Re-Imagineers: Gail Tifford, An inspiring Personal Story From Grief to Healing

In your early 50s, you became both a widow when your husband passed away and an empty nester when your kids went off to college.  You had to begin the process of reimagining what your life would become. What wisdom can you share with our readers who might find themselves in a similar circumstance?

On New Year’s Day 2021, I remember waking up and pinching myself. I had two exceptional children, an adoring husband of almost 25 years, an adorable dog and even a white picket fence. I was a C-Suite executive, held a seat on the board of a public company, was about to join the board of a private company, and achieved professionally more than I ever could have dreamed. I also felt blessed to have so many wonderful friends and family. I was a big believer in karma (I still am!) and felt that by treating people with kindness and respect was the main reason I was living such a full life. So, I certainly was unprepared for the news almost 12 weeks later that would cause my world to crash. My husband Craig had been diagnosed with terminal Stage 4 esophageal cancer, and we knew then that his odds of surviving the rest of 2021 were slim to none. Craig passed away on December 19, 2021, after the most noble battle with the most horrible disease imaginable.

The first few months after his passing were a bit of a blur. And I am forever grateful to my family, friends and colleagues who managed to keep me afloat and helped me understand what it really means to show up, to listen, to support and to hold space. This support bolstered me while I tried to keep the family afloat and make some life-defining choices. So whether it’s wisdom, advice or just plain common sense, I truly feel there is nothing more important than who you choose to surround yourself with. Find your tribe. We are fortunate to have the freedom to pick who we spend time with, who we are comforted by in the hard times and laugh with through the good. As many of us know, life can be unpredictable and unexpectedly altered in a moment. So, for the moments we are here on this earth, surround yourself with people who make your light shine brighter. Who truly care for you and your health and well-being. Who love to laugh with you and hug you when you need to cry. Who always tells you the truth no matter how hard it is to hear. To act without being told what to do. To love unconditionally. For me, my tribe was the key to my survival. 

The next nugget of advice I can share (and to this day share it all the time as I talk to hundreds of people who are looking for new jobs, new careers, and some even a new life). Be very clear about what is important to you – what do you WANT and what do you NEED. Knowing this may change over time, but that is OK. As someone who has worked 24/7 since I was 22 years old and had just first handedly witnessed the fragility of life, I decided I WANTED freedom and flexibility. Freedom to spend time with my son and daughter, my family, and my friends. Flexibility to travel, see the world and experience different cultures.  I NEEDED a paycheck, health insurance, and a job that was fulfilling, where I could help make a difference in people’s lives. Those priorities guided the next big decisions I would make, including selling the family home, moving to Florida, making a career transition to the world of executive recruiting and creating my bucket list of world travel that I am well on my way to completing.

It is now almost three years since my husband passed, and I do not have one regret about the decisions I made as they were all in furtherance of my priorities, which still hold true to this day.

You had a long and successful career in corporate America, including a role as Global Chief Brand Officer for a major company. In 2022, you made a major pivot into a new career. Tell us about that and what led to the decision to move into this new area?

As I mentioned above, when I redefined my priorities, it was clear that  showing up to an office every day and leading authentically after my heart had been shattered was not going to work for me.  This created a dilemma for me as it was the only life I had known and now I was the only breadwinner in my family, still supporting two children and scared of what I would do next. But as I mentioned above, when you surround yourself with incredible people, amazing things will happen. So when Todd Zangrillo from True Search called me to see if I would consider a career in executive recruiting – I was at first incredulous but then touched and excited. For he had seen something in me that I hadn’t even seen in myself. And gave me an opportunity to start my next chapter in a career that was able to give me not only what I needed but also what I wanted. It has now been over 2 years and I feel so grateful for the executives who trust me with helping them build their teams and companies and the candidates who trust me to guide them through a life changing decision.

As part of your reimagination, you left your home state of Connecticut and relocated to Florida. What led to that decision and how are you settling into your new life?  What advice would you give to someone who is thinking about moving to a new place?

My husband and I had been restoring a historic home in Florida with the intent of someday becoming snowbirds. He got so much joy out of restoring and rebuilding this home and would spend nights and weekends picking out flooring, appliances, windows and outdoor stones. After he passed away, I felt torn between two homes. My “old” home which was the idyllic place to have raised our children but was too big for me alone and where I felt incredibly lonely with every corner reminding me of the life we lived. I had friends and family nearby, yet I had never felt more alone. My “new” home in Florida was one that was smaller, more manageable and where I still felt Craig’s presence but in a “he built this for me knowing I would be living there alone” kind of way. I had a few friends but certainly not the community I had in Connecticut. I chose Florida for many reasons that had to do with my WANTS and NEEDS and I love the life I have created there: biking to my trainer, watching sunrises on the beach, and staring at the stars at nights amidst the palm trees. I do spend a lot more time on airplanes but am ok with that because when I leave, I cannot wait to see the people waiting for me in the cities that I am visiting and when I fly back to Florida, I cannot wait to get home to my little slice of paradise.

My biggest piece of advice though is not perhaps what you would think. Not “go introduce yourself to your neighbors” or “take up pickleball”, though they might be good ideas. But for me, the advice is do the work. Heal your trauma. Love what you do. And who you do it with. Because the best piece of advice is adherence to the old proverb ‘home is where the heart is’. No matter where I am, my heart is full of love, warmth and happy memories, And that is why I am always home.

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