned was to be completely unashamed of my background — what I or anyone else had done previously did not define me as a person. I see this a lot in education where someone would express ‘I am a teacher’ as opposed to ‘I teach’. It is important to separate yourself and not be ashamed, especially when searching for something new.

What does ‘generalist’ mean to you?

From my perspective, a generalist is someone who desires to learn a broad spectrum of different skills, and gets a high from diving into the unknown.

As a founding member of Generalist World, I’ve spoken to so many people in who also have these squiggly backgrounds, too, and I began to notice patterns.

They love learning, and figuring stuff out. We love to get our hands on something we haven't done before. When you see something within reach that you want to discover more about, the operation side kicks in and all you want to do is lean into it.

This was a gradual realisation for me. The process of not becoming what I set out to be, and then 5 years speeding by. I realized how quickly life passes. I was suddenly hit by a reckoning, where a question within myself surfaced:

“Is what I am doing benefiting me beyond my paycheck? Am I really gaining anything from this career, or am I just coasting?”

One of my biggest lightbulb moments happened when I embraced my neurodivergence. The moment of ‘hey, I have a squiggly brain, not just a squiggly career’. 

I could finally recognise, in reflection, that I deal with change extremely well, as someone who has had to adapt to different environments consistently. I could now start to apply that to a career context.

Instead of staying in one business where I could have worked my way to the top and had a linear path, I would rather lean into things that excite me — that pique my curiosity. To prioritize that feeling of flow,where I suddenly look up, and 4 hours have passed by.

How has being a generalist, or even neurodivergent, worked in your favour?

The big unlock came when I learned to speak about my generalism, and my neurodivergence, in a way that carried no stigma, or negative connotation.

Growing up, my Dad had a very linear perspective on business; he valued loyalty and building yourself up in one career (which definitely works for some people!)

He found a bit of shame in committing to something for only 5 years, or only trying something for 6 months then ‘giving up’. Seeing other people being incredibly successful on their squiggly paths in ways that I also value, made me realise I don't have to feel any shame and I should just own it. And because of this, I am happier with the path I am on now.

I have also learnt that being a generalist or neurodivergent can be exhausting. It is so important to have ‘pause points’ to allow yourself to recharge and give yourself time to figure out what is next.

How do you think about what’s next for your career path?

I’ve come to realize I massively value the opportunity to progress. If there’s no opportunities where I can upskill and be continuously learning, I would consider moving on somewhere different, or advocating for something different within that company.

Over the years, I have also shifted my meaning of success, and I have disconnected myself from the salary, title, and stage of the company being the most important metrics. Now, having a fully flexible schedule feels like I have moved up in life, that is my promotion (for more flexible companies, check out our friends at Flexa!)

Any parting advice?

It is so important to find people and companies who will support you; where you don’t have to try and ‘sell yourself’ — but where you can just be yourself. This might make your job search a little longer or more arduous while you find a great fit, but when you do, it’s worth it.

Look upon your windy path and think of it as evidence of your strength, your experiences, and your skills. It’s your unique combination that will allow you to thrive in a world full of technological change, cultual shifts, and endless possibilities.