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It's All Relative

My name is Caitilin O’Connor and I am the newest employee of Blackwood Family Enterprise Services; I’m also the daughter of Patrick O’Connor, the President and Founder. I’ve been working at Blackwood for a year now and was asked to write a blog post about my experience being the G2 in a family business. So I figured as an accounting student, what a great way to show off my skills! Here goes nothing…


A Little About Me

I’m a 25 year old student at the University of Winnipeg planning to graduate with a Bachelor of Business Administration, streaming in Accounting. I’m the second of three daughters, the middle child (so I’ve experienced struggle), and the only one working at Blackwood. I was working fulltime as the Program Coordinator at my local Community Centre until last year when I decided to go back to school fulltime, which created the opportunity for me to begin working at Blackwood.


Blackwood and I

My relationship with my father’s business has traditionally been one of unfamiliarity. I didn’t know what he did. I did, however, always know that if I licked envelopes for an hour or two, I could earn $20 from him – which is all a kid needs at age 12.

Fast forward to now and my relationship with my father’s business is one of admiration.

When my parents first suggested I start working at Blackwood, I was a little hesitant. I understood what an amazing opportunity it was, but I didn’t want something I didn’t feel I deserved. This worked, because as it turns out, my parents didn’t want to give me something I didn’t deserve either! Thus began the tricky yet wonderful balance of being a part of the ‘family’ AND the ‘business’ in family business.


Pros and Cons

Being the second generation has its perks and its drawbacks, much like anything. You get a great opportunity to work within an already established business, but… you are also brought into an already established business. This team you’re now joining may not share the same values or have the work culture and environment you excel in. Both parties have to adapt and see what works and what doesn’t.

Currently succession is not a topic of discussion, however, I still encounter what I think are typical situations that come about when working in a family business. Little things, like remembering not to call my mom and dad, ‘mom’ and ‘dad’. It may seem odd, but for some reason all credibility is lost when people hear you drop the ‘d-bomb’ in the middle of a meeting.

A surprising result has been that my relationship with my parents has changed for the positive. We have a new level of understanding and respect for each other. Working so closely with them I feel has been a bonding experience.

One of the biggest hurdles has been getting away from the label of “boss’s kid”. The bottom-line is that, regardless of my qualifications, my DNA had something to do with me becoming a Blackwood employee. Since my date of hire, it has been up to me to prove myself to my coworkers as a needed part of the team. This may mean I have to work a bit harder at first, but it’s your work that will set you apart from this title.

Honestly, there’s a list of things that you encounter, and the list just keeps growing as you work through different situations. But for me, the good has far outweighed any bad. Being a part of this amazing company, with my mom and dad, is so cool to me. Though for now I don’t see this as my long-term plan, I will never regret giving it a try and seeing what it has to offer. I know I’ll gain so much from this, and I hope that I will have had, in turn, an impact on the company and my coworkers too.

When I sat down to write this I researched some other articles about being a G2 in a family business, and found one in particular that I really connected with. I highly recommend reading this article if you are considering working in your family business, hiring a family member, or are just generally interested in learning about the dynamics of family members working together.

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