Lisa Hamilton | Crain's Toronto

In this ongoing series, we ask executives, entrepreneurs and business leaders about mistakes that have shaped their business philosophy.

Lisa Hamilton


The Annie E. Casey Foundation, a private philanthropic foundation founded in 1948 and headquartered in Baltimore, is devoted to creating a brighter future for children. Its work focuses on strengthening families, building stronger communities and ensuring access to opportunity. The foundation makes grants that help federal agencies, states, counties, cities and neighborhoods create more innovative, cost-effective responses to the issues that negatively affect children: poverty, unnecessary disconnection from family and communities with limited access to opportunity.

The Mistake:

My mistake was leaving a position that I enjoyed to accept another, less satisfying position that would advance my career.

I had worked a long time to become president of the UPS Foundation. I worked really long and hard to get that opportunity in the foundation, and I really enjoyed it. I was presented with an opportunity in public relations that would have advanced my career in a totally different area, and it turned out to not be the best opportunity for me, given what I was passionate about.

I have changed roles quite a few times, and I had a number of positions that built my skills and enabled me to take on that role as president of the foundation. When I got this opportunity in PR it wasn’t unusual for me to try something different and figure out how to build my skills.

I hadn’t been in the position running the foundation very long. I hadn’t exhausted all that I could have learned. But when doors open you never know where they could lead, it’s not always perfect timing.

Even though I’d only had the foundation job for two years, I thought, “This is a special opportunity, I should go through this door, you never know when it might open again.” In retrospect I should have stayed at what I was really enjoying and was great at. It took me about a year in that new role to realize it wasn’t the right fit. Although I did a good job in the new position, it was very different and very stressful, and not really my passion.

As the head of PR it was a much more significant business role. I’d been told if successful in this new job, I’d get my boss’ job, who was the head of communications for the company. It was positioning me on a path upward to the C-suite. It was a huge opportunity that I was being given. I’m African American and a woman — those opportunities don’t really open up every day for people like me. I thought if I was respected that much and being given this chance, it was something I should take advantage of and seriously consider.

It’s a blessing if you’re fortunate to have people giving you offers. But you have to be clear about which ones you want to take or you can end up in a place you don’t want to go.

It can be difficult to be trapped in someone else’s dream if it’s not your vision for yourself.

The Lesson:

The lesson is you always have to think about what’s right for you. Even when doors open and other people think you could be great for something, if you aren’t clear that that’s what you want for yourself, you can’t substitute someone else’s judgment if that isn’t your aspiration.

There’s something about reflecting on where you want your career to go, and being clear about what your own aspirations are. Part of that is to be self-aware enough not to be seduced by a variety of opportunities that might be placed in front of you. It can be difficult to be trapped in someone else’s dream if it’s not your vision for yourself.

I was very flexible in seizing opportunities that were presented to me throughout my career. I was thankful for the opportunity and gained great skills, but it really took some time for me to accept that this PR job was more about the allure of bigger opportunities, and it wasn’t a sufficient enough reason for me to continue in that role.

I was approached by the now-president at the Casey Foundation about a job there. I didn’t seek it out — it was just fortuitous that I was invited to do something I’d been thinking about. If I hadn’t been approached with that opportunity, I probably would have pursued another job in philanthropy, because I was clear that it was my passion and what I was best suited to do.

The Annie E. Casey Foundation is on Twitter at @AECFNews.

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