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Five Turning Points of My Career

with Caroline O'Driscoll

Caroline O’Driscoll is a force of nature. Tax partner in our Cork office, with 20+ years advising companies in the technology sector and supporting teenage girls to pursue STEM careers as co-founder of I Wish. But that’s only half of her story, read it all here.

"Education will set you free"

My guidance counsellor at school told me I’d probably need to emigrate to get a job. It was the early 90s and it was more challenging to find employment, but I decided to study law at UCC, which led to me becoming the first tax graduate trainee at a Big 4 professional services firm in Cork.

Culturally, it was a different time. I am from a working-class background and was the first in my family to go to university so it was harder to break into business circles - but I never let that limit me. 

My father had to leave school early for economic reasons and he believed that education was the way to participate in a way that he didn’t have the opportunity to do. I passionately believe in the power of education - it is one of life’s great levellers. My approach was that if I got my exams and worked hard, I could be at that table. My parents believed I could do anything once I had my education. That helped me to build my confidence in those early days. 

“I always looked different” 

As I started to move through my career, I was always a bit different, especially for an accountant! My hair has been every colour under the rainbow and there were times when that wasn’t accepted. I remember being asked to change my hair before a big pitch, which crushed me as an individual. The way that diversity and inclusion have evolved is brilliant in that sense - it’s about all of us, it’s about celebrating difference, and we don’t all have to be the same.  

There is still a way to go regarding female representation at senior levels, but things are improving. It’s not until any minority group hits 30% representation that you have a voice and influence. We still don’t fully have that in corporate Ireland and we have more work to do.  

“Your whole frame of reference changes” 

In 2010, shortly before I had my daughter, Darcy, I became a partner in another firm. Returning to work triggered somewhat of a crisis of confidence for me. I was out of the business for six or seven months and it was hard to come back. You feel like you’ve forgotten everything!   

Your whole frame of reference changes. You’ve got a new baby, you feel pulled in many different ways. I was also a new partner, so I had to build a new portfolio of clients and I really focused on building a network. There were lots of lunches, dinners, events, and travel which was tough with a very young baby. There weren’t many female partners who had been on that journey, so it wasn’t really understood, and the workplace supports weren’t really there. Professional services firms are a lot more conscious of that now.

On reflection, the feminism I grew up with was more focused on equality; if you walked and acted like a man, and participated like a man, you’d get on in the business. But that’s not diversity, and it’s certainly not inclusive. We must respect and celebrate differences. Women do have babies, sometimes they want to take some time out, and sometimes it’s more than six months - it’s two or three years. How we develop our programmes to then support women to return to the workplace is crucial. 

“Take confidence from those who place their confidence in you” 

Your career can often be like Lego blocks, you take on one thing and it can be the building block that brings you to something else. My career wasn’t made up of big moments, it was little moments and opportunities I took along the way.  The biggest game changer was when I met Gillian Keating, my co-founder at I Wish. I met her at a time when I was trying to find my way, at a time when I was feeling a little lost.   

She was president of Cork Chamber and reached out to me about doing something for women in STEM. I couldn’t believe that this inspiring role model had reached out to little ole me but I went home that evening full of self-doubt, thinking ‘I can’t do something like this, what do I know about STEM, am I good enough?’.   

What I realised was that she had placed her confidence in me, and saw something that I maybe didn’t see in myself. That’s something I’ve learned from her - ‘take confidence from those who place their confidence in you’.   

She transformed everything for me as a mentor, as a sounding board, and as a friend. I found my mojo again, and my sense of purpose. As well as founding I Wish (a volunteer-led social enterprise to encourage teenage girls to pursue STEM careers), it also led me to join Deloitte in 2019. While it was one of the scariest things I have done, it has been an amazing experience. The opportunity to take on a more senior role, and focus on the tech sector in particular, was something I was interested in. It was such a great move for me - I feel like I’ve found my tribe and a place where I can be me.  

“Be clear about what you want” 

I think it’s vital to know your worth and be clear about what you want. That self-awareness is really important so that you just don’t tumble into things, and you don't end up wondering ‘What if?’. If I feel I’m hitting a bump on the road, I take some time out for coaching and I’ve benefitted enormously from that.

It’s also very important to invest in the relationship that you have with your boss. Sometimes we can focus too much on the negative, on what we are not doing. Don’t be afraid to tell your boss what you are achieving.  I send an email to my Head of Tax every six weeks, and when we come to our year-end discussion, she already has a good picture of what I’ve done. 

I've been so fortunate and I feel a huge responsibility to pay it forward to the next generation of female leaders. It’s vital to reach out to women - understand where they want to get to, what their challenges are, and how you can support them in that. Mentorship for me is about getting to know the person and helping them to tease out where they want to go. The sponsorship piece is where you make it happen. You advocate for them, and you make sure that they’re on track.   

A mistake I made in my early career was that I used to compartmentalize a lot. There was the corporate Caroline and the personal Caroline and the two rarely met.  But most of the time I was pretending! What I like about Deloitte is that you bring your whole self to the table - you are who you are, all of you.   

I Wish is very much part of my personal journey, it is a legacy that I am proud of. I’m also an international tax partner. I am a proud mum to a crazy cool 11-year-old girl. I like Zumba. I read whenever I can. West Cork is my happy place. I am all of those things. I now bring all of me to work and I just thrive on that and I hope my teams do too.  

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